2-Amino-5-nitrothiazole - ≥98%(HPLC) , CAS No.121-66-4

CAS: 121-66-4 Cat. No.: A151201 Molecular Weight: 145.14 Beilstein Registry Number: 126797 EC Number: 204-490-9

GRADE & PURITY ≥98%(HPLC)

Synonyms

CAS-121-66-4 | 2-amino-5-nitro-1,3-thiazole | 5-Nitro-2-thiazolamine | AM20080158 | HSDB 4022 | 2-AMINO-5-NITROTHIAZOLE [IARC] | 2-AMINO-5-NITROTHIAZOLE [MI] | Oprea1_237935 | STR02181 | PD162659 | 2-AMINO-4-NITROTHIAZOLE | Aminonitrothiazole | 2-AMINO-5-

Storage

Room temperature

Shipped In

Normal

Overview

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

Specifications

Synonyms

CAS-121-66-4 | 2-amino-5-nitro-1, 3-thiazole | 5-Nitro-2-thiazolamine | AM20080158 | HSDB 4022 | 2-AMINO-5-NITROTHIAZOLE [IARC] | 2-AMINO-5-NITROTHIAZOLE [MI] | Oprea1_237935 | STR02181 | PD162659 | 2-AMINO-4-NITROTHIAZOLE | Aminonitrothiazole | 2-AMINO-5-

Specifications & Purity

≥98%(HPLC)

Storage

Room temperature

Shipped In

Normal

Purity

≥98%(HPLC)

Names and Identifiers

• Pubchem Sid: 488180810
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/488180810
• Canonical Smiles: C1=C(SC(=N1)N)[N+](=O)[O-]
• IUPAC Name: 5-nitro-1,3-thiazol-2-amine
• InChIKey: MIHADVKEHAFNPG-UHFFFAOYSA-N
• INCHI: 1S/C3H3N3O2S/c4-3-5-1-2(9-3)6(7)8/h1H,(H2,4,5)
• Isomeric SMILES: C1=C(SC(=N1)N)[N+](=O)[O-]
• WGK Germany: 3
• RTECS: XJ2800000
• UN Number: 2811
• Packing Group: I
• Molecular Weight: 145.14
• Beilstein: 126797
• Reaxy-Rn: 126797
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=126797&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organoheterocyclic compounds
    • Class Azoles
      • Subclass Thiazoles

• Kingdom: Organic compounds
• Superclass: Organoheterocyclic compounds
• Class: Azoles
• Subclass: Thiazoles
• Intermediate Tree Nodes: Not available
• Direct Parent: Nitrothiazoles
• Alternative Parents: Nitroaromatic compounds Heteroaromatic compounds Isothioureas Propargyl-type 1,3-dipolar organic compounds Organic oxoazanium compounds Azacyclic compounds Organopnictogen compounds Organonitrogen compounds Organic zwitterions Organic oxides Hydrocarbon derivatives
• Molecular Framework: Aromatic heteromonocyclic compounds
• Substituents: Nitroaromatic compound - Nitrothiazole - Heteroaromatic compound - Isothiourea - C-nitro compound - Organic nitro compound - Organic oxoazanium - Allyl-type 1,3-dipolar organic compound - Propargyl-type 1,3-dipolar organic compound - Organic 1,3-dipolar compound - Azacycle - Organic nitrogen compound - Organic zwitterion - Organonitrogen compound - Organic oxygen compound - Organopnictogen compound - Organic oxide - Hydrocarbon derivative - Aromatic heteromonocyclic compound
• Description: This compound belongs to the class of organic compounds known as nitrothiazoles. These are compounds containing a thiazole ring which bears a nitro group.
• External Descriptors: C-nitro compound - thiazoles

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Associated Targets(Human)

NR3C1 Tclin Glucocorticoid receptor (14987 Activities)

Discover Target: NR3C1

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PRKAA2 Tchem AMP-activated protein kinase, alpha-2 subunit (1328 Activities)

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PLK1 Tchem Serine/threonine-protein kinase PLK1 (28605 Activities)

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ALOX15B Tchem Arachidonate 15-lipoxygenase, type II (7244 Activities)

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ALDH1A1 Tchem Aldehyde dehydrogenase 1A1 (77053 Activities)

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ALOX15 Tchem Arachidonate 15-lipoxygenase (7108 Activities)

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Lymphoblastoid cell (5959 Activities)

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HPGD Tchem 15-hydroxyprostaglandin dehydrogenase [NAD+] (24926 Activities)

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GMNN Tbio Geminin (128009 Activities)

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ATXN2 Tbio Ataxin-2 (54410 Activities)

Discover Target: ATXN2

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IDH1 Tclin Isocitrate dehydrogenase [NADP] cytoplasmic (40980 Activities)

Discover Target: IDH1

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Associated Targets(non-human)

Leishmania amazonensis (3813 Activities)

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Trypanosoma cruzi (99888 Activities)

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Trichomonas vaginalis (2376 Activities)

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Giardia intestinalis (1290 Activities)

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Rattus norvegicus (775804 Activities)

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Vero (26788 Activities)

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Nfe2l2 Nuclear factor erythroid 2-related factor 2 (214 Activities)

Discover Target: Nfe2l2

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Rorc Nuclear receptor ROR-gamma (89407 Activities)

Discover Target: Rorc

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Mechanisms of Action

Chemical and Physical Properties

• Solubility: 95% ethanol: soluble 1g/150g at 20 °C； diethyl ether: soluble 1g/250g at 20 °C； chloroform: insoluble； water: slightly soluble； hot Methanol：very faint turbidity；
• Melt Point(°C): 202℃
• Molecular Weight: 145.140 g/mol
• XLogP3: 0.800
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 0
• Exact Mass: 144.995 Da
• Monoisotopic Mass: 144.995 Da
• Topological Polar Surface Area: 113.000 Ų
• Heavy Atom Count: 9
• Formal Charge: 0
• Complexity: 125.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 0
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1

References

1. Yadong Wang, Li Ma, Jun Yuan, Zongmin Zhu, Xiaoming Liu, Dengsong Li, Liqing He, Fei Xiao.  (2023)  Furfural-based P/N/S flame retardant towards high-performance epoxy resins with flame retardancy, toughness, low dielectric properties and UV resistance.  POLYMER DEGRADATION AND STABILITY,      [PMID:] [10.1016/j.polymdegradstab.2023.110343]