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4'-Nitroacetanilide

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4'-Nitroacetanilide Basic information

Product Name:
4'-Nitroacetanilide
Synonyms:
  • P-NITROACETANILIDE
  • N-ACETYL-4-NITROANILINE
  • 4-Nitroacetanilide, GC 97%
  • LABOTEST-BB LT00455738
  • p-nitro-acetanilid
  • p-Nitrophenylacetanilide
  • 4μ-Nitroacetanilide, Acetic acid 4-nitroanilide
  • 4'-Nitroacetanilide,97%,pract.
CAS:
104-04-1
MF:
C8H8N2O3
MW:
180.16
EINECS:
203-169-0
Product Categories:
  • Intermediates of Dyes and Pigments
  • Aromatic Carboxylic Acids, Amides, Anilides, Anhydrides & Salts
  • Anilines, Amides & Amines
  • Nitro Compounds
Mol File:
104-04-1.mol
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4'-Nitroacetanilide Chemical Properties

Melting point:
213-215 °C(lit.)
Boiling point:
312.97°C (rough estimate)
Density 
1.340
refractive index 
1.6180 (estimate)
storage temp. 
2-8°C
solubility 
2.2g/l
pka
13.91±0.70(Predicted)
form 
Solid
color 
Yellow to green-yellow or green-brown
Water Solubility 
2.2g/L(room temperature)
Merck 
14,6581
BRN 
2211962
Stability:
Stable. Combustible. Incompatible with strong oxidizing agents.
CAS DataBase Reference
104-04-1(CAS DataBase Reference)
EPA Substance Registry System
Acetamide, N-(4-nitrophenyl)- (104-04-1)
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Safety Information

Hazard Codes 
Xi
Risk Statements 
36/37/38
Safety Statements 
26-36
WGK Germany 
3
RTECS 
AE5075000
TSCA 
Yes
HS Code 
29242990

MSDS

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4'-Nitroacetanilide Usage And Synthesis

Chemical Properties

solid

Uses

Manufacture of nitraniline.

Preparation

Preparation of 4'-Nitroacetanilide from acetanilide.
Principle: Aromatic compounds can be conveniently nitrated by the use of the nitrating mixture, which is normally a mixture of concentrated nitric acid and concentrated sulphuric acid. The function of sulphuric acid is to convert nitric acid into a highly reactive, electrophilic, nitronium ion, NO2+, which is the effective nitrating agent. Nitration of activated aromatic compounds is carried out under milder condition whereas deactivated rings require drastic conditions. Activating groups are o, p-directing, while deactivating groups are m-directing for electrophilic substitution.
Reaction:

Procedure: Take 0.5 g acetanilide in 0.6 ml glacial acetic acid and add 1 ml conc. H2SO4 in a beaker. Cool the mixture in ice salt bath (5-10°C). To this add a mixture of 0.2 ml conc. H2SO4 and 0.25 ml conc. HNO3 dropwise. Maintain the temperature below 10°C during addition. After addition is over allow the mixture to attain room temperature and leave it for 30 minutes. Pour the mixture on to crushed ice (20 g) with stirring. Filter the separated product and wash with cold water. Dry the product, record the practical yield and re-crystallize it.
Re-crystallization: Dissolve the crude product in minimum amount of ethyl alcohol in a beaker by heating on a water bath. Filter the hot solution and cool the filtrate. The crystals of the product separate out. Filter, dry and record the melting point and TLC (using toluene as solvent).

Synthesis Reference(s)

Journal of the American Chemical Society, 75, p. 5905, 1953 DOI: 10.1021/ja01119a037
Tetrahedron Letters, 28, p. 1669, 1987 DOI: 10.1016/S0040-4039(00)95389-9

Purification Methods

Precipitate the anilide from 80% H2SO4 by adding ice, then wash with water, and crystallise from aqueous EtOH. Dry it in air. [Beilstein 12 IV 1632.]

4'-Nitroacetanilide Preparation Products And Raw materials

Preparation Products

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