4'-Nitroacetanilide Property

Melting point:

213-215 °C(lit.)

Boiling point:

312.97°C (rough estimate)

Density 

1.340

refractive index 

1.6180 (estimate)

storage temp. 

Store below +30°C.

solubility 

2.2g/l

form 

Solid

pka

13.91±0.70(Predicted)

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)

Safety

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36

WGK Germany 

3

RTECS 

AE5075000

TSCA 

Yes

HS Code 

29242990

Toxicity

rat,LDLo,intraperitoneal,500mg/kg (500mg/kg),National Academy of Sciences, National Research Council, Chemical-Biological Coordination Center, Review. Vol. 5, Pg. 10, 1953.

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P271Use only outdoors or in a well-ventilated area.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

4'-Nitroacetanilide Chemical Properties,Usage,Production

Chemical Properties

solid

Uses

Manufacture of nitraniline.

Uses

4-Nitroacetanilide was used as a test substrate and its hydrolysis was determined by UV spectroscopic measurements. It was also used to prepare 4-aminoacetanilide.

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.]