4-Chloro-1-(2-methylpropyl)-1H-imidazo[4,5-c]quinoline

Base Information

• Chemical Name: 4-Chloro-1-(2-methylpropyl)-1H-imidazo[4,5-c]quinoline
• CAS No.: 99010-64-7
• Molecular Formula: C14H14ClN3
• Molecular Weight: 259.738
• Hs Code.: 2934990002
• European Community (EC) Number: 619-386-2,939-507-5
• NSC Number: 672965
• UNII: NJ5E4GY4NY
• DSSTox Substance ID: DTXSID50327633
• Wikidata: Q72454728
• ChEMBL ID: CHEMBL192111
• Mol file: 99010-64-7.mol

Synonyms:99010-64-7;4-Chloro-1-(2-methylpropyl)-1H-imidazo[4,5-c]quinoline;4-Chloro-1-isobutyl-1H-imidazo[4,5-c]quinoline;4-chloro-1-(2-methylpropyl)imidazo[4,5-c]quinoline;Chlorodeaminoimiquimod;NSC672965;NJ5E4GY4NY;NSC-672965;4-chloro-1-(2-methylpropyl)-1h-imidazo(4,5-c)quinoline;4-chloro-1-isobutyl-imidazo[4,5-c]quinoline;4-chloro-1-isobutyl-1H-imidazo(4,5-c)quinoline;4-chloro-1-isobutyl-1H-imidazo [4,5-c]quinoline;1H-Imidazo(4,5-C)quinoline, 4-chloro-1-(2-methylpropyl)-;Trifloxysulfuronsodium;UNII-NJ5E4GY4NY;Chlorodeaminoimiquimod [USP];CHEMBL192111;SCHEMBL1774913;DTXSID50327633;AMY18247;MFCD06658174;AKOS015899334;AB25764;AC-26311;AS-16115;NCI60_025857;CHLORODEAMINOIMIQUIMOD [USP IMPURITY];CS-0154218;FT-0642385;4-chloro-1-isobutyl-1H-imidazo[4,5-c]-quinoline;A845944;4-chloro-1-isobuty-I-1H-imidazo[4,5-c]quinoline;1H-Imidazo[4,5-c]quinoline,4-chloro-1-(2-methylpropyl)-;4-Chloro-1-(2-methylpropyl)- 1H-imidazo[4,5-c]quinoline;4-chloro-1-(2-methylpropyl)-1H-imidazo[4,5-c]-quinoline;4-chloro-1-(2-methylpropyl)-1H-imidazo[4.5-c]-quinoline;4-chloro-l-(2-methylpropyl)-1H-imidazo[4,5-c]quinoline;4-chloro-1-(2-methylpropyl)-1H-imidazo [4,5-c]-quinoline;1-[2-METHYLPROPYL]-1H-2-CHLOROIMIDAZO-[4,5-C]QUINOLINE

Chemical Property of 4-Chloro-1-(2-methylpropyl)-1H-imidazo[4,5-c]quinoline

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 212.3oC
• Refractive Index: 1.804
• Boiling Point: 427.5 °C at 760 mmHg
• PKA: 3.15±0.30(Predicted)
• Flash Point: 212.3 °C
• PSA: 30.71000
• Density: 1.29 g/cm³
• LogP: 3.89390
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Solubility.: Chloroform (Sparingly), Methanol (Slightly)
• XLogP3: 3.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 259.0876252
• Heavy Atom Count: 18
• Complexity: 297

Purity/Quality:

99% ^*data from raw suppliers

Desamino Chloroimiquimod ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)CN1C=NC2=C1C3=CC=CC=C3N=C2Cl
• Uses: Desamino Chloroimiquimod (Imiquimod USP Related Compound C) is a pharmacologically active compound related to Imiquimod (I475000), an immune response modifier. It stimulates the production of Interferon-a.

Technology Process of 4-Chloro-1-(2-methylpropyl)-1H-imidazo[4,5-c]quinoline

There total 1 articles about 4-Chloro-1-(2-methylpropyl)-1H-imidazo[4,5-c]quinoline 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:

1-(2-methylpropyl)-1H-imidazo[4,5-c]quinoline (99010-24-9) → 4-Chloro-1-(2-methylpropyl)-1H-imidazo[4,5-c]quinoline (99010-64-7)

Guidance literature:

Multi-step reaction with 2 steps

1: peracetic acid / ethanol / 2.5 h / 60 °C

2: 49 percent / POCl₃ / CH₂Cl₂ / 0.25 h / Heating

With peracetic acid; trichlorophosphate; In ethanol; dichloromethane;

DOI:10.1021/jm049211v

Reference yield: 95.0%

4-Chloro-1-(2-methylpropyl)-1H-imidazo[4,5-c]quinoline (99010-64-7) + 5-(4-aminophenyl)-1,3,4-thiadiazole-2-thiol (664993-18-4) → 4-(5-((1-isobutyl-1H-imidazo[4,5-c]quinolin-4-yl)thio)-1,3,4-thiadiazol-2-yl)aniline

Guidance literature:

With triethylamine; In N,N-dimethyl-formamide; at 60 ℃; for 24h;

DOI:10.1016/j.bioorg.2020.104293

Reference yield: 92.0%

4-Chloro-1-(2-methylpropyl)-1H-imidazo[4,5-c]quinoline (99010-64-7) + 5-p-methylphenyl-2-mercapto-1,3,4-thiadiazole → 2-((1-isobutyl-1H-imidazo[4,5-c]quinolin-4-yl)thio)-5-(p-tolyl)-1,3,4-thiadiazole

Guidance literature:

With triethylamine; In N,N-dimethyl-formamide; at 60 ℃; for 24h;

DOI:10.1016/j.bioorg.2020.104293

upstream raw materials:

1-(2-methylpropyl)-1H-imidazo[4,5-c]quinoline

Downstream raw materials:

imiqimod

N-benzyl-1-isobutyl-1H-imidazo[4,5-c]quinolin-4-amine

1-isobutyl-1H-imidazo[4,5-c]quinolin-4-guanidine

2-[(1-isobutyl-1H-imidazo[4,5-c]quinolin-4-yl)amino]benzoic acid

Refernces