5-Nitrobenzimidazole

Base Information

• Chemical Name: 5-Nitrobenzimidazole
• CAS No.: 94-52-0
• Deprecated CAS: 89843-47-0
• Molecular Formula: C7H5N3O2
• Molecular Weight: 163.136
• Hs Code.: 29339990
• European Community (EC) Number: 202-341-2
• NSC Number: 58858,3068
• UN Number: 2811
• UNII: A7V95AYT2T
• DSSTox Substance ID: DTXSID8020965
• Nikkaji Number: J68.954H
• Wikidata: Q27273738
• ChEMBL ID: CHEMBL164921
• Mol file: 94-52-0.mol

Synonyms:5-NITROBENZIMIDAZOLE;94-52-0;6-Nitrobenzimidazole;5-nitro-1H-benzo[d]imidazole;5-Nitro-1H-benzimidazole;1H-Benzimidazole, 5-nitro-;6-Nitro-1H-benzimidazole;1H-Benzimidazole, 6-nitro-;5(6)-Nitrobenzimidazole;5-nitro-1H-1,3-benzodiazole;6-Nitro-benzimidazole;Benzimidazole, 5-nitro-;Benzimidazole, 6-nitro-;NCI-C01912;5-Nitro-1H-benzoimidazole;CCRIS 442;6-nitro-1H-1,3-benzodiazole;HSDB 2864;NSC 3068;EINECS 202-341-2;MFCD00005604;NSC 58858;UNII-A7V95AYT2T;A7V95AYT2T;AI3-52609;MLS002637666;CHEMBL164921;89843-47-0;DTXSID8020965;Benzimidazole, 5(or 6)-nitro-;NSC-3068;NSC-58858;DTXCID60965;WLN: T56 BM DNJ HNW;CAS-94-52-0;6-Nitro-1H-benzo[d]imidazole;4msa;1H-BENZIMIDAZOLE,5-NITRO-;5-nitrobenzimidazol;6-nitrobenzimidazol;2ZM;5-nitrobenzoimidazol;5-nitrobenzoimidazole;5-nitro-benzimidazole;4n9c;5(6)-nitro-benzimidazole;6-Nitro-1H-benzoimidazole;1h-benzimidazole,6-nitro-;1h-bencimidazol, 6-nitro-;1H-bencimidazol, 5-nitro-;Oprea1_525754;Oprea1_664147;SCHEMBL271340;Benzimidazole 5-nitro-(8CI);5-nitro-1H-1,3-benzimidazole;NSC3068;1H-Benzimidazole 5-nitro-(9CI);HMS3079A05;5-NITROBENZIMIDAZOLE [HSDB];BCP26862;NSC58858;Tox21_201684;Tox21_302828;BDBM50208881;MFCD00040457;STK299272;AKOS000275609;AKOS003790796;AKOS015970456;CS-W010848;LS-1964;s10799;NCGC00091868-01;NCGC00091868-02;NCGC00091868-03;NCGC00091868-04;NCGC00091868-05;NCGC00091868-06;NCGC00256398-01;NCGC00259233-01;AC-11286;AM808099;AS-46775;Benzimidazole 5(or 6)-nitro-(6CI7CI);SMR001305771;SY003312;BB 0219456;EU-0067493;FT-0620702;N0152;Benzimidazole, 5(or 6)-nitro- (6CI,7CI);EN300-34514;2-[(4,6-Dimethoxypyrimidin-2-yl)thio]benzoicacid;AE-641/30196001;SR-01000394488;SR-01000394488-1;W-100194;Q27273738;F0020-1984

Chemical Property of 5-Nitrobenzimidazole

Chemical Property:

• Appearance/Colour: white or pale yellow powder
• Vapor Pressure: 9.35E-09mmHg at 25°C
• Melting Point: 207-210 °C
• Refractive Index: 1.74
• Boiling Point: 475.7 °C at 760 mmHg
• PKA: 10.95±0.10(Predicted)
• Flash Point: 241.5 °C
• PSA: 74.50000
• Density: 1.525 g/cm³
• LogP: 1.99430
• Storage Temp.: Store below +30°C.
• Solubility.: 0.5g/l
• Water Solubility.: <0.01 g/100 mL at 16.5℃
• XLogP3: 1.6
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 163.038176411
• Heavy Atom Count: 12
• Complexity: 192
• Transport DOT Label: Poison

Purity/Quality:

99%, ^*data from raw suppliers

5-Nitrobenzimidazole ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi,Xn
• Hazard Codes: Xi,Xn
• Statements: 36/37/38-40-22
• Safety Statements: 26-45-36/37

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Nitrogen Compounds -> Imidazoles
• Canonical SMILES: C1=CC2=C(C=C1[N+](=O)[O-])NC=N2
• Uses: Antifogging agent in photographic developers. 5-Nitrobenzimidazole acts as a reagent in the synthesis of benzimidazoles derivatives with antibacterial and antifungal activities. It also functions as a reagent in the synthesis of xanthine oxidase, a key enzyme that catalyze xanthine to uric acid causing hyperuricemia in humans.

Technology Process of 5-Nitrobenzimidazole

There total 36 articles about 5-Nitrobenzimidazole which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

formic acid (64-18-6) + 4-Nitrophenylene-1,2-diamine (99-56-9) → 5-nitrobenzimidazole (94-52-0)

Guidance literature:

With hydrogenchloride; In water; for 8h; Reflux;

DOI:10.3390/molecules200815206

Reference yield: 95.0%

N,N-dimethyl-formamide (68-12-2,33513-42-7) + 4-Nitrophenylene-1,2-diamine (99-56-9) → 5-nitrobenzimidazole (94-52-0)

Guidance literature:

With hydrogenchloride; In water; at 150 ℃; for 0.0333333h; Microwave irradiation;

DOI:10.1039/c5ra00021a

Reference yield: 93.0%

orthoformic acid triethyl ester (122-51-0) + 4-Nitrophenylene-1,2-diamine (99-56-9) → 5-nitrobenzimidazole (94-52-0)

Guidance literature:

With TiO₂ modified with bis-3-(trimethoxysilylpropyl)-ammonium hydrogen sulfate; In neat (no solvent); at 90 ℃; for 0.333333h;

DOI:10.1039/c8nj00171e

upstream raw materials:

benzoimidazole

formic acid

4-Nitrophenylene-1,2-diamine

Vilsmeier reagent

Downstream raw materials:

4-ethyl-5-aminobenzimidazole

C₁₄H₁₂N₄O

2-hydroxy-5-(6-nitro-1H-benzimidazol-2-yl)benzoic acid

Refernces

• 1、 Li, Hu,Li, Zhengyi,Wu, Hongguo,Yang, Song,Yu, Zhaozhuo,Zhang, Lilong,Zhu, Kaixun. "A substituent- And temperature-controllable NHC-derived zwitterionic catalyst enables CO2upgrading for high-efficiency construction of formamides and benzimidazoles". supporting information. p. 5759 - 5765. Retrieved 2021/08/23.
• 2、 Han, Limin,Hong, Hailong,Li, Xiao,Yang, Yue,Zhang, Junhua,Zhu, Ning. "Reductive cyclization of o-phenylenediamine with CO2 and BH3NH3 to synthesize 1H-benzoimidazole derivatives". supporting information. . Retrieved 2021/09/28.