2-Nitroimidazole - ≥98% , CAS No.527-73-1

CAS: 527-73-1 Cat. No.: N119956 Formula: C₃H₃N₃O₂ Peso molecolare: 113.07 Beilstein Registry Number: 116444 Numero EC: 208-425-5

GRADE & PURITY ≥98%

Synonyms

s2267 | azomycin-(2-nitroimidazole) | SCHEMBL17145914 | EINECS 208-425-5 | Ro 05-9129 | SCHEMBL4794199 | HY-N0195 | NSC 105831 | FT-0601241 | Azomycin (2-Nitroimidazole) | 2 -nitroimidazole | Nitroimidazoles | Q27135639 | UNII-K8E96XL55D | 2-NITRO-1H-IMID

Storage

Room temperature

Shipped In

Normal

Panoramica

2-Nitroimidazole is a natural antibiotic.
Used to prepare nitroimidazole substituted boronic acids as precursors for imaging hypoxic tissue. Also used to prepare potential site-selective radiosensitizers for estrogen receptor-rich tumors.

Specifications

Sinonimi

s2267 | azomycin-(2-nitroimidazole) | SCHEMBL17145914 | EINECS 208-425-5 | Ro 05-9129 | SCHEMBL4794199 | HY-N0195 | NSC 105831 | FT-0601241 | Azomycin (2-Nitroimidazole) | 2 -nitroimidazole | Nitroimidazoles | Q27135639 | UNII-K8E96XL55D | 2-NITRO-1H-IMID

Specifiche e purezza

≥98%

Meccanismi biochimici e fisiologici

Macrolide antibiotic agent. Hypoxia labeling agent. Selectively accumulates in hypoxic cells. Inhibits bacterial protein synthesis. Shows bactericidal effects against Gram-positive, Gram-negative bacteria and anaerobic bacteria in vivo.

Condizioni di conservazione di stoccaggio

Room temperature

Spedito in

Normal

Tipo di azione

INHIBITOR

Nota

Wherever possible, you should prepare and use solutions on the same day. However, if you need to make up stock solutions in advance, we recommend that you store the solution as aliquots in tightly sealed vials at -20°C. Generally, these will be useable for up to one month. Before use, and prior to opening the vial we recommend that you allow your product to equilibrate to room temperature for at least 1 hour. Need more advice on solubility, usage and handling? Please visit our frequently asked questions (FAQ) page for more details.

Purezza

≥98%

Nomi e identificatori

• Pubchem Sid: 504751989
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/504751989
• Sorrisi canonici: C1=CN=C(N1)[N+](=O)[O-]
• IUPAC Name: 2-nitro-1H-imidazole
• InChIKey: YZEUHQHUFTYLPH-UHFFFAOYSA-N
• INCHI: 1S/C3H3N3O2/c7-6(8)3-4-1-2-5-3/h1-2H,(H,4,5)
• Isomeri SMILES: C1=CN=C(N1)[N+](=O)[O-]
• WGK Germania: 3
• RTECS: NI7875000
• Numero UN: 2811
• Gruppo di imballaggio: III
• Peso molecolare: 113.07
• Beilstein: 116444
• Reaxy-Rn: 116444
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=116444&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organic 1,3-dipolar compounds
    • Classe Allyl-type 1,3-dipolar organic compounds
      • Subclass Organic nitro compounds
        • Level5 C-nitro compounds
          • Level6 Nitroaromatic compounds

• Kingdom: Organic compounds
• Superclass: Organic 1,3-dipolar compounds
• Classe: Allyl-type 1,3-dipolar organic compounds
• Subclass: Organic nitro compounds
• Intermediate Tree Nodes: C-nitro compounds
• Direct Parent: Nitroaromatic compounds
• Alternative Parents: Imidazoles Heteroaromatic compounds 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 - Azole - Imidazole - Heteroaromatic compound - Organic oxoazanium - Propargyl-type 1,3-dipolar organic compound - Organoheterocyclic compound - Azacycle - Organic nitrogen compound - Hydrocarbon derivative - Organic oxide - Organic zwitterion - Organonitrogen compound - Organopnictogen compound - Organic oxygen compound - Aromatic heteromonocyclic compound
• Descrizione: This compound belongs to the class of organic compounds known as nitroaromatic compounds. These are c-nitro compounds where the nitro group is C-substituted with an aromatic group.
• External Descriptors: C-nitro compound - imidazoles

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

Obiettivi associati (umani)

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Discover Target: ACHE

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Obiettivi associati (non umani)

Hdac6 Histone deacetylase 6 (222 Activities)

