521270-78-0

Basic information

• Product Name: 1-(2-isocyanophenyl)ethan-1-one
• Synonyms: 1-(2-isocyanophenyl)ethan-1-one
• CAS NO: 521270-78-0
• Molecular Weight: 145.161
• Mol File: 521270-78-0.mol
• Article Data: 8

Chemical Properties

• CAS DataBase Reference: 1-(2-isocyanophenyl)ethan-1-one(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(2-isocyanophenyl)ethan-1-one(521270-78-0)
• EPA Substance Registry System: 1-(2-isocyanophenyl)ethan-1-one(521270-78-0)

Safety Data

• Hazardous Substances Data: 521270-78-0(Hazardous Substances Data)

Upstream product

• 5257-06-7 N-(2-acetylphenyl)formamide 
• 551-93-9 2-aminoacetophenone 
• 1885-29-6 anthranilic acid nitrile 
• 2258-42-6 formyl acetic anhydride 
• 103529-16-4 2-[(trimethylsilyl)ethynyl]aniline 
• 52670-38-9 2-ethynylaniline 
• 615-43-0 2-iodophenylamine 

Downstream Products

• 112158-32-4 1-isocyano-2-(1-methylethenyl)benzene 
• 141305-99-9 3-(4-methoxybenzyl)quinazolin-4(3H)-one 
• 1451070-60-2 3-benzyl-4-methylene-3,4-dihydroquinazoline 
• 1451070-61-3 3-(4-methylbenzyl)-4-methylene-3,4-dihydroquinazoline 
• 1451070-62-4 3-(4-chlorobenzyl)-4-methylene-3,4-dihydroquinazoline 
• 1451070-63-5 C₁₇H₁₆N₂O 
• 1451070-64-6 3-(2,4-dimethoxybenzyl)-4-methylene-3,4-dihydroquinazoline 
• 700-46-9 4-methylquinazoline 
• 10501-56-1 4-methylquinazoline 3-oxide 
• 611-36-9 quinolin-4-ol 
• 134470-65-8 1-(2-isothiocyanatophenyl)ethan-1-one 
• 4789-76-8 4-methyl-2-phenylquinoline 
• 5465-86-1 ML 204 

Relevant articles and documents

A convenient synthesis of quinolines by reactions of o-isocyano-β- methoxystyrenes with nucleophiles

2,4-Disubstituted quinolines have been synthesized by reactions of o-isocyano-β-methoxystyrenes, which can be easily prepared from commercially available o-aminophenyl ketones in three steps, with alkyl(or aryl)lithiums in generally good yields. Subsequently, o-isocyano-β- methoxystyrenes have also proved to react efficiently with lithium dialkylamides to afford the corresponding 4-substituted N,N-dialkylquinolin-2-amines in satisfactory yields. Graphical Abstract.

Copper-Catalyzed Chemoselective Cyclization Reaction of 2-Isocyanoacetophenone: Synthesis of 4-Hydroxyquinoline Compounds

A copper-catalyzed intramolecular cyclization reaction of 2-isocyanoacetophenone derivatives to afford 4-hydroxyquinolines chemoselectively is described. The transformation proceeds through enol tautomerism and a subsequent C-C bond formation. Compared to previous methods, this study provides a new protocol for the construction of 4-hydroxyquinoline compounds from functionalized isocyanides under mild conditions.

Isocyanide cyclization reactions: 4-methylene-4H-benzo[d][1,3]oxazine, 3-benzyl-4-methylene-3,4-dihydroquinazolines and 3-(4-benzyl)-3H-quinazolin-4- ones - Experiment and theory

2-Isocyanoacetophenone (3a) was found to be an easily accessible starting material for the unexpected formation of various heterocyclic systems. Thus, a hitherto unknown rather unstable 4-methylene-4H-benzoxazine derivative 4, which could be characterized by NMR spectroscopy, was formed in situ by the reaction of 3a in the presence of weak acids. In the presence of benzylamines, a new class of 3,4-dihydroquinazoline derivatives 6 and their oxidation products, quinazolin-4-ones 9, were obtained. The starting materials and products were completely characterized by spectroscopic and X-ray analysis. The scope and limitations of these cyclization reactions were investigated under various reaction conditions. High-level quantum chemical calculations were carried out to elucidate the mechanisms leading to scaffolds 4 and 6. The calculations suggest that the formation of 4 and 6 involves the generation of an unusual six-membered N-heterocyclic carbene or its C-protonated form as a reaction intermediate, followed by tautomerisation. This mechanism might also be applicable to other isocyanide cyclization reactions. Copyright