6-Chloro-2,8-dimethylquinoline

Base Information

• Chemical Name: 6-Chloro-2,8-dimethylquinoline
• CAS No.: 948289-20-1
• Molecular Formula: C₁₁H₁₀ClN
• Molecular Weight: 191.66
• Hs Code.: 2933499090
• DSSTox Substance ID: DTXSID90589132
• Wikidata: Q82482299
• Mol file: 948289-20-1.mol

Synonyms:6-Chloro-2,8-dimethylquinoline;948289-20-1;DTXSID90589132;MFCD08274964;AKOS006280759;AB44505;AS-10932;DB-080035;A916259

Chemical Property of 6-Chloro-2,8-dimethylquinoline

Chemical Property:

• Vapor Pressure: 0.00232mmHg at 25°C
• Boiling Point: 297.9°C at 760 mmHg
• PKA: 5.05±0.50(Predicted)
• Flash Point: 162.1°C
• PSA: 12.89000
• Density: 1.188g/cm³
• LogP: 3.50500
• XLogP3: 3.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 191.0501770
• Heavy Atom Count: 13
• Complexity: 183

Purity/Quality:

98%min ^*data from raw suppliers

6-Chloro-2,8-dimethylquinoline ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=NC2=C(C=C1)C=C(C=C2C)Cl

Technology Process of 6-Chloro-2,8-dimethylquinoline

There total 4 articles about 6-Chloro-2,8-dimethylquinoline 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: 88.0%

4-Hydroxy-4-methyl-2-pentanone (123-42-2) + 2-amino-3-methyl-5-chlorobenzaldehyde (151446-29-6) → 6-chloro-2,8-dimethylquinoline (948289-20-1)

Guidance literature:

With chloro[1,3-bis(2,6-di-i-propylphenyl)imidazol-2-ylidene]copper(I); sodium t-butanolate; In toluene; at 70 ℃; chemoselective reaction; Inert atmosphere; Schlenk technique;

DOI:10.1039/c6ob01452f

Reference yield: 71.0%

ethyl vinyl ether (109-92-2,25104-37-4) + 4-chloro-2-methylbenzeneamine (95-69-2) → 6-chloro-2,8-dimethylquinoline (948289-20-1)

Guidance literature:

With 2,4,6-triphenylpyrylium tetrafluoroborate; In acetonitrile; at 20 ℃; for 16h; Irradiation;

DOI:10.1039/c9ob02259g

Reference yield:

(2-amino-5-chloro-3-methylphenyl)methanol (775331-65-2) → 6-chloro-2,8-dimethylquinoline (948289-20-1)

Guidance literature:

Multi-step reaction with 2 steps

1: manganese(IV) oxide / dichloromethane / Inert atmosphere

2: chloro[1,3-bis(2,6-di-i-propylphenyl)imidazol-2-ylidene]copper(I); sodium t-butanolate / toluene / 70 °C / Inert atmosphere; Schlenk technique

With manganese(IV) oxide; chloro[1,3-bis(2,6-di-i-propylphenyl)imidazol-2-ylidene]copper(I); sodium t-butanolate; In dichloromethane; toluene;

DOI:10.1039/c6ob01452f

upstream raw materials:

4-Hydroxy-4-methyl-2-pentanone

2-amino-3-methyl-5-chlorobenzaldehyde

(2-amino-5-chloro-3-methylphenyl)methanol

2-amino-5-chloro-3-methylbenzoic acid

Refernces

• 1、 Zhang, Song-Lin,Deng, Zhu-Qin. "Synthesis of quinolines and naphthyridines: Via catalytic retro-aldol reaction of β-hydroxyketones with ortho -aminobenzaldehydes or nicotinaldehydes". supporting information. p. 8966 - 8970. Retrieved 2016/10/05.