Discover Target: Hdac6

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rep Replicase polyprotein 1ab (378 Activities)

Discover Target: rep

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BCHE Cholinesterase (8742 Activities)

Discover Target: BCHE

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Meccanismi d'azione

Proprietà chimiche e fisiche

• Solubilità: NH4OH: soluble 50 mg/mL, clear, yellow to orange
• Punto di fusione (°C): 287°C
• Peso molecolare: 113.080 g/mol
• XLogP3: 0.100
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 113.023 Da
• Monoisotopic Mass: 113.023 Da
• Topological Polar Surface Area: 74.500 Ų
• Heavy Atom Count: 8
• Formal Charge: 0
• Complexity: 99.200
• 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

Riferimenti

1. Kai Wang, Wentao Zhou, Xiangyu Jin, Xuwei Shang, Xiaomei Wu, Lijuan Wen, Sufen Li, Yiling Hong, Jia Ke, Yichong Xu, Hong Yuan, Fuqiang Hu.  (2023)  Enhanced brain delivery of hypoxia-sensitive liposomes by hydroxyurea for rescue therapy of hyperacute ischemic stroke.  Nanoscale,  15  (27): (11625-11646).  [PMID:37377137] [10.1039/D3NR01071F]

2. Yifan Luo, Chao Li, Yiwen Zhang, Peixin Liu, Hongyi Chen, Zhenhao Zhao, Yu Wang, Zheng Zhou, Haolin Song, Boyu Su, Chufeng Li, Xuwen Li, Tongyu Zhang, Haoyu You, Yuxing Wu, Zonghua Tian, Shilin Zhang, Yun Guo, Hongrui Fan, Qinjun Chen, Chen Jiang, Tao Sun.  (2023)  Gradient tumor microenvironment-promoted penetrating micelles for hypoxia relief and immunosuppression reversion in pancreatic cancer treatment.  Acta Biomaterialia,      [PMID:37276955] [10.1016/j.actbio.2023.05.047]

3. Yao Li, Mengying Liu, Yan Zheng, Zheng Wang, Yanjun Zhao.  (2023)  Coenzyme-depleting nanocarriers for enhanced redox cancer therapy under hypoxia.  JOURNAL OF COLLOID AND INTERFACE SCIENCE,      [PMID:36931212] [10.1016/j.jcis.2023.03.057]

4. Mengjie Pu, Daqi Ye, Jinquan Wan, Bentuo Xu, Wei Sun, Wei Li.  (2022)  Zinc-based metal–organic framework nanofibers membrane ZIF-65/PAN as efficient peroxymonosulfate activator to degrade aqueous ciprofloxacin.  SEPARATION AND PURIFICATION TECHNOLOGY,      [PMID:] [10.1016/j.seppur.2022.121716]

5. Meng Tingting, Li Yinghong, Tian Ying, Ma Mingxing, Shi Kequan, Shang Xuwei, Yuan Hong, Hu Fuqiang.  (2022)  A Hypoxia-Sensitive Drug Delivery System Constructed by Nitroimidazole and its Application in the Treatment of Hepatocellular Carcinoma.  AAPS PHARMSCITECH,  23  (6): (1-11).  [PMID:35711068] [10.1208/s12249-022-02316-7]

6. Ying Xu, Peng Chen, Lei Tang, Xiaojun Zhang, Feng Shi, Xuyang Ning, Jingli Bi, Yang Qu, Hongfei Liu.  (2022)  Hypoxia responsive and tumor-targeted mixed micelles for enhanced cancer therapy and real-time imaging.  COLLOIDS AND SURFACES B-BIOINTERFACES,      [PMID:35512561] [10.1016/j.colsurfb.2022.112526]

7. Jinxing Chen, Liang Huang, Qingqing Wang, Weiwei Wu, He Zhang, Youxing Fang, Shaojun Dong.  (2019)  Bio-inspired nanozyme: a hydratase mimic in a zeolitic imidazolate framework.  Nanoscale,  11  (13): (5960-5966).  [PMID:30888366] [10.1039/C9NR01093A]

8. Wenjie Ma, Qin Jiang, Ping Yu, Lifen Yang, Lanqun Mao.  (2013)  Zeolitic Imidazolate Framework-Based Electrochemical Biosensor for in Vivo Electrochemical Measurements.  ANALYTICAL CHEMISTRY,      [PMID:23815314] [10.1021/ac401576u]

