2-(CHLOROMETHYL)-3-NITROIMIDAZO[1,2-A]PYRIDINE

Base Information

• Chemical Name: 2-(CHLOROMETHYL)-3-NITROIMIDAZO[1,2-A]PYRIDINE
• CAS No.: 129179-30-2
• Molecular Formula: C8H6ClN3O2
• Molecular Weight: 211.608
• Hs Code.: 2933998090
• Mol file: 129179-30-2.mol

Synonyms:

Chemical Property of 2-(CHLOROMETHYL)-3-NITROIMIDAZO[1,2-A]PYRIDINE

Chemical Property:

• PSA: 63.12000
• LogP: 2.50450

Purity/Quality:

99% ^*data from raw suppliers

2-(chloromethyl)-3-nitroimidazo[1,2-a]pyridine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-(CHLOROMETHYL)-3-NITROIMIDAZO[1,2-A]PYRIDINE

There total 2 articles about 2-(CHLOROMETHYL)-3-NITROIMIDAZO[1,2-A]PYRIDINE 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: 80.0%

2-chloromethylimidazo[1,2-a]pyridine (57892-76-9) → 2-(chloromethyl)-3-nitro-1H-imdiazo[1,2-a]pyridine (129179-30-2)

Guidance literature:

With sulfuric acid; nitric acid; at 20 ℃;

DOI:10.1016/j.bmc.2013.09.002

Reference yield:

2-aminopyridine (504-29-0) → 2-(chloromethyl)-3-nitro-1H-imdiazo[1,2-a]pyridine (129179-30-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 66 percent / 1,2-dimethoxy-ethane / 2 h / 20 °C

2: 76 percent / conc. H₂SO₄, HNO₃ (d=1.38) / 2 h / 20 °C

With sulfuric acid; nitric acid; In 1,2-dimethoxyethane;

DOI:10.1016/S0040-4020(01)87129-5

Reference yield: 60.0%

2-(chloromethyl)-3-nitro-1H-imdiazo[1,2-a]pyridine (129179-30-2) + benzenesulfonyl chloride (98-09-9) → 3-nitro-2-phenylsulfonylmethylimidazo[1,2-a]pyridine

Guidance literature:

With sodium hydrogencarbonate; sodium sulfite; In water; at 120 ℃; for 1h; under 3750.38 Torr; Microwave irradiation; Sealed tube;

DOI:10.1016/j.bmc.2013.09.002

upstream raw materials:

2-chloromethylimidazo[1,2-a]pyridine

2-aminopyridine

Downstream raw materials:

E-2-(2-phenyl cyclopentylidenemethyl) 3-nitroimidazo<1,2-a>pyridine

E-2-(2-phenyl propen-1-yl) 3-nitroimidazo<1,2-a>pyridine

2-cyclohexylidenemethyl 3-nitroimidazo<1,2-a>pyridine

Refernces

Synthesis by the S(RN)1 reaction of a new series of imidazo[1,2-a]pyridine derivatives with pharmacological potentialities

10.1016/S0040-4020(01)87129-5

The study investigates the SRN1 reaction between 2-chloromethyl-3-nitroimidazo[1,2-a]pyridine and various nitronate anions, including those from aliphatic, cyclic, and heterocyclic nitroalkanes, to synthesize new potential pharmacological derivatives. The reaction involves the C-alkylation of 2-chloromethyl-3-nitroimidazo[1,2-a]pyridine by nitronate anions, followed by base-promoted nitrous acid elimination to form products with a trisubstituted double bond at the 2-position. Key chemicals include 2-chloromethyl-3-nitroimidazo[1,2-a]pyridine as the starting material, various nitroalkanes (e.g., 2-nitropropane, nitrocyclopentane) as sources of nitronate anions, and tetrabutylammonium hydroxide as a phase-transfer catalyst. The synthesized compounds are being evaluated for their potential pharmacological properties, particularly their affinity for specific receptors related to anxiolytic and hypnotic effects.