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3-Bromothiophene

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3-Bromothiophene Basic information

Product Name:
3-Bromothiophene
Synonyms:
  • 3-bromo-thiophen
  • beta-Bromothiophene
  • thiophene,3-bromo-
  • β-bromothiophene
  • TIMTEC-BB SBB003930
  • TIMTEC-BB SBB003931
  • ALPHA-THIENYL BROMIDE
  • 3-THIENYL BROMIDE
CAS:
872-31-1
MF:
C4H3BrS
MW:
163.04
EINECS:
212-821-3
Product Categories:
  • Heterocycles
  • Halides
  • Thiophenes & Benzothiophenes
  • Thiophene&Benzothiophene
  • Miscellaneous
  • Thiophene Derivatives (for Conduting Polymer Research)
  • Thiophenes
  • Functional Materials
  • Reagents for Conducting Polymer Research
  • Thiophen
  • Thiophenes & Benzothiophenes
  • Heterocycle-oher series
  • alkyl bromide
  • bc0001
Mol File:
872-31-1.mol
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3-Bromothiophene Chemical Properties

Melting point:
<-10°C
Boiling point:
150 °C (lit.)
Density 
1.74 g/mL at 25 °C (lit.)
refractive index 
n20/D 1.591(lit.)
Flash point:
140 °F
storage temp. 
Keep in dark place,Sealed in dry,2-8°C
solubility 
Chloroform (Slightly), Methanol (Slightly)
form 
Liquid
Specific Gravity
1.740
color 
Clear colorless to slightly yellow
Water Solubility 
IMMISCIBLE
Sensitive 
Light Sensitive/Stench
BRN 
105338
CAS DataBase Reference
872-31-1(CAS DataBase Reference)
NIST Chemistry Reference
Thiophene, 3-bromo-(872-31-1)
EPA Substance Registry System
3-Bromothiophene (872-31-1)
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Safety Information

Hazard Codes 
T,Xi,N,Xn
Risk Statements 
10-25-41-51/53-36/37/38-23/24/25-20/21/22-43-36/37
Safety Statements 
26-36/37/39-45-61-38-28A-16-24/25-23-36-36/37-24/35
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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3-Bromothiophene Usage And Synthesis

Chemical Properties

clear colourless to slightly yellow liquid. It is not soluble in water, but can dissolve in common organic solvents such as chloroform, benzene, ether, and tetrahydrofuran.

Uses

3-Bromothiophene is used in the preparation of derivatives such as thienylenic alpha, μ-diformyl-alpha-oligothiophenes and 3-lithiothiophene. It is also used in the synthesis of 3-lithiothiophene by reacting with n-butyllithium.

Uses

3-Bromothiophene can be used as a reactant to synthesize:
3,3-Bithiophene via borylation followed by Suzuki coupling.
3-Alkylthiophenes by NiDPPP++ catalyzed cross-coupling with Grignard reagents.
3-Lithiothiophene by treating with n-butyllithium in hexane.
Derivatives of thienylenic α, ω?diformyl?α?oligothiophenes.
N-(2-(3-bromothiophen-2-yl)phenyl)methanesulfonamides by coupling at the 2-position with N-arylmethanesulfonamides, mediated by iodobenzene diacetate (178721).

Preparation

Preparation of 3-bromothiophene using 2,5-dibromothiophene
2,5-Dibromothiophene (121g, 0.5 moles), tris (3,6-dioxaheptyl) amine (1.0g, 0.003 mole), thiophene (500 cm3) and sodium amide (58.5g, 1.5 mole) were successively charged to a flask which had previously been purged with nitrogen. The reaction mixture was stirred and heated under nitrogen at 50-60°C for 6 hours. The product, after work up as described in Example 3, was found to contain 138.5g 3-bromothiophene and 2.6g 2-bromothiophene. The yield of 3-bromothiophene was 85% and the monobromothiophenes were in the ratio of 2 parts 2-bromothiophene to 98 parts 3-bromothiophene.

Reactions

3-Bromothiophene is an electron-rich aromatic hydrocarbon bromide. The bromine atom in it has good electrophilicity. It can perform a Suzuki coupling reaction under the catalysis of metal palladium, and react with different aryl or alkenyl borates. The corresponding substitution products are generated. This reaction is one of the very important methods in organic synthesis, which can build C-C bonds and form complex organic molecular structures.

Synthesis Reference(s)

Journal of the American Chemical Society, 74, p. 2965, 1952 DOI: 10.1021/ja01132a004
Synthetic Communications, 11, p. 25, 1981 DOI: 10.1080/00397918108064278

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