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CAS No. : | 51760-21-5 |
Formula : | C10H9BrO4 |
M.W : | 273.08 |
SMILES Code : | O=C(OC)C1=CC(Br)=CC(C(OC)=O)=C1 |
MDL No. : | MFCD00078709 |
InChI Key : | QUJINGKSNJNXEB-UHFFFAOYSA-N |
Pubchem ID : | 103954 |
GHS Pictogram: |
![]() |
Signal Word: | Warning |
Hazard Statements: | H315-H319-H335 |
Precautionary Statements: | P261-P264-P271-P280-P304+P340-P302+P352-P305+P351+P338-P312-P362+P364-P403+P233-P501 |
Num. heavy atoms | 15 |
Num. arom. heavy atoms | 6 |
Fraction Csp3 | 0.2 |
Num. rotatable bonds | 4 |
Num. H-bond acceptors | 4.0 |
Num. H-bond donors | 0.0 |
Molar Refractivity | 56.7 |
TPSA ? Topological Polar Surface Area: Calculated from |
52.6 ?2 |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
2.67 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
2.32 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
2.02 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
2.52 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
2.31 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
2.37 |
Log S (ESOL):? ESOL: Topological method implemented from |
-3.03 |
Solubility | 0.257 mg/ml ; 0.00094 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (Ali)? Ali: Topological method implemented from |
-3.06 |
Solubility | 0.236 mg/ml ; 0.000864 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-3.4 |
Solubility | 0.108 mg/ml ; 0.000396 mol/l |
Class? Solubility class: Log S scale |
Soluble |
GI absorption? Gatrointestinal absorption: according to the white of the BOILED-Egg |
High |
BBB permeant? BBB permeation: according to the yolk of the BOILED-Egg |
Yes |
P-gp substrate? P-glycoprotein substrate: SVM model built on 1033 molecules (training set) |
No |
CYP1A2 inhibitor? Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set) |
Yes |
CYP2C19 inhibitor? Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set) |
Yes |
CYP2C9 inhibitor? Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set) |
No |
CYP2D6 inhibitor? Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set) |
No |
CYP3A4 inhibitor? Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set) |
No |
Log Kp (skin permeation)? Skin permeation: QSPR model implemented from |
-6.32 cm/s |
Lipinski? Lipinski (Pfizer) filter: implemented from |
0.0 |
Ghose? Ghose filter: implemented from |
None |
Veber? Veber (GSK) filter: implemented from |
0.0 |
Egan? Egan (Pharmacia) filter: implemented from |
0.0 |
Muegge? Muegge (Bayer) filter: implemented from |
0.0 |
Bioavailability Score? Abbott Bioavailability Score: Probability of F > 10% in rat |
0.55 |
PAINS? Pan Assay Interference Structures: implemented from |
0.0 alert |
Brenk? Structural Alert: implemented from |
1.0 alert: heavy_metal |
Leadlikeness? Leadlikeness: implemented from |
No; 1 violation:MW<0.0 |
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) |
1.9 |
* 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% | With sulfuric acid; for 24h;Reflux; | B (8 g, 0.033 mol) was dissolved in 120 mL methanol under stirring and 6 mL cone. H2SO4 was subsequently added to the mixture. The reaction was heated to reflux for 24 hours. After cooling down to room temperature the solvent was removed through rotovap. The obtained solid was dispersed in 40 mL DI water and the aqueous phase was extracted by dichloromethane (40 mL X 3). The combined organic layer was washed with saturated NaHCCL and brine and dried over MgSCL. Crude product was obtained upon removal of the solvent which was recrystallized from methanol to give pure C (8.3 g, 91 % yield). |
76.6% | With sulfuric acid; for 20h;Reflux; | A solution of conc. sulphuric acid (8 ml) in methanol (30 ml) was added dropwise to a solution of B (13.2 g,0.054 mol) in methanol (150 ml). The reaction mixture was refluxed for 20 h. After cooling to room temperature, the product was obtained as colourless crystals. After filtration, the product was washed with cold methanol to give C 11.3g (Yield. 76.6%). 1H-NMR(CDCl3): delta = 3.96 (s, 6H), 8.35 (d, 2H), 8.6 (t, 1H). |
76.6% | for 20h;Reflux; | A solution of conc. sulphuric acid (8 ml) in methanol (30 ml) was added dropwise to a solution of B (13.2 g, 0.054 mol) in methanol (150 ml). The reaction mixture was refluxed for 20 h. Afier cooling to room temperature, the product was obtained as colourless crystals. After filtration, the product was washed with cold methanol to give C 11.3 g (Yield. 76.6%). ?H-NMR (CDC13): oe=3.96 (s, 6H), 8.35 (d, 2H), 8.6 (t, 1H). |
