28790-86-5

Basic information

• Product Name: 2,3,4-trimethylcyclopent-2-en-1-one
• Synonyms: 2,3,4-trimethylcyclopent-2-en-1-one;2,3,4-Trimethyl-2-cyclopenten-1-one;2,3,4-TriMethyl-2-cyclopentenone
• CAS NO: 28790-86-5
• Molecular Formula: C₈H₁₂O
• Molecular Weight: 124.18
• Mol File: 28790-86-5.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 183.7°Cat760mmHg
• Flash Point: 67.1°C
• Appearance: /
• Density: 0.923g/cm³
• Vapor Pressure: 0.759mmHg at 25°C
• Refractive Index: 1.461
• CAS DataBase Reference: 2,3,4-trimethylcyclopent-2-en-1-one(CAS DataBase Reference)
• NIST Chemistry Reference: 2,3,4-trimethylcyclopent-2-en-1-one(28790-86-5)
• EPA Substance Registry System: 2,3,4-trimethylcyclopent-2-en-1-one(28790-86-5)

Safety Data

• Hazardous Substances Data: 28790-86-5(Hazardous Substances Data)

Usage

Uses

2,3,4-Trimethyl-2-cyclopentenone, is an intermediate that can be used in various chemical synthesis. It is used for the synthesis of cyclic saturated compounds.

Synthesis Reference(s)

Synthetic Communications, 8, p. 71, 1978 DOI: 10.1080/00397917808062098

InChI:InChI=1/C8H12O/c1-5-4-8(9)7(3)6(5)2/h5H,4H2,1-3H3

Upstream product

• 115818-80-9 3-methyl-hepta-2,6-dien-4-one 
• 2630-54-8 5-methyl-hepta-1,5-dien-3-yne 
• 591-63-9 n-butyl crotonate 
• 101231-89-4 (S)-2,3-Dimethyl-2-vinyl-cyclobutanone 
• 67-56-1 methanol 
• 201230-82-2 carbon monoxide 
• 3142-85-6 3-methyl-hept-6-en-4-yn-3-ol 
• 54543-04-3 Dimethyl ((Z)-3-Methyl-2-oxo-3-pentenyl)phosphonate 
• 28895-02-5 3,4-dimethyl-2,5-hexanedione 
• 6831-84-1 1-diazo-2-butanone 
• 6203-88-9 2-acetoxy-2-butene 

Downstream Products

• 19374-46-0 (1α,2β,3α)-1,2,3-trimethyl-cyclopentane 
• 2613-69-6 (1α,2α,3α)-1,2,3-trimethyl-cyclopentane 
• 116531-01-2 optically inactive 4-hydroxy-1.2.3-trimethyl-cyclopentane 
• 6628-79-1 3-methyllevulinic acid 
• 64-19-7 acetic acid 
• 40459-94-7 2,3,4-trimethylcyclopent-2-en-1-ol 
• 109391-23-3 (d,l)-2,3-dihydroxy-2,3,4-trimethylcyclopentanone 
• 151598-89-9 1,4-bis<1,1'-(2,3,4-trimethylcyclopentadienyl)>butane 
• 28783-61-1 2,3,4-trimethyl-cyclopent-2-enone-(2,4-dinitro-phenylhydrazone) 

Relevant articles and documents

Coupling of Methanol and Carbon Monoxide over H-ZSM-5 to Form Aromatics

The conversion of methanol into aromatics over unmodified H-ZSM-5 zeolite is generally not high because the hydrogen transfer reaction results in alkane formation. Now circa 80 % aromatics selectivity for the coupling reaction of methanol and carbon monoxide over H-ZSM-5 is reported. Carbonyl compounds and methyl-2-cyclopenten-1-ones (MCPOs), which were detected in the products and catalysts, respectively, are considered as intermediates. The latter species can be synthesized from the former species and olefins. 13C isotope tracing and 13C liquid-state NMR results confirmed that the carbon atoms of CO molecules were incorporated into MCPOs and aromatic rings. A new aromatization mechanism that involves the formation of the above intermediates and co-occurs with a dramatically decreased hydrogen transfer reaction is proposed. A portion of the carbons in CO molecules are incorporated into aromatic, which is of great significance for industrial applications.

Nazarov cyclisation of dienone-esters and tetrahydropyrones using trimethylsilyltriflate

Cyclopentenone esters have been synthesized via a Nazarov cyclisation of the corresponding α,α'-dienone esters or tetrahydro-γ-pyrone esters employing trimethylsilyltriflate at room temperature. The dienone esters were synthesised by a short two-step acylation-Knoevenagel sequence.

OPTICALLY ACTIVE 2-VINYLCYCLOBUTANONES

Enzymatic resolution of dimethyl 2-methylsuccinate, acyloin cyclization and base induced ring contraction provided 1-hydroxycyclopropanecarboxylic acids with high optical purity (>95percent e.e).Their derivatives opened a regio- and stereoselective way to optically active 2-vinylcyclobutanones (>84-90percent e.e), providing useful building blocks for further ring expansions.