22597-46-2

Basic information

• Product Name: 4,4-DIMETHYLPENT-2-ENAL
• Synonyms: 4,4-DIMETHYLPENT-2-ENAL
• CAS NO: 22597-46-2
• Molecular Formula: C₇H₁₂O
• Molecular Weight: 112.17
• Mol File: 22597-46-2.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 147.1°C at 760 mmHg
• Flash Point: 44.3°C
• Appearance: /
• Density: 0.83g/cm³
• Vapor Pressure: 4.51mmHg at 25°C
• Refractive Index: 1.427
• CAS DataBase Reference: 4,4-DIMETHYLPENT-2-ENAL(CAS DataBase Reference)
• NIST Chemistry Reference: 4,4-DIMETHYLPENT-2-ENAL(22597-46-2)
• EPA Substance Registry System: 4,4-DIMETHYLPENT-2-ENAL(22597-46-2)

Safety Data

• Hazardous Substances Data: 22597-46-2(Hazardous Substances Data)

Usage

Synthesis Reference(s)

Canadian Journal of Chemistry, 70, p. 2040, 1992 DOI: 10.1139/v92-257Tetrahedron Letters, 29, p. 1631, 1988 DOI: 10.1016/S0040-4039(00)82003-1

InChI:InChI=1/C7H12O/c1-7(2,3)5-4-6-8/h4-6H,1-3H3/b5-4+

Upstream product

• 762-62-9 4,4-dimethylpent-1-ene 

Downstream Products

• 22430-49-5 trans,trans-2,2,7,7-tetramethylocta-3,5-diene 
• 93222-97-0 (3Z,5E)-2,2,7,7-tetramethyloctadiene 
• 104272-51-7 (E)-N-(4,4-dimethylpent-2-enyl)benzenamine 
• 29569-93-5 (E)-4,4-dimethyl-1-phenylpent-2-en-1-one 
• 107415-43-0 4,4-dimethyl-pent-2t-enal-(2,4-dinitro-phenylhydrazone) 
• 80674-59-5 3-Hydroxy-6,6-dimethyl-3-phenyl-(E)-4-heptensaeure 

Relevant articles and documents

Palladium/Copper-catalyzed Oxidation of Aliphatic Terminal Alkenes to Aldehydes Assisted by p-Benzoquinone

The development of an anti-Markovnikov Wacker-type oxidation for simple aliphatic alkenes is a significant challenge. Herein, a variety of aldehydes can be selectively obtained from various unbiased aliphatic terminal alkenes using PdCl2(MeCN)2/CuCl in the presence of p-benzoquinone (BQ) under mild reaction conditions. Isomerization of the terminal alkene to the internal alkene was suppressed via slow addition of the starting material to the reaction mixture. In addition to the Pd catalyst, CuCl and BQ were essential in order to obtain the anti-Markovnikov product with high selectivity. Terminal alkenes bearing a halogen substituent afforded their corresponding aldehydes with high anti-Markovnikov selectivity. The halogen acts as a directing group in the reaction. DFT calculations indicate that a μ-chloro Pd(II)?Cu(I) bimetallic species with BQ coordinated to Cu is the catalytically active species in the case of a terminal alkene without a directing group.