4-(5-Nitro-1H-benzo[d]imidazol-2-yl)thiazole

Base Information

• Chemical Name: 4-(5-Nitro-1H-benzo[d]imidazol-2-yl)thiazole
• CAS No.: 3575-05-1
• Molecular Formula: C10H6N4O2S
• Molecular Weight: 246.24500
• Hs Code.: 2934999090
• ChEMBL ID: CHEMBL370771
• DSSTox Substance ID: DTXSID90468559
• Wikidata: Q82295812
• Mol file: 3575-05-1.mol

Synonyms:3575-05-1;4-(5-Nitro-1H-benzo[d]imidazol-2-yl)thiazole;6-Nitro-2-(4-thiazolyl)-1H-benzimidazole;CHEMBL370771;4-(6-nitro-1H-benzimidazol-2-yl)-1,3-thiazole;5-nitro-2-(1,3-thiazol-4-yl)-1H-1,3-benzodiazole;5-nitro-2-(1,3-thiazol-4-yl)-1H-benzimidazole;6-Nitro-2-(1,3-thiazol-4-yl)-1H-benzimidazole;DTXSID90468559;BDBM50180736;MFCD09971573;AKOS009222604;AKOS032947671;FT-0743631;EN300-31868;5-nitro-2-(4-thiazolyl)-1h-benzo[d]imidazole;5-nitro-2-thiazol-4-yl-1(3)H-benzoimidazole;I11712;Z335575046

Chemical Property of 4-(5-Nitro-1H-benzo[d]imidazol-2-yl)thiazole

Chemical Property:

• Melting Point: 247-249 °C
• Boiling Point: 537.8±48.0 °C(Predicted)
• PKA: 8.76±0.10(Predicted)
• PSA: 115.63000
• Density: 1.589±0.06 g/cm3(Predicted)
• LogP: 3.11780
• XLogP3: 2.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 1
• Exact Mass: 246.02114662
• Heavy Atom Count: 17
• Complexity: 311

Purity/Quality:

99%min ^*data from raw suppliers

6-Nitro-2-(4-thiazolyl)-1H-benzimidazole ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC2=C(C=C1[N+](=O)[O-])NC(=N2)C3=CSC=N3
• Uses: 6-Nitro-2-(4-thiazolyl)-1H-benzimidazole is used in the preparation of methionine aminopeptidase inhibitors.

Technology Process of 4-(5-Nitro-1H-benzo[d]imidazol-2-yl)thiazole

There total 5 articles about 4-(5-Nitro-1H-benzo[d]imidazol-2-yl)thiazole 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: 62.0%

1,3-thiazole-4-carbaldehyde (3364-80-5) + 4-Nitrophenylene-1,2-diamine (99-56-9) → 4-(6-nitro-1H-benzo[d]imidazol-2-yl)thiazole (3575-05-1)

Guidance literature:

With sodium metabisulfite; In N,N-dimethyl-formamide; at 120 ℃;

DOI:10.1016/j.bmc.2015.03.085

Reference yield: 55.0%

thiabendazole (148-79-8,98002-42-7) → 5-nitro-2-thiazol-4-yl-1(3)H-benzoimidazole (3575-05-1)

Guidance literature:

With sulfuric acid; nitric acid; at 20 ℃; for 2h;

DOI:10.1021/jm050476z

Reference yield:

1,3-thiazole-4-carbaldehyde (3364-80-5) + 4-Nitrophenylene-1,2-diamine (99-56-9) → 5-nitro-2-thiazol-4-yl-1(3)H-benzoimidazole (3575-05-1)

Guidance literature:

With sodium metabisulfite; In N,N-dimethyl-formamide; at 120 ℃;

DOI:10.3390/molecules22020213

upstream raw materials:

thiabendazole

1,3-thiazole-4-carbaldehyde

4-Nitrophenylene-1,2-diamine

Downstream raw materials:

5-aminothiabendazole

Refernces

• 1、 Zhang, Chao,Zhong, Bo,Yang, Simin,Pan, Liangkun,Yu, Siwang,Li, Zhongjun,Li, Shuchun,Su, Bin,Meng, Xiangbao. "Synthesis and biological evaluation of thiabendazole derivatives as anti-angiogenesis and vascular disrupting agents". supporting information. p. 3774 - 3780. Retrieved 2015/08/03.
• 2、 Hoff,Fisher,Bochis,Lusi,Waksmunski,Egerton,Yakstis,Cuckler,Campbell. "A new broad-spectrum anthelmintic: 2-(4-thiazolyl)-5-isopropoxycarbonylamino-benzimidazole.". . p. 550 - 551. Retrieved 2007/10/05.