Methyl 3-amino-2-methylbenzoate Chemical Properties

Boiling point:

300 °C (lit.)

Density 

1.146 g/mL at 25 °C (lit.)

refractive index 

n20/D 1.573(lit.)

Flash point:

220 °F

storage temp. 

under inert gas (nitrogen or Argon) at 2–8 °C

solubility 

Chloroform (Sparingly), Methanol (Slightly)

form 

Liquid

pka

3.31±0.10(Predicted)

color 

Colorless to brown

CAS DataBase Reference

18583-89-6(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

2922498590

MSDS

• Language:English Provider:SigmaAldrich

Methyl 3-amino-2-methylbenzoate Usage And Synthesis

Chemical Properties

off-white powder

Uses

Methyl 3-Amino-2-methylbenzoate can be used in petroleum recovery process.

Synthesis

A. General procedure for the synthesis of methyl 3-amino-2-methylbenzoate: 10 g (66.2 mmol) of 3-amino-2-methylbenzoic acid and 20 g of p-toluenesulfonic acid monohydrate were dissolved in 400 mL of methanol and the reaction was carried out at reflux overnight. After completion of the reaction, the reaction solution was diluted with a mixture of ethyl acetate and 1 M potassium carbonate solution. After cooling, the organic and aqueous layers were separated. The organic layer was washed sequentially with 1M potassium carbonate solution and saturated brine, dried over anhydrous sodium sulfate, filtered, and concentrated to give 9.23 g of an orange oily product in 85% yield. The product was characterized as follows: 1H NMR (CDCl3): δ 2.34 (s, 3H), 3.73 (br.s, 2H), 3.88 (s, 3H), 6.81 (d, J = 7.96 Hz, 1H), 7.05 (t, J = 7.78 Hz, 1H), 7.19-7.30 (m, 1H). IR (CHCl3): 3406, 3027, 3012, 2.30 (m). 3027, 3012, 2978, 2953, 1718, 1621, 1467, 1435, 1315, 1301, 1265, 1196, 1159, 1108, 1066, 1045, 810 cm-1. MS (FD): m/e 165 (M+, 100).

References

[1] Patent: US5952343, 1999, A
[2] Patent: US5461154, 1995, A
[3] Patent: US5484926, 1996, A
[4] Patent: US6555541, 2003, B1

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