N1-(3-Aminophenyl)acetamide Chemical Properties

Melting point:

86-88 °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 crystal

pka

14.82±0.70(Predicted)

color 

White to Gray to Brown

Water Solubility 

1-5 g/100 mL at 24 ºC

InChI

InChI=1S/C8H10N2O/c1-6(11)10-8-4-2-3-7(9)5-8/h2-5H,9H2,1H3,(H,10,11)

InChIKey

PEMGGJDINLGTON-UHFFFAOYSA-N

SMILES

C(NC1=CC=CC(N)=C1)(=O)C

CAS DataBase Reference

102-28-3(CAS DataBase Reference)

EPA Substance Registry System

3'-Aminoacetanilide (102-28-3)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36-37/39

WGK Germany 

3

RTECS 

AD8050000

TSCA 

Yes

HazardClass 

IRRITANT

HS Code 

29214200

Toxicity

mouse,LD50,intravenous,320mg/kg (320mg/kg),U.S. Army Armament Research & Development Command, Chemical Systems Laboratory, NIOSH Exchange Chemicals. Vol. NX#02899,

MSDS

• Language:English Provider:N1-(3-Aminophenyl)acetamide
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS

N1-(3-Aminophenyl)acetamide Usage And Synthesis

Chemical Properties

light brown crystalline powder

Uses

3'-Aminoacetanilide is mainly used as reaction intermediates dyes and disperse dyes.

General Description

Gray solid.

Air & Water Reactions

Soluble in water.

Reactivity Profile

Amines are chemical bases. They neutralize acids to form salts plus water. These acid-base reactions are exothermic. The amount of heat that is evolved per mole of amine in a neutralization is largely independent of the strength of the amine as a base. Amines may be incompatible with isocyanates, halogenated organics, peroxides, phenols (acidic), epoxides, anhydrides, and acid halides. Flammable gaseous hydrogen is generated by amines in combination with strong reducing agents, such as hydrides.

Health Hazard

ACUTE/CHRONIC HAZARDS: When heated to decomposition N1-(3-Aminophenyl)acetamide emits toxic fumes.

Fire Hazard

Flash point data concerning N1-(3-Aminophenyl)acetamide are not available, however, N1-(3-Aminophenyl)acetamide is probably combustible.

Synthesis

m-Nitroacetanilide (1 g, 5.66 mmol) was dissolved in 100 mL of methanol and a catalytic amount of 10% palladium/activated charcoal (~0.015 g) was added. The reaction mixture was cooled via an ice bath and sodium borohydride (1 g, 26.43 mmol) was added in batches. Subsequently, the mixture was stirred vigorously for 1 hour. The reaction process was monitored by thin layer chromatography (TLC) using toluene-acetone (5:2, v/v) as unfolding agent. Upon completion of the reaction, the product was purified by silica gel column chromatography with toluene-acetone (5:2, v/v) as eluent. A white solid product was obtained in 75% yield with a melting point of 86-88 °C. Elemental analysis (C8H10N2O, Mr=150.18) Calculated values: C 63.98%, H 6.71%, N 18.65%; measured values: C 63.76%, H 6.50%, N 18.53%.1H NMR (400 MHz, DMSO-d6) δ: 9.58 (s, 1H, NH), 6.92 (t, 1H, H-2, J = 2.00 Hz), 6.88 (t, 1H, H-4, J = 8.00 Hz), 6.64 (dd, 1H, H-6, J1 = 0.80 Hz, J2 = 8.00 Hz), 6.23 (dd, 1H, H-5, J1 = 1.60 Hz, J2 = 8.00 Hz), 5.00 (bs, 2H, NH2), 1.99 (s, 3H , CH3-CO).13C NMR (100 MHz, DMSO-d6) δ: 167.85 (C=O), 148.85 (C1), 139.85 (C3), 128.75 (C4), 109.04 (C5), 106.93 (C6), 104.67 (C2), 23.98 (CH3-CO).

References

[1] Green Chemistry, 2018, vol. 20, # 1, p. 130 - 135
[2] Supramolecular Chemistry, 2010, vol. 22, # 10, p. 586 - 597
[3] Bioorganic Chemistry, 2014, vol. 57, p. 13 - 29
[4] Chemical & Pharmaceutical Bulletin, 1989, vol. 37, # 3, p. 615 - 617
[5] Journal of Chemical Research, 2006, # 4, p. 223 - 224

N1-(3-Aminophenyl)acetamide(102-28-3)Related Product Information

• Acetanilide
• 3-(METHYLTHIO)ANILINE
• m-Anisidine
• N1-(3-Aminophenyl)acetamide
• N-(4-DIMETHYLAMINO-3,5-DINITROPHENYL)MALEIMIDE
• N-(3-Nitro-Phenyl)-3-Oxo-Butyramide
• N,N'-1,3-Phenylene bismaleimide
• ALPHA-CHLORO-3-NITROACETANILIDE
• 3-Hydroxy-N-(3-nitrophenyl)-2-naphthalenecarboxamide
• 3'-NITROACETANILIDE
• 3'-Amino-4'-methoxyacetanilide
• Metrizamide
• N-(3-BIS(2-HYDROXYETHYL)AMINOPHENYL)ACETAMIDE
• 2-[(3-acetamidophenyl)(2-cyanoethyl)amino]ethyl acetate
• 3-(N,N-Diethylamino)acetanilide
• 3'-AMINOACETANILIDE HYDROCHLORIDE
• N-(2-Methoxy-4-aminophenyl)acetamide
• 4'-Aminoacetanilide