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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.)

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

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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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
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
Voltammetric determination of 2-amino-6-nitrobenzothiazole at two different silver amalgam electrodes.
Deylova D, et al.
Electrochimica Acta, 62, 335-340 (2012)
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)

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