4-Hydroxy-8-cyanoquinoline

Base Information

• Chemical Name: 4-Hydroxy-8-cyanoquinoline
• CAS No.: 848128-91-6
• Molecular Formula: C₁₀H₆N₂O
• Molecular Weight: 170.17
• Hs Code.: 2933499090
• DSSTox Substance ID: DTXSID20564078
• Wikidata: Q72481746
• Mol file: 848128-91-6.mol

Synonyms:848128-91-6;4-HYDROXY-8-CYANOQUINOLINE;4-Hydroxyquinoline-8-carbonitrile;127285-55-6;4-Oxo-1,4-dihydro-quinoline-8-carbonitrile;4-OXO-1H-QUINOLINE-8-CARBONITRILE;4-Oxo-1,4-dihydroquinoline-8-carbonitrile;MFCD08063205;8-Quinolinecarbonitrile, 4-hydroxy-;CL1013;SCHEMBL2983782;DTXSID20564078;VFERFNFGHIWLEM-UHFFFAOYSA-N;AMY10095;CFA28555;YIB12891;AKOS006287638;SB67978;AC-23312;AS-45950;SY241160;CS-0137789;G10612;A917638;4-Hydroxyquinoline-8-carbonitrile pound 80%+ pound(c)

Chemical Property of 4-Hydroxy-8-cyanoquinoline

Chemical Property:

• Boiling Point: 402.7±25.0 °C(Predicted)
• PKA: 3.17±0.40(Predicted)
• PSA: 56.91000
• Density: 1.36
• LogP: 1.81208
• XLogP3: 1.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 170.048012819
• Heavy Atom Count: 13
• Complexity: 299

Purity/Quality:

99% ^*data from raw suppliers

4-Hydroxy-8-cyanoquinoline ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(=C2C(=C1)C(=O)C=CN2)C#N

Technology Process of 4-Hydroxy-8-cyanoquinoline

There total 1 articles about 4-Hydroxy-8-cyanoquinoline 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:

2-{[(2,2-dimethyl-4,6-dioxo-1,3-dioxan-5-ylidene)methyl]amino}benzonitrile (1020252-22-5) → 4-hydroxy-8-cyanoquinoline (848128-91-6,127285-55-6)

Guidance literature:

In diphenylether; at 300 ℃; for 0.0833333h; microwave irradiation;

DOI:10.1016/j.bmcl.2004.12.037

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:

4-hydroxy-8-cyanoquinoline (848128-91-6,127285-55-6) → N-{trans-4-[(8-cyanoquinolin-4-yl)oxy]cyclohexyl}-3-fluorobenzamide

Guidance literature:

Multi-step reaction with 4 steps

1.1: thionyl chloride; N,N-dimethyl-formamide / dichloromethane / 4 h / 40 °C / Large scale

2.1: 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; palladium diacetate; potassium phosphate / 1,4-dioxane / 10.5 h / 101 °C / Large scale

3.1: hydrogenchloride / methanol; 1,4-dioxane / 12.5 h / 20 °C / Large scale

4.1: triethylamine / dichloromethane / 15 °C / Large scale

4.2: 10 h / 15 - 20 °C / Large scale

With hydrogenchloride; potassium phosphate; thionyl chloride; palladium diacetate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; triethylamine; N,N-dimethyl-formamide; In 1,4-dioxane; methanol; dichloromethane;

DOI:10.1021/acs.oprd.0c00484

upstream raw materials:

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

Downstream raw materials:

4-chloro-8-cyanoquinoline

Refernces