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[ CAS No. 56-91-7 ] {[proInfo.proName]}

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Chemical Structure| 56-91-7
Chemical Structure| 56-91-7
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Product Details of [ 56-91-7 ]

CAS No. :56-91-7 MDL No. :MFCD00010203
Formula : C8H9NO2 Boiling Point : -
Linear Structure Formula :- InChI Key :QCTBMLYLENLHLA-UHFFFAOYSA-N
M.W : 151.16 Pubchem ID :65526
Synonyms :
Aminomethylbenzoic acid;α-Amino-p-toluic acid

Calculated chemistry of [ 56-91-7 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 11
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.12
Num. rotatable bonds : 2
Num. H-bond acceptors : 3.0
Num. H-bond donors : 2.0
Molar Refractivity : 41.07
TPSA : 63.32 ?2

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -8.32 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.07
Log Po/w (XLOGP3) : -1.55
Log Po/w (WLOGP) : 0.69
Log Po/w (MLOGP) : 1.05
Log Po/w (SILICOS-IT) : 0.82
Consensus Log Po/w : 0.42

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -0.07
Solubility : 128.0 mg/ml ; 0.847 mol/l
Class : Very soluble
Log S (Ali) : 0.73
Solubility : 807.0 mg/ml ; 5.34 mol/l
Class : Highly soluble
Log S (SILICOS-IT) : -1.8
Solubility : 2.4 mg/ml ; 0.0159 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.0

Safety of [ 56-91-7 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 56-91-7 ]

* 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.

  • Downstream synthetic route of [ 56-91-7 ]

