Skip to Content
Merck
All Photos(1)

Documents

106224

Sigma-Aldrich

3-Bromothiophene

97%

Synonym(s):

3-Thienyl bromide

Sign Into View Organizational & Contract Pricing
All Photos(1)

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.)

SMILES string

Brc1ccsc1

InChI

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

InChI key

XCMISAPCWHTVNG-UHFFFAOYSA-N

Looking for similar products? Visit Product Comparison Guide

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)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

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.
Room temperature stable 3-lithiothiophene: a facile synthesis of 3-functional thiophenes.
Wu X, et al.
Tetrahedron Letters, 35(22), 3673-3674 (1994)
Cyclopalladated ferrocenylimine: a highly effective catalyst for the borylation/suzuki coupling reaction
Ning Ma, et al.
Tetrahedron, 63, 4625-4625 (2007)
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)
M Zangoli et al.
Nanoscale, 9(26), 9202-9209 (2017-06-27)
We report that nanoparticles prepared from appropriately functionalized polythiophenes once administered to live cells can acquire phototransduction properties under illumination, becoming photoactive sites able to absorb visible light and convert it to an electrical signal through cell membrane polarization. Amine-reactive
View All Related Papers

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service