4'-Bromoacetanilide Property

Melting point:

165-169 °C(lit.)

Boiling point:

353.4°C (estimate)

Density 

1.72

refractive index 

1.6120 (estimate)

storage temp. 

Store below +30°C.

solubility 

alcohol: moderately soluble

form 

Crystalline Powder or Crystals

pka

14.25±0.70(Predicted)

color 

White to beige or light gray

Water Solubility 

Insoluble

Merck 

14,1399

BRN 

2208091

Stability:

Stable. Incompatible with strong oxidizing agents.

CAS DataBase Reference

103-88-8(CAS DataBase Reference)

NIST Chemistry Reference

Acetamide, N-(4-bromophenyl)-(103-88-8)

EPA Substance Registry System

Acetamide, N-(4-bromophenyl)- (103-88-8)

Safety

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36

RIDADR 

2811

WGK Germany 

3

RTECS 

AD9625000

Hazard Note 

Irritant

TSCA 

Yes

HazardClass 

6.1(b)

PackingGroup 

III

HS Code 

29242998

Toxicity

mouse,LD50,intraperitoneal,250mg/kg (250mg/kg),National Technical Information Service. Vol. AD277-689,

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

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

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

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

4'-Bromoacetanilide Chemical Properties,Usage,Production

Chemical Properties

4'-Bromoacetanilide is a white to light beige crystalline solid with a melting point of 168°C and a relative density of 1.717. It is soluble in benzene, chloroform, and ethyl acetate, slightly soluble in alcohol and hot water, and insoluble in cold water. This compound can be prepared by brominating acetanilide and is commonly used as an intermediate in organic synthesis.

Uses

4'-Bromoacetanilide is used as an internal standard for phenylurea and the respective metabolic products in oysters. It has also been used as a reagent in the production of a new ligand to form a coordination compex between gadolinium(III) and T=titanium(IV) oxide. It was used in the synthesis of new ligand for anchoring Gd(III) chelates onto TiO2 surface.

Uses

4-Bromoacetanilide was used as internal standard in determination of several phenylurea and triazine herbicides and their transformation products in oyster. It was used in the synthesis of new ligand for anchoring Gd(III) chelates onto TiO₂ surface.

Preparation

Preparation of 4'-Bromoacetanilide from Acetanilide.
Principle: Aromatic compounds can be conveniently brominated by the use of brominating agent, which is normally a solution of bromine in acetic acid. Bromination of activated aromatic compounds usually give 2, 4, 6-tribromo derivatives while moderately activating group like anilide give preferably the para bromo product.
Reaction:

Procedure: Dissolve 0.5 g acetanilide in 0.6 ml glacial acetic acid and add 2.5 ml bromine solution in acetic acid (25% w/v). Shake the mixture for 1 h. After 1 h, 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 a solvent).

Synthesis Reference(s)

Canadian Journal of Chemistry, 50, p. 1233, 1972 DOI: 10.1139/v72-193
Synthetic Communications, 23, p. 779, 1993 DOI: 10.1080/00397919308009839

Purification Methods

Crystallise the anilide from aqueous MeOH or EtOH. Purify it by zone refining. [Beilstein 12 IV 1504.]