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ChemicalBook >> CAS DataBase List >>4-Bromophenol

4-Bromophenol

CAS No.
106-41-2
Chemical Name:
4-Bromophenol
Synonyms
P-BROMOPHENOL;Para Bromo Phenol;4-Bromphenol;Phenol, 4-bromo-;NSC 4970;p-Bromphenol;4-BROMOPHENOL;BROMOPHENOL-4;P-Bromophenlo;4-bromo-pheno
CBNumber:
CB7181317
Molecular Formula:
C6H5BrO
Molecular Weight:
173.01
MDL Number:
MFCD00002313
MOL File:
106-41-2.mol
MSDS File:
SDS
TDS File:
TDS
Last updated:2026-06-30 08:02:02
Product description Number Pack Size Price
4-Bromophenol 99% B75808 5g $41.2
4-Bromophenol 99% B75808 100g $83.8
4-Bromophenol >98.0%(GC)(T) B0787 25g $19
4-Bromophenol >98.0%(GC)(T) B0787 100g $33
4-Bromophenol TRC-B686405-5G 5g $77
More product size

4-Bromophenol 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
Henry's Law Constant 6.7×101 mol/(m3Pa) at 25℃, Abraham et al. (1994)
InChI 1S/C6H5BrO/c7-5-1-3-6(8)4-2-5/h1-4,8H
InChIKey GZFGOTFRPZRKDS-UHFFFAOYSA-N
SMILES Oc1ccc(Br)cc1
CAS DataBase Reference 106-41-2(CAS DataBase Reference)
EWG's Food Scores 1
FDA UNII LAO4J0183I
NIST Chemistry Reference 4-Bromophenol(106-41-2)
EPA Substance Registry System Phenol, 4-bromo- (106-41-2)
UNSPSC Code 12352100
NACRES NA.22

SAFETY

Risk and Safety Statements

Symbol(GHS)  Exclamation Mark (GHS07)Health Hazard (GHS08)Environment (GHS09)
GHS07,GHS08,GHS09
Signal word  Warning
Hazard statements  H302-H315-H319-H361-H411
Precautionary statements  P501-P273-P270-P202-P201-P264-P280-P302+P352-P391-P308+P313-P337+P313-P305+P351+P338-P362+P364-P332+P313-P301+P312+P330-P405
PPE dust mask type N95 (US), Eyeshields, Gloves
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  TSCA listed
HazardClass  6.1(b)
PackingGroup  III
HS Code  29081000
Storage Class 11 - Combustible Solids
Hazard Classifications Acute Tox. 4 Oral
Skin Irrit. 2
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.
NFPA 704
0
2 0

4-Bromophenol price More Price(52)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich B75808 4-Bromophenol 99% 106-41-2 5g $41.2 2026-04-30 Buy
Sigma-Aldrich B75808 4-Bromophenol 99% 106-41-2 100g $83.8 2026-04-30 Buy
TCI Chemical B0787 4-Bromophenol >98.0%(GC)(T) 106-41-2 25g $19 2026-04-30 Buy
TCI Chemical B0787 4-Bromophenol >98.0%(GC)(T) 106-41-2 100g $33 2026-04-30 Buy
TRC TRC-B686405-5G 4-Bromophenol 106-41-2 5g $77 2026-06-03 Buy
Product number Packaging Price Buy
B75808 5g $41.2 Buy
B75808 100g $83.8 Buy
B0787 25g $19 Buy
B0787 100g $33 Buy
TRC-B686405-5G 5g $77 Buy

4-Bromophenol Chemical Properties,Uses,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

Synthesis

m-Bromoaniline (50 g) is dissolved by boiling in a mixture of water (400 ml) and sulfuric acid (50 ml). The solution is then cooled to 10℃ and diazotized by the addition of sodium nitrite (21 g) dissolved in a small amount of water, The resulting diazonium salt solution is run in a thin stream during fifteen to thirty minutes into a boiling mixture of water (300 ml) and sulfuric acid (100 ml) contained in a flask fitted with a dropping funnel, a steam inlet tube reaching to the bottom of the flask, and an efficient condenser set for downward distillation. During the addition of the diazonium salt solution the acid solution is heated so that its volume remains constant, and steam is passed in at such a rate that at the end of the addition approximately 1 liter of distillate has been collected. Steam distillation is then continued until 2-liters of distillate has been collected. To this is added sodium chloride (150 g), and the phenol is extracted with ether, using portions of 200, 100, and 100 ml. The ether is removed from the combined extracts and the product is distilled under reduced pressure. Eight runs of 50 g, each of m-bromoaniline gave 330 g of crude m-bromophenol boiling at 100-140℃ (20-30 mm.). Redistillation gave 313 g (77.8%) of m-bromophenol which boiled at 125-130℃ at 25 mm. Treatment of this 313 g of product with sodium hydroxide and methyl sulfate gave 285 g of m-bromoanisole (4-bromophenol), b. p. 100℃ at 20 mm[1].

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.]

References

[1] Koelsch, C. Frederick. “The Preparation of m-Bromophenol.” Journal of the American Chemical Society 61 4 (1939): 969.

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