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Synonyms: Sodium citrate; Trisodium citrate anhydrous
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CAS No. : | 68-04-2 |
Formula : | C6H5Na3O7 |
M.W : | 258.07 |
SMILES Code : | O=C(CC(C([O-])=O)(O)CC([O-])=O)[O-].[Na+].[Na+].[Na+] |
Synonyms : |
Sodium citrate; Trisodium citrate anhydrous
|
MDL No. : | MFCD00012462 |
InChI Key : | HRXKRNGNAMMEHJ-UHFFFAOYSA-K |
Pubchem ID : | 6224 |
GHS Pictogram: |
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Signal Word: | Warning |
Hazard Statements: | H317-H319 |
Precautionary Statements: | P280-P305+P351+P338 |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
91.5% | With triethylamine; In toluene; at 110℃; under 397.54 Torr; for 17h;Heating / reflux; | A 1 L four-necked flask equipped with a stirrer, thermometer, water separator and reflux tube was charged with 294.1 g (1.0 mole) of tri<strong>[68-04-2]sodium citrate</strong> dihydrate, 404.3 g (3.3 moles) of ethyl monochloroacetate, 0.3 g of triethylamine and 77.5 g of toluene, and the mixture was heated to 110C over a period of 30 minutes while being stirred under a reduced pressure of about 53 kPa. Toluene started to reflux at the same temperature (110C), and after the refluxing reached a stable state, 11.8 g of triethylamine was added over a period of 10 hours. Sixteen hours after the start of the reaction, 36.0 g (2.0 moles) of crystal water of tri<strong>[68-04-2]sodium citrate</strong> dihydrate had been recovered. Since no more water generation was observed, the reaction mixture was stirred at the same temperature and pressure for 1 hour, and the reaction was judged to be complete. After the reaction was complete, the reaction mixture was cooled to 40C, 560.0 g of a 1% aqueous hydrochloric acid solution was added, and the sodium chloride and quaternary ammonium salt of triethylamine generated as by-products were removed. Subsequently, the organic layer was neutralized by adding sodium carbonate in an amount corresponding to twice the acid value of the organic layer (14.2 g) and 185.0g of water. Subsequently, the organic layer was washed with 185.0 g of water and then heated to 120C. Toluene was recovered until the pressure reached about 5 kPa, and steam distillation was performed at the same pressure for 1 hour to remove low-boiling components from the reaction product. Thus, 412.4 g of a reddish yellow transparent liquid was obtained. The yield was 91.5% and the acid value of the product was 0.126 (mg KOH/g). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
aluminium chloride; In dichloromethane; methoxybenzene; | EXAMPLE 7 Sodium (6R,7R)-7-phenylacetamido-3-[(S)-tetrahydrofuran-2-yl]ceph-3-em-4-carboxylate A solution of the cephem ester from Example 6 (45 mg) in dry dichloromethane (1 ml) was added to a stirred solution of aluminium chloride (27 mg) in a mixture of anisole (1.5 ml) and dry dichloromethane (0.5 ml) at -40 C. After 15 minutes at (40 C. the cooling bath was removed and the mixture was treated with tri<strong>[68-04-2]sodium citrate</strong> (3.5 ml of a 0.5M aqueous solution). After stirring for a further 15 minutes the mixture was diluted with water (10 ml) and dichloromethane (5 ml). The aqueous layer was separated and the organic layer was re-extracted with water (5 ml). The combined aqueous layers were washed with dichloromethane, evaporated to low volume, and chromatographed on HP20 SS eluding with THF/water mixtures. The appropriate fractions were combined, concentrated, and freeze dried to give the title compound as an amorphous solid (26 mg), d ppm (D2O) 1.66-2.01 (3H, m), 2.12-2.22 (1H, m), 3.28 and 3.46 (2H, ABq, J 17.7 Hz), 3.61 and 3.69 (2H, ABq, J 14.8 Hz), 3.74-3.92 (2H, m), 4.67-4.73 (1H, m), 5.07 (1H, d, J 4.6 Hz), 5.57 (1H, d, J 4.6 Hz), 7.29-7.40 (5H, m). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
