4-Bromophenol Property

Melting point:

61-64 °C (lit.)

Boiling point:

235-236 °C (lit.)

Density 

1.84

refractive index 

1.5085 (estimate)

Flash point:

235-238°C

storage temp. 

room temp

solubility 

14g/l

form 

Crystalline Solid

pka

9.37(at 25℃)

color 

Pinkish-brown

Water Solubility 

It is insoluble in water. It is soluble in 5%ethanol.

λmax

282nm(EtOH)(lit.)

Merck 

14,1428

BRN 

1680024

CAS DataBase Reference

106-41-2(CAS DataBase Reference)

NIST Chemistry Reference

4-Bromophenol(106-41-2)

EPA Substance Registry System

Phenol, 4-bromo- (106-41-2)

Safety

Hazard Codes 

Xn,Xi

Risk Statements 

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

Safety Statements 

26-37/39-36

RIDADR 

2811

WGK Germany 

2

RTECS 

SJ7960000

F 

8-10-23

Hazard Note 

Irritant

TSCA 

Yes

HazardClass 

6.1(b)

PackingGroup 

III

HS Code 

29081000

Hazardous Substances Data

106-41-2(Hazardous Substances Data)

Toxicity

mouse,LD50,intraperitoneal,411mg/kg (411mg/kg),Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 44(12), Pg. 19, 1979.

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

H315Causes skin irritation

Precautionary statements

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P270Do not eat, drink or smoke when using this product.

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

P301+P312IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.

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

P332+P313IF SKIN irritation occurs: Get medical advice/attention.

4-Bromophenol Chemical Properties,Usage,Production

Chemical Properties

4-Bromophenol is a pinkish-brown crystalline solid. four-sided biconical crystal precipitated from ether or chloroform. The melting point is 66.4 ℃, and a small amount of water can reduce the melting point a lot. Soluble in water, chloroform, easily soluble in ethanol, ether and glacial acetic acid, soluble in 7 parts of water.

Uses

4-Bromophenol is used as an intermediate in medicine grade. It is also used as a phenol that is used in Stille reactions. It is used in the intermediate of organic synthesis, flame retardant and pharmaceutical industry.

Application

4-Bromophenol is a phenolic derivative that It can used as a reagent in Stille reactions or Intermediates of Liquid Crystals.

Preparation

4-Bromophenol is synthesized by bromination of phenol. The bromine and carbon disulfide solution was added to the phenolic carbon disulfide solution, and the addition was started below 5°C, and the addition was completed under stirring for 2 hours. Phenol and bromine are approximately equimolar ingredients. Distill the reactant to remove carbon disulfide, and then conduct fractional distillation under reduced pressure to collect fractions at 145-150°C (3.32-3.99kPa) to obtain the product. Yield 80-84%.

Definition

ChEBI: 4-bromophenol is a bromophenol containing only hydroxy and bromo substituents that are para to one another. It has a role as a mouse metabolite, a persistent organic pollutant, a human xenobiotic metabolite, a rat metabolite, a human urinary metabolite and a marine metabolite.

Synthesis Reference(s)

Tetrahedron, 45, p. 7869, 1989 DOI: 10.1016/S0040-4020(01)85800-2
The Journal of Organic Chemistry, 23, p. 280, 1958 DOI: 10.1021/jo01096a033

Purification Methods

Crystallise the phenol from CHCl3, CCl4, pet ether (b 40-60o), or water and dry it at 70o under vacuum for 2hours. [Beilstein 6 IV 1043.]