1-isobutyl-1H-imidazo[4,5-c]quinoline-5-oxide

Base Information

• Chemical Name: 1-isobutyl-1H-imidazo[4,5-c]quinoline-5-oxide
• CAS No.: 99010-63-6
• Molecular Formula: C14H15N3O
• Molecular Weight: 241.293
• Hs Code.: 2934990002
• European Community (EC) Number: 695-357-8
• UNII: HRF2WX8EPT
• DSSTox Substance ID: DTXSID70474153
• Wikidata: Q82303970
• Mol file: 99010-63-6.mol

Synonyms:99010-63-6;1-isobutyl-1H-imidazo[4,5-c]quinoline-5-oxide;Desamino Imiquimod N-Oxide;1-(2-methylpropyl)-5-oxidoimidazo[4,5-c]quinolin-5-ium;HRF2WX8EPT;1-Isobutyl-1H-imidazo(4,5-C)quinoline N-oxide;1-(2-Methylpropyl)-5-oxidoimidazo(4,5-C)quinolin-5-ium;1-(2-methylpropyl)-1H-imidazo[4,5-c]quinolin-5-ium-5-olate;1H-Imidazo(4,5-C)quinoline, 1-(2-methylpropyl)-, 5-oxide;1-Isobutyl-1H-imidazo[4,5-c]quinoline 5-Oxide (Desaminoimiquimod N-Oxide);1-Isobutyl-1H-imidazo[4,5-c]quinoline 5-oxide;Imiquimod Related Compound B;UNII-HRF2WX8EPT;SCHEMBL3192664;1-(2-methylpropyl)-1h-imidazo[4,5-c]quinoline 5-oxide;DTXSID70474153;RBKTVDLDAPUNMV-UHFFFAOYSA-N;ZDA01063;AC-31040;CS-0154219;1-isobutyl-1H-imidazo[4,5-c]quinolin-5-oxide;1-isobutyl-1H-imidazo [4,5-c]quinolin-5-oxide

Chemical Property of 1-isobutyl-1H-imidazo[4,5-c]quinoline-5-oxide

Chemical Property:

• Melting Point: 211-214℃ (methanol ethyl ether )
• Boiling Point: 452.8±55.0 °C(Predicted)
• PKA: 4.16±0.30(Predicted)
• PSA: 43.28000
• Density: 1.24±0.1 g/cm3(Predicted)
• LogP: 3.27400
• Storage Temp.: -20°C Freezer, Under inert atmosphere
• Solubility.: Chloroform (Slightly), Methanol (Slightly)
• XLogP3: 2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 241.121512110
• Heavy Atom Count: 18
• Complexity: 297

Purity/Quality:

98% or more ^*data from raw suppliers

DesaminoImiquimodN-Oxide ^*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=C3[N+](=C2)[O-]
• Uses: Desamino Imiquimod N-Oxide (Imiquimod USP Related Compound B) is a pharmacologically active compound related to Imiquimod (I475000), an immune response modifier. It stimulates the production of Interferon-a.

Technology Process of 1-isobutyl-1H-imidazo[4,5-c]quinoline-5-oxide

There total 8 articles about 1-isobutyl-1H-imidazo[4,5-c]quinoline-5-oxide 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: 79.0%

1-isobutyl-1H-imidazo[4,5-c]quinolin-5-ium chloride → 1-(2-methylpropyl)-1H-imidazo[4,5-c]quinoline 5N-oxide (99010-63-6)

Guidance literature:

1-isobutyl-1H-imidazo[4,5-c]quinolin-5-ium chloride; With sodium hydrogencarbonate; In dichloromethane; water;

With peracetic acid; In dichloromethane; water;

Reference yield:

1-(2-methylpropyl)-1H-imidazo[4,5-c]quinoline (99010-24-9) → 1-(2-methylpropyl)-1H-imidazo[4,5-c]quinoline 5N-oxide (99010-63-6)

Guidance literature:

With peracetic acid; In ethanol; at 60 ℃; for 2.5h;

DOI:10.1021/jm049211v

Reference yield:

3-Amino-4-(2-methylpropylamino)-quinoline (99010-09-0) + orthoformic acid triethyl ester (122-51-0) → 1-(2-methylpropyl)-1H-imidazo[4,5-c]quinoline 5N-oxide (99010-63-6)

Guidance literature:

With dihydrogen peroxide; sodium hydrogencarbonate; In n-heptane; acetic acid;

upstream raw materials:

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

3-Amino-4-(2-methylpropylamino)-quinoline

N-(2-methylpropyl)-3-nitro-4-quinolinamine

quinolin-4-ol

Downstream raw materials:

imiqimod

N-benzoyl-1-(2-methylpropyl)-1H-imidazo[4,5-c]quinolin-4-amine

Refernces

• 1、 -. "Process for the preparation of imidazo[4,5-c]-quinolin-4-amines". Page/Page column 3. . Retrieved 2008/06/13.
• 2、 Gerster, John F.,Lindstrom, Kyle J.,Miller, Richard L.,Tomai, Mark A.,Birmachu, Woubalem,Bomersine, Shannon N.,Gibson, Shiela J.,Imbertson, Linda M.,Jacobson, Joel R.,Knafla, Roy T.,Maye, Peter V.,Nikolaides, Nickolas,Oneyemi, Folakemi Y.,Parkhurst, Gwen J.,Pecore, Sharon E.,Reiter, Michael J.,Scribner, Lisa S.,Testerman, Tracy L.,Thompson, Natalie J.,Wagner, Tammy L.,Weeks, Charles E.,Andre, Jean-Denis,Lagain, Daniel,Bastard, Yvon,Lupu, Michel. "Synthesis and structure - Activity-relationships of 1H-imidazo[4,5-c] quinolines that induce interferon production". . p. 3481 - 3491. Retrieved 2007/10/03.