64% | aluminium chloride; In dichloromethane; water; methoxybenzene; | (b) Sodium (6R,7R)-7-[2-(2-aminothiazol-4-yl)-2-(Z)-methoxyiminoacetamido]-3-[(R) -tetrahydrofuran-2-yl]ceph-3-em-4-carboxylate Aluminium chloride (740 mg, 5.55 mmol) was added to anisole (32 ml) and dry dichloromethane (15 ml) at -20 C. and stirred for 15 min. The temperature of the cooling bath was then lowered to -40 C. before addition of a solution of 4-methoxybenzyl (6R,7R)-7-[2-(2-aminothiazol-4-yl)-2-(Z)-methoxyiminoacetamido) -3- [ (R) -tetrahydrofuran-2-yl) ceph-3-em-4-carboxylate (1.06 g, 1.85 mmol) in dichloromethane (10 ml). After 10 min., the solution was treated with tri<strong>[68-04-2]sodium citrate</strong> (0.5M, 54 ml) and then vigorously stirred for 10 min. at room temperature. The aqueous phase was separated, washed with dichloromethane (x2) and concentrated in vacuo. The residue was chromatographed on HP20SS eluding with water, then 1% THF in water. Fractions containing the product, (h.p.l.c. analysis), were combined and freeze-dried to give the title compound (560 mg, 64%); numax (KBr) 3399, 1762, 1669, 1603, 1529, 1038 cm-1; deltaH (d6 -DMSO, 250 MHz) 1.50-1.91 (4 H, m), 3.25 and 3.38 (2 H, ABq, J 16.8 Hz), 3.60-3.82 (2 H, m), 3.84 (3 H, s), 4.96 (1 H, d, J 4.7 Hz), 5.20 (1 H, dd, J 8.6, 6.0 Hz), 5.48 (1 H, dd, J 8.1, 4.7 Hz), 6.76 (1 H, s), 7.23 (2 H, br. s, exch.), 9.50 (1 H, d, J 8.1 Hz, exch.). [Mass spectrum: +ve ion (thioglycerol) MH+ (476), MNa+ (498)]. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
zirconium(IV) oxide; | (ii) The above <strong>[68-04-2]sodium citrate</strong> solution was added to 500 gm of zirconium hydroxychloride solution which contains 20.0% ZrO2. The reaction batch was mixed continuously while the <strong>[68-04-2]sodium citrate</strong> was being added. A clear solution of sodium zirconium citrate was obtained after the addition of <strong>[68-04-2]sodium citrate</strong> solution was completed. | |
zirconium(IV) oxide; | (ii) The above <strong>[68-04-2]sodium citrate</strong> solution was added to 500 g of zirconium hydroxychloride solution which contains 20.0% ZrO2. The reaction batch was mixed continuously while the <strong>[68-04-2]sodium citrate</strong> was being added. A clear solution of sodium zirconium citrate was obtained after the addition of <strong>[68-04-2]sodium citrate</strong> solution was completed. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
48.7% | With citric acid; In 1,2-dimethoxyethane; water; | EXAMPLE 9 To a solution of 1.62 g of 2,3-diamino-3-(ethylthio)acrylonitrile in 26 ml of DME and 87 ml of water were added 113 ml of 0.1M citric acid and 9.5 ml of a 0.1M <strong>[68-04-2]sodium citrate</strong> aqueous solution to adjust the pH to be 3.2. The reaction mixture was stirred with bubbling air at 20 C. for 4 hours, followed by the same procedures in Example 3. 0.44 g of the 3,6-diamino-2,5-pyrazinedicarbonitrile as red crystals was obtained. (yield: 48.7%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
aluminium chloride; In dichloromethane; water; methoxybenzene; | (f) Sodium (6S,7S)-7-[2-(2-Aminothiazol-4-yl)-2-(Z)-methoxyiminoacetamido]-8-oxo-3-(tetrahydrofuran-2-yl)-1-aza-4-oxabicyclo[4.2.0]oct-2-ene-2-carboxylate (I) A stirred mixture of anisole (2.38 ml) and dichloromethane (1.2 ml) under argon was cooled to -20 C. and treated with aluminium chloride (61 mg). The mixture was stirred at -20 C. for 15 min. an then a slurry of 4-methoxybenzyl (6S,7S)-7-[2-(2-aminothiazol-4-yl)-2-(Z)-methoxyiminoacetamido]-8-oxo-3-(tetrahydrofuran-2-yl)-1-aza-4-oxabicyclo[4.2.0]oct-2-ene-2-carboxylate (I) (88 mg) in dichloromethane (7.5 ml) was added. The mixture was stirred for 5 min. and then tri<strong>[68-04-2]sodium citrate</strong> (5.2 ml of 0.5M) was added and the mixture stirred for 10 min. The aqueous phase was separated and washed twice with dichloromethane, then evaporated. The product was purified by HP20SS chromatography of the residue (water with increasing proportions of acetone as eluent). Fractions containing product were combined and evaporated and the residue dissolved in water (4 ml) and freeze-dried to give the title compound (27 mg). numax (KBr) 1757, 1662 and 1617 cm-1; delta[(CD3)2 SO]1.68-1.95 (4H, m), 3.58-3.77 (4H, m), 3.84 (3H, s), 4.35 (1H, m), 5.51 (1H, dd, J 3.91 and 8.83 Hz), 5.68 (1H, t, J 6.84), 6.78 (1H, s), 7.25 (2H, s), 9.91 (1H, d, J 8.83 Hz). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
