96-38-8

Basic information

• Product Name: Methylcyclopentadiene
• Synonyms: 1-Methyl-2,4-cyclopentadiene;5-Methyl-1,3-cyclopentadiene;5-Methylcyclopentadiene;5α-Methyl-1,3-cyclopentadiene
• CAS NO: 96-38-8
• Molecular Formula: C₆H₈
• Molecular Weight: 80.1277
• Mol File: 96-38-8.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 80.4°Cat760mmHg
• Flash Point: °C
• Appearance: /
• Density: 0.84g/cm³
• Vapor Pressure: 94.8mmHg at 25°C
• Refractive Index: 1.477
• CAS DataBase Reference: Methylcyclopentadiene(CAS DataBase Reference)
• NIST Chemistry Reference: Methylcyclopentadiene(96-38-8)
• EPA Substance Registry System: Methylcyclopentadiene(96-38-8)

Safety Data

• Hazardous Substances Data: 96-38-8(Hazardous Substances Data)

Usage

General Description

Methylcyclopentadiene, also known as MCPD, is a colorless liquid with a strong, unpleasant odor. It is a cyclic diene that is primarily used in the production of plastics, resins, and specialty chemicals. MCPD is a highly reactive compound and is often used as a building block for the synthesis of various chemical compounds. It is also used as a monomer in the production of synthetic rubbers and elastomers. The chemical is also known to be highly flammable and requires careful handling and storage to prevent accidents. Additionally, MCPD is known to be toxic to aquatic organisms and should be disposed of in accordance with local environmental regulations. Overall, methylcyclopentadiene is a versatile and important chemical in the manufacturing of various industrial products.

InChI:InChI=1/C6H8/c1-6-4-2-3-5-6/h2-6H,1H3

Upstream product

• 100-66-3 methoxybenzene 
• 50-00-0 formaldehyd 
• 115-11-7 isobutene 
• 2203-80-7 5-methylhex-1-yne 

Downstream Products

• 123748-85-6 (1S,2S,6S,7R)-1-Methyl-4-oxa-tricyclo[5.2.1.0^2,6]dec-8-ene-3,5-dione 
• 131588-72-2 Tetraethylammonium-5-methyl-1,2,3,4-tetrakis(phenylthio)cyclopentadienid 
• 108-88-3 toluene 
• 76847-17-1 diethyl 2,3-diaza-7-methylbicyclo<2.2.1>hept-5-ene-2,3-dicarboxylate 
• 221885-27-4 methyl (2R,3S,4R)-2-(benzyloxy)-4-hydroxy-3-methylpentanoate 
• 221885-33-2 (2R,3S,4R)-2,4-dibenzyloxy-3-methylpentanoic acid 
• 357274-61-4 Acetic acid (1R,4S,5R)-4-benzyloxy-5-methyl-cyclopent-2-enyl ester 
• 357274-62-5 (3R,4S,5S)-3-Benzyloxy-5-hydroxymethyl-4-methyl-dihydro-furan-2-one 
• 357274-64-7 (S)-2-((2R,3S,4R)-2,4-Bis-benzyloxy-3-methyl-pentanoylamino)-3-hydroxy-2-methyl-propionic acid benzyl ester 

Relevant articles and documents

Isoprene synthesis from formaldehyde and isobutene over Keggin-type heteropolyacids supported on silica

Gas phase Prins condensation of isobutene with formaldehyde has been studied over different Keggin-type heteropolyacids supported on amorphous silica. The catalysts were characterized by elemental analysis, X-ray diffraction, low temperature nitrogen adsorption, TPD of ammonia, FTIR of adsorbed pyridine and NMR spectroscopy. The activity of the supported heteropoly compounds was found to increase in the following order: H4SiMo12O40 3PMo12O40 4SiW12O40 ≈ H3PW12O40. The lower activity of the supported molybdenum heteropolyacids was attributed to their low thermal stability and partial decomposition during catalyst activation, which resulted in lower acidity. The variation of HPA content from 5 to 33 wt% was also shown to increase catalyst activity. Based on the relationship between the content of weak Br?nsted sites, the amount and type of carbonaceous deposits and the catalytic activity, it was concluded that the generation of working active sites over HPA catalysts involves the formation of unsaturated branched surface species over weak Br?nsted sites. These active carbonaceous species are responsible for selective isoprene synthesis. The best catalyst performance is observed over the catalyst with 20 wt% of H3PW12O40, which shows an isoprene yield of 48% with a selectivity of 63%.

On the Thermal Cycloisomerization of Long-Chain Alkylacetylenes in the Gas Phase

The thermal cycloisomerization of some alkylacetylenes was investigated in a tubular quartz reactor.At 570 deg C 1-hexyne (1) rearranges to 3-methyl-1-cyclopentene (5) with a selectivity of about 27 by a reaction sequence including an acetylene-vinylidene rearrangement and 1,5-C,H insertion of the intermediately formed alkylidenecarbene species. 5-methyl-1-hexyne (2) behaves analogously forming 3,3-dimethyl-1-cyclopentene (6), while 2-hexyne (3) provides 1-methyl-1-cyclopentene (7) indicating that the acetylene-vinylidene rearrangement is obviuosly not restricted to 1,2-H shifts.The mechanism of the cycloisomerization of alkylacetylenes is investigated by means of D-labeled parent alkynes.The results show that the unimolecular cycloisomerization via alkylidenecarbenes obviously can be an important channel despite the dominance of a radical chain course. - Keywords: Alkyne/ Carbene/ Cycloisomerization/ Pyrolysis