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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:
105724
EC Number:
221-229-4
MDL number:
MFCD00005316
UNSPSC Code:
12352100
PubChem Substance ID:
24849873
NACRES:
NA.22

Quality Level

100

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 Code

10 - Combustible liquids

WGK

WGK 3

Flash Point(F)

152.6 °F - closed cup

Flash Point(C)

67 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

FSL

Group 4: Flammable liquids
Type 2 petroleums
Hazardous rank III
Water insoluble liquid

JAN Code

160474-5G:
160474-VAR:
160474-BULK:
160474-25G:

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Certificates of Analysis (COA)

Lot/Batch Number
STBG8292
STBB8567V
STBB8687V
S39471
08210DE

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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
Tetrahedron Letters, 48, 4831-4831 (2007)
Synlett, 555-555 (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)

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