[ 56-91-7 ] Synthesis Path-Downstream   1~9

  • 1
  • [ 56-91-7 ]
  • [ 501-53-1 ]
  • [ 58933-52-1 ]
YieldReaction ConditionsOperation in experiment
87% With sodium hydroxide; In tetrahydrofuran; water; at 0 - 20℃; for 16h; Benzyl chloroformate (10.3 mL, 72.7 mmol) and 2 M NaOH solution (33 mL, 66 mmol) were simultaneously added dropwise to a stirred solution of 4-aminomethylbenzoic acid (29) (10.0 g, 66.2 mmol) in 2 M NaOH solution (33 mL) and THF (30 mL) at 0 C. The mixture was stirred at 20 C for 16 h, then the organic solvent was evaporated and the residue acidified with 2 M HC1 until the pH of the mixture was 2-3. The precipitate was filtered, washed with water (250 mL), washed with EtOH (50 mL), and finally washed with Et20 (100 mL). The solid was dried under vacuum to give acid 2 (16.43 g, 87%) as a white powder: mp 190-192 C [lit. (Loge et. al., J. Enzyme Inhibit. Med. Chem. 2002, 17, 381-390) mp (toluene) 194-195 C; 1H NMR δ 7.85 (br d, 2 H, H-2, H-6), 7.82 (br t, J = 6.1 Hz, 1 H, NHC02), 7.30-7.40 (m, 5 H, H-2', H-3', H-4', H-5', H-6'), 7.27 (br d, J = 8.2 Hz, 2 H, H-3, H-5), 5.05 (s, 2 H, OCH2), 4.24 (d, J = 6.1 Hz, 2 H, CH2N).
87% With sodium hydroxide; In tetrahydrofuran; at 0 - 20℃; for 16h; Benzyl chloroformate (10.3 mL, 72.7 mmol) and 2 M NaOH solution (33 mL, 66 mmol) were simultaneously added dropwise to a stirred solution of 4-aminomethylbenzoic acid (29) (10.0 g, 66.2 mmol) in 2 M NaOH solution (33 mL) and THF (30 mL) at 0 C. The mixture was stirred at 20 C. for 16 h, then the organic solvent was evaporated and the residue acidified with 2 M HCl until the pH of the mixture was 2-3. The precipitate was filtered, washed with water (250 mL), washed with EtOH (50 mL), and finally washed with Et2O (100 mL). The solid was dried under vacuum to give acid 2 (16.43 g, 87%) as a white powder: mp 190-192 C. [lit. (Loge et. al., J. Enzyme Inhibit. Med. Chem. 2002, 17, 381-390) mp (toluene) 194-195 C.; 1H NMR δ 7.85 (br d, 2H, H-2, H-6), 7.82 (br t, J=6.1 Hz, 1H, NHCO2), 7.30-7.40 (m, 5H, H-2', H-3', H-4', H-5', H-6'), 7.27 (br d, J=8.2 Hz, 2H, H-3, H-5), 5.05 (s, 2H, OCH2), 4.24 (d, J=6.1 Hz, 2H, CH2N).
87% With sodium hydroxide; In tetrahydrofuran; at 0 - 20℃; for 16h; Benzylchloroformate (10.3 mL, 72.7 mmol) and 2 M NaOH solution (33 mL, 66 mmol) weresimultaneously added dropwise to a stirred solution of 4-aminomethylbenzoicacid (1) (10.0 g, 66.2 mmol) in 2 M NaOH solution (33 mL) and THF (30 mL) at 0C. The mixture was stirred at 20 C. for 16 h, then the organic solvent wasevaporated and the residue acidified with 2 M HCl until the pH of the mixturewas 2-3. The precipitate was filtered, washed with water (250 mL), washed withEtOH (50 mL), and finally washed with Et2O (100 mL). The solid was dried undervacuum to give acid 2 (16.43 g, 87%)
32% With sodium hydrogencarbonate; In water; acetone; at 0 - 20℃; 4-(Aminomethyl)benzoic acid (4.53 g, 30.0 mmol) was dissolved in acetone (50 mL), sodium hydrogen carbonate (sat, 50 mL), and water (50 mL). After cooling to 0 C and an additional adding of ice (ca 10 mL) to the reaction mixture, benzyl chloroformate (4.5 mL, 31.5 mmol) in acetone (25 ml) was added dropwise. The mixture was allowed to attain room temperature and then stirred overnight. The mixture was diluted with water and washed with dichloromethane. The water layer was acidified with HCI (1 M) and extracted with ethyl acetate. The organic layer was basified with NaOH (aq) and a precipitate was formed. This was filtered off, washed with acetone and dichloromethane. Recrystallization from methanol yielded pure product (2.76 g, 9.67 mmol, 32%). 3C NMR (101 MHz, DMSO-cfe) δ ppm 43.77, 65.79, 127.31 , 128.01 , 128.16, 128.69, 129.45, 129.69, 137.32, 145.24, 156.72, 167.39
With hydrogenchloride; In tetrahydrofuran; sodium hydroxide; Step A. Preparation of 4-(N-CBz-aminomethyl)-benzoic acid 10.0 g (66 mmol) of 4-aminomethylbenzoic acid was dissolved in 33 ml of 2N NaOH solution (66 mmol) and 30 ml of THF. 12.45 g (73 mmol) of benzyl chloroformate and 37.5 ml of 2N NaOH solution was added in aliquots at 0 C. over 20 minutes. The reaction was stirred at room temperature over night and concentrated in vacuo to remove THF. 2N HCl was added to acidify to pH2-3. The precipitated solid was recovered by filtration and washed with ether to remove excess benzyl chloroformate. The solid was dried in vacuo to give 18.8 g of the desired product. 400 MHz 1H NMR (CD3OD): 4.31 (s, 2H); 5.09 (s, 2H); 7.30 (m, 7H); 7.91 (d, 2H).
With potassium carbonate; In water; for 16h; Compound 34 (4.00 g, 26.5 mmol) in aq. K2CO3 (1.0 M, 144 mL) was stirred vigorously with BnOCOCl (4.52 g, 26.5 mmol) for 16 h. The precipitate was collected by filtration and dried. This material was stirred with SOCl2 (10 mL) under Ar for 16 h. The evaporation residue was suspended in CH2Cl2 and filtered. Evaporation gave the crude acyl chloride, which was used immediately. This acyl chloride in dry THF (70 mL) was stirred with 2-aminobenzamide 12 (1.96 g, 14.4 mmol), pyridine (1.48 g, 18.7 mmol) and DMAP (0.35 g, 2.88 mmol) under Ar for 16 h. The evaporation residue, in EtOAc, was washed twice with water and twice with brine. Drying, evaporation and chromatography (EtOAc/CH2Cl2 2:3) gave 35 (5.1 g, 88%) as a white solid: mp 180-183 C;

