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4-Bromophenol

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4-Bromophenol Basic information

Product Name:
4-Bromophenol
Synonyms:
  • BROMOPHENOL-4
  • 4-BROMOHYDROXYBENZENE
  • 4-Bromophenol p-Bromophenol
  • 4-BROMOPHENOL
  • AKOS BBS-00004402
  • P-BROMOPHENOL
  • 4-Bromophbenol
  • 4-Bromophenoles
CAS:
106-41-2
MF:
C6H5BrO
MW:
173.01
EINECS:
203-394-4
Product Categories:
  • intermediates
  • alcohol| alkyl bromide
  • Building Blocks for Liquid Crystals
  • Bromo
  • Halogenated
  • Volatiles/ Semivolatiles
  • Aromatic Phenols
  • Halides
  • Phenyls & Phenyl-Het
  • Heterocyclic Compounds
  • Functional Materials
  • Phenols (Building Blocks for Liquid Crystals)
  • Phenyls & Phenyl-Het
  • A-BAlphabetic
  • Organic Building Blocks
  • Oxygen Compounds
  • Phenols
  • Alpha Sort
  • B
  • BI - BZChemical Class
Mol File:
106-41-2.mol
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4-Bromophenol Chemical Properties

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)
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Safety Information

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
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.

MSDS

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4-Bromophenol Usage And Synthesis

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.]

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