2-Chloroquinoline-3-carbonyl chloride

Base Information

• Chemical Name: 2-Chloroquinoline-3-carbonyl chloride
• CAS No.: 136812-19-6
• Molecular Formula: C10H5Cl2NO
• Molecular Weight: 226.062
• DSSTox Substance ID: DTXSID00383305
• Wikidata: Q82174969
• Mol file: 136812-19-6.mol

Synonyms:2-chloroquinoline-3-carbonyl chloride;136812-19-6;2-chloro-3-quinolinecarbonyl chloride;2-Chloro-3-quinoline carbonyl chloride;2-CHLORO-3-QUINOLINECARBONYLCHLORIDE;SCHEMBL30025;DTXSID00383305;QZUMFCDPDBLWBV-UHFFFAOYSA-N;2-chloroquinoline-3-carbonylchloride;MFCD06200869;AS-31460;CS-0270738;FT-0729676;EN300-1459126;A905959

Chemical Property of 2-Chloroquinoline-3-carbonyl chloride

Chemical Property:

• Vapor Pressure: 5.56E-05mmHg at 25°C
• PSA: 29.96000
• LogP: 3.26720
• XLogP3: 3.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 224.9748192
• Heavy Atom Count: 14
• Complexity: 234

Purity/Quality:

98%min ^*data from raw suppliers

2-Chloro-3-quinolinecarbonylChloride ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: C1=CC=C2C(=C1)C=C(C(=N2)Cl)C(=O)Cl

Technology Process of 2-Chloroquinoline-3-carbonyl chloride

There total 5 articles about 2-Chloroquinoline-3-carbonyl chloride 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: 55.0%

2-chloro-3-quinoline carboxaldehyde (73568-25-9) → 2-chloroquinoline-3-carbonyl chloride (136812-19-6)

Guidance literature:

With chlorine; In various solvent(s); at 120 - 130 ℃; for 2h;

DOI:10.1080/00397919108021784

Reference yield:

2-chloro-3-quinolinecarboxylic acid (73776-25-7) → 2-chloroquinoline-3-carbonyl chloride (136812-19-6)

Guidance literature:

With thionyl chloride;

DOI:10.1002/ardp.19382760505

Reference yield:

2-Chloroquinoline (612-62-4) → 2-chloroquinoline-3-carbonyl chloride (136812-19-6)

Guidance literature:

Multi-step reaction with 2 steps

1.1: lithium diisopropylamide / tetrahydrofuran; hexane / 0.33 h

1.2: 65 percent / tetrahydrofuran; hexane

2.1: oxalyl chloride / dimethylformamide; CH₂Cl₂ / 2 h / 20 °C

With oxalyl dichloride; lithium diisopropyl amide; In tetrahydrofuran; hexane; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/j.tetasy.2004.11.004

upstream raw materials:

2-chloro-3-quinolinecarboxylic acid

2-chloro-3-quinoline carboxaldehyde

2-oxo-1,2-dihydro-quinoline-3-carboxylic acid

2-Chloroquinoline

Downstream raw materials:

methyl 4-(2-chloroquinoline-3-carboxamido)benzoate

C₂₄H₁₆F₂N₂O₄

4-(2-(2,4-difluorophenoxy)quinoline-3-carboxamido)benzoic acid

5-(2-(2-chloro-4-fluorophenoxy)quinoline-3-carboxamido)picolinic acid

Refernces

• 1、 Fuchs, Ferdinand C.,Eller, Gernot A.,Holzer, Wolfgang. "Heterocyclic analogs of thioflavones: Synthesis and NMR spectroscopic investigations". experimental part. p. 3814 - 3832. Retrieved 2010/03/03.
• 2、 Leleu, Stephane,Papamicael, Cyril,Marsais, Francis,Dupas, Georges,Levacher, Vincent. "Preparation of axially chiral quinolinium salts related to NAD+ models: New investigations of these biomimetic models as 'chiral amide-transferring agents'". . p. 3919 - 3928. Retrieved 2007/10/03.