2758-18-1

Basic information

• Product Name: 3-Methyl-2-cyclopenten-1-one
• Synonyms: 1-Methyl-1-cyclopenten-3-one;3-methyl-2-cyclopenten-1-on;3-Methyl-cyclopent-2-enone;3-METHYL-2-CYCLOPENTEN-1-ONE FOR SYNTHES;3-Methyl-2-cyclopenten-1-one, GC 98%;3-Methyl-2-cyclopentenone 97%;3-Methyl-2-cyclopenten-1-one, 97%+;3-Methyl-2-cyclopenten-1-one, stabilised
• CAS NO: 2758-18-1
• Molecular Formula: C₆H₈O
• Molecular Weight: 96.13
• EINECS: 220-421-5
• Product Categories: Organic Building Blocks;Pyridines;ketone;C3 to C6;Carbonyl Compounds;Ketones;Building Blocks;C3 to C6;Carbonyl Compounds;Chemical Synthesis
• Mol File: 2758-18-1.mol
• Article Data: 76

Chemical Properties

• Melting Point: 3-5 °C(lit.)
• Boiling Point: 74 °C15 mm Hg(lit.)
• Flash Point: 150 °F
• Appearance: Clear light yellow to yellow-brown/Liquid
• Density: 0.971 g/mL at 25 °C(lit.)
• Vapor Pressure: 2.74mmHg at 25°C
• Refractive Index: n20/D 1.488(lit.)
• Storage Temp.: Refrigerator (+4°C)
• Water Solubility: miscible
• BRN: 1280476
• CAS DataBase Reference: 3-Methyl-2-cyclopenten-1-one(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Methyl-2-cyclopenten-1-one(2758-18-1)
• EPA Substance Registry System: 3-Methyl-2-cyclopenten-1-one(2758-18-1)

Safety Data

• Statements: 36/38
• Safety Statements: 24/25
• RIDADR: 1224
• WGK Germany: 3
• TSCA: Yes
• PackingGroup: III
• Hazardous Substances Data: 2758-18-1(Hazardous Substances Data)

Usage

Description

May be prepared by dehydrohalogenation of 2-chloro-l-methylcyclopentan-3-one.

Chemical Properties

Different sources of media describe the Chemical Properties of 2758-18-1 differently. You can refer to the following data:
1. 1-Methyl-1-cyclopenten-3-one has a sweet-floral, warm-spicy and diffusive yet quite tenacious odor.
2. clear light yellow to yellow-brownish liquid

Occurrence

Reported found in roasted onion, cooked pork, black tea, soybean and dried bonito

Uses

Different sources of media describe the Uses of 2758-18-1 differently. You can refer to the following data:
1. 3-Methyl-2-cyclopentenone was used in the synthesis of 2-hydroxy-3-methyl-2-cyclopentenone.
2. It is an important raw material and intermediate used in Organic Synthesis, Pharmaceuticals, Agrochemicals.

Preparation

By dehydrohalogenation of 2-chloro-1-methyl-cyclopentan-3-one.

Synthesis Reference(s)

Journal of the American Chemical Society, 101, p. 494, 1979 DOI: 10.1021/ja00496a044The Journal of Organic Chemistry, 55, p. 371, 1990

General Description

3-Methyl-2-cyclopenten-1-one is a component of smoke flavoring.

InChI:InChI=1/C6H8O/c1-5-2-3-6(7)4-5/h4H,2-3H2,1H3

Upstream product

• 110-13-4 2,5-hexanedione 
• 17024-44-1 2,3-epoxy-3-methylcyclopentanone 
• 96816-51-2 diethyl(hex-2,5-dione-1-yl)phosphonate 
• 110874-84-5 3-methyl-2-<(dimethylthiocarbamoyl)oxy>-2-cyclopenten-1-one 
• 917-64-6 methyl magnesium iodide 
• 5682-74-6 3-isobutoxy-2-cyclopentenone 
• 854817-78-0 2-chloro-3-methyl-cyclopentanone 
• 7732-18-5 water 
• 2935-44-6 hexane-2,5-diol 
• 3859-41-4 1,3-cyclopentadione 
• 763-32-6 2-methyl-1-buten-4-ol 
• 108-29-2 5-methyl-dihydro-furan-2-one 
• 10493-98-8 2-hydroxy-2-cyclopenten-1-one 
• 10575-36-7 (1E,4E)-hexa-1,4-dien-3-one 

