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106224

Sigma-Aldrich

3-Bromothiophene

97%

Synonym(s):

3-Thienyl bromide

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About This Item

Empirical Formula (Hill Notation):
C4H3BrS
CAS Number:
872-31-1
Molecular Weight:
163.04
Beilstein:
105338
EC Number:
212-821-3
MDL number:
MFCD00005464
UNSPSC Code:
12352100
PubChem Substance ID:
24846726
NACRES:
NA.22

Assay

97%

refractive index

n20/D 1.591 (lit.)

bp

150 °C (lit.)

density

1.74 g/mL at 25 °C (lit.)

functional group

bromo

SMILES string

Brc1ccsc1

InChI

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

InChI key

XCMISAPCWHTVNG-UHFFFAOYSA-N

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Application

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).

Signal Word

Danger

Hazard Classifications

Acute Tox. 1 Inhalation - Acute Tox. 2 Dermal - Acute Tox. 3 Oral - Aquatic Chronic 2 - Eye Irrit. 2 - Flam. Liq. 3 - Skin Sens. 1 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

3 - Flammable liquids

WGK

WGK 3

Flash Point(F)

125.6 °F - closed cup

Flash Point(C)

52 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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Alexandre Jean et al.
Organic letters, 9(13), 2553-2556 (2007-05-29)
Oxidation of N-aromatic methanesulfonamides with iodobenzene diacetate in the presence of substituted thiophene promotes interesting coupling reactions in moderate to good yields.
Cyclopalladated ferrocenylimine: a highly effective catalyst for the borylation/suzuki coupling reaction
Ning Ma, et al.
Tetrahedron, 63, 4625-4625 (2007)
Room temperature stable 3-lithiothiophene: a facile synthesis of 3-functional thiophenes.
Wu X, et al.
Tetrahedron Letters, 35(22), 3673-3674 (1994)
Synthesis and characterization of 3−hexyl multi−substituted α, ω−diformyl−α−oligothiophenes (n= 3, 6, 8).
Olinga T, et al.
Macromolecular Chemistry and Physics, 198(4), 1091-1107 (1997)
A convenient synthesis of 3-alkylthiophenes.
Pham CV, et al.
Synthetic Communications, 16(6), 689-696 (1986)
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