2-Amino-6-methylbenzoic acid Chemical Properties

Melting point:

128-130 °C (dec.) (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 

Soluble in methanol.

pka

1.95±0.31(Predicted)

form 

powder to crystal

color 

White to Light yellow to Dark green

BRN 

2803391

InChI

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

InChIKey

XHYVBIXKORFHFM-UHFFFAOYSA-N

SMILES

C(O)(=O)C1=C(C)C=CC=C1N

CAS DataBase Reference

4389-50-8(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36-24/25

WGK Germany 

3

F 

10

Hazard Note 

Irritant

HS Code 

29224999

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

2-Amino-6-methylbenzoic acid Usage And Synthesis

Chemical Properties

Beige to pink powder

Uses

2-Amino-6-methylbenzoic acid reacts with cyanogen bromide to prepare 2-amino-5-methyl-benzo[d][1,3]oxazin-4-one.

reaction suitability

reaction type: solution phase peptide synthesis

Synthesis

General procedure for the synthesis of 2-amino-6-methylbenzoic acid from 2-methyl-6-nitrobenzoic acid: Pd/C catalyst (150 mg) was added to a methanol (35 mL) solution of 2-methyl-6-nitrobenzoic acid (1.5 g, 8.29 mmol). The reaction mixture was stirred for 2 hours at room temperature under hydrogen atmosphere. Upon completion of the reaction, the mixture was filtered to remove the catalyst and the filtrate was subsequently concentrated to give 2-amino-6-methylbenzoic acid (1.2 g) in yellow solid form. The product was characterized by liquid chromatography-mass spectrometry (LCMS, ESI mode): the calculated value of C8H9NO2 [M+H]+ was 152 and the measured value was 152, as expected.

References

[1] Patent: US5753664, 1998, A
[2] Tetrahedron Letters, 1984, vol. 25, # 8, p. 839 - 842
[3] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1982, # 8, p. 1637 - 1648
[4] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1982, # 8, p. 1701 - 1714
[5] Journal fuer Praktische Chemie (Leipzig), 1985, vol. 327, # 5, p. 865 - 867

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