Downstream Products

• 859446-70-1 4-(α-hydroxy-benzyl)-3-methyl-cyclopent-2-enone 
• 114718-24-0 (2'E,3RS,S_SR_S)-3-methyl-3-<3'-<(4-methylphenyl)sulfinyl>prop-2'-enyl>cyclopentanone 
• 74758-71-7 3-Methyl-3-phenylselanyl-cyclopentanone 
• 39858-69-0 3-methyl-3-(3-phenylpropyl)cyclopentanone 
• 82222-80-8 3-methyl-3-((4-methylphenyl)sulfonyl)cyclopentanone 
• 67263-03-0 3-(dimethyl(phenyl)silyl)-3-methylcyclopentanone 
• 116830-98-9 3-((E)-1-Benzenesulfonyl-3-chloro-2-methyl-allyl)-3-methyl-cyclopentanone 
• 116830-97-8 3-(1-Benzenesulfonyl-2-chloromethyl-allyl)-3-methyl-cyclopentanone 
• 114678-75-0 1-<3'-methyl-1'-(phenylsulfinyl)but-2'-enyl>-3-methylcyclopent-2-en-1-ol 
• 137905-51-2 (E)-1-phenylsulphenyl-1-(1-hydroxy-3-methyl-2-cyclopentenyl)-2,4-pentadiene 
• 137905-50-1 (Z)-1-phenylsulphenyl-3-(1-methyl-3-oxocyclopentyl)-1,4-pentadiene 
• 137905-50-1 (E)-1-phenylsulphenyl-3-(1-methyl-3-oxocyclopentyl)-1,4-pentadiene 
• 117012-17-6 3-(1-Benzenesulfonyl-2-methylsulfanyl-allyl)-3-methyl-cyclopentanone 
• 114790-60-2 3,6-dimethyl-3-(1-methyl-3-oxocyclopentyl)-1-(phenylsulfinyl)cyclohexene 

Relevant articles and documents

Vapor-phase intramolecular aldol condensation of 2,5-hexanedione to 3-methylcyclopent-2-enone over ZrO2-supported Li2O catalyst

Vapor-phase intramolecular aldol condensation of 2,5-hexanedione to produce 3-methylcyclopent-2-enone was performed over several ZrO2-supported alkali and alkali earth metal oxides. Among the tested catalysts, ZrO2-supported Li2O showed a stable catalytic activity. A high 2,5-hexanedione conversion of 99% with a 3-methylcyclopent-2-enone selectivity of 96% was achieved over a 20?mol% Li2O-loaded ZrO2catalyst at 250?°C.

Synthesis of Bio-Based Methylcyclopentadiene from 2,5-Hexanedione: A Sustainable Route to High Energy Density Jet Fuels

The sustainable, bio-based, platform chemical, 2,5-hexanedione [HD (1)], was efficiently converted to methylcyclopentadiene [MCPD (4)] through a three-step process consisting of intramolecular aldol condensation, catalytic chemoselective hydrogenation, and dehydration. Base-catalyzed aldol condensation of 1 resulted in the formation of 3-methyl-2-cyclopenten-1-one [MCO (2)], which was then converted to 3-methyl-2-cyclopenten-1-ol [MCP (3)] by chemoselective reduction with a ternary Ru catalyst system [RuCl2(PPh3)3/NH2(CH2)2NH2/KOH]. The hydrogenation proceeded with 96 % chemoselectivity. 3 was then dehydrated over AlPO4/MgSO4 at 70 °C under reduced pressure to yield 4, which can undergo an ambient temperature [4+2]-Diels-Alder cyclization to generate dimethyldicyclopentadiene (DMDCPD), a commodity chemical useful for the preparation of high-performance fuels and polymers. Through this approach, advanced jet fuels and materials can be conveniently produced from sustainable cellulosic feedstocks.

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Calcium and nitrogen species loaded into SBA-15-a promising catalyst tested in Knoevenagel condensation

Mesoporous silica of the SBA-15 type was used as a support for basic active centers generated by the incorporation of calcium species and (3-aminopropylo)trimethoxysilane (APTMS) or imidazole. The samples were characterized by low temperature N2 adsorption/desorption, XRD, XPS, FTIR spectroscopy, CO2-TPD, and elemental and thermal analyses. Calcium containing samples were analysed in 2,5-hexanedione dehydration and cyclization, while the activities of all the samples were examined in Knoevenagel condensation between benzaldehyde and malononitrile. It was demonstrated that the calcium species interacted with a silica support increasing the stabilization of organosilanes on the SBA-15 surface. A very high activity of the catalysts in Knoevenagel condensation indicated a synergistic interaction between calcium and the organic modifiers.

Transformation of γ-ketoaldehyde acetals into 3-substituted-2-cyclopentenones via cyanophosphates under mild conditions

The reaction of cyanophosphates, which are readily derived from γ-ketoaldehyde acetals, with TMSN3 (3 eq)/Bu2SnO (0.3 eq) in refluxing toluene directly furnished 3-substituted-2-cyclopentenones in modest to good yield under mild conditions. The present method was further applied toward the synthesis of dechlorotrichodenone C isolated from Trichoderma asperellum.

Producing methylcyclopentadiene dimer and trimer based high-performance jet fuels using 5-methyl furfural

Methylcyclopentadiene dimer and trimer based fuels are synthesized from 5-methyl furfural for the first time with yields as high as 74.4%. They exhibit both high density and high thermal stability that are better than those of widely used fossil based jet fuels such as JP-10 and JP-7, and represent types of high-performance fuels. This work also provides a potential and scale-up feasible route for synthesizing high-performance jet fuels from biomass.