500-00-5

Basic information

• Product Name: p-menth-3-ene
• Synonyms: p-menth-3-ene;4-Methyl-1-(1-methylethyl)cyclohexene;Menthomenthene;Δ3 p-Mentene;4-methyl-1-propan-2-ylcyclohexene;4-methyl-1-propan-2-yl-cyclohexene
• CAS NO: 500-00-5
• Molecular Formula: C₁₀H₁₈
• Molecular Weight: 138.24992
• EINECS: 207-896-4
• Mol File: 500-00-5.mol
• Article Data: 32

Chemical Properties

• Melting Point: 25-26 °C
• Boiling Point: 166.85°C
• Flash Point: 43.3°C
• Appearance: /
• Density: 0.8102 (estimate)
• Vapor Pressure: 1.69mmHg at 25°C
• Refractive Index: 1.4604 (estimate)
• CAS DataBase Reference: p-menth-3-ene(CAS DataBase Reference)
• NIST Chemistry Reference: p-menth-3-ene(500-00-5)
• EPA Substance Registry System: p-menth-3-ene(500-00-5)

Safety Data

• Hazardous Substances Data: 500-00-5(Hazardous Substances Data)

Usage

Synthesis Reference(s)

Tetrahedron Letters, 17, p. 463, 1976 DOI: 10.1016/S0040-4039(00)77883-X

InChI:InChI=1/C10H18/c1-8(2)10-6-4-9(3)5-7-10/h6,8-9H,4-5,7H2,1-3H3

Upstream product

• 2216-51-5 (-)-menthol 
• 104-15-4 toluene-4-sulfonic acid 
• 586-62-9 Terpinolene 
• 99-86-5 1-methyl-4-isopropyl-1,3-cyclohexadiene 
• 71-43-2 benzene 
• 67-56-1 methanol 
• 16052-42-9 (1R,2S,5R)-menthyl chloride 
• 64-17-5 ethanol 
• 60-29-7 diethyl ether 
• 28953-96-0 2-chloro-1-isopropyl-4-methyl-cyclohexane 
• 854823-95-3 4-chloro-p-menthane 
• 7732-18-5 water 
• 554-59-6 trans-Carane 
• 554-59-6 cis-Carane 

Downstream Products

• 53067-10-0 3,7-dimethyl-1,6-octanediol 
• 100-21-0 terephthalic acid 
• 470-65-5 p-menthane-4-ol 
• 854823-95-3 4-chloro-p-menthane 
• 116836-10-3 4-bromo-p-menthane 
• 35551-82-7 4-chloro-p-menthan-3-ol 
• 5980-81-4 p-menth-3-en-2-yl hydroperoxide 
• 61585-35-1 p-menth-1-ene 
• 1124-27-2 p-4⁽⁸⁾-menthene 
• 1879-07-8 cis-p-8-menthene 
• 1678-82-6 trans-1,4-menthane 
• 6069-98-3 cis-1-isopropyl-4-methyl-cyclohexane 
• 176916-54-4 3,4-dibromo-p-menthane 
• 99-82-1 Menthane 

Relevant articles and documents

Continuous synthesis of menthol from citronellal and citral over Ni-beta-zeolite-sepiolite composite catalyst

One-pot continuous synthesis of menthols both from citronellal and citral was investigated over 5 wt% Ni supported on H-Beta-38-sepiolite composite catalyst at 60–70 °C under 10–29 bar hydrogen pressure. A relatively high menthols yield of 53% and 49% and stereoselectivity to menthol of 71–76% and 72–74% were obtained from citronellal and citral respectively at the contact time 4.2 min, 70 °C and 20 bar. Citral conversion noticeably decreased with time-on-stream under 10 and 15 bar of hydrogen pressure accompanied by accumulation of citronellal, the primary hydrogenation product of citral, practically not affecting selectivity to menthol. A substantial amount of defuctionalization products observed during citral conversion, especially at the beginning of the reaction (ca. 1 h), indicated that all intermediates could contribute to formation of menthanes. Ni/H-Beta-38-sepiolite composite material prepared by extrusion was characterized by TEM, SEM, XPS, XRD, ICP-OES, N2 physisorption and FTIR techniques to perceive the interrelation between the physico-chemical and catalytic properties.

Synthesis of isobenzofuran derivatives from renewable 2-carene over halloysite nanotubes

Condensation of a terpene 2-carene with 4-methoxybenzaldehyde over a range of acid aluminosilicates including halloysite nanotubes (HNT) was studied for as a model for preparation of isobenzofuran derivatives with a pharmaceutical potential. The catalysts were characterized by FTIR with pyridine, UV by adsorption of 2-phenylethylamine from the aqueous phase, SEM, TEM and N2 physisorption. The largest selectivity to the desired product (ca. 70%) over halloysite nanotubes is associated with weak acidity of these catalysts (45 μmol/g), allowing avoiding side isomerization and condensation reactions. Moreover, the highest yield on air-dry HNT clearly indicates that weak Br?nsted sites favored the reaction. On the contrary, over strong Br?nsted and Lewis acids (Amberlyst-15, scandium triflate), the yield of isobenzofurans did not exceed 16% with formation of mainly 2-carene isomerization products. DFT calculations showed that interactions of the aldehyde with cyclopropane moiety of 2-carene giving isobenzofurans are more beneficial than an alternative direct attack of a proton, leading to side reactions. A possibility to reuse of HNT catalyst was confirmed. Overall, halloysite is a highly effective catalyst for production of isobenzofuran compounds based on 2-carene.

Highly efficient rhodium-phosphite catalyzed hydroformylation of camphene and other terpenes

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