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133507

Sigma-Aldrich

2-Amino-5-nitrothiazole

97%

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About This Item

Empirical Formula (Hill Notation):
C3H3N3O2S
CAS Number:
121-66-4
Molecular Weight:
145.14
Beilstein:
126797
EC Number:
204-490-9
MDL number:
MFCD00005326
UNSPSC Code:
12352100
PubChem Substance ID:
24848112
NACRES:
NA.22

Assay

97%

form

solid

mp

195-200 °C (dec.) (lit.)

solubility

95% ethanol: soluble 1g/150g at 20 °C
diethyl ether: soluble 1g/250g at 20 °C
chloroform: insoluble
water: slightly soluble

SMILES string

Nc1ncc(s1)[N+]([O-])=O

InChI

1S/C3H3N3O2S/c4-3-5-1-2(9-3)6(7)8/h1H,(H2,4,5)

InChI key

MIHADVKEHAFNPG-UHFFFAOYSA-N

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General description

2-Amino-5-nitrothiazole(ANT) is a hypoxic radiosensitizing drug. ANT forms square-planar complex, trans-[PdCl2(ANT)2] with palladium in methanol.

Application

2-Amino-5-nitrothiazole was used as diazo component in the synthesis of monoazo disperse dyes. It was used as matrix during matrix-assisted laser desorption/ionization time-of-flight mass spectrometric study of oligonucleotide and protein.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H302,H315,H319,H335

Hazard Classifications

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 3

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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Reaction of 2-amino-5-nitrothiazole with palladium salts.
Farrell N and Carneiro TM.
Inorgorganica Chimica Acta, 126(2), 137-139 (1987)
Analysis of Oligonucleotide and Protein via Matrix-assisted Laser Desorption/Ionization Time-of-flight Mass Spectrometry Using 2-Amino-5-nitrothiazole as an Effective Matrix [J].
ZHOU LH, et al.
Chemical Research in Chinese Universities, 12, 012-012 (2004)
Synthesis and Spectral Properties of Hetaryl Monoazo dyes derived from 2-amino-5-nitrothiazole.
OTUTU JO, et al.
Orient. J. Chem., 27(4), 2011-2011 (1389)
Evaluation of 2-amino-5-nitrothiazole as a hypoxic cell radiosensitizer.
S Rockwell et al.
Radiation research, 90(3), 575-585 (1982-06-01)
T Eric Ballard et al.
Bioorganic & medicinal chemistry letters, 20(12), 3537-3539 (2010-05-22)
Head group analogues of the antibacterial and antiparasitic drug nitazoxanide (NTZ) are presented. A library of 39 analogues was synthesized and assayed for their ability to suppress growth of Helicobacter pylori, Campylobacter jejuni, Clostridium difficile and inhibit NTZ target pyruvate:ferredoxin
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