  • 2
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  • [ 123986-64-1 ]
  • 3
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  • [ 156866-52-3 ]
  • 4
  • [ 56-91-7 ]
  • [ 24424-99-5 ]
  • [ 156866-52-3 ]
YieldReaction ConditionsOperation in experiment
[0261] To a solution of 5.0 g of 4-aminomethylbenzoic acid in 40 ml of dioxane-water (1:1) was added 6.0 g of NaHCO3 and a solution of 7.6 g of di-tertiary butyl dicarbonate in 20 ml of dioxane in order at room temperature, and the mixture was stirred at room temperature for 4 days. The solvent was distilled off under reduced pressure, and the residue was neutralized with aqueous hydrochloric acid. The precipitated solid was collected by filtration, and dried under reduced pressure to give 8.0 g of a carboxylic acid. The carboxylic acid (0.85 g) was dissolved in 10 ml of THF, to which was added 0.60 g of 1,1'-carbonylbis-1H-imidazole under ice-cooling, and the mixture was stirred at 50° C. for 40 minutes. To the resulting solution was added 0.43 g of N,O-dimethylhydroxylamine hydrochloride and 0.7 ml of triethylamine (Et3N) in order under ice-cooling, and the mixture was stirred overnight at room temperature. Water was added to the mixture, and the mixture was extracted with ethyl acetate (EtOAc). The resulting organic layer was dried over anhydrous sodium sulfate, filtered, and evaporated under reduced pressure. The resulting residue was purified by silica gel column chromatography to give 0.98 g of an amide. The amide (0.98 g) was dissolved in 10 ml of THF, to which was added 0.12 g of lithium aluminum hydride at -78° C., and the mixture was stirred at the same temperature for 40 minutes. There was added 2.0 g of Na2SO4.10H2O and the mixture was warmed up to room temperature and stirred for 3 hours. The reaction mixture was filtered and evaporated under reduced pressure to give 0.76 g of tertiary (t-)butyl 4-formylbenzylcarbamate.
  • 5
  • [ 56-91-7 ]
  • [ 13139-17-8 ]
  • [ 58933-52-1 ]
YieldReaction ConditionsOperation in experiment
85% Aminomethyl benzoic acid (6.0 g, 39.7 mmol) and Na2CO3 (8.41 g, 79.4 mmol) were dissolved in H2O (40 mL). To this mixture was added a solution Cbz-Osu (10.4 g, 41.7 mmol) in THF (40 mL). The resulting solution was stirred at room temperature overnight, then concentrated. The residue was acidified with 2N HCl to pH=2, which led to a solid precipitate. The product was collected by filtration and dried in vacuum overnight to give 9.6 g, 85% of a white solid (4).
  • 6
  • [ 56-91-7 ]
  • [ 1885-14-9 ]
  • [ 58933-52-1 ]
YieldReaction ConditionsOperation in experiment
Synthesis Example 41-1: Synthesis of 4-(N-Cbz aminomethyl) benzoic acid (Compound XVII-4) 5 mg of commercially available 4-aminomethyl benzoic acid was dissolved in 33 ml of a 1 mol/l sodiumhydroxide aqueous solution. Under stirring at room temperature, 5.2 ml of benzylchloroformate, and 40 ml of a 1 mol/l sodium hydroxide aqueous solution were gradually added to the solution at the same time. After 3 hours, a 1 mol/l hydrochloric acid was added to the reaction solution to adjust the pH thereof to pH = 3. A precipitated product was filtrated through a glass filter G4. Then, filtrate was washed with water, and with hexane, followed by drying under reduced pressure. Consequently, 8.162 g of the above-mentioned compound was obtained as a white solid product. 1H-NMR(500MHz,DMSO-d6):δ=4.26 (2H,d,J=6.3Hz), 5.05 (2H,s), 7.30-7. 40 (7H,m), 7.88 (2H,d,J=8.3Hz), 7.91 (1H,t,J=6.3Hz).
