4-Amino-3-methylbenzoic acid Chemical Properties

Melting point:

169-171 °C (lit.)

Boiling point:

273.17°C (rough estimate)

Density 

1.2023 (rough estimate)

refractive index 

1.5810 (estimate)

storage temp. 

Keep in dark place,Inert atmosphere,Room temperature

solubility 

DMSO (Slightly), Methanol (Slightly)

form 

Solid

pka

4.93±0.10(Predicted)

color 

Pale Brown to Light Brown

BRN 

2802615

Stability:

Light Sensitive

InChI

InChI=1S/C8H9NO2/c1-5-4-6(8(10)11)2-3-7(5)9/h2-4H,9H2,1H3,(H,10,11)

InChIKey

NHFKECPTBZZFBC-UHFFFAOYSA-N

SMILES

C(O)(=O)C1=CC=C(N)C(C)=C1

CAS DataBase Reference

2486-70-6(CAS DataBase Reference)

NIST Chemistry Reference

4-Amino-3-methylbenzoic acid(2486-70-6)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-37/39-24/25

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

29224999

MSDS

• Language:English Provider:3-Methyl-4-aminobenzoic acid
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

4-Amino-3-methylbenzoic acid Usage And Synthesis

Chemical Properties

beige or light buff to orange

Uses

4-Amino-3-methylbenzoic Acid is used in preparation of Amide-substituted Benzo[d]imidazole compounds as selective inhibitors of indoleamine-2,3-dioxygenases.

reaction suitability

reaction type: solution phase peptide synthesis

Synthesis

At room temperature and under hydrogen atmosphere, 3-methyl-4-nitrobenzoic acid (100 g, 552.04 mmol) was dissolved in methanol (2000 mL) followed by addition of palladium carbon catalyst (5.0 g). The reaction mixture was stirred continuously at room temperature for 24 hours. Upon completion of the reaction, the solid catalyst was removed by filtration. The filtrate was concentrated under reduced pressure to give the light yellow solid product 4-amino-3-methylbenzoic acid (80 g, 96% yield).

References

[1] Advanced Synthesis and Catalysis, 2010, vol. 352, # 9, p. 1451 - 1454
[2] Patent: WO2014/66795, 2014, A1. Location in patent: Paragraph 0175
[3] Journal of Organic Chemistry, 2008, vol. 73, # 21, p. 8631 - 8634
[4] Patent: CN106831460, 2017, A. Location in patent: Paragraph 0029-0059
[5] Patent: CN107501106, 2017, A. Location in patent: Paragraph 0025-0047

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