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106224

Sigma-Aldrich

3-Bromothiophene

97%

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Synonym(s):
3-Thienyl bromide
Empirical Formula (Hill Notation):
C4H3BrS
CAS Number:
Molecular Weight:
163.04
Beilstein:
105338
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.22

Quality Level

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

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This Item
C81217B77207633054
3-Bromothiophene 97%

Sigma-Aldrich

106224

3-Bromothiophene

refractive index

n20/D 1.591 (lit.)

refractive index

n20/D 1.621 (lit.)

refractive index

n20/D 1.546 (lit.)

refractive index

n20/D 1.612

bp

150 °C (lit.)

bp

103 °C/22 mmHg (lit.)

bp

237-238 °C (lit.)

bp

-

density

1.74 g/mL at 25 °C (lit.)

density

1.332 g/mL at 25 °C (lit.)

density

1.31 g/mL at 25 °C (lit.)

density

-

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

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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)
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
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)

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