24264-08-2

Basic information

• Product Name: 2-ethylbut-1-en-1-one
• Synonyms: 1-Buten-1-one, 2-ethyl-
• CAS NO: 24264-08-2
• Molecular Formula: C₆H₁₀O
• Molecular Weight: 98.143
• Mol File: 24264-08-2.mol
• Article Data: 5

Chemical Properties

• Melting Point: -71.05°C (estimate)
• Boiling Point: 90.4°C at 760 mmHg
• Flash Point: 4.2°C
• Density: 0.795g/cm³
• Vapor Pressure: 56.3mmHg at 25°C
• Refractive Index: 1.399
• CAS DataBase Reference: 2-ethylbut-1-en-1-one(CAS DataBase Reference)
• NIST Chemistry Reference: 2-ethylbut-1-en-1-one(24264-08-2)
• EPA Substance Registry System: 2-ethylbut-1-en-1-one(24264-08-2)

Safety Data

• Hazardous Substances Data: 24264-08-2(Hazardous Substances Data)

Upstream product

• 510-20-3 diethyl malonic acid 
• 54502-37-3 2-ethylbutyric anhydride 
• 26074-53-3 2-bromo-2-ethylbutyryl bromide 
• 57613-20-4 diethylmalonic acid anhydride 
• 34804-01-8 3,3-diethyl-thietane-2,4-dione 

Downstream Products

• 95284-59-6 5-Dimethylamino-2,2-dimethyl-4,4,6,6-tetraaethyl-1,3-cyclohexandion 
• 591-50-4 iodobenzene 
• 1609030-55-8 (±)-3,3-diethyl-4-phenyloxetan-2-one 
• 124-38-9 carbon dioxide 
• 96-22-0 pentan-3-one 
• 88-09-5 2-Ethylbutanoic acid 
• 90720-34-6 3-(tert-Butyl-dimethyl-silanyloxy)-1-(4-chloro-phenyl)-4-ethyl-hex-3-en-1-one 
• 90720-25-5 3-(tert-Butyl-dimethyl-silanyloxy)-3-(4-chloro-phenyl)-2,2-diethyl-cyclobutanone 
• 90720-38-0 3-(tert-Butyl-dimethyl-silanyloxy)-4-ethyl-1-(4-methoxy-phenyl)-hex-3-en-1-one 
• 90720-29-9 3-(tert-Butyl-dimethyl-silanyloxy)-2,2-diethyl-3-(4-methoxy-phenyl)-cyclobutanone 
• 90720-43-7 4-Ethyl-1-(4-methoxy-phenyl)-hexane-1,3-dione 
• 90720-36-8 3-(tert-Butyl-dimethyl-silanyloxy)-4-ethyl-1-phenyl-hex-3-en-1-one 
• 90720-27-7 3-(tert-Butyl-dimethyl-silanyloxy)-2,2-diethyl-3-phenyl-cyclobutanone 

Relevant articles and documents

-

-

Lewis acid-promoted ketene-alkene [2 + 2] cycloadditions

Described are the first examples of ketene-alkene [2 + 2] cycloadditions promoted by Lewis acids. Notable features of this method include (1) substantial rate acceleration relative to traditional thermal reactions, (2) good diastereoselectivities and yields for the formation of the cyclobutanone products, and (3) inverse diastereoselectivity compared with related thermal cycloadditions for many examples. These studies not only provide access to synthetically versatile cyclobutanones that cannot be prepared by traditional thermal cycloadditions but also address important mechanistic questions regarding ketene-alkene [2 + 2] cycloaddition reactions.

Kinetics and Mechanism of Hydration of Alkylketenes

The hydration reactivities of CH2=C=O (1), t-Bu2C=C=O (5), Et2C=C=O (7), (CH2)4C=C=O (8), (CH2)5C=C=O (9), and t-BuCH=C=O (10) in H2O or H2O/CH3CN mixtures have been examined, including acid and base catalysis and solvent and structural isotope effects.These results provide the first systematic comparison of structural effects on the hydration of aliphatic ketenes, as well as the first measurements of base-induced hydration and pH-rate profiles for this process.The significant steric and electronic effects of the substituents observed lead to the interpretation that the acid-catalyzed reaction involves rate-limiting proton transfer to Cβ perpendicular to the ketene plane, while the H2O- and OH--induced reactions involve nucleophilic attack in the ketene plane.These results resolve the many conflicting previous reports and interpretations regarding ketene hydration.