4-Bromoaniline Chemical Properties

Melting point:

56-62 °C (lit.)

Boiling point:

230-250 °C

Density 

1.497

refractive index 

1.5680 (estimate)

Flash point:

222-224°C

storage temp. 

Store below +30°C.

solubility 

ethanol: soluble0.5g/10 mL, clear, colorless to almost colorless

form 

crystalline

pka

3.86(at 25℃)

color 

white to light yellow

Odor

Sweetish

Water Solubility 

<0.1 g/100 mL at 23 ºC

Merck 

14,1404

BRN 

742031

Dielectric constant

13.0（-7℃）

Stability:

Stable. Combustible. Incompatible with strong oxidizing agents, peroxides, acids, acid chlorides, acid anhydrides, chloroformates. May be air sensitive.

InChIKey

WDFQBORIUYODSI-UHFFFAOYSA-N

CAS DataBase Reference

106-40-1(CAS DataBase Reference)

NIST Chemistry Reference

4-Bromoaniline(106-40-1)

EPA Substance Registry System

p-Bromoaniline (106-40-1)

Safety Information

Hazard Codes 

Xn

Risk Statements 

21/22-36/37/38-20/21/22

Safety Statements 

26-36/37-36/37/39

RIDADR 

UN 2811 6.1/PG 3

WGK Germany 

3

RTECS 

BW9280000

F 

8-9-23

Hazard Note 

Harmful

TSCA 

Yes

HazardClass 

6.1

PackingGroup 

III

HS Code 

29214210

Hazardous Substances Data

106-40-1(Hazardous Substances Data)

Toxicity

LD50 orally in Rabbit: 456 mg/kg LD50 dermal Rat 536 mg/kg

MSDS

• Language:English Provider:p-bromophenylamine
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

4-Bromoaniline Usage And Synthesis

Chemical Properties

Gray-brown crystals with a peculiar odor. When heated or burned, they break down and release harmful fumes that contain hydrogen bromide and nitrogen oxides. When dissolved in water, it acts as a mild base. It reacts with acids and powerful oxidizing agents. The compound 4-bromoaniline consists of a hydrophobic benzene ring and an amino group that assists in carrying substances and improving PSC stability.

Uses

4-Bromoaniline is a brominated aniline that is commonly used as a building block in the preparation of pharmaceutical and organic compounds. It is used in the preparation of azo dyes and is condensed with formaldehyde to prepare dihydroquinazolines. In addition, 4-Bromoaniline is also used as an intermediate in the production of other chemicals such as metobromuron, a herbicide, and resorantel, an antiparasitic agent.

Preparation

4-bromoaniline can be made by reacting aniline with bromine with a protection with acetyl chloride.

Synthesis Reference(s)

The Journal of Organic Chemistry, 40, p. 1867, 1975 DOI: 10.1021/jo00900a053
Synthetic Communications, 19, p. 3047, 1989 DOI: 10.1080/00397918908052699

General Description

P-bromoaniline is a brown solid with a sweet odor. (NTP, 1992)

Air & Water Reactions

4-Bromoaniline is sensitive to prolonged exposure to air. Vapor may form highly reactive mixtures in air . Insoluble in water.

Reactivity Profile

Vapor may form highly reactive mixtures in air.

Fire Hazard

Flash point data are not available for 4-Bromoaniline, but 4-Bromoaniline is probably combustible.

Synthesis

RGO/Cu NPs (25 mg), arylboronic acid (1.0 mmol), K2CO3(1.3 mmol), 25-28% aqueous ammonia (5 mmol) and methanol(4 mL) were added to a 50 mL round-bottomed flask. The reactionmixture was stirred under reflux conditions for the appropriatetime. After completion of the reaction as monitored by TLC, themixture was filtered, and the solvent of the filtrate was removedunder vacuum with the aid of a rotary evaporator. The residue waspurified by column chromatography on silica gel to afford 4-Bromoaniline.

Purification Methods

Crystallise the aniline (with appreciable loss) from aqueous EtOH. The benzoyl derivative has m 204o (from EtOH). [Beilstein 12 IV 1497.]

4-Bromoaniline(106-40-1)Related Product Information

• N,N-Dimethylaniline
• 4-Amino-benzenesulfonic acid monosodium salt
• 4-Aminophenylacetic acid
• 4-Chloroaniline
• Aniline
• Sulfanilic acid
• 4-Fluoroaniline
• POLYANILINE
• N-Methylaniline
• p-Anisidine
• p-Toluidine
• 2-BENZOYLACETANILIDE
• Bromobenzene
• Diphenylamine
• Sulfanilamide
• 4-Aminobenzoic acid
• 2-Bromo-4,6-dinitroaniline
• 4-Dimethylaminobenzaldehyde