The following are for examples of substances suitable for adjusting the pH: sodium hydroxide, potassium hydroxide, tromethamine, trisodium citrate, sodium monohydrogen phosphate, potassium monohydrogen phosphate. | ||
Example 3 37.3 kg of citric acid are dissolved in 32.1 kg of demineralised water and the solution is reacted to give monosodium citrate by addition of 17.3 kg of 45% strength sodium hydroxide solution. | ||
EXAMPLE 3 A white dispersion of carboxymethyl ethyl cellulose was prepared in the same manner as in Example 1 except that 81.5 parts of an aqueous solution of sodium citrate obtained by adding 3 parts by volume of a 0.1 M aqueous solution of sodium hydroxide to 1 part by volume of a 0.1 M aqueous solution of citric acid was employed instead of the aqueous sodium lactate solution. |
EXAMPLE 2 1.110 kg of potassium phenoxymethylpenicillin is mixed with 0.050 kg of maize starch. A solution of 0.1 kg of sodium citrate is prepared in 0.1 liter of distilled water. | ||
In FIG. 2 are shown the U.V. spectra of the indicated compounds namely: trisodium citrate PAC PHC trisodium isocitrate | ||
Sodium citrate 0.27% sodium saccharin | ||
Solutions were not prepared with bicarbonate below pH 7 because bicarbonate will decompose at a lower pH. 1. Sodium Lactate Sodium Bicarbonate Sodium Citrate Sodium Pyruvate | ||
4. Preparation of Trisodium Citrate Solution: In a separate 400 mL glass beaker equipped with a magnetic stirbar, and using a stirrer/hot-plate, make a solution by mixing 150-mL's deionized water, 33.7 grams citric acid, and 42.0 grams 50% sodium hydroxide. Use a cooling water bath to cool the solution to 30-32 C. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
aluminium chloride; In dichloromethane; methoxybenzene; | (i) Sodium (6R,7R)-7-[2-(2-Aminothiazol-4-yl)-2-(Z)methoxyiminoacetamido]-3-(1,1-dioxotetrahydrothien-2-yl)ceph-3-em-4-carboxylate Anisole (3 ml) and dichloromethane (3 ml), under argon were cooled to -20 C. and treated with aluminium chloride (0.118 g) for 15m. The solution was then further cooled to -40 C. and a solution of the cephalosporin (0.185 g) from example 3(h) in dichloromethane (3 ml) added. After 15m., 0.5M tri<strong>[68-04-2]sodium citrate</strong> (8 ml) was added. The reaction mixture was then worked up and purified as described in Example 3(f). The title compound was obtained as an amorphous white solid, (0.128 g, 82%); numax (KBr) 1766, 1671, 1617 and 1529cm-1; deltaH ((CD3)2 SO) 1.83-2.02 (1H, m), 2.06-2.20 (3H, m), 2.95-3.17 (2H, m), 3.46 (2H, s), 3.85 (3H, s), 5.03 (1H, d, J4.7 Hz), 5.38 (1H, t, J9.5 Hz), 5.54 (1H, dd, J4.7, 8.2 Hz collapses to d, J4.7 Hz with D2 O), 6.78 (1H, s), 7.25 (2H, br.s, exchangeable with D2 O) and 9.61 (1H, d, J8.2 Hz, exchangeable with D2 O); [mass spectrum: +ve ion (thioglycerol) MH+ (502), MNa+ (524)]. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium hydroxide; | Preparation A An aqueous solution of folic acid, dihydrofolic acid and citric acid was prepared using sodium hydroxide solution. The pH value of the solution was 10.4. 100 g solution contained 16 mmol folic acid disodium salt, 1 mmol dihydrofolic acid, sodium salt, and 5 mmol tri<strong>[68-04-2]sodium citrate</strong>. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
410 mg (56%) | With sodium hydrogen sulfate; In dichloromethane; ethyl acetate; | E. [1S-[1alpha,2alpha(Z),3alpha,4alpha]]-7-[3-[4-[[(4-Cyclohexylbutyl)amino]carbonyl]-2-oxazolyl]-7-oxabicyclo[2.2.1]hept-2-yl]-5-heptenoic acid, methyl ester To a stirred solution of Part D oxazoline (730 mg, 1.50 mmol) in 15 mL of dry CH2 Cl2 was added 1.10 g of NiO2. This mixture was stirred at room temperature for one hour, then 0.74 g of NiO2 was added. This mixture was stirred at room temperature for an additional hour and a second portion of 0.74 g of NiO2 was added. This mixture was stirred at room temperature for one more hour and then diluted with 80 mL of EtOAc, 50 mL of 3M NaHSO3 solution and 50 mL of 1M <strong>[68-04-2]sodium citrate</strong> solution. The aqueous layer was separated and extracted with EtOAc (3*120 mL). The combined organic extracts were dried (MgSO4), filtered and concentrated in vacuo. This was chromatographed on 30 g of Merck silica gel 60 using 2% CH3 OH in CH2 Cl2 as eluant to give 410 mg (56%) of title oxazole. TLC: silica gel, 2% CH3 OH/CH2 Cl2, Rf 0.31, Ce(SO4)2. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