With hydrogenchloride; sodium hydroxide; In 1,4-dioxane; C. 4-Benzyloxycarbonylaminomethylbenzoic acid 4-(Aminomethyl)benzoic acid 15.1 g (100 mmol) was dissolved in 200 mL dioxane and 100 mL 1.000 N NaOH and cooled in a 0 C. ice bath. The mixture was treated dropwise with benzylchloroformate 14.3 mL (100 mmol) followed by the dropwise addition of 100 mL of 1.000 N NaOH. The mixture was stirred at room temperature for 18 hours. The mixture was neutralized by adding 100 mL of 1.000 N HCl followed by dilution with dichloromethane. A white solid precipitated out which was filtered. The solid was dried in vacuo to afford 10.8 g (38.9%). 1H NMR (300 MHz, DMSO-d6): δ 4.24 (d, 2H, J=6.2 Hz); 5.01 (s, 2H); 7.31-7.34 (m, 7H); 7.84-7.88 (m, 3H); 12.85 (s, 1H).
With hydrogenchloride; sodium hydroxide; Example 41-1 Synthesis of 4-(N-Cbz-aminomethyl)benzoic acid (Compound XVII-4) Commercially available 4-aminomethylbenzoic acid (5 g) was dissolved in 1 mol/l aqueous solution of sodium hydroxide (33 ml). Benzylchloroformate (5.2 ml) and 1 mol/l aqueous solution sodium hydroxide (40 ml) were gradually and simultaneously added while stirring at roomtemperature. After 3 hours, 1 mol/l hydrochloric acid was added to the reaction solution to adjust the pH to 3, and the deposited precipitate was collected by filtration through glass filter G4. The precipitate was washed with water and hexane, and dried under reduced pressure to obtain the title compound (8.162 g) as a white solid. 1H-NMR(500MHz,DMSO-d6):δ=4.26(2H,d,J=6.3Hz),5.05(2H,s), 7.30-7.40(7H,m),7.88(2H,d,J=8.3Hz),7.91(1H,t,J=6.3Hz).
  • 7
  • [ 56-91-7 ]
  • [ 530-62-1 ]
  • [ 123986-64-1 ]
  • [ 1160823-18-6 ]
YieldReaction ConditionsOperation in experiment
4-[([(4-[(tert-butoxycarbonyl)amino methyl}benzyl)oxy]carbonyl}amino) methyl]benzoic acid. To a suspension of CDI (340 mgd, 2.1 mmol) in THF (1.6 mL) was added tert-butyl [4-(hydroxymethyl)benzyl]carbamate (500 mg, 2.1 mmol)) in THF (0.7 mL) and the mixture was aged for 1 hour at ambient temperature. The resulting mixture was then added to a stirring solution of 4-(aminomethyl)benzoic acid (320 mg, 2.1 mmol), TEA (0.3 mL, 2.1 mmol), and DBU (0.3 mL, 2.1 mmol)) in THF (3.5 mL). After stirring at ambient temperature for 5 hours the reaction mixture was concentrated in vacuo, diluted with water, then acidified with HCl. The white precipitate was filtered away, washed with water then dissolved in DCM:EtOAc (some MeOH was added for solubility) dried over anhydrous MgSO4 and concentrated in vacuo to give the title compound. cal'd [M+Na]+437, exp. 437
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