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2-Amino-4-methylbenzamide

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2-Amino-4-methylbenzamide Basic information
Product Name:2-Amino-4-methylbenzamide
Synonyms:2-AMINO-4-METHYLBENZAMIDE;Benzamide, 2-amino-4-methyl- (9CI);2-Amino-4-methylbenzamide ,98%;-Amino-4-methylbenzamide;Benzamide, 2-amino-4-methyl-
CAS:39549-79-6
MF:C8H10N2O
MW:150.18
EINECS:
Product Categories:AMIDE;Amines;Phenyls & Phenyl-Het;Phenyls & Phenyl-Het
Mol File:39549-79-6.mol
2-Amino-4-methylbenzamide Structure
2-Amino-4-methylbenzamide Chemical Properties
Melting point 147 °C
Boiling point 282.8±28.0 °C(Predicted)
density 1.185±0.06 g/cm3(Predicted)
storage temp. Keep in dark place,Inert atmosphere,Room temperature
pka15.98±0.50(Predicted)
AppearanceLight yellow to yellow Solid
CAS DataBase Reference39549-79-6(CAS DataBase Reference)
Safety Information
Hazard Codes Xn
Risk Statements 36/37/38-20/21/22-36-22
Safety Statements 26-36/37/39-36/37-36
HS Code 29242100
MSDS Information
2-Amino-4-methylbenzamide Usage And Synthesis
Synthesis
2-Amino-4-methylbenzonitrile

26830-96-6

2-Amino-4-methylbenzamide

39549-79-6

The general procedure for the synthesis of 2-amino-4-methylbenzamide using 2-amino-4-methylbenzonitrile as starting material was as follows: to a suspension of 2-amino-4-methylbenzonitrile (800 mg, 6.1 mmol) in water (1 mL), concentrated sulfuric acid (3 mL) was slowly added. The mixed solution was placed in an oil bath preheated to 120 °C and the reaction was stirred for 20 min. Immediately after completion of the reaction, the reaction mixture was cooled in an ice bath. Subsequently, the reaction solution was adjusted to alkaline by dropwise addition of 5% sodium hydroxide solution and the precipitated solid was collected by vacuum filtration. Finally, 484.4 mg of 2-amino-4-methylbenzamide was obtained in 53% yield as a light brown solid. The product was characterized by 1H NMR (DMSO-d6): δ 7.63 (br s, 1H), 7.42 (d, 1H), 6.95 (br s, 1H), 6.55 (br s, 2H), 6.45-6.48 (m, 1H), 6.29 (ddd, 1H), 2.16 (s, 3H). The mass spectrum (ES) showed a m/z of 134 (M-16).

References[1] Journal of the American Chemical Society, 2008, vol. 130, # 47, p. 15786 - 15787
[2] Journal of Organic Chemistry, 2006, vol. 71, # 1, p. 382 - 385
[3] Patent: WO2006/74223, 2006, A2. Location in patent: Page/Page column 51
[4] Patent: WO2013/100632, 2013, A1. Location in patent: Page/Page column 49; 50
[5] Patent: US2014/371219, 2014, A1. Location in patent: Paragraph 0342; 0343
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