200 mg (42%) | With sodium hydrogen sulfate; In dichloromethane; ethyl acetate; | D. [1S-[1alpha,2alpha(Z),3alpha,4alpha]]-6-[3-[4-[[[2-(4-Chlorophenyl)ethyl]amino]carbonyl]-2-oxazolyl]-7-oxabicyclo[2.2.1]hept-2-yl]-4-hexenoic acid, methyl ester To a stirred solution of Part C oxazoline (480 mg, 1.01 mmol) in 20 mL of CH2 Cl2 was added 480 mg of NiO2. The reaction mixture was stirred at room temperature for 1 hour at which time another 480 mg of NiO2 was added. The mixture was stirred at room temperature for 3 hours and 480 mg of NiO2 was added. This mixture was stirred for another 15.5 hours and one more portion of 480 mg of NiO2 was added. The reaction mixture was stirred for 1:5 hours and diluted with 100 mL of ethyl acetate. To the resulting mixture was added 20 mL of 3M NaHSO3 solution and 30 mL of 1M <strong>[68-04-2]sodium citrate</strong> solution. The organic layer was separated and the aqueous layer was extracted with ethyl acetate (2*100 mL). The combined organic extracts were washed with brine (1*50 mL), dried (MgSO4), filtered, and concentrated in vacuo. This was chromatographed on 45 g of Merck silica gel 60 using 2% CH3 OH in CH2 Cl2 as eluant to give 200 mg (42%) of title ester. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
200 mg (42%) | With sodium hydrogen sulfate; In dichloromethane; ethyl acetate; | D. [1S-[1alpha,2alpha(Z),3a,4a]]-6-[3-[4-[[(2-Cyclohexylethyl)amino]carbonyl]-2-oxazolyl]-7-oxabicyclo[2.2.1]hept-2-yl]-4-hexenoic acid, methyl ester To a stirred solution of Part C oxazoline (480 mg, 1.01 mmol) in 20 mL of CH2 Cl2 was added 480 mg of NiO2. The reaction mixture was stirred at room temperature for 1 hour at which time another 480 mg of NiO2 was added. The mixture was stirred at room temperature for 3 hours and 480 mg of NiO2 was added. This mixture was stirred for another 15.5 hours and one more portion of 480 mg of NiO2 was added. The reaction mixture was stirred for 1.5 hours and diluted with 100 mL of ethyl acetate. To the resulting mixture was added 20 mL of 3M NaHSO3 solution and 30 mL of 1M <strong>[68-04-2]sodium citrate</strong> solution. The organic layer was separated and the aqueous layer was extracted with ethyl acetate (2*100 mL). The combined organic extracts were washed with brine (1*50 mL), dried (MgSO4), filtered, and concentrated in vacuo. This was chromatographed on 45 g of Merck silica gel 60 using 2% CH3 OH in CH2 Cl2 as eluant to give 200 mg (42%) of title ester. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With hydrogenchloride; sodium hydroxide; In ethyl acetate; | EXAMPLE 6 Benzhydryl 7-(S)-(2-phenylacetamido)-3-hydroxymethyl-3-cephem-4-carboxylate sulfone 7-(S)-(2-Phenylacetamido)-3-acetoxymethyl-3-cephem-4-carboxylic acid (15 g) was dissolved in a buffer solution (0.05 M <strong>[68-04-2]sodium citrate</strong> plus 0.075 M sodium phosphate, pH 7.0, 1500 ml) while maintaining the pH of the solution between pH 7.0-7.2 by the addition of 1 N sodium hydroxide. The solution was then percolated through the IMER (at 60 to 100 ml/h). The collected effluent (1250 ml) was layered with ethyl acetate (600 ml) and the resultant emulsion was chilled to 0 C. in an ice-alcohol bath. Diphenyldiazomethane (5.0 g) was added to the stirred emulsion, and the mixture was stirred for an additional 2.5 h, while the pH of the reaction mixture was maintained at about 2.5 by the addition of 1 N hydrochloric acid. The phases were separated and the aqueous phase was extracted with ethyl acetate (400 ml, 2*). The ethyl acetate extracts and the ethyl acetate phase were combined, washed with 0.3 M sodium phosphate solution (pH 7, 2*) and saturated aqueous sodium bicarbonate solution (300 ml, 1*). The combined ethyl acetate solution was dried over magnesium sulfate, filtered, and the solvent was removed in vacuo to give a yellow foam. The foam was pulverized, yielding 12.6 g of benzhydryl 7-(S)-(2-phenylacetamido)-3-hydroxymethyl-3-cephem-4-carboxylate sulfone: n.m.r. delta 3.60 (s, 2, 2-phenylacetamido CH2), 4.06 (s, 2, C3 '-H), 4.22 (ABq, 2, C2 -H), 5.10 (dd, 1, C7 -H), 5.47 (d, 1, C6 -H), 6.90 (s, 1, benzhydryl methine), 7.2 to 7.6 (m, 15, aromatic protons), 9.07 (d, 1, amido proton). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With hydrogenchloride; sodium hydroxide; In dichloromethane; | EXAMPLE 12 Benzhydryl 7-(S)-[D-(5-(2,4-dichlorobenzoxycarbonylamino))- 5-(benzhydryl carboxylate)valeramido]-3-hydroxymethyl-3-cephem-4-carboxylate sulfone Benzhydryl 7-(S)-[D-(5-(2,4-dichlorobenzoxycarbonylamino))-5-(benzhydryl carboxylate)valeramido]-3-acetoxymethyl-3-cephem-4-carboxylate sulfone (14.7 g) was added to a 0.2 M <strong>[68-04-2]sodium citrate</strong> solution (pH adjusted to 7.0 by the addition of 1 N sodium hydroxide to yield a 1% solution of sulfone), and the solution was percolated through an IMER (50 to 35 ml/h). The eluant was refrigerated and diluted with ethyl acetate. Diphenyldiazomethane (10.0 g) was added to the cold eluant and the pH of the mixture was adjusted to 3.5 by the addition of 1 N hydrochloric acid. After stirring the mixture for 4 h, the layers were separated and the aqueous layer was extracted with ethyl acetate (250 ml, 2*). The ethyl acetate layer and extracts were combined, washed with a saturated sodium chloride solution, then dried over magnesium sulfate and filtered. Diphenyldiazomethane (1.6 g) was added to the filtrate and the solution was stirred overnight. Additional diphenyldiazomethane (1.0 g) was added. The mixture was stirred for approx. 6 h, and was then evaporated to yield 22.3 g of yellow foam. The foam was triturated with diethyl ether, the liquid decanted, the pale yellow solid dissolved in methylene chloride, and the solution evaporated to dryness in vacuo. The trituration procedure was repeated yielding a foam (14.9 g, 78% yield) of benzhydryl 7-(S)-[D-(5-(2,4-dichlorobenzoxycarbonylamino))-5-(benzhydryl carboxylate)valeramido]-3-hydroxymethyl-3-cephem-4-carboxylate sulfone: n.m.r. (DMSO d6) delta 1.40-2.45 (br. m., 6, valeramido methylenes), 4.04 (d, 2, C3 '-H), 4.11 (ABq, 2, C2 -H), 4.54 (m, 1, valeramido methine), 5.06 (dd, 1, C7 -H, J=2.5, 8), 5.21 (t, 1, hydroxy proton), 5.40 (d, 1, C6 -H, J=2.5), 6.79 (s, 1, benzhydryl methine on valeramido ester), 6.89 (s, 1, benzhydryl methine on C-4 ester), 7.2 to 7.7 (br. m., 23, aromatic protons), 8.85 (d, 2, S-amido proton), 8.97 (d, 1, C-7 amido proton). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With hydrogenchloride; sodium hydroxide; sodium acetate; In aqueous sodium citrate; water; ethyl acetate; | EXAMPLE 1 Sodium 7-(S)-benzamido-3-hydroxymethyl-3-cephem-4-carboxylate sulfone 7-(S)-Benzamido-3-acetoxymethyl-3-cephem-4-carboxylic acid sulfone (13.2 g) was dissolved in 0.2M aqueous <strong>[68-04-2]sodium citrate</strong> solution (38.9 g <strong>[68-04-2]sodium citrate</strong> in 630 ml water). The pH of this solution was adjusted to 7.0 by the addition of 1.0 N sodium hydroxide solution (approximately 30 ml). The solution was then percolated through the IMER (40-50 ml/h). The effluent (680 ml) collected from the IMER was layered with ethyl acetate (800 ml), chilled to 0 C. in an ice-alcohol bath, then the pH was adjusted to 2.5 by the addition of 1 N hydrochloric acid. The layers were separated and the aqueous layer was extracted with ethyl acetate (400 ml, 2*). The ethyl acetate extracts and the ethyl acetate layer were combined. Ice was added to the combined ethyl acetate solution which was then washed with an acidified saturated aqueous sodium chloride solution (250 ml, 2*). The solution was dried over magnesium sulfate and filtered. Sodium acetate (2.8 g) was added to the filtrate and the solution was stirred at room temperature for 3 h. and refrigerated overnight. The cream-colored crystals which deposited were collected by suction filtration, then washed with cold ethyl acetate. The crystals were allowed to air-dry first and then were dried in vacuo to yield 8.6 g of sodium 7-(S)-benzamido-3-hydroxymethyl-3-cephem-4-carboxylate: F.A.B.M.S. (m+1)=389. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With Potassium borohydride; sodium chloride; In hydrogenchloride; methanol; acetone; | h. Preparation of 7-[2-hydroxy-5-(3-hydroxyalk-1-enyl)-3-(2-tetrahydropyranyloxy)cyclopentyl]heptanoic acids A solution of 7-[2-oxo-5-(3-oxooct-1-enyl)-3-(2-tetrahydropyranyloxy)cyclopentyl]heptanoic acid [0.45 g.; prepared as described above in Example 2(g)] in methanol (10 ml.) was added to a stirred 2% w/v aqueous solution of <strong>[68-04-2]sodium citrate</strong> (100 ml.) at -5C. Potassium borohydride (1.6 g.) was then added portionwise, allowing the pH to change to pH 8 and then maintaining at pH 8 by the addition, when necessary, of quantities of 10% w/v aqueous citric acid solution. When the addition of the potassium borohydride was complete, the solution was stirred for 90 minutes, meanwhile maintaining the pH at pH 8 by means of the addition of further quantities of the citric acid solution, and allowing it to attain room temperature. The solution was then treated with acetone (50 ml.), treated with a further quantity of the citric acid solution to bring the pH to pH 4, saturated with sodium chloride and extracted three times with diethyl ether. The combined ethereal extracts were washed with a saturated solution of sodium chloride in 2N hydrochloric acid, and then with a saturated aqueous solution of sodium chloride, and dried over magnesium sulphate. The solvent was removed in vacuo to give crude 7-[2-hydroxy-5-(3-hydroxyoct-1-enyl)-3-(2-tetrahydropyranyloxy)cyclopentyl]heptanoic acid (0.34 g.), numax 1700 cm-1, 980 cm-1, which was used as starting material in the following preparation (i) of 7-[2,3-dihydroxy-5-(3-hydroxyoct-1-enyl)cyclopentyl]heptanoic acid without further purification being necessary. |
Tags: Citric acid trisodium | Alcohols | Carboxylic Acid Salts | Aliphatic Chain Hydrocarbons | 68-04-2
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P230 | Keep wetted |
P231 | Handle under inert gas. |
P232 | Protect from moisture. |
P233 | Keep container tightly closed. |
P234 | Keep only in original container. |
P235 | Keep cool |
P240 | Ground/bond container and receiving equipment. |
P241 | Use explosion-proof electrical/ventilating/lighting/equipment. |
P242 | Use only non-sparking tools. |
P243 | Take precautionary measures against static discharge. |
P244 | Keep reduction valves free from grease and oil. |
P250 | Do not subject to grinding/shock/friction. |
P251 | Pressurized container: Do not pierce or burn, even after use. |
P260 | Do not breathe dust/fume/gas/mist/vapours/spray. |
P261 | Avoid breathing dust/fume/gas/mist/vapours/spray. |
P262 | Do not get in eyes, on skin, or on clothing. |
P263 | Avoid contact during pregnancy/while nursing. |
P264 | Wash hands thoroughly after handling. |
P265 | Wash skin thouroughly after handling. |
P270 | Do not eat, drink or smoke when using this product. |
P271 | Use only outdoors or in a well-ventilated area. |
P272 | Contaminated work clothing should not be allowed out of the workplace. |
P273 | Avoid release to the environment. |
P280 | Wear protective gloves/protective clothing/eye protection/face protection. |
P281 | Use personal protective equipment as required. |
P282 | Wear cold insulating gloves/face shield/eye protection. |
P283 | Wear fire/flame resistant/retardant clothing. |
P284 | Wear respiratory protection. |
P285 | In case of inadequate ventilation wear respiratory protection. |
P231 + P232 | Handle under inert gas. Protect from moisture. |
P235 + P410 | Keep cool. Protect from sunlight. |
Response | |
Code | Phrase |
P301 | IF SWALLOWED: |
P304 | IF INHALED: |
P305 | IF IN EYES: |
P306 | IF ON CLOTHING: |
P307 | IF exposed: |
P308 | IF exposed or concerned: |
P309 | IF exposed or if you feel unwell: |
P310 | Immediately call a POISON CENTER or doctor/physician. |
P311 | Call a POISON CENTER or doctor/physician. |
P312 | Call a POISON CENTER or doctor/physician if you feel unwell. |
P313 | Get medical advice/attention. |
P314 | Get medical advice/attention if you feel unwell. |
P315 | Get immediate medical advice/attention. |
P320 | |
P302 + P352 | IF ON SKIN: wash with plenty of soap and water. |
