3-Aminomethylbenzoic acid hydrochloride Chemical Properties

Melting point:

242-244℃

storage temp. 

Inert atmosphere,2-8°C

form 

Solid

Appearance

White to off-white Solid

Water Solubility 

Slightly soluble in water.

BRN 

3697656

CAS DataBase Reference

876-03-9(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xn

Risk Statements 

22-36/37/38

Safety Statements 

26

WGK Germany 

3

HS Code 

29224999

MSDS

• Language:English Provider:SigmaAldrich

3-Aminomethylbenzoic acid hydrochloride Usage And Synthesis

Chemical Properties

Solid

Uses

It is used as pharmaceutical intermediate. Derivatives of benzylamine and benzamidine were found to be competitive inhibitors of the proteolytic enzymes trypsin, plasmin, and thrombin.

Synthesis

Step 6 Synthesis of 3-(aminomethyl)benzoic acid hydrochloride: 3-cyanobenzoic acid (5.88 g, 40 mmol) was suspended in 50 mL of tetrahydrofuran (THF), stirred and heated gently until completely dissolved. Subsequently, 50 mL of isopropanol was added and the solution was cooled to room temperature. To the cooled solution, 4.2 mL of pre-cooled concentrated hydrochloric acid was slowly added, followed by 300 mg of platinum(IV) oxide catalyst. The reaction mixture was subjected to hydrogenation under 55 psi hydrogen pressure overnight. Upon completion of the reaction, 50 mL of ether was added to precipitate the product, the precipitate was collected by filtration and washed with ether. The resulting solid was dissolved in methanol, filtered to remove the catalyst, and finally the solvent was removed by distillation under reduced pressure to afford 6.2 g (82% yield) of the target product 3-(aminomethyl)benzoic acid hydrochloride. The structure of the product was confirmed by 1H-NMR (DMSO-d6): δ = 4.08 (d, 2H); 7.53 (t, 1H); 7.80 (d, 1H); 7.94 (d, 1H); 8.10 (s, 1H); 8.65 (s, 3H).

References

[1] Journal of the American Chemical Society, 1994, vol. 116, # 8, p. 3220 - 3230
[2] Patent: US5635477, 1997, A

3-Aminomethylbenzoic acid hydrochloride(876-03-9)Related Product Information

• Ethyl 2-(Chlorosulfonyl)acetate
• Topotecan hydrochloride
• 3-(Trifluoromethyl)benzoic acid
• Methyl 4-(bromomethyl)benzoate
• o-Toluic acid
• Methyl 4-methylbenzoate
• Folic acid
• m-Toluic acid
• p-Toluic acid
• methylbenzoic acid
• 3-Aminomethylbenzoic acid
• phosphoric acid
• 3-Aminomethylbenzoic acid hydrochloride