124168

Sigma-Aldrich

2-Bromothiophene

98%

Synonym(s):
2-Thienyl bromide
Empirical Formula (Hill Notation):
C4H3BrS
CAS Number:
Molecular Weight:
163.04
Beilstein/REAXYS Number:
104663
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.22

Quality Level

assay

98%

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.

Packaging

10, 50, 250 g in glass bottle

Signal Word

Danger

Hazard Statements

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

RIDADR

UN 2929 3(6.1) / PGII

WGK Germany

WGK 3

Flash Point(F)

125.6 °F - closed cup

Flash Point(C)

52 °C - closed cup

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)
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)
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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