P321 | |
P322 | |
P330 | Rinse mouth. |
P331 | Do NOT induce vomiting. |
P332 | IF SKIN irritation occurs: |
P333 | If skin irritation or rash occurs: |
P334 | Immerse in cool water/wrap n wet bandages. |
P335 | Brush off loose particles from skin. |
P336 | Thaw frosted parts with lukewarm water. Do not rub affected area. |
P337 | If eye irritation persists: |
P338 | Remove contact lenses, if present and easy to do. Continue rinsing. |
P340 | Remove victim to fresh air and keep at rest in a position comfortable for breathing. |
P341 | If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing. |
P342 | If experiencing respiratory symptoms: |
P350 | Gently wash with plenty of soap and water. |
P351 | Rinse cautiously with water for several minutes. |
P352 | Wash with plenty of soap and water. |
P353 | Rinse skin with water/shower. |
P360 | Rinse immediately contaminated clothing and skin with plenty of water before removing clothes. |
P361 | Remove/Take off immediately all contaminated clothing. |
P362 | Take off contaminated clothing and wash before reuse. |
P363 | Wash contaminated clothing before reuse. |
P370 | In case of fire: |
P371 | In case of major fire and large quantities: |
P372 | Explosion risk in case of fire. |
P373 | DO NOT fight fire when fire reaches explosives. |
P374 | Fight fire with normal precautions from a reasonable distance. |
P376 | Stop leak if safe to do so. Oxidising gases (section 2.4) 1 |
P377 | Leaking gas fire: Do not extinguish, unless leak can be stopped safely. |
P378 | |
P380 | Evacuate area. |
P381 | Eliminate all ignition sources if safe to do so. |
P390 | Absorb spillage to prevent material damage. |
P391 | Collect spillage. Hazardous to the aquatic environment |
P301 + P310 | IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician. |
P301 + P312 | IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell. |
P301 + P330 + P331 | IF SWALLOWED: Rinse mouth. Do NOT induce vomiting. |
P302 + P334 | IF ON SKIN: Immerse in cool water/wrap in wet bandages. |
P302 + P350 | IF ON SKIN: Gently wash with plenty of soap and water. |
P303 + P361 + P353 | IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower. |
P304 + P312 | IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell. |
P304 + P340 | IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing. |
P304 + P341 | IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing. |
P305 + P351 + P338 | IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. |
P306 + P360 | IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes. |
P307 + P311 | IF exposed: call a POISON CENTER or doctor/physician. |
P308 + P313 | IF exposed or concerned: Get medical advice/attention. |
P309 + P311 | IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician. |
P332 + P313 | IF SKIN irritation occurs: Get medical advice/attention. |
P333 + P313 | IF SKIN irritation or rash occurs: Get medical advice/attention. |
P335 + P334 | Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages. |
P337 + P313 | IF eye irritation persists: Get medical advice/attention. |
P342 + P311 | IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician. |
P370 + P376 | In case of fire: Stop leak if safe to Do so. |
P370 + P378 | In case of fire: |
P370 + P380 | In case of fire: Evacuate area. |
P370 + P380 + P375 | In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion. |
P371 + P380 + P375 | In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion. |
Storage | |
Code | Phrase |
P401 | |
P402 | Store in a dry place. |
P403 | Store in a well-ventilated place. |
P404 | Store in a closed container. |
P405 | Store locked up. |
P406 | Store in corrosive resistant/ container with a resistant inner liner. |
P407 | Maintain air gap between stacks/pallets. |
P410 | Protect from sunlight. |
P411 | |
P412 | Do not expose to temperatures exceeding 50 oC/ 122 oF. |
P413 | |
P420 | Store away from other materials. |
P422 | |
P402 + P404 | Store in a dry place. Store in a closed container. |
P403 + P233 | Store in a well-ventilated place. Keep container tightly closed. |
P403 + P235 | Store in a well-ventilated place. Keep cool. |
