2'-AMINOACETANILIDE Chemical Properties

Melting point:

133-137 °C(lit.)

Boiling point:

271.72°C (rough estimate)

Density 

1.1392 (rough estimate)

refractive index 

1.6180 (estimate)

storage temp. 

Keep in dark place,Inert atmosphere,Room temperature

form 

powder to crystalline

pka

14.73±0.70(Predicted)

color 

Light orange to Light red

Water Solubility 

107.5g/L(22 ºC)

CAS DataBase Reference

34801-09-7(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

2924297099

MSDS

• Language:English Provider:SigmaAldrich

2'-AMINOACETANILIDE Usage And Synthesis

Chemical Properties

White Powder

Uses

2′-Aminoacetanilide may be used in the preparation of:

• 2-Methylbenzimidazole.
• N-(2-(1,3-Dimethyl-2,4-dioxo-5-phenyl-3,4-dihydro-1H-pyrrolo[3,4-d]pyrimidin-6(2H)-yl)phenyl)-5-methylfuran-2-carboxamide, a potent cystic fibrosis transmembrane conductance regulator (CFTR) inhibitor.
• Azobenzothiazole dyes, N-[2-(6-nitrobenzothiazol-2-ylazo)phenyl]acetamide and N-[2-(benzothiazol-2-ylazo)phenyl]acetamide.

General Description

2′-Aminoacetanilide (2-aminoacetanilide, o-aminoacetanilide) can be prepared by the catalytic hydrogenation of 2-nitroacetanilide using 10%Pd/C (palladium/carbon).

Synthesis

The general procedure for the synthesis of 2'-aminoacetanilide from 2-nitroacetanilide was as follows: first, 2-nitroacetanilide (1.0 g, 5.6 mmol) was dissolved in ethanol (EtOH) and the solution was purged with nitrogen to remove oxygen. Subsequently, palladium hydroxide (Pd(OH)2, 20% by weight, carbon carrier, 200 mg) was added to the solution as a catalyst. The reaction mixture was shaken under hydrogen (H2, 20 psi) atmosphere for 2 hours. Upon completion of the reaction, it was filtered through a 0.22 μm cellulose acetate membrane (Corning) to remove the catalyst. The filtrate was concentrated under vacuum to afford the white crystalline solid product 2'-aminoacetanilide (800 mg, 96% yield). The structure of the product was confirmed by 1H NMR (300 MHz, d6-DMSO) and LRMS (ES pos.): 1H NMR δ: 9.12 (s, 1H), 7.14 (dd, J = 7.8,1.3 Hz, 1H), 6.88 (dt, J = 7.6,1.5 Hz, 1H), 6.70 (dd, J = 8.0,1.3 Hz, 1H), 6.52 (dt, J = 7.5,1.4 Hz, 1H), 4.85 (br s, 2H), 2.03 (s, 3H); LRMS (ES pos.) m/z = 151 (M + 1).

References

[1] Journal of Organic Chemistry, 2008, vol. 73, # 23, p. 9235 - 9244
[2] Patent: US6667300, 2003, B2. Location in patent: Page column 98
[3] Chemistry - A European Journal, 2015, vol. 21, # 26, p. 9493 - 9504
[4] Russian Journal of Organic Chemistry, 1997, vol. 33, # 11, p. 1676 - 1677
[5] Russian Journal of Organic Chemistry, 1997, vol. 33, # 11, p. 1676 - 1677

2'-AMINOACETANILIDE(34801-09-7)Related Product Information

• 2'-NITROBENZANILIDE
• 2'-NITROACETANILIDE
• 4-Acetamido-3-nitrobenzoic acid
• ALPHA-CHLORO-2-NITROACETANILIDE
• N1-(4,5-DICHLORO-2-NITROPHENYL)ACETAMIDE
• 4'-BROMO-2'-NITROACETANILIDE
• 2,4-DINITROACETANILIDE
• 4-METHOXY-2-NITROACETANILIDE
• 3-(N,N-DIACETHOXYETHYL)AMINOACETANILIDE,3'-Bis(2-acetoxyethyl)aminoacetanilide
• 2-[(3-acetamidophenyl)(2-cyanoethyl)amino]ethyl acetate
• P-AMINOACETANILIDE-3-SULFONIC ACID,4-aminoacetanilide-3-sulfonic acid
• 2-METHOXY-4-AMINOACETANILIDE
• 3-Aminoacetanilide HCl,M-AMINOACETANILIDE,3-AMINOACETANILIDE,3'-AMINOACETANILIDE
• 4-AMINOACETANILIDE HYDROCHLORIDE
• 3-(N-Cyanoethyl)aminoacetanilide
• N,N-DIALLYL-3-AMINOACETANILIDE
• 3'-AMINOACETANILIDE HYDROCHLORIDE
• 4'-Aminoacetanilide