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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

Quality Level

100

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

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

FSL

Group 4: Flammable liquids
Type 2 petroleums
Hazardous rank III
Water insoluble liquid

JAN Code

106224-VAR:
106224-25G:
106224-BULK:
106224-5G:
106224-100G:

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Certificates of Analysis (COA)

Lot/Batch Number
STBK7549
STBJ6641
STBH9626
STBH6971
STBH6190

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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)
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
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.
A convenient synthesis of 3-alkylthiophenes.
Pham CV, et al.
Synthetic Communications, 16(6), 689-696 (1986)
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