2-CYANO-4-METHYLQUINOLINE

Base Information

• Chemical Name: 2-CYANO-4-METHYLQUINOLINE
• CAS No.: 10590-69-9
• Molecular Formula: C11H8 N2
• Molecular Weight: 168.19462
• Hs Code.: 2933499090
• Mol file: 10590-69-9.mol

Synonyms:Quinaldonitrile,4-methyl- (6CI,7CI,8CI); 4-Methyl-2-cyanoquinoline;4-Methylquinoline-2-carbonitrile

Chemical Property of 2-CYANO-4-METHYLQUINOLINE

Chemical Property:

• Vapor Pressure: 4.57E-05mmHg at 25°C
• Refractive Index: 1.635
• Boiling Point: 349.9°Cat760mmHg
• Flash Point: 121.8°C
• PSA: 36.68000
• Density: 1.17g/cm³
• LogP: 2.41488
• Storage Temp.: 2-8°C

Purity/Quality:

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

4-Methylquinoline-2-carbonitrile 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 2-CYANO-4-METHYLQUINOLINE

There total 8 articles about 2-CYANO-4-METHYLQUINOLINE 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: 87.0%

4-methylquinoline 1-oxide (4053-40-1) + trimethylsilyl cyanide (7677-24-9) → 4-methylquinoline-2-carbonitrile (10590-69-9)

Guidance literature:

In neat (no solvent); at 130 ℃; for 0.0833333h; Wavelength; regioselective reaction; Sealed tube; Inert atmosphere; Microwave irradiation;

DOI:10.1002/adsc.201901103

Reference yield: 84.0%

2-chloro-4-methylquinoline (634-47-9) + 2-hydroxy-2-methylpropanenitrile (75-86-5) → 4-methylquinoline-2-carbonitrile (10590-69-9)

Guidance literature:

With [Pd(cinnamyl)Cl]2; N-ethyl-N,N-diisopropylamine; XPhos; In butan-1-ol; for 2h; Inert atmosphere;

DOI:10.1021/acs.oprd.6b00229

Reference yield: 82.0%

(4-methyl-quinolin-2-yl)-methanol (33787-85-8) → 4-methylquinoline-2-carbonitrile (10590-69-9)

Guidance literature:

With ammonium hydroxide; iodine; at 40 ℃; for 14h;

DOI:10.1002/ejoc.201701321

upstream raw materials:

4-methylquinoline 1-oxide

trimethylsilyl cyanide

2-chloro-4-methylquinoline

2-hydroxy-2-methylpropanenitrile

Downstream raw materials:

N,4-dimethyl-N-phenylquinoline-2-amine

2-cyclohexyl-4-methylquinoline

Refernces

• 1、 Sarmah, Bikash Kumar,Konwar, Monuranjan,Bhattacharyya, Dipanjan,Adhikari, Priyanka,Das, Animesh. "Regioselective Cyanation of Six-Membered N-Heteroaromatic Compounds Under Metal-, Activator-, Base- and Solvent-Free Conditions". supporting information. p. 5616 - 5625. Retrieved 2019/11/22.
• 2、 Xu, Feng,Li, Yuqin,Huang, Xin,Fang, Xinjie,Li, Zhuofei,Jiang, Hongshuo,Qiao, Jingyi,Chu, Wenyi,Sun, Zhizhong. "Hypervalent Iodine(III)-Mediated Regioselective Cyanation of Quinoline N-Oxides with Trimethylsilyl Cyanide". supporting information. p. 520 - 525. Retrieved 2018/12/13.