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16350

Sigma-Aldrich

Bromobenzene

≥99.5% (GC)

Synonym(s):

1-Bromobenzene, Bromobenzol, Monobromobenzene, Phenyl bromide

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About This Item

Empirical Formula (Hill Notation):
C6H5Br
CAS Number:
108-86-1
Molecular Weight:
157.01
Beilstein/REAXYS Number:
1236661
EC Number:
203-623-8
MDL number:
MFCD00000055
UNSPSC Code:
12352100
PubChem Substance ID:
57647528
NACRES:
NA.22

vapor density

5.41 (vs air)

Quality Level

200

vapor pressure

10 mmHg ( 40 °C)

assay

≥99.5% (GC)

form

liquid

autoignition temp.

1051 °F

expl. lim.

36.5 %

refractive index

n20/D 1.559 (lit.)
n20/D 1.559

bp

156 °C (lit.)

mp

−31 °C (lit.)

solubility

alcohol: soluble 10.4g/100g at 25 °C
diethyl ether: soluble 71.3g/100g at 25 °C
water: insoluble 0.045g/100g at 30 °C (practically)
benzene: miscible
chloroform: miscible
hydrocarbons: miscible (petr.)

density

1.491 g/mL at 25 °C (lit.)

functional group

bromo

SMILES string

Brc1ccccc1

InChI

1S/C6H5Br/c7-6-4-2-1-3-5-6/h1-5H

InChI key

QARVLSVVCXYDNA-UHFFFAOYSA-N

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Application

Bromobenzene was used in the synthesis of four-armed star chain transfer agent required for preparation of amphiphilic star graft copolymers.

Biochem/physiol Actions

Bromobenzene induces hepatic necrosis via the formation of a reactive metabolite that arylates vital cellular macromolecules.

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Warning

Hazard Classifications

Aquatic Chronic 2 - Flam. Liq. 3 - Skin Irrit. 2

Storage Class

3 - Flammable liquids

wgk_germany

WGK 2

flash_point_f

123.8 °F - closed cup

flash_point_c

51.0 °C - closed cup

ppe

Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter

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Certificates of Analysis (COA)

Lot/Batch Number
BCCF7091
BCCC3505
BCCB2050
BCBW5525
BCBT5468

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Star-like PAA-g-PPO well-defined amphiphilic graft copolymer synthesized by ATNRC and SET-NRC reaction.
Li Y, et al.
Journal of Polymer Science: Part A, General Papers, 48(10), 2084-2097 (2010)
Bromobenzene-induced liver necrosis. Protective role of glutathione and evidence for 3,4-bromobenzene oxide as the hepatotoxic metabolite.
D J Jollow et al.
Pharmacology, 11(3), 151-169 (1974-01-01)
Xiaolin Pan et al.
Organic & biomolecular chemistry, 10(10), 1969-1975 (2012-01-26)
Diverse 11H-indeno[1,2-c]quinolines are produced via a palladium-catalyzed three-component reaction of 2-alkynylbromobenzene, 2-alkynylaniline, and electrophile. This conversion tolerates a wide variety of functionality and substitution patterns on the 11H-indeno[1,2-c]quinoline ring.
Hiroyuki Asakura et al.
The journal of physical chemistry. A, 116(16), 4029-4034 (2012-04-14)
A homocoupling reaction mechanism of bromobenzene mediated by the [Ni(cod)(bpy)] (cod = 1,5-cyclooctadiene; bpy = 2,2'-bipyridine) complex was investigated by means of in situ time-resolved X-ray absorption fine structure (XAFS) and factor analysis. A dimer intermediate [Ni(bpy)(Ph)Br](2) proposed in the
Lukas Werner et al.
The Journal of organic chemistry, 76(24), 10050-10067 (2011-10-20)
Four generations of chemoenzymatic approaches to oseltamivir are presented. The first two generations relied on the use of cyclohexadiene-cis-diol derived enzymatically from bromobenzene. The third and fourth generation used the corresponding diol obtained from ethyl benzoate by fermentation with E.
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Protocols

US EPA Method 8260: GC Analysis of Volatiles on SPB®-624 after Purge & Trap using "K" Trap, Fast GC Analysis

US EPA Method 8260 describes the analysis of volatile organic compounds in solid wastes and ground waters. This application illustrates the analysis of many compounds commonly analyzed by this method using purge and trap coupled to GC-MS.

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