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190241

Sigma-Aldrich

2-Amino-6-nitrobenzothiazole

≥97%

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About This Item

Empirical Formula (Hill Notation):
C7H5N3O2S
CAS Number:
6285-57-0
Molecular Weight:
195.20
EC Number:
228-513-7
MDL number:
MFCD00005786
UNSPSC Code:
12352100
PubChem Substance ID:
24851422
NACRES:
NA.22

Quality Level

100

Assay

≥97%

mp

247-249 °C (lit.)

functional group

nitro

SMILES string

Nc1nc2ccc(cc2s1)[N+]([O-])=O

InChI

1S/C7H5N3O2S/c8-7-9-5-2-1-4(10(11)12)3-6(5)13-7/h1-3H,(H2,8,9)

InChI key

GPNAVOJCQIEKQF-UHFFFAOYSA-N

General description

Voltammetric behavior of 2-amino-6-nitrobenzothiazole has been investigated using direct current voltammetry and differential pulse voltammetry.

Application

2-Amino-6-nitrobenzothiazole has been used:
  • as model analyte for voltammetric determination of electrochemically reducible organic substances
  • in the synthesis of 2-methyl-4-nitro-2H-pyrazole-3-carboxylic acid[2-(cyclohexanecarbonylamino)benzothiazol-6-yl]amide derivatives
  • in the preparation of push-pull nonlinear optical chromophores containing thiazole and benzothiazole acceptors
  • as a base in dye production by diazotation reaction

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Classifications

Acute Tox. 4 Dermal - Acute Tox. 4 Inhalation - Acute Tox. 4 Oral - Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 2

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
MKCQ3435
MKCP0900
MKCN3315
MKCL6341
MKCH7253

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Voltammetric determination of 2-amino-6-nitrobenzothiazole at two different silver amalgam electrodes.
Deylova D, et al.
Electrochimica Acta, 62, 335-340 (2012)
Masao Yoshida et al.
Bioorganic & medicinal chemistry letters, 15(14), 3328-3332 (2005-06-16)
Based on 2-methyl-4-nitro-2H-pyrazole-3-carboxylic acid[2-(cyclohexanecarbonylamino)benzothiazol-6-yl]amide (1), which shows selective cytotoxicity against tumorigenic cell lines, 2,6-dichloro-N-[2-(cyclopropanecarbonylamino)benzothiazol-6-yl]benzamide (13b) was designed and synthesized as a biologically stable derivative containing no nitro group. The highly potent derivative 13b exhibited excellent in vivo inhibitory effect on
Synthesis and characterization of thermally stable second-order nonlinear optical side-chain polyimides containing thiazole and benzothiazole push-pull chromophores.
Tambe SM, et al.
Opt. Mater., 31(6), 817-825 (2009)
Dana Deýlová et al.
Talanta, 102, 68-74 (2012-11-28)
New type of bismuth film electrode prepared by electrodeposition of bismuth film on a silver solid amalgam substrate (BiF-AgSAE) was tested as a sensor for voltammetric determination of electrochemically reducible organic substances using 2-amino-6-nitrobenzothiazole (ANBT) as a model analyte. Using

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