72248-92-1

Basic information

• Product Name: 2-Methylquinoline-3-carbonitrile
• Synonyms: 2-Methylquinoline-3-carbonitrile
• CAS NO: 72248-92-1
• Molecular Formula: C₁₁H₈N₂
• Molecular Weight: 168.19462
• Mol File: 72248-92-1.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 324.8°C at 760 mmHg
• Flash Point: 115.8°C
• Appearance: /
• Density: 1.17g/cm³
• Vapor Pressure: 0.00024mmHg at 25°C
• Refractive Index: 1.635
• CAS DataBase Reference: 2-Methylquinoline-3-carbonitrile(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Methylquinoline-3-carbonitrile(72248-92-1)
• EPA Substance Registry System: 2-Methylquinoline-3-carbonitrile(72248-92-1)

Safety Data

• Hazardous Substances Data: 72248-92-1(Hazardous Substances Data)

Usage

InChI:InChI=1/C11H8N2/c1-8-10(7-12)6-9-4-2-3-5-11(9)13-8/h2-6H,1H3

Upstream product

• 5765-44-6 5-methylisoxazole 
• 529-23-7 o-aminobenzaldehyde 
• 72844-86-1 (E)-N-(2-(2-cyanovinyl)phenyl)acetamide 
• 614-76-6 N-acetyl-2-bromoaniline 
• 89-95-2 2-methyl-benzyl alcohol 
• 763-33-7 (E)-3-aminocrotononitrile 
• 2469-99-0 Cyanoaceton 
• 72844-90-7 o-(2-trans-Cyanoethenyl)thioacetanilide 
• 612-62-4 2-Chloroquinoline 
• 75-05-8 acetonitrile 
• 1118-61-2 3-Aminocrotononitrile 

Downstream Products

• 147329-81-5 2-styrylquinoline-3-carbonitrile 
• 147329-87-1 3-Phenyl-3,4-dihydro-2H-benzo[b][1,6]naphthyridin-1-one 
• 635-79-0 2-methylquinoline-3-carboxylic acid 

Relevant articles and documents

Ru(III)-catalyzed construction of variously substituted quinolines from 2-aminoaromatic aldehydes (ketones) and isoxazoles: Isoxazoles as cyclization reagent and cyano sources

A Ru(Ⅲ)-catalyzed annulation reaction of 2-aminoaromatic aldehydes (ketones) and isoxazoles to afford diverse 3-cyanoquinolines has been developed. Notably, isoxazole acted as a cyclization reagent and nontoxic cyano source via N-O bond cleavage and fragm

Utility of 3-Aminocrotononitrile in the Synthesis of New Methyl 1,4-Dihydropyridine, Methylquinoline and Thiophene Derivatives: The Reactivity of Methyl Function in Alkyl 1,4-Dihydropyridine and Methyl Quinoline Derivatives Towards Some Electrophilic Reagents

New alkyl 1,4-dihydropyridine and methyl quinoline derivatives were prepared from the reaction of 3-aminocrotononitrile with some aliphatic ketones, cinnamaldehyde and salicylaldehyde. The methyl function in some of methyl 1,4-dihydropyridine and methyl quinoline derivatives towards electrophilic reagents proved to be highly active under mild conditions.

Photochemical Synthesis. Conversion of o-Vinylthioanilides to Quinolines

Quinoline derivatives are formed in fair to good yields when acetonitrile solutions of o-vinylthioanilides are irradiated with Pyrex-filtered light.The transformation is a singlet reaction and involves intramolecular cycloaddition of the thioamide, yielding unstable thietanes, as the initial step.In the case of o-(1-trans-propenyl)thioacetanilide (2a) the corresponding thietane has been detected by 1H NMR spectroscopy by irradiating a toluene solution of the compound at -78 deg C.The quantum yield of quinoline formation from 2a appeared to be solvent dependent.Concomitant with quinoline formation, triplet cis-trans isomerization of the vinyl moiety takes place.In the case of 2a the quantum yield for trans -> cis isomerization is 0.506.A variable-temperature 1H NMR study of 2,3-dimethylquinoline in toluene solution has also been performed.For the 2,3-dimethylquinoline-toluene complex the enthalpy and entropy of formation are -1.03 +/- 0.10 kcal/mol and -3.7 +/- 0.2 gibbs/mol, respectively.