9. Quanliang Mao, Mengyin Gu, Chengyuan Hong, Huiying Wang, Xinzhong Ruan, Zhusheng Liu, Bo Yuan, Mengting Xu, Chen Dong, Lei Mou, Xiang Gao, Guangyu Tang, Tianxiang Chen, Aiguo Wu, Yuning Pan.  (2024)  A Contrast-Enhanced Tri-Modal MRI Technique for High-Performance Hypoxia Imaging of Breast Cancer.  Small,      [PMID:38366271] [10.1002/smll.202308850]

10. Wenjuan Yang, Lingling Tian, Ning Zhao, Lingyan Feng, Bingpu Zhou, Yongheng Zhu, Xinghua Gao, Yuan Zhang.  (2024)  Zeolitic Imidazolate Frameworks Based Anticancer Drug Delivery System Associated with Dual Action of Surface Charge and Lewis Base Ligand.  Advanced Therapeutics,      [PMID:] [10.1002/adtp.202300447]

11. Fengxiang Liu, Shipeng Ning, Xia Wang, Xiaoyuan Fan, Bin Wan, Fei Sun, Lili Du, Kefan Shi, Xinpeng Zou, Ruihong Zhu, Mingxing Li, Wenwen Shen, Zhonggui He, Kaiyuan Wang, Jin Sun.  (2025)  Pulsatile sequential drug release system for cascade tumor deep penetration and differentiation therapy to enhance chemoimmunotherapy.  Science Advances,  11  (36):   [PMID:40901943] [10.1126/sciadv.adr8001]

12. Yumei Zhang, Yunqi Song, Kemin Xie, Yujie Tang, Yao Yao.  (2025)  Synergistic enhancement in In2O3/In-MOM: Homologous heterojunction with engineered oxygen vacancies for ultrasensitive ethanol sensing.  JOURNAL OF ALLOYS AND COMPOUNDS,      [PMID:] [10.1016/j.jallcom.2025.184001]

13. Zhe Yu, Fudan Zhu, Tianxiao Chen, Jiayao Li, Qingliang Feng, Fengchun Yang, Xin Zhang.  (2023)  Sensitive photoelectrochemical detection of azomycin on Bi2S3/Bi2WO6 heterojunction using ascorbic acid as a hole-trapping agent.  JOURNAL OF PHOTOCHEMISTRY AND PHOTOBIOLOGY A-CHEMISTRY,      [PMID:] [10.1016/j.jphotochem.2023.114637]

14. Shuofeng Li, Weihua Liu, Qianqian Wang, Mingming Xu, Yangjuan An, Lin Hao, Chun Wang, Qiuhua Wu, Zhi Wang.  (2022)  Constructing magnetic covalent organic framework EB-COF@Fe3O4 for sensitive determination of five benzoylurea insecticides.  FOOD CHEMISTRY,      [PMID:35152018] [10.1016/j.foodchem.2022.132362]

15. Qing Cheng, Yuqi Zhang, Yingying Cao, Long Liu, Yanqiang Zhang.  (2026)  Manipulating d-Band Center of Cu(I)-MOFs for Catalytic Ignition of [BMIM]N(CN) 2 IL-H 2 O 2 Propellants.  Journal of Materials Chemistry A,      [PMID:] [10.1039/D5TA09529H]

16. Bin Wang, Na Yin, Xinrui Liu, Yi Guan, Haiyang Xu, Ying Yu, Yang Bai, Yue Cao, Ziqian Wang, Shiqi Bai, Shaopeng Zhang, Donghao Qu, Wanying Li, Zhijia Lv, Yunqian Li, Hongquan Yu, Yinghui Wang.  (2026)  Biomimetic sequentially gated nanotuners based on amorphous metal–organic frameworks for reprogramming the metabolism-ferroptosis-immunity crosstalk in gliomas.  Materials Today Bio,      [PMID:41809378] [10.1016/j.mtbio.2026.102973]

Domande frequenti

What is the purity of this product?

This product is supplied at ≥98% purity (chemical assay). Lot-specific values are stated on the Certificate of Analysis.

How should this product be stored?

Store at room temperature.

How is this product shipped?

This product ships under standard ambient conditions. No temperature-controlled packaging is required.

What are the CAS number, molecular formula and molecular weight?

The CAS Number is 527-73-1, the molecular formula is C3H3N3O2, and the molecular weight is 113.07 g/mol. InChIKey YZEUHQHUFTYLPH-UHFFFAOYSA-N.

What documentation is provided?

Available product documentation, including Certificates of Analysis (COA), Safety Data Sheets (SDS), and specification sheets, is shown in the product document area. Document availability and access follow the current site policy.