With sulfuric acid; In N,N-dimethyl-formamide; at 70℃; for 24h; | 6 g of <strong>[23351-91-9]5-bromoisophthalic acid</strong> (0.024 mol) was added to 80 mL of methanol.Slowly add 6 mL of concentrated sulfuric acid with stirring.It was refluxed at 70 C for 24 hours, cooled to room temperature, and dried.The resulting solid was dissolved in ethyl acetate and then aqueous sodium hydrogen carbonate (5%)Wash to neutral, dry anhydrous sodium sulfate, filter, spin dry,A white solid was obtained. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
5-Bromoisophthalic acid. To a solution of dimethyl 5-bromoisophthalate (5.00 g, 18.3 mmol) in 150 mL of MeOH was added KOH (5.14 g, 91.5 mmol). The reaction was refluxed for 3 hours. The reaction was cooled and the solvent was removed in vacuo. The remaining residue was dissolved in 100 mL water and acidified with 35 mL of 3N HCl solution and extracted with EtOAc. The combined organic extracts were washed with brine, dried over Na2SO4, filtered, and concentrated to give 5-bromoisophthalic acid as a white solid. 1H NMR (400 MHz, DMSO) delta 13.44 (b, 2H), 8.41(m, 1H), 8.25(m, 2H | ||
Step A: Bis Hydrolysis To a solution of dimethyl 5-bromoisorhohthalate (10 g, 36.6 mmol) in MeOH (200 mL) and THF (200 mL) was added IN NaOH (91.5 mL, 91.5 mmol) and the reaction mixture was stirred at rt for 5 h, quenched with IN HCl (92 mL), concentrated in vacuo to ca. 250 mL. The white solid was filtered, washed with water and dried over P2O5, under high vacuum, at 50 °C. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
0.9%; 4.9%; 7.2%; 0.2%; 19.6%; 7.0%; 50.4% | With sulfuric acid; sulfur trioxide; bromine; at 120℃; for 7h; | Into a 100 ml pressure and sealable glass tube, 9.70 g (50 mmol) of dimethyl isophthalate, 30.00 g of 10 wt percent fuming sulfuric acid and 10.40 g (100 mmol) of bromine were charged, and the content was stirred at 120° C. for 7 hours. After the conclusion of the reaction, the content was cooled to room temperature, and placed in a beaker containing ice water to give a solid. The resulting solid was filtered off, washed with cooling, and further dried under reduced pressure to give 11.95 g of a crude crystal of the aimed product (reaction yield: 50.4percent 5-bromoisophthalic acid, 19.6percent isophthalic acid, 4.9percent 2,5-dibromoisophthalic acid, 7.2percent 4,5-dibromoisophthalic acid, 7.0percent dimethyl 5-bromoisophthalate, 1.5percent dimethyl isophthalate, 0.9percent dimethyl 2,5-dibromoisophthalate and 0.2percent dimethyl 4,5-dibromoisophthalate). Then, dimethyl esters were derived from the crystal by heating and stirring it with 65.50 g (2.04 mol) of methanol and 1.75 g (30 mol percent) of sulfuric acid in an autoclave at 120° C. [0038] In succession, the esters were subjected to rectification to give 6.73 g (yield: 49.3percent, vacuum boiling point: 159° C./4.8mmHg) of aimed dimethyl 5-bromoisophthalate and 1.67 g (yield: 17.2percent, vacuum boiling point: 133° C./4.8mmHg) of dimethyl isophthalate corresponding to a raw material. The resulting crystals were identified as dimethyl 5-bromoisophthalate and 5-bromoisophthalic acid by MASS, 1H-NMR and melting point. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
83.3% | With sodium tetrahydroborate; In tetrahydrofuran; methanol; at 0℃; for 5.0h;Cooling with ice; | A three-necked flask having a capacity of 2 liters was charged with 109.2g of dimethyl 5-bromo-isophthalate and then with 400 ml of tetrahydrofuran (THF), to prepare a solution of dimethyl 5-bromoisophthalate. The solution was mixed with 16.6g of sodium borohydride and the resultant mixture liquid was agitated while cooling the mixture liquid with ice pieces. Separately, 40.5 ml of methyl alcohol were dissolved in 150 ml of THF, the resultant solution was mixed in the ice-cooled mixture liquid. Then, the resultant reaction mixture liquid was agitated for 5 hours while cooling with ice pieces. The reaction mixture liquid was added with 380 ml of water to terminate the reaction, and then mixed with a 1 mole hydrochloric acid solution to adjust the pH value of the reaction mixture liquid to 7.0. The resultant reaction mixture liquid was subjected to an extraction treatment with 380 ml of ethyl acetate and then with 200 ml of ethyl acetate. The resultant organic extract liquids were mixed with each other, and the resultant mixed extract liquid was washed with 300 ml of water and then with 80 ml of a saturated aqueous common salt solution, and the resultant washed extract liquid was dried with a drying agent consisting of anhydrous magnesium sulfate. The dried extract liquid was filtered to separate the drying agent, and the resultant filtrate was concentrated. A crude product of the target compound, namely methyl 5-bromo-3-(hydroxymethyl)benzoate was obtained in an amount of 96.5g. In the crude product, the mass ratio of the target compound, namely methyl 5-bromo-3-(hydroxymethyl)benzoate to the by-product