6-Nitro-2-phenyl-1H-benzo[D]imidazole

Base Information

• Chemical Name: 6-Nitro-2-phenyl-1H-benzo[D]imidazole
• CAS No.: 1571-85-3
• Molecular Formula: C13H9N3O2
• Molecular Weight: 239.233
• Hs Code.: 2933990090
• DSSTox Substance ID: DTXSID20353944
• Nikkaji Number: J2.177.160K
• Wikidata: Q82131816
• ChEMBL ID: CHEMBL1164403
• Mol file: 1571-85-3.mol

Synonyms:1571-85-3;6-NITRO-2-PHENYL-1H-BENZO[D]IMIDAZOLE;6-nitro-2-phenyl-1H-benzimidazole;1H-Benzimidazole, 5-nitro-2-phenyl-;1H-BENZIMIDAZOLE, 6-NITRO-2-PHENYL-;5-nitro-2-phenyl-1H-benzimidazole;CHEMBL1164403;5-Nitro-2-phenyl-1H-benzoimidazole;2-phenyl-5-nitrobenzimidazole;MLS000560373;1H-BENZIMIDAZOLE,6-NITRO-2-PHENYL-;Cambridge id 5175874;Oprea1_232925;Oprea1_261004;Oprea1_473321;SCHEMBL2245102;DTXSID20353944;FHOXCSDDMCCTPM-UHFFFAOYSA-N;HMS2551H07;BDBM50553732;MFCD00441943;STK009456;AKOS000275608;AKOS003245363;5-Nitro-2-phenyl-1H-benzo[d]imidazole;DS-10110;SMR000175416;BB 0219455;CS-0030087;5-NITRO-2-PHENYL-1H-1,3-BENZODIAZOLE;A907663;SR-01000389398;SR-01000389398-1

Chemical Property of 6-Nitro-2-phenyl-1H-benzo[D]imidazole

Chemical Property:

• Melting Point: 203 °C
• Boiling Point: 482.6±37.0 °C(Predicted)
• PKA: 9?+-.0.10(Predicted)
• PSA: 74.50000
• Density: 1.389±0.06 g/cm3(Predicted)
• LogP: 3.66130
• Storage Temp.: Sealed in dry,Room Temperature
• XLogP3: 3.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 239.069476538
• Heavy Atom Count: 18
• Complexity: 312

Purity/Quality:

98%min ^*data from raw suppliers

6-NITRO-2-PHENYL-1H-BENZO[D]IMIDAZOLE 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)C2=NC3=C(N2)C=C(C=C3)[N+](=O)[O-]

Technology Process of 6-Nitro-2-phenyl-1H-benzo[D]imidazole

There total 50 articles about 6-Nitro-2-phenyl-1H-benzo[D]imidazole 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: 99.0%

benzoic acid anhydride (93-97-0) + 4-Nitrophenylene-1,2-diamine (99-56-9) → 2-phenyl-5-nitrobenzimidazole (1571-85-3)

Guidance literature:

In 1-methyl-pyrrolidin-2-one; water; at 445 ℃; for 0.00277778h; under 337534 Torr; Supercritical conditions;

Reference yield: 98.0%

benzaldehyde (100-52-7) + 4-Nitrophenylene-1,2-diamine (99-56-9) → 2-phenyl-5-nitrobenzimidazole (1571-85-3)

Guidance literature:

With sulfonated rice husk ash; at 80 ℃; for 0.333333h; Green chemistry;

DOI:10.1007/s11164-015-2075-5

Reference yield: 94.0%

4-Nitrophenylene-1,2-diamine (99-56-9) + benzoic acid (65-85-0,8013-63-6) → 2-phenyl-5-nitrobenzimidazole (1571-85-3)

Guidance literature:

With polyphosphoric acid; at 140 ℃; for 8h;

DOI:10.2174/13862073113166660058

upstream raw materials:

N,N'-(4-nitro-o-phenylene)-bis-benzamide

benzaldehyde

4-Nitrophenylene-1,2-diamine

2-phenyl-1H-benzoimidazole

Downstream raw materials:

2-Phenyl-1H-benzimidazol-6⁽⁵⁾-amine

N-(2-phenyl-1⁽³⁾H-benzoimidazol-5-yl)-benzamide

C₂₀H₁₄N₄O₃

C₂₀H₁₄ClN₃O

Refernces

• 1、 Lopez-Alvarado, Pilar,Avendano, Carmen,Menendez, J. Carlos. "New Synthetic Applications of Aryllead Triacetates. N-Arylation of Azoles". . p. 5678 - 5682. Retrieved 1995.
• 2、 Sofi, Firdoos Ahmad,Sharma, Rohit,Rawat, Ravi,Chakraborti, Asit K.,Bharatam, Prasad V.. "Visible light promoted tandem dehydrogenation-deaminative cyclocondensation under aerobic conditions for the synthesis of 2-aryl benzimidazoles/quinoxalines fromortho-phenylenediamines and arylmethyl/ethyl amines". supporting information. p. 4569 - 4573. Retrieved 2021/03/22.
• 3、 Geng, Zhenzhen,Zhang, Hong-Yu,Yin, Guohui,Zhang, Yuecheng,Zhao, Jiquan. "A one-pot synthesis of benzimidazoles via aerobic oxidative condensation of benzyl alcohols with o-phenylenediamines catalyzed by [MIMPs]+Cl-/NaNO2/TEMPO". . p. 557 - 565. Retrieved 2020/03/30.