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Merck
CN

18441

3-Bromothiophene

technical, ≥95% (GC)

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
EC Number:
212-821-3
UNSPSC Code:
12352100
PubChem Substance ID:
24851112
Beilstein/REAXYS Number:
105338
MDL number:
MFCD00005464

Key Documents

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grade

technical

assay

≥95% (GC)

refractive index

n20/D 1.591 (lit.), n20/D 1.592

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

Application

3-Bromothiophene was used in the preparation of:
  • N-acyldithieno[3,2-b:2′,3′-d]pyrrole via copper-catalyzed amidation
  • 1-benzyl-6′-methoxy-6′,7′-dihydrospiro[piperidine-4,4′-thieno[3.2- c]pyran]
  • 3-alkylthiophenes

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

Regulatory Information

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Christoph Oberdorf et al.
Journal of medicinal chemistry, 51(20), 6531-6537 (2008-09-26)
Herein, the synthesis and pharmacological evaluation of thiophene bioisosteres of the highly potent spirocyclic benzopyran 1 are detailed. The synthesis of 1-benzyl-6'-methoxy-6',7'-dihydrospiro[piperidine-4,4'-thieno[3.2- c]pyran] (2a) was performed starting with 3-bromothiophene (3). After introduction of the acetaldehyde substructure (7), halogen metal exchange
Sean J Evenson et al.
Organic letters, 12(18), 4054-4057 (2010-08-24)
A new class of dithieno[3,2-b:2',3'-d]pyrroles (DTPs) incorporating N-acyl groups have been prepared from 3-bromothiophene via copper-catalyzed amidation. The utilization of various electron-withdrawing acyl groups has allowed stabilization of the HOMO and LUMO energy levels of these popular building blocks for
A convenient synthesis of 3-alkylthiophenes.
Pham CV, et al.
Synthetic Communications, 16(6), 689-696 (1986)

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