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538507

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.)

functional group

bromo

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

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Certificates of Analysis (COA)

Lot/Batch Number
MKBW7566V
MKBG2242V
MKBD9075
MKBB1205
02828EJ

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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)
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)
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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