6564-95-0

Basic information

• Product Name: 4-oxobutyl acetate
• Synonyms: 4-oxobutyl acetate;4-acetoxybutyraldehyde
• CAS NO: 6564-95-0
• Molecular Formula: C₆H₁₀O₃
• Molecular Weight: 130.1418
• Mol File: 6564-95-0.mol
• Article Data: 10

Chemical Properties

• Boiling Point: 59-60 °C(Press: 1 Torr)
• Appearance: /
• Density: 1.0612 g/cm3
• CAS DataBase Reference: 4-oxobutyl acetate(CAS DataBase Reference)
• NIST Chemistry Reference: 4-oxobutyl acetate(6564-95-0)
• EPA Substance Registry System: 4-oxobutyl acetate(6564-95-0)

Safety Data

• Hazardous Substances Data: 6564-95-0(Hazardous Substances Data)

Usage

Synthesis Reference(s)

Journal of the American Chemical Society, 70, p. 383, 1948 DOI: 10.1021/ja01181a119

Upstream product

• 591-87-7 Allyl acetate 
• 201230-82-2 carbon monoxide 
• 56703-55-0 but-3-yn-1-yl acetate 

Downstream Products

• 26976-72-7 4-acetoxybutyric acid 
• 6191-71-5 heptene-4 ol-1 
• 21676-08-4 (E)-undec-4-en-1-ol 
• 21676-07-3 (Z)-undec-4-en-1-ol 
• 114423-64-2 trans,trans-3-(10'-acetoxy-6'-decenyl)-1,2-bis<(dimethylthexylsilyl)oxy>cyclohexane 
• 166166-16-1 (Z)-N-<3-(tert-butyldiphenylsiloxy)hex-4-enyl>-4-acetoxybutylideneamine N-oxide 
• 837364-66-6 (3S,4R)-3-(hydroxymethyl)-4-(4-methoxyphenylamino)heptane-1,7-diyl diacetate 
• 1040726-54-2 4-benzylcarbamoyl-4-[benzyl-(2-chloroacetyl)amino]butyl acetate 
• 1395897-86-5 (S)-5-((tert-butoxycarbonyl)amino)-4-oxo-5-phenylpentyl acetate 
• 1374694-54-8 (S)-4-oxo-4-(2-phenyl-1,2,3,4-tetrahydroisoquinolin-1-yl)butyl acetate 
• 1431323-25-9 (+)-(R)-methyl 6 acetoxy-2-hydroxy-3-oxo-2-phenylhexanoate 
• 1040726-58-6 1,4-dibenzyl-3-(3-acetoxypropyl)piperazine-2,5-dione 

Relevant articles and documents

Hydroformylation of unsaturated esters and 2,3-dihydrofuran under solventless conditions at room temperature catalysed by rhodium: N-pyrrolyl phosphine catalysts

Rhodium complexes of the type HRh(CO)L3 (where L is an N-pyrrolyl phosphine, such as P(NC4H4)3, PPh(NC4H4)2, or PPh2(NC4H4)) were applied in the hydroformylation of less reactive unsaturated substrates, namely allyl acetate, butyl acrylate, methyl acrylate, 2,3-dihydrofuran and vinyl acetate. Even at room temperature, these catalysts enabled complete substrate conversion and high chemoselectivity towards the corresponding aldehydes. High conversion of vinyl acetate (88% in 6 h) to the branched aldehyde was obtained with HRh(CO)[P(NC4H4)3]3 at 25 °C. An increase of the turnover frequency, TOF, up to 2000 mol mol-1 h-1 was achieved in this reaction under 20 bar of syngas (H2/CO = 1) at 80 °C. The introduction of chiral phosphines, BINAP or Ph-BPE, to this system resulted in the production of a branched aldehyde with enantioselectivity, ee, up to 44 and 81%, respectively. High activity combined with high enantioselectivity was achieved due to the formation of the mixed rhodium hydrides HRh(CO)[P(NC4H4)3](BINAP) and HRh(CO)[P(NC4H4)3](Ph-BPE), identified by the NMR method.

Allyl acetate hydroformylation process

A process for the production of 4-acetoxybutyraldehyde is described. The process comprises reacting allyl acetate with a mixture of carbon monoxide and hydrogen in the presence of a solvent and a catalyst comprising a rhodium complex and a diphosphine. The diphoshine is a substituted or unsubstituted 2,2′-bis(dihydrocarbylphosphino)diphenyl ether. The process gives a high ratio of 4-acetoxybutyraldehyde:3-acetoxy-2-methylpropionaldehyde.

Self-assembled bidentate ligands for ru-catalyzed anti-Markovnikov hydration of terminal alkynes

(Figure Presented) In pairs: Bidentate ligands are generated by the self-assembly of monodentate ligands through complementary hydrogen bonding. A ruthenium complex bearing such self-assembled heterodimeric ligands is used as the catalyst in the regioselective hydration of terminal alkynes. FG = functional group, Piv = pivaloyl.