1-(3-Chloro-2-hydroxypropyl)-2-methyl-4-nitroimidazole

Base Information

• Chemical Name: 1-(3-Chloro-2-hydroxypropyl)-2-methyl-4-nitroimidazole
• CAS No.: 14419-11-5
• Molecular Formula: C7H10 Cl N3 O3
• Molecular Weight: 219.628
• DSSTox Substance ID: DTXSID30932264
• Mol file: 14419-11-5.mol

Synonyms:14419-11-5;1-(3-Chloro-2-hydroxypropyl)-2-methyl-4-nitroimidazole;Ornidazole Isomer (Impurity);BRN 0616417;1-chloro-3-(2-methyl-4-nitroimidazol-1-yl)propan-2-ol;1-chloro-3-(2-methyl-4-nitro-1H-imidazol-1-yl)propan-2-ol;alpha-(Chloromethyl)-2-methyl-4-nitro-1H-imidazole-1-ethanol;1H-Imidazole-1-ethanol, alpha-(chloromethyl)-2-methyl-4-nitro-;Ornidazole Impurity D;SCHEMBL11418348;DTXSID30932264;BCP33789;LS-78599

Chemical Property of 1-(3-Chloro-2-hydroxypropyl)-2-methyl-4-nitroimidazole

Chemical Property:

• Vapor Pressure: 1.23E-08mmHg at 25°C
• Melting Point: 151-153 °C
• Boiling Point: 443.2°Cat760mmHg
• PKA: 13.29±0.20(Predicted)
• Flash Point: 221.9°C
• PSA: 83.87000
• Density: 1.53g/cm³
• LogP: 1.22260
• Storage Temp.: Amber Vial, -20°C Freezer, Under inert atmosphere
• Solubility.: DMSO (Slightly), Methanol (Slightly)
• XLogP3: 0.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 219.0410689
• Heavy Atom Count: 14
• Complexity: 211

Purity/Quality:

99% ^*data from raw suppliers

OrnidazoleIsomer(Impurity) ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=NC(=CN1CC(CCl)O)[N+](=O)[O-]
• Uses: An isomeric impurity of Ornidazole, which maintains anti-infective properties. An isomeric impurity of Ornidazole (0688500), which maintains anti-infective properties.

Technology Process of 1-(3-Chloro-2-hydroxypropyl)-2-methyl-4-nitroimidazole

There total 3 articles about 1-(3-Chloro-2-hydroxypropyl)-2-methyl-4-nitroimidazole 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: 60.0%

2-methyl-4-nitro-1H-imidazole (696-23-1) + epichlorohydrin (106-89-8,24969-06-0,13403-37-7) → (±)-1-chloro-3-(2-methyl-4-nitro-1H-imidazol-1-yl)propan-2-ol (14419-11-5)

Guidance literature:

With potassium carbonate;

DOI:10.1016/S0957-4166(97)00260-7

Reference yield: 60.0%

2-methyl-5-nitro-1H-imidazole (696-23-1,88054-22-2) + epichlorohydrin (106-89-8,24969-06-0,13403-37-7) → (±)-1-chloro-3-(2-methyl-4-nitro-1H-imidazol-1-yl)propan-2-ol (14419-11-5)

Guidance literature:

With potassium carbonate; at 110 - 115 ℃; for 0.25h;

DOI:10.1016/j.ejmech.2016.09.006

Reference yield:

→ (±)-1-chloro-3-(2-methyl-4-nitro-1H-imidazol-1-yl)propan-2-ol (14419-11-5)

Guidance literature:

2-Methyl-4(5)-nitro-imidazol, Epichlorhydrin: Enwarmen unter Zusatz von wasserfreim K2CO3 bei 100gradC (S.531);

upstream raw materials:

2-methyl-4-nitro-1H-imidazole

epichlorohydrin

2-methyl-5-nitro-1H-imidazole

Downstream raw materials:

2-methyl-4-nitro-1-(oxiran-2-ylmethyl)-1H-imidazole

Benzo[1,3]dioxole-5-carbaldehyde O-[2-hydroxy-3-(2-methyl-4-nitro-imidazol-1-yl)-propyl]-oxime

2-Nitro-benzaldehyde O-[2-hydroxy-3-(2-methyl-4-nitro-imidazol-1-yl)-propyl]-oxime

4-Nitro-benzaldehyde O-[2-hydroxy-3-(2-methyl-4-nitro-imidazol-1-yl)-propyl]-oxime

Refernces

• 1、 Mandalapu, Dhanaraju,Kushwaha, Bhavana,Gupta, Sonal,Singh, Nidhi,Shukla, Mahendra,Kumar, Jitendra,Tanpula, Dilip K.,Sankhwar, Satya N.,Maikhuri, Jagdamba P.,Siddiqi, Mohammad I.,Lal, Jawahar,Gupta, Gopal,Sharma, Vishnu L.. "2-Methyl-4/5-nitroimidazole derivatives potentiated against sexually transmitted Trichomonas: Design, synthesis, biology and 3D-QSAR study". . p. 820 - 839. Retrieved 2016.
• 2、 Suwinski,Salwinska,Watras,Widel. "Synthesis and some physico-chemical properties of 1-(2-hydroxy-3-alkoxypropyl)-4-nitroimidazoles". . p. 529 - 535. Retrieved 2007/10/05.