3-methyl-3H-imidazo[4,5-f]quinolin-2-amine

Base Information

• Chemical Name: 3-methyl-3H-imidazo[4,5-f]quinolin-2-amine
• CAS No.: 76180-96-6
• Molecular Formula: C11H10N4
• Molecular Weight: 198.227
• Hs Code.: 29334900
• European Community (EC) Number: 689-809-3
• UNII: 30GL3D3T0G
• DSSTox Substance ID: DTXSID4020745
• Nikkaji Number: J45.287D
• Wikidata: Q27120486
• NCI Thesaurus Code: C44309
• Metabolomics Workbench ID: 43996
• ChEMBL ID: CHEMBL1233049
• Mol file: 76180-96-6.mol

Synonyms:2-amino-3-methyl-3H-imidazo(4,5-f)quinoline;2-amino-MIQ

Chemical Property of 3-methyl-3H-imidazo[4,5-f]quinolin-2-amine

Chemical Property:

• Appearance/Colour: light tan crystalline solid or tan powder
• Vapor Pressure: 1.34E-08mmHg at 25°C
• Melting Point: >300 °C
• Refractive Index: 1.4260 (estimate)
• Boiling Point: 458.7 °C at 760 mmHg
• Flash Point: 231.2 °C
• PSA: 56.73000
• Density: 1.41 g/cm³
• LogP: 2.28490
• Storage Temp.: Refrigerator
• Solubility.: DMSO (Slightly, Heated), Methanol (Slightly)
• XLogP3: 1.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 198.090546336
• Heavy Atom Count: 15
• Complexity: 245

Purity/Quality:

98%Min ^*data from raw suppliers

2-Amino-3-methyl-3H-imidazo[4,5-f]quinoline ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T
• Hazard Codes: T

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Nitrogen Compounds -> Quinolines
• Canonical SMILES: CN1C2=C(C3=C(C=C2)N=CC=C3)N=C1N
• Uses: IQ is highly mutagenic in the Ames test. Investigations have shown that this compound may be present in broiled fish, fried beef, commercial beef extracts and protein pyrolysates

Technology Process of 3-methyl-3H-imidazo[4,5-f]quinolin-2-amine

There total 31 articles about 3-methyl-3H-imidazo[4,5-f]quinolin-2-amine 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: 42.0%

bromocyane (506-68-3) + N6-Methyl-isoquinoline-5,6-diamine → 2-amino-3-methyl-3H-imidazo<4,5-f>isoquinoline (76180-96-6,147293-15-0)

Guidance literature:

In acetonitrile;

Reference yield:

N,N-dimethyl-formamide dimethyl acetal (4637-24-5) + imidazo<4,5-f>quinoline-2(3H)-thione (107002-97-1) → 2-Amino-3-methylimidazo[4,5-f]quinoline (76180-96-6) + 2-amino-1-methylimidazo[4,5-f]-quinoline (102408-25-3)

Guidance literature:

With potassium permanganate; ammonia; sodium; iron(III) chloride; Yield given. Multistep reaction. Yields of byproduct given; 1.) toluene, reflux, 5 h, 2.) acetic acid, 25 deg C, 1.5 h, 3.) reflux, 8 h;

Reference yield:

6-methoxyisoquinoline (52986-70-6) → 2-amino-3-methyl-3H-imidazo<4,5-f>isoquinoline (76180-96-6,147293-15-0)

Guidance literature:

Multi-step reaction with 4 steps

1: 75 percent / KNO₃, H₂SO₄ / 24 h / 20 °C

2: 85 percent / H₂O

3: H₂ / Ni

4: 42 percent / acetonitrile

With sulfuric acid; hydrogen; potassium nitrate; nickel; In water; acetonitrile;

upstream raw materials:

tetramethyl ammoniumhydroxide

2-amino-3H-imidazo<4,5-f>quinoline

bromocyane

5-amino-6-methylaminoquinoline

Downstream raw materials:

O⁶-benzyl-8-[(3-methyl-3H-imidazo[4,5-f]quinolin-2-yl)amino]-N9-[3',5'-O-(1,1,3,3-tetrakis(isopropyl)-1,3-disiloxanediyl)-β-D-2'-deoxyribofuranosyl]guanine

6-benzyloxy-N²-[bis-(4-methoxy-phenyl)-phenyl-methyl]-9-[4-(tert-butyl-dimethyl-silanyloxy)-5-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-furan-2-yl]-N⁸-(3-methyl-3H-imidazo[4,5-f]quinolin-2-yl)-9H-purine-2,8-diamine

N-[3-(3-Methyl-3H-imidazo[4,5-f]quinolin-2-ylamino)-propyl]-4-nitro-benzamide

4-Amino-N-[3-(3-methyl-3H-imidazo[4,5-f]quinolin-2-ylamino)-propyl]-benzamide

Refernces

• 1、 Yoshida,Saito,Mizusaki. "Isolation of 2-amino-3-methyl-imidazo-[4,5-f]quinoline as mutagen from the heated product of a mixture of creatine and proline". . p. 241 - 243. Retrieved 1984.
• 2、 Ronne, Erik,Grivas, Spiros,Olsson, Kjell. "Synthetic Routes to the Carcinogen IQ and Related 3H-Imidazoquinolines". . p. 823 - 830. Retrieved 2007/10/02.