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194395

Sigma-Aldrich

1,3-Dibromobenzene

97%

Synonym(s):

1-Bromo-3-bromobenzene, m-Dibromobenzene

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About This Item

Empirical Formula (Hill Notation):
C6H4Br2
CAS Number:
108-36-1
Molecular Weight:
235.90
Beilstein:
1904538
EC Number:
203-574-2
MDL number:
MFCD00000078
UNSPSC Code:
12352100
PubChem Substance ID:
24851649
NACRES:
NA.22

vapor density

8.16 (vs air)

vapor pressure

5 mmHg ( 66 °C)

Assay

97%

form

liquid

refractive index

n20/D 1.608 (lit.)

bp

218-219 °C (lit.)

mp

−7 °C (lit.)

density

1.952 g/mL at 25 °C (lit.)

functional group

bromo

SMILES string

Brc1cccc(Br)c1

InChI

1S/C6H4Br2/c7-5-2-1-3-6(8)4-5/h1-4H

InChI key

JSRLURSZEMLAFO-UHFFFAOYSA-N

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General description

1,3-Dibromobenzene undergoes solid-supported [KF-Al2O3] palladium-catalyzed polyarylation reaction with phenyl boronic acid under microwave irradiation to yield conjugated polyaryls.

Application

1,3-Dibromobenzene was used in the synthesis of [n]metacyclophanes via Suzuki coupling reaction.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

10 - Combustible liquids

WGK

WGK 2

Flash Point(F)

200.1 °F - closed cup

Flash Point(C)

93.4 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
MKCS5469
MKCP7494
MKCM9956
MKCM4165
MKCL4576

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Microwave-assisted Suzuki coupling on a KF-alumina surface: synthesis of polyaryls. Microwave-assisted Suzuki coupling on a KF-alumina surface: synthesis of polyaryls.
Basu B, et al.
Tetrahedron Letters, 44(19), 3817-3820 (2003)
Beverly B Smith et al.
The Journal of organic chemistry, 67(15), 5333-5337 (2002-07-20)
Reaction of the bis-9-BBN adduct of several dienes with 1,3-dibromobenzene via Suzuki coupling leads to a series of [n]metacyclophanes ranging in size from 10 to 17 atom members. In each case, two carbon-carbon bonds are formed in one reaction vessel.
J A Szymańska
Archives of toxicology, 71(1-2), 99-106 (1996-01-01)
Rats were used to study acute and subacute hepatotoxicity of 1,3-dibromobenzene (1,3-dBB). In the single-exposure experiment, maximum hepatic 1,3-dBB concentrations were found to occur 1 to 12 h after the exposure, depending on the dose. Maximum concentrations of covalently bound
A Sapota et al.
Chemosphere, 39(13), 2229-2238 (1999-11-27)
The distribution, excretion and metabolism of 1,3-dibromobenzene following a single i.p. administration to rats 100 or 300 mg/kg was investigated using radiotracer [3H] and GC-MS technique. After 72 hours about 74 to 90% were excreted in urine. The highest radioactivity
J A Szymańska et al.
Journal of applied toxicology : JAT, 16(1), 35-41 (1996-01-01)
Various doses of dibromobenzene isomers (1,2-dBB, 1,3-dBB, 1,4-dBB) were administered (i.p.) to BALB mice. The levels of reduced glutathione (GSH) and malondialdehyde (MDA) in the liver, and glutamate-pyruvate transaminase (GPT) (EC.2.6.1.2) gamma-glutamyltransferase (gamma-GT) (EC.2.3.2.2) and triglycerides (TG) in the serum
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