2-(chloromethyl)-1-methyl-5-nitro-1H-1,3-benzodiazole

Base Information

• Chemical Name: 2-(chloromethyl)-1-methyl-5-nitro-1H-1,3-benzodiazole
• CAS No.: 20443-39-4
• Molecular Formula: C9H8ClN3O2
• Molecular Weight: 225.6317
• Hs Code.: 2933990090
• NSC Number: 167861
• DSSTox Substance ID: DTXSID70304865
• Wikidata: Q82051138
• ChEMBL ID: CHEMBL2287771
• Mol file: 20443-39-4.mol

Synonyms:20443-39-4;2-(chloromethyl)-1-methyl-5-nitro-1H-1,3-benzodiazole;2-(chloromethyl)-1-methyl-5-nitrobenzimidazole;2-(Chloromethyl)-1-methyl-5-nitro-1H-benzo[d]imidazole;2-(Chloromethyl)-1-methyl-5-nitro-1H-benzimidazole;NSC 167861;NSC167861;CHEMBL2287771;DTXSID70304865;MFCD01073119;AKOS015850541;NE-0724;NSC-167861;FT-0682840;J-506284

Chemical Property of 2-(chloromethyl)-1-methyl-5-nitro-1H-1,3-benzodiazole

Chemical Property:

• Vapor Pressure: 9.34E-07mmHg at 25°C
• Melting Point: 191-192 °C(Solv: ethanol (64-17-5))
• Boiling Point: 416.3°Cat760mmHg
• PKA: 2.80±0.10(Predicted)
• Flash Point: 205.6°C
• PSA: 63.64000
• Density: 1.5g/cm³
• LogP: 2.74350
• XLogP3: 1.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 225.0305042
• Heavy Atom Count: 15
• Complexity: 258

Purity/Quality:

98%min ^*data from raw suppliers

2-(Chloromethyl)-1-methyl-5-nitro-1H-1,3-benzodiazole >95% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CN1C2=C(C=C(C=C2)[N+](=O)[O-])N=C1CCl

Technology Process of 2-(chloromethyl)-1-methyl-5-nitro-1H-1,3-benzodiazole

There total 3 articles about 2-(chloromethyl)-1-methyl-5-nitro-1H-1,3-benzodiazole 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: 71.0%

chloroacetic acid (79-11-8) + N1-methyl-4-nitrobenzene-1,2-diamine (41939-61-1) → 2-(chloromethyl)-1-methyl-5-nitro-1H-benzo[d]imidazole (20443-39-4)

Guidance literature:

With hydrogenchloride; In water; for 4h; Reflux;

DOI:10.1021/jf3053934

Reference yield: 68.5%

chloroacetyl chloride (79-04-9) + N1-methyl-4-nitrobenzene-1,2-diamine (41939-61-1) → 2-(chloromethyl)-1-methyl-5-nitro-1H-benzo[d]imidazole (20443-39-4)

Guidance literature:

chloroacetyl chloride; N₁-methyl-4-nitrobenzene-1,2-diamine; With triethylamine; In ethyl acetate; at 0 - 20 ℃; for 0.5h;

With acetic acid; In ethyl acetate; for 20h; Reflux;

DOI:10.1016/j.ejmech.2017.08.031

Reference yield:

→ 2-(chloromethyl)-1-methyl-5-nitro-1H-benzo[d]imidazole (20443-39-4)

Guidance literature:

4-Nitro-2-amino-N-methylanilin, Chloressigsaeure;

DOI:10.1007/BF00469869

upstream raw materials:

chloroacetic acid

N₁-methyl-4-nitrobenzene-1,2-diamine

chloroacetyl chloride

Downstream raw materials:

1-(4-((1-methyl-5-nitro-1H-benzo[d]imidazol-2-yl)methoxy)-phenyl)ethanone

propyl 4-((1-methyl-5-nitro-1H-benzo[d]imidazol-2-yl)methoxy)benzoate

2-((4-fluorophenoxy)methyl)-1-methyl-5-nitro-1H-benzo[d]imidazole

2-((4-chlorophenoxy)methyl)-1-methyl-5-nitro-1H-benzo[d]imidazole

Refernces

• 1、 Bai, Yu-Bin,Zhang, An-Ling,Tang, Jiang-Jiang,Gao, Jin-Ming. "Synthesis and antifungal activity of 2-chloromethyl-1 H -benzimidazole derivatives against phytopathogenic fungi in vitro". . p. 2789 - 2795. Retrieved 2013/06/04.