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2-Bromothiophene

Basic information General description Application Product Introduction Safety Supplier Related

2-Bromothiophene Basic information

Product Name:
2-Bromothiophene
Synonyms:
  • TIMTEC-BB SBB003931
  • 2 - broMine thiophene
  • 2-bromothiophene:2-thienyl bromide
  • INDIP-020
  • Clopidogrel Impurity 74
  • 2-BROMOTHIOPHENE, 98%2-BROMOTHIOPHENE, 98%2-BROMOTHIOPHENE, 98%2-BROMOTHIOPHENE, 98%
  • 2-THIENYL BROMIDE
  • 2-BROMOTHIOPHENE
CAS:
1003-09-4
MF:
C4H3BrS
MW:
163.04
EINECS:
213-699-4
Product Categories:
  • Heterocycle-oher series
  • Thiophene&Benzothiophene
  • Halides
  • Thiophenes & Benzothiophenes
  • Thiophenes & Benzothiophenes
  • Heterocycles
  • Thiophenes
  • Sulfur & Selenium Compounds
  • bc0001
  • K00001
Mol File:
1003-09-4.mol
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2-Bromothiophene Chemical Properties

Melting point:
-10 °C
Boiling point:
149-151 °C (lit.)
Density 
1.684 g/mL at 25 °C (lit.)
refractive index 
n20/D 1.586(lit.)
Flash point:
140 °F
storage temp. 
2-8°C
form 
Liquid
color 
Clear colorless to slightly brownish
Specific Gravity
1.684
Water Solubility 
IMMISCIBLE
Sensitive 
Light Sensitive
BRN 
104663
InChIKey
TUCRZHGAIRVWTI-UHFFFAOYSA-N
CAS DataBase Reference
1003-09-4(CAS DataBase Reference)
NIST Chemistry Reference
Thiophene, 2-bromo-(1003-09-4)
EPA Substance Registry System
Thiophene, 2-bromo- (1003-09-4)
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Safety Information

Hazard Codes 
T,N,Xn
Risk Statements 
10-25-41-51/53-36/37/38-23/24-22-20/21/22
Safety Statements 
26-36/37/39-45-61-16-36
RIDADR 
UN 2929 6.1/PG 2
WGK Germany 
3
8
Hazard Note 
Irritant
TSCA 
T
HazardClass 
6.1
PackingGroup 
II
HS Code 
29349990

MSDS

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2-Bromothiophene Usage And Synthesis

General description

2-Bromothiophene undergoes metallation-alkylation reaction with various electrophiles to generate various 5-alkylated 2-bromo products. It is coupled with 4-bromoallyl phenyl ether to produce allyl thiophene ether, which is a new type of organic thin film transistor dielectric material.

Application

In dimethylformamide containing tetramethylammonium perchlorate, 2-bromothiophene is electrochemically reduced many mono- and dihalothiophenes on a carbon cathode by cyclic voltammetry and controlled potential electrolysis.

Product Introduction

The 2-Bromothiophene(casno:1003-09-4) is an organic compound with the formula C4H3BrS. The IUPAC name of this chemical is 2-bromothiophene. With the CAS registry number 1003-09-4, it is also named as Bromothiophene. The product's categories are Thiophenes; Halides; Thiophenes & Benzothiophenes; Thiophene & Benzothiophene; Thiophenes & Benzothiophenes. Besides, 2-Bromothiophene(casno:1003-09-4) is a colorless to light yellow transparent liquid, which should be stored in a closed dark and cool place. 2-Bromothiophene(casno:1003-09-4) can be used for organic synthesis and pharmaceutical intermediates.

Chemical Properties

colorless to light yellow liquid. Soluble in ether and acetone, insoluble in water.

Uses

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

Preparation

2-Bromothiophene is synthesized by bromination of thiophene, which is achieved through the following steps: dissolve thiophene in acetic acid, and add bromine in glacial acetic acid solution below 10°C. Water was added to the reaction mixture to precipitate an oily liquid. Extract with ether. Add potassium carbonate to the extract to remove acetic acid, dry it, distill off the ether, and then conduct vacuum distillation to collect fractions at 42-46°C (1.73kPa) to obtain 2-bromothiophene with a yield of 55%.

Synthesis Reference(s)

Journal of the American Chemical Society, 79, p. 5474, 1957 DOI: 10.1021/ja01577a039
Synthesis, p. 890, 1988 DOI: 10.1055/s-1988-27740

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.

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