4-Bromophenol | Pharmaceutical Grade | 99.99% Purity | 10mg 20mg 30mg Vials | Lyophilized Powder | CAS 106-41-2

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;Bromo;Halogenated;Volatiles/ Semivolatiles;Aromatic Phenols;Halides;Phenyls & Phenyl-Het;Heterocyclic Compounds;Functional Materials;Phenols ();Phenyls & Phenyl-Het;A-BAlphabetic;Organic Building Blocks;Oxygen Compounds;Phenols;Alpha Sort;B;BI - BZChemical Class
Mol File: 106-41-2.mol
Shop 4-Bromophenol106-41-2-Detailed Image 1

4-Bromophenol Chemical Properties
Melting point 61-64 °C (lit.)
Boiling point 235-236 °C (lit.)
density 1.84
refractive index 1.5085 (estimate)
Fp 235-238°C
storage temp. room temp
solubility 14g/l
pka 9.37(at 25℃)
form Crystalline Solid
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)
NIST Chemistry Reference 4-Bromophenol(106-41-2)
EPA Substance Registry System Phenol, 4-bromo- (106-41-2)

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
F 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.
MSDS Information
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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, 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.

4-Bromophenol Preparation Products And Raw materials
Raw materials Bromine-->Carbon disulfide
Preparation Products 1-Benzofuran-5-carbaldehyde-->BENZOFURAN-5-BORONIC ACID-->5-BROMO-2-BENZOXAZOLINONE 97-->2-Amino-4-bromophenol-->5-BROMO-2(3H)-BENZOXAZOLONE-->6-BROMO-2H-1,4-BENZOXAZIN-3(4H)-ONE-->1-BENZOFURAN-5-CARBONITRILE-->6-bromo-3,4-dihydro-2H-chromen-4-ol-->5-Bromo-1-benzofuran-->N-[2-(4-Bromophenoxy)ethyl]pyrrolidine-->4-Bromoanisole-->4-Benzyloxybenzeneboronic acid-->4-ISOBUTOXYPHENYLBORONIC ACID-->4-Bromo-2-nitrophenol-->4-Bromo-2-chlorophenol-->6-Bromo-2,3-dihydro-4H-chromen-4-one-->4-Hydroxyphenylboronic acid-->-->Disperse Red 207-->3-(4-BROMOPHENOXY)PROPANOIC ACID-->O,O-Di(4-bromophenyl)thiophosphoryl chloride