Quinoline-4-carbonitrile

Base Information

• Chemical Name: Quinoline-4-carbonitrile
• CAS No.: 2973-27-5
• Molecular Formula: C10H6N2
• Molecular Weight: 154.171
• Hs Code.: 2933499090
• European Community (EC) Number: 689-987-2
• NSC Number: 113049
• DSSTox Substance ID: DTXSID70296998
• Nikkaji Number: J805.481I
• Wikidata: Q72505840
• Mol file: 2973-27-5.mol

Synonyms:quinoline-4-carbonitrile;4-cyanoquinoline;2973-27-5;4-Quinolinecarbonitrile;MFCD00972111;Cinchoninonitrile;NSC113049;N-M-TOLYLPHTHALAMICACID;SCHEMBL828123;DTXSID70296998;AMY16014;BBL103914;STL557724;AKOS005257007;NSC-113049;SB36445;AC-28312;DS-13338;CS-0044994;FT-0660320;A18591;EN300-170895;J-524191;Z1165164711

Chemical Property of Quinoline-4-carbonitrile

Chemical Property:

• Appearance/Colour: White to off-white microcrystalline solid
• Vapor Pressure: 0.0325mmHg at 25°C
• Melting Point: 103-104oC
• Refractive Index: 1.654
• Boiling Point: 243.2 °C at 760 mmHg
• PKA: 1.55±0.13(Predicted)
• Flash Point: 95.2 °C
• PSA: 36.68000
• Density: 1.21 g/cm³
• LogP: 2.10648
• Storage Temp.: Sealed in dry,Room Temperature
• XLogP3: 2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 154.053098200
• Heavy Atom Count: 12
• Complexity: 203

Purity/Quality:

98%,99%, ^*data from raw suppliers

4-Cyanoquinoline 97% ^*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)C#N

Technology Process of Quinoline-4-carbonitrile

There total 3 articles about Quinoline-4-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: 66.0%

quinoline (91-22-5) + trimethylsilyl cyanide (7677-24-9) → quinoline-2-carbonitrile (1436-43-7) + quinoline-4-carbonitrile (2973-27-5)

Guidance literature:

quinoline; With trifluoromethylsulfonic anhydride; In chloroform; at 20 ℃; for 1h; Inert atmosphere; Sealed tube;

trimethylsilyl cyanide; In chloroform; at 60 ℃; for 3h; Inert atmosphere; Sealed tube;

With 4-methyl-morpholine; In chloroform; at 60 ℃; for 17h; Overall yield = 85 %; Inert atmosphere; Sealed tube;

DOI:10.1002/chem.201703931

Reference yield:

Quinoline N-oxide (1613-37-2) → quinoline-4-carbonitrile (2973-27-5) + quinoline-2-carboxylic acid (93-10-7,1199266-78-8)

Guidance literature:

With dimethyl sulfate; Behandeln des Reaktionsprodukts mit KCN in wss. Dioxan;

Reference yield:

1-methyl-4-cyano-quinolinium iodide (64275-22-5) → quinoline-4-carbonitrile (2973-27-5) + methyl iodide (74-88-4)

Guidance literature:

bei der trocknen Destillation;

upstream raw materials:

Quinoline N-oxide

1-methyl-4-cyano-quinolinium iodide

quinoline

trimethylsilyl cyanide

Downstream raw materials:

4-ethylquinoline

1-(quinolin-4-yl)propan-1-one

4-acetylquinoline

phenyl(quinolin-4-yl)methanone

Refernces

• 1、 Yamaguchi, Kazuya,Xu, Ning,Jin, Xiongjie,Suzuki, Kosuke,Mizuno, Noritaka. "Regioselective direct oxidative C-H cyanation of quinoline and its derivatives catalyzed by vanadium-containing heteropoly acids". supporting information. p. 10034 - 10037. Retrieved 2015/06/22.