P410 + P403 | Protect from sunlight. Store in a well-ventilated place. |
P410 + P412 | Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF. |
P411 + P235 | Keep cool. |
Disposal | |
Code | Phrase |
P501 | Dispose of contents/container to ... |
P502 | Refer to manufacturer/supplier for information on recovery/recycling |
Physical hazards | |
Code | Phrase |
H200 | Unstable explosive |
H201 | Explosive; mass explosion hazard |
H202 | Explosive; severe projection hazard |
H203 | Explosive; fire, blast or projection hazard |
H204 | Fire or projection hazard |
H205 | May mass explode in fire |
H220 | Extremely flammable gas |
H221 | Flammable gas |
H222 | Extremely flammable aerosol |
H223 | Flammable aerosol |
H224 | Extremely flammable liquid and vapour |
H225 | Highly flammable liquid and vapour |
H226 | Flammable liquid and vapour |
H227 | Combustible liquid |
H228 | Flammable solid |
H229 | Pressurized container: may burst if heated |
H230 | May react explosively even in the absence of air |
H231 | May react explosively even in the absence of air at elevated pressure and/or temperature |
H240 | Heating may cause an explosion |
H241 | Heating may cause a fire or explosion |
H242 | Heating may cause a fire |
H250 | Catches fire spontaneously if exposed to air |
H251 | Self-heating; may catch fire |
H252 | Self-heating in large quantities; may catch fire |
H260 | In contact with water releases flammable gases which may ignite spontaneously |
H261 | In contact with water releases flammable gas |
H270 | May cause or intensify fire; oxidizer |
H271 | May cause fire or explosion; strong oxidizer |
H272 | May intensify fire; oxidizer |
H280 | Contains gas under pressure; may explode if heated |
H281 | Contains refrigerated gas; may cause cryogenic burns or injury |
H290 | May be corrosive to metals |
Health hazards | |
Code | Phrase |
H300 | Fatal if swallowed |
H301 | Toxic if swallowed |
H302 | Harmful if swallowed |
H303 | May be harmful if swallowed |
H304 | May be fatal if swallowed and enters airways |
H305 | May be harmful if swallowed and enters airways |
H310 | Fatal in contact with skin |
H311 | Toxic in contact with skin |
H312 | Harmful in contact with skin |
H313 | May be harmful in contact with skin |
H314 | Causes severe skin burns and eye damage |
H315 | Causes skin irritation |
H316 | Causes mild skin irritation |
H317 | May cause an allergic skin reaction |
H318 | Causes serious eye damage |
H319 | Causes serious eye irritation |
H320 | Causes eye irritation |
H330 | Fatal if inhaled |
H331 | Toxic if inhaled |
H332 | Harmful if inhaled |
H333 | May be harmful if inhaled |
H334 | May cause allergy or asthma symptoms or breathing difficulties if inhaled |
H335 | May cause respiratory irritation |
H336 | May cause drowsiness or dizziness |
H340 | May cause genetic defects |
H341 | Suspected of causing genetic defects |
H350 | May cause cancer |
H351 | Suspected of causing cancer |
H360 | May damage fertility or the unborn child |
H361 | Suspected of damaging fertility or the unborn child |
H361d | Suspected of damaging the unborn child |
H362 | May cause harm to breast-fed children |
H370 | Causes damage to organs |
H371 | May cause damage to organs |
H372 | Causes damage to organs through prolonged or repeated exposure |
H373 | May cause damage to organs through prolonged or repeated exposure |
Environmental hazards | |
Code | Phrase |
H400 | Very toxic to aquatic life |
H401 | Toxic to aquatic life |
H402 | Harmful to aquatic life |
H410 | Very toxic to aquatic life with long-lasting effects |
H411 | Toxic to aquatic life with long-lasting effects |
H412 | Harmful to aquatic life with long-lasting effects |
H413 | May cause long-lasting harmful effects to aquatic life |
H420 | Harms public health and the environment by destroying ozone in the upper atmosphere |
Sorry,this product has been discontinued.
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* Cat. No.:
* CAS No :
* Product Name :
* Additional Information :
Calculate the required mass, volume, or concentration of the solution. The Ambeed Molarity calculator is based on the following equation:
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