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Sigma-Aldrich

2-Amino-6-bromobenzothiazole

97%

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About This Item

Empirical Formula (Hill Notation):
C7H5BrN2S
CAS Number:
15864-32-1
Molecular Weight:
229.10
MDL number:
MFCD00152229
UNSPSC Code:
12352100
PubChem Substance ID:
24878338
NACRES:
NA.22

Assay

97%

form

solid

mp

213-217 °C (lit.)

SMILES string

Nc1nc2ccc(Br)cc2s1

InChI

1S/C7H5BrN2S/c8-4-1-2-5-6(3-4)11-7(9)10-5/h1-3H,(H2,9,10)

InChI key

VZEBSJIOUMDNLY-UHFFFAOYSA-N

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General description

Reaction of 4-bromoaniline with acetic acid and potassium thiocynate in solution of bromine in acetic acid yields 2-amino-6-bromobenzothiazole. 2-Amino-6-bromobenzothiazole can also be synthesized from 2-aminobenzothiazole via monobromination with silica-supported quinolinium tribromide.

Application

2-Amino-6-bromobenzothiazole may be used in the synthesis of the following
  • 2-amino-6-arylbenzothiazole compounds:
  • 6-p-tolylbenzo[d]thiazole-2-amine
  • 6-(4chlorophenyl)benzo[d]thiazole-2-amine
  • 6-(4-methoxyphenyl)benzo[d]thiazole-2-amine
  • 6-(3,5-bis(triflouromethyl)phenyl)benzo[d]thiazole-2-amine
  • 6-phenylbenzo[d]thiazole-2-amine
It may be employed as a ligand (L) in the synthesis of organometallic derivatives of Rh(I) [Rh(CO)2(L)(Cl)].

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H302,H317,H319

Hazard Classifications

Acute Tox. 4 Oral - Eye Irrit. 2 - Skin Sens. 1

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

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Silica-supported quinolinium tribromide: a recoverable solid brominating reagent for regioselective monobromination of aromatic amines.
Li Z, et al.
Journal of the Brazilian Chemical Society, 21(3), 496-501 (2010)
Efficient synthesis of 2-amino-6-arylbenzothiazoles via Pd (0) Suzuki cross coupling reactions: potent urease enzyme inhibition and nitric oxide scavenging activities of the products.
Gull Y, et al.
Molecules (Basel), 18(8), 8845-8857 (2013)
Synthesis, cytostatic, and antitumor properties of new Rh (I) thiazole complexes.
Craciunescu, D. G., et al.
Biological trace element research, 8(4), 251-261 (1985)
Claire Bagnéris et al.
Proceedings of the National Academy of Sciences of the United States of America, 111(23), 8428-8433 (2014-05-23)
Voltage-gated sodium channels are important targets for the development of pharmaceutical drugs, because mutations in different human sodium channel isoforms have causal relationships with a range of neurological and cardiovascular diseases. In this study, functional electrophysiological studies show that the

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