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544531

Sigma-Aldrich

2-Bromo-5-nitrothiophene

97%

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About This Item

Empirical Formula (Hill Notation):
C4H2BrNO2S
CAS Number:
13195-50-1
Molecular Weight:
208.03
EC Number:
236-155-8
MDL number:
MFCD00022493
UNSPSC Code:
12352100
PubChem Substance ID:
24878772
NACRES:
NA.22

Assay

97%

mp

44-48 °C (lit.)

SMILES string

[O-][N+](=O)c1ccc(Br)s1

InChI

1S/C4H2BrNO2S/c5-3-1-2-4(9-3)6(7)8/h1-2H

InChI key

ZPNFMDYBAQDFDY-UHFFFAOYSA-N

General description

2-Bromo-5-nitrothiophene is a heteroaryl halide that can be prepared from thiophene by bromination followed by nitration. It participates in the synthesis of oligothiophene precursors for generating (porphinato)zinc(II)-based chromophores.

Application

2-Bromo-5-nitrothiophene may be used in the preparation of:
  • 3-bromo-4-(5-nitro-2-thienyl)-6-ethoxypyridine
  • 5-chloro-2-methoxy-4-(5-nitrothien-2-yl)-pyridine
  • 5-(5-nitrothien-2-yl)pyrimidine
  • 2-methoxy-5-(5-nitrothien-2-yl)pyrimidine

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
BCBV3426
BCBT0916
BCBN9564V
BCBG5363V
BCBC9463V

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5-Pyrimidylboronic acid and 2-methoxy-5-pyrimidylboronic acid: new heteroarylpyrimidine derivatives via Suzuki cross-coupling reactions.
Saygili N, et al.
Organic & Biomolecular Chemistry, 2(6), 852-857 (2004)
New Shelf-stable halo-and alkoxy-substituted Pyridylboronic acids and their Suzuki cross-coupling reactions to yield heteroarylpyridines.
Parry PR, et al.
Synthesis, 2003(07), 1035-1038 (2003)
Oligo (2,5?thienyleneethynylene) s with Terminal Donor?Acceptor Substitution.
Meier H, et al.
European Journal of Organic Chemistry, 2006(2), 405-413 (2006)
Design, synthesis, linear, and nonlinear optical properties of conjugated (porphinato) zinc (II)-based donor-acceptor chromophores featuring nitrothiophenyl and nitrooligothiophenyl electron-accepting moieties.
Zhang TG, et al.
Journal of the American Chemical Society, 127(27), 9710-9720 (2005)
Functionalized pyridylboronic acids and their Suzuki cross-coupling reactions to yield novel heteroarylpyridines
Parry PR, et al.
The Journal of Organic Chemistry, 67(21), 7541-7543 (2002)

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