106224
3-Bromothiophene
97%
Synonym(s):
3-Thienyl bromide
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About This Item
Empirical Formula (Hill Notation):
C4H3BrS
CAS Number:
Molecular Weight:
163.04
UNSPSC Code:
12352100
NACRES:
NA.22
PubChem Substance ID:
EC Number:
212-821-3
Beilstein/REAXYS Number:
105338
MDL number:
Assay:
97%
Quality Level
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
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).
signalword
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
3 - Flammable liquids
wgk
WGK 3
flash_point_f
125.6 °F - closed cup
flash_point_c
52 °C - closed cup
ppe
Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter
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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)
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.