consisting of 5-bromo-3-(hydroxymethyl)benzyl alcohol was 88:10, as determined by NMR measurement. The crude product was dissolved in 160 ml of methyl alcohol; the resultant solution was placed in a separatory funnel and mixed with 160 ml of water and 1000 ml of xylene; and the resultant mixture liquid was subjected to a phase separation. The resultant organic phase fraction was collected, washed with 160 ml of a solution of methyl alcohol in water in volume ratio of 1:1, then with 160 ml of water and finally with 160 ml of a saturated aqueous common salt solution. The washed organic phase fraction was dried with a drying agent consisting of anhydrous magnesium sulfate. The dried solution was subjected to a filtration procedure to remove the drying agent from the organic phase fraction. Then, the filtrate was concentrated. The target compound, namely, purified methyl 5-bromo-3-(hydroxymethyl)benzoate was obtained in an amount of 81.98g. The yield thereof was 83.3%. In the resultant purified product, a mass ratio of the target compound, methyl 5-bromo-3-(hydroxymethyl)benzoate to a by-product, namely, 5-bromo-3-(hydroxymethyl)benzyl alcohol was 96:1.8, determined by the NMR measurement. The results of the 1H-NMR measurement (200 MHz, delta ppm, CDCl3) were as follows 3.93(s, 3H), 4.74 (d, J = 5.6 Hz, 2H) 7.73 (s, 1H), 7.95 (s, 1H), 8.09 (s, 1H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
89% | With sulfuric acid; sodium hydrogencarbonate; In methanol; | [Preparation of dimethyl 5-bromoisophthalate from <strong>[23351-91-9]5-bromoisophthalic acid</strong>] Into a 500 ml flask equipped with a stirrer and a Dimroth condenser, 110 g of <strong>[23351-91-9]5-bromoisophthalic acid</strong> obtained above, 500 ml of methanol and 10 g of a concentrated sulfuric acid were placed and the resultant mixture was heated under the refluxing condition for 6 hours. After the reaction mixture was cooled by being left standing, the cooled mixture was added dropwise to 1 liter of distilled water and the obtained mixture was neutralized with a 5percent by weight aqueous solution of sodium hydrogencarbonate. The formed precipitates were separated by filtration and washed twice with 2 liters of distilled water. The obtained white solid substance was dried at 50OEC under a reduced pressure for 2 days and 109 g (0.4 moles) of dimethyl 5-bromoisophthalate was obtained (the yield: 89percent). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
To a stirred solution of dimethyl 5-bromoisophthalate (5.4 g, 20 mmol) in methanol (300 mL) at 0 0C was slowly added sodium tetrahydroborate (1O g, 0.28 mol). The mixture was stirred at rt for 3 h, and then treated with water (300 mL). The volatiles were removed in vacuo and the aqueous phase was extracted with CH2Cl2 (100 niL x 3). The combined organic layers were washed with brine, dried over anhydrous MgSO4, and concentrated in vacuo. The resulting oil was purified by flash chromatography to afford the title compound. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
75% | With caesium carbonate;tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; In 1,4-dioxane; at 105℃; for 2h;Inert atmosphere; | Step b) 5-(5-Methyl-l,l-dioxo-llambda*6*-ri,2,51thiadiazolidin-2-yl)-isophthalic acid dimethyl ester (Acid- 12b^; Tris(dibenzylideneacetone)palladium (27 mg, 0.029 mmol) was added to a degassed mixture of 5-bromo-isophthalic acid dimethyl ester (159 mg, 0.583 mmol), 2-methyl-[l,2,5]thiadiazolidine 1,1 -dioxide (Acid- 12a) (79 mg, 0.583 mmol), Cs2CO3 (474 mg, 1.46 mmol) and Xantphos (50.6 mg, 0.0874 mmol) in dioxane (5 ml). The mixture was heated at 105 0C under N2 for 2 h, the solvent was evaporated and the residue purified by flash chromatography using 2% MeOH in DCM as eluent, which gave the title compound (143 mg, 75%) as a yellow solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | 5-bromobenzene-l, 3 -dicarboxylic acid (5 g, 20.4 mmol, 1.0 eq) was dissolved in DMF (150 mL). CS2CO3 (33.2 g, 102 mmol, 5.0 eq) was added and the reaction stirred for 30 min. Mel (7.2 g, 51 mmol, 2.5 eq) was added dropwise and the solution was stirred at room temperature overnight. Water was added and the aqueous layer was extracted with EtOAc. The combined organic extracts were dried (Na2S04), filtered and evaporated in vacuo to give the title compound as a colourless oil (5 g, 90 percent).LC-MS: m z 274.9 [M+H] |
Tags: 51760-21-5 synthesis path| 51760-21-5 SDS| 51760-21-5 COA| 51760-21-5 purity| 51760-21-5 application| 51760-21-5 NMR| 51760-21-5 COA| 51760-21-5 structure
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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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