4-Chloroquinoline-6-carbonitrile

Base Information

• Chemical Name: 4-Chloroquinoline-6-carbonitrile
• CAS No.: 219763-83-4
• Molecular Formula: C10H5ClN2
• Molecular Weight: 188.616
• Hs Code.: 2933499090
• DSSTox Substance ID: DTXSID90608059
• Wikidata: Q72459288
• Mol file: 219763-83-4.mol

Synonyms:4-chloroquinoline-6-carbonitrile;219763-83-4;4-CHLORO-6-CYANOQUINOLINE;4-CHLORO-QUINOLINE-6-CARBONITRILE;4-Chloro-6-quinolinecarbonitrile;SCHEMBL730084;DTXSID90608059;FLRGXIDFVYOCLP-UHFFFAOYSA-N;MFCD08063204;AKOS006287637;SB15640;AS-50545;DB-066669;A4714;CS-0054421;P10548

Chemical Property of 4-Chloroquinoline-6-carbonitrile

Chemical Property:

• Boiling Point: 340.299 °C at 760 mmHg
• Flash Point: 159.608 °C
• PSA: 36.68000
• Density: 1.363 g/cm³
• LogP: 2.75988
• Storage Temp.: Sealed in dry,Store in freezer, under -20°C
• XLogP3: 2.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 188.0141259
• Heavy Atom Count: 13
• Complexity: 232

Purity/Quality:

97% ^*data from raw suppliers

4-Chloroquinoline-6-carbonitrile ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: C1=CC2=NC=CC(=C2C=C1C#N)Cl

Technology Process of 4-Chloroquinoline-6-carbonitrile

There total 4 articles about 4-Chloroquinoline-6-carbonitrile 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: 50.0%

4-Hydroxy-6-quinolinecarbonitrile (642477-81-4,219763-82-3) → 4-chloroquinoline-6-carbonitrile (219763-83-4)

Guidance literature:

With trichlorophosphate; In 1,4-dioxane; at 90 ℃; for 1.5h;

Reference yield:

zinc(II) cyanide (557-21-1) + 4-chloro-6-iodo-quinoline (40107-07-1) → 4-chloroquinoline-6-carbonitrile (219763-83-4)

Guidance literature:

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; In N,N-dimethyl-formamide; at 50 ℃; for 17h; Inert atmosphere; Sealed tube;

Reference yield:

4-[(2,2-dimethyl-4,6-dioxo-[1,3]dioxan-5-ylidenemethyl)-amino]-benzonitrile (219763-81-2) → 4-chloroquinoline-6-carbonitrile (219763-83-4)

Guidance literature:

Multi-step reaction with 2 steps

1: diphenyl ether / 0.08 h / 300 °C / microwave irradiation

2: POCl₃ / 3 h / Heating

With trichlorophosphate; In diphenylether;

DOI:10.1016/j.bmcl.2004.12.037

upstream raw materials:

4-Hydroxy-6-quinolinecarbonitrile

4-[(2,2-dimethyl-4,6-dioxo-[1,3]dioxan-5-ylidenemethyl)-amino]-benzonitrile

zinc(II) cyanide

4-chloro-6-iodo-quinoline

Downstream raw materials:

4-bromoquinoline-6-carboxylic acid methyl ester

4-bromoquinoline-6-carboxylic acid

Refernces

• 1、 -. "QUINOLINE-BASED COMPOUNDS AND METHODS OF INHIBITING CDK8/19". Paragraph 0108; 0117-0118. . Retrieved 2020/03/09.
• 2、 -. "Aurora Kinase Modulators and Method of Use". Paragraph 0505. . Retrieved 2014/11/27.