4-Chloroquinoline-8-carbonitrile

Base Information

• Chemical Name: 4-Chloroquinoline-8-carbonitrile
• CAS No.: 132664-45-0
• Molecular Formula: C10H5ClN2
• Molecular Weight: 188.61300
• Hs Code.: 2933499090
• DSSTox Substance ID: DTXSID80564079
• Wikidata: Q82448661
• Mol file: 132664-45-0.mol

Synonyms:4-Chloroquinoline-8-carbonitrile;132664-45-0;4-CHLORO-8-CYANOQUINOLINE;4-Chloro-8-quinolinecarbonitrile;4-chloro-quinoline-8-carbonitrile;8-Quinolinecarbonitrile, 4-chloro-;8-cyano-4-chloroquinoline;SCHEMBL317372;DTXSID80564079;OXKQMBHOOISBLS-UHFFFAOYSA-N;MFCD08063206;ZB0134;AKOS006287639;SB68353;CS-0144183;F72153

Chemical Property of 4-Chloroquinoline-8-carbonitrile

Chemical Property:

• Melting Point: 210-211 °C(Solv: acetone (67-64-1))
• Boiling Point: 340.3±22.0 °C(Predicted)
• PKA: 0.34±0.30(Predicted)
• PSA: 36.68000
• Density: 1.36±0.1 g/cm3(Predicted)
• LogP: 2.75988
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• XLogP3: 2.7
• 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:

98%min ^*data from raw suppliers

4-Chloro-quinoline-8-carbonitrile- ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

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

Technology Process of 4-Chloroquinoline-8-carbonitrile

There total 6 articles about 4-Chloroquinoline-8-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: 82.0%

8-cyano-1,4-dihydro-4-oxoquinolone (127285-55-6) → 4-chloro-8-cyanoquinoline (132664-45-0)

Guidance literature:

With trichlorophosphate; for 1h; Heating;

DOI:10.1248/cpb.38.2919

Reference yield: 81.0%

4-hydroxy-8-cyanoquinoline (848128-91-6,127285-55-6) → 4-chloro-8-cyanoquinoline (132664-45-0)

Guidance literature:

With thionyl chloride; N,N-dimethyl-formamide; In dichloromethane; at 40 ℃; for 4h; Large scale;

DOI:10.1021/acs.oprd.0c00484

Reference yield:

2-{[(2,2-dimethyl-4,6-dioxo-1,3-dioxan-5-ylidene)methyl]amino}benzonitrile (1020252-22-5) → 4-chloro-8-cyanoquinoline (132664-45-0)

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:

8-cyano-1,4-dihydro-4-oxoquinolone

4-hydroxy-8-cyanoquinoline

2-{[(2,2-dimethyl-4,6-dioxo-1,3-dioxan-5-ylidene)methyl]amino}benzonitrile

8-cyano-1,4-dihydro-4-oxoquinolone-3-carboxylic acid

Downstream raw materials:

methyl 4-bromo-quinoline-8-carboxylate

3-(8-cyanoquinolin-4-ylamino)-4-(4-fluorophenyl)pyrrolidine-1-carboxylic acid tert-butyl ester

tert-butyl 3-{[8-(aminocarbonyl)quinolin-4-yl]amino}-4-(4-fluorophenyl)pyrrolidine-1-carboxylate

4-((4-(4-fluorophenyl)pyrrolidin-3-yl)amino)quinoline-8-carboxamide