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106224 Aldrich

3-Bromothiophene

97%

Synonym: 3-Thienyl bromide

  • CAS Number 872-31-1

  • Empirical Formula (Hill Notation) C4H3BrS

  • Molecular Weight 163.04

  •  Beilstein Registry Number 105338

  •  EC Number 212-821-3

  •  MDL number MFCD00005464

  •  PubChem Substance ID 24846726

  • Popular Documents:  FTNMR (PDF)  

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Properties

Related Categories Building Blocks, C4 to C6, Chemical Synthesis, Halogenated Heterocycles, Heterocyclic Building Blocks,
assay   97%
refractive index   n20/D 1.591(lit.)
bp   150 °C(lit.)
density   1.74 g/mL at 25 °C(lit.)

Description

Packaging

5, 25, 100 g in glass bottle

Application

3-Bromothiophene was used in the synthesis and characterization of derivatives of thienylenic α, ω−diformyl−α−oligothiophenes1.

General description

3-Bromothiophene undergoes NiDPPP++ catalyzed cross-coupling with Grignard reagents to form 3-alkylthiophenes2. 3-Bromothiophene reacts with n-butyllithium in hexane to form 3-lithiothiophene3.

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Safety & Documentation

Safety Information

Symbol 
Signal word 
Danger
Precautionary statements 
RIDADR 
UN 2929 3(6.1) / PGII
WGK Germany 
3
Flash Point(F) 
125.6 °F
Flash Point(C) 
52 °C

Protocols & Articles

Peer-Reviewed Papers

References

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1. Synthesis and characterization of 3−hexyl multi−substituted α, ω−diformyl−α−oligothiophenes (n= 3, 6, 8). Olinga T, et al. Macromol. Chem. Phys. 198(4), 1091-1107, (1997)

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

3. Room temperature stable 3-lithiothiophene: a facile synthesis of 3-functional thiophenes. Wu X, et al. Tetrahedron Lett. 35(22), 3673-3674, (1994)

Tetrahedron 63, 4625, (2007)

Novel method of aromatic coupling between N-aryl methanesulfonamide and thiophene derivatives. Org. Lett. 9, 2553, (2007)

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Beil. 17,V,1,306

Aldrich MSDS 1, 289:D / Corp MSDS 1 (1), 582:C / FT-IR 1 (2), 593:C / FT-IR 2 (3), 3469:D / FT-NMR 1 (3), 46:A / IR-Spectra (3), 1207:F / IR-Spectra (2), 1052:D / NMR-Reference 2 (2), 467:D / RegBook 1 (2), 2331:M / Sigma FT-IR 1 (2), 347:D / Structure Index 1, 367:C:3 / Vapor Phase 3, 1468:D

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