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160474

Sigma-Aldrich

2-Bromothiazole

98%

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About This Item

Empirical Formula (Hill Notation):
C3H2BrNS
CAS Number:
3034-53-5
Molecular Weight:
164.02
Beilstein/REAXYS Number:
105724
EC Number:
221-229-4
MDL number:
MFCD00005316
UNSPSC Code:
12352100
PubChem Substance ID:
24849873
NACRES:
NA.22

assay

98%

form

liquid

refractive index

n20/D 1.593 (lit.)

bp

171 °C (lit.)

density

1.82 g/mL at 25 °C (lit.)

functional group

bromo

storage temp.

2-8°C

SMILES string

Brc1nccs1

InChI

1S/C3H2BrNS/c4-3-5-1-2-6-3/h1-2H

InChI key

RXNZFHIEDZEUQM-UHFFFAOYSA-N

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Application

2-Bromothiazole was used to N-arylate 5- and 7-azaindoles. 2-Bromothiazole was also used as starting reagent in the synthesis of:
  • 2-cyanothiazole via cpper-catalyzed cyanation
  • 2,4,5-trisubstituted thiazoles
  • novel electron-deficient fused pyrrolo[3,2-d:4,5-d′]bisthiazole
  • 3-(2′-thiazoyl)indoles

Storage Class

10 - Combustible liquids

wgk_germany

WGK 3

flash_point_f

152.6 °F - closed cup

flash_point_c

67 °C - closed cup

ppe

Eyeshields, Gloves, multi-purpose combination respirator cartridge (US)

Certificates of Analysis (COA)

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Synlett, 555-555 (2007)
Tetrahedron Letters, 48, 4831-4831 (2007)
Mohammed Al-Hashimi et al.
Organic letters, 12(23), 5478-5481 (2010-11-12)
The synthesis of a novel electron-deficient fused pyrrolo[3,2-d:4,5-d']bisthiazole is reported from 2-bromothiazole. This was copolymerized with thiophene, selenophene, thienothiophene, and bithiophene by microwave-assisted Stille polycondensation. The resulting polymers exhibited small optical band gaps combined with low-lying HOMO energy levels and
Synthesis of camalexin and related phytoalexins.
Ayer WA, et al.
Tetrahedron, 48(14), 2919-2924 (1992)
Cora Dunst et al.
The Journal of organic chemistry, 76(16), 6972-6978 (2011-07-09)
A general method for the synthesis of 2,4,5-trisubstituted thiazoles has been developed. Starting from commercially available 2-bromothiazole, successive metalations using TMPMgCl·LiCl or TMP(2)Zn·2MgCl(2)·2LiCl lead to the corresponding magnesated or zincated thiazoles which readily react with various electrophiles providing highly functionalized

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