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Sigma-Aldrich

2-Bromothiophene

98%

Synonym(s):

2-Thienyl bromide

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About This Item

Empirical Formula (Hill Notation):
C4H3BrS
CAS Number:
1003-09-4
Molecular Weight:
163.04
Beilstein/REAXYS Number:
104663
EC Number:
213-699-4
MDL number:
MFCD00005417
UNSPSC Code:
12352100
PubChem Substance ID:
24847601
NACRES:
NA.22

assay

98%

form

liquid

refractive index

n20/D 1.586 (lit.)

bp

149-151 °C (lit.)

density

1.684 g/mL at 25 °C (lit.)

storage temp.

2-8°C

SMILES string

Brc1cccs1

InChI

1S/C4H3BrS/c5-4-2-1-3-6-4/h1-3H

InChI key

TUCRZHGAIRVWTI-UHFFFAOYSA-N

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General description

2-Bromothiophene undergoes metalation-alkylation reaction with various electrophiles to form various 5-alkylated 2-bromo products. It undergoes coupling with 4-bromo allyl phenyl ether to form allyl phenyl thiophene ether, which is a novel potential dielectric material for organic thin film transistors.

Application

2-Bromothiophene has been used in electrochemical reduction of a number of mono- and dihalothiophenes at carbon cathodes in dimethylformamide containing tetramethylammonium perchlorate by cyclic voltammetry and controlled-potential electrolysis.

signalword

Danger

Hazard Classifications

Acute Tox. 2 Oral - Eye Dam. 1 - Flam. Liq. 3

Storage Class

3 - Flammable liquids

wgk_germany

WGK 3

flash_point_f

125.6 °F - closed cup

flash_point_c

52 °C - closed cup

ppe

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

Certificates of Analysis (COA)

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R A Ingle et al.
The Journal of chemical physics, 147(1), 013914-013914 (2017-07-10)
The ultraviolet photochemistry of 2-bromothiophene (C
Synlett, 974-974 (2007)
First example of base-promoted tandem alkylation-bromination of 2-bromothiophene via halogen dance process: a remarkable temperature effect.
Peyron C, et al.
Tetrahedron Letters, 46(19), 3315-3318 (2005)
Novel self assembled monolayers of allyl phenyl thiophene ether as potential dielectric material for organic thin film transistors.
Sathyapalan A, et al
Thin Solid Films, 516(16), 5645-5648 (2008)
Mohammad S. Mubarak et al.
The Journal of organic chemistry, 61(23), 8074-8078 (1996-11-15)
Cyclic voltammetry and controlled-potential electrolysis have been employed to probe the electrochemical reduction of a number of mono- and dihalothiophenes at carbon cathodes in dimethylformamide containing tetramethylammonium perchlorate. Reduction of 2-bromo-, 3-bromo-, 2-chloro-, 3-chloro-, and 2-iodothiophene gives rise to a
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