547-61-5

Basic information

• Product Name: (-)-TRANS-PINOCARVEOL
• Synonyms: (1S,3R,5S)-6,6-DIMETHYL-2-METHYLENEBICYCLO[3.1.1]HEPTAN-3-OL;[1S-(1alpha,3alpha,5alpha)]-6,6-dimethyl-2-methylenebicyclo[3.1.1]heptan-3-ol;(-)-TRANS-PINOCARVEOL 96+%;(1S,3R,5S)-2-Methylene-6,6-dimethylbicyclo[3.1.1]heptane-3-ol;(1S,5S)-6,6-Dimethyl-2-methylenebicyclo[3.1.1]heptan-3α-ol;[1S,3R,5S,(-)]-Pin-2(10)-en-3-ol;(1S,5S)-6,6-dimethyl-2-methylene-norpinan-3-ol;(1S,5S)-7,7-dimethyl-4-methylidene-bicyclo[3.1.1]heptan-3-ol
• CAS NO: 547-61-5
• Molecular Formula: C₁₀H₁₆O
• Molecular Weight: 152.23
• EINECS: 208-927-4
• Mol File: 547-61-5.mol
• Article Data: 33

Chemical Properties

• Melting Point: 5 °C
• Boiling Point: 217.5°Cat760mmHg
• Flash Point: 90.1°C
• Appearance: milky white/liquid
• Density: 0.979 g/mL at 20 °C(lit.)
• Vapor Pressure: 0.0283mmHg at 25°C
• Refractive Index: n20/D 1.500
• PKA: 14.91±0.40(Predicted)
• BRN: 5730571
• CAS DataBase Reference: (-)-TRANS-PINOCARVEOL(CAS DataBase Reference)
• NIST Chemistry Reference: (-)-TRANS-PINOCARVEOL(547-61-5)
• EPA Substance Registry System: (-)-TRANS-PINOCARVEOL(547-61-5)

Safety Data

• Safety Statements: 23-24/25
• WGK Germany: 3
• F: 9-23
• Hazardous Substances Data: 547-61-5(Hazardous Substances Data)

Usage

General Description

(-)-trans-Pinocarveol is an allyl alcohol. It is formed during the allylic oxidation of β-pinene using hydrogen peroxide-selenium dioxide or from the isomerization of α-pinene oxide over zirconium oxide.

InChI:InChI=1/C10H16O/c1-6-8-4-7(5-9(6)11)10(8,2)3/h7-9,11H,1,4-5H2,2-3H3/t7-,8+,9+/m0/s1

Upstream product

• 58434-29-0 myrtenyl hydroperoxide 
• 22321-84-2 pinocarveyl hydroperoxide 
• 177698-19-0 Beta-pinene 
• 25488-94-2 5,7,7-trimethyl-3-oxa-tricyclo[4.1.1.0^2,4]octane 
• 80-56-8 Pinene 
• 1686-14-2 α-pinene epoxide 
• 18172-67-3 beta-pinene 
• 515-00-4 myrtenol 
• 17004-05-6 3-amino-β-pinene 
• 22321-84-2 trans-pinocarveyl hydroperoxide 
• 50-00-0 formaldehyd 
• 7785-26-4 2,6,6-trimethylbicyclo[3.1.1]hept-2-ene 

Downstream Products

• 18172-67-3 (?)-β-pinene 
• 7785-26-4 2,6,6-trimethylbicyclo[3.1.1]hept-2-ene 

Relevant articles and documents

Design of stable mixed-metal MIL-101(Cr/Fe) materials with enhanced catalytic activity for the Prins reaction

This work highlights the benefit of designing mixed-metal (Cr/Fe) MOFs for enhanced chemical stability and catalytic activity. A robust and stable mixed-metal MIL-101(Cr/Fe) was prepared through a HF-free direct hydrothermal route with Fe3+ content up to 21 wt%. The incorporation of Fe3+ cations in the crystal structure was confirmed by 57Fe M?ssbauer spectrometry. The catalytic performance of the mixed metal MIL-101(Cr/Fe) was evaluated in the Prins reaction. MIL-101(Cr/Fe) exhibited a higher catalytic activity compared to MIL-101(Cr), improved chemical stability compared to MIL-101(Fe) and a higher catalytic activity for bulky substrates compared to MIL-100(Fe). In situ infra-red spectroscopy study suggests that the incorporation of Fe3+ ions in MIL-101 structure leads to an increase in Lewis acid sites. It was thus concluded that the predominant role of Cr3+ ions was to maintain the crystal structure, while Fe3+ ions enhanced the catalytic activity.

Solvent and additive-free selective aerobic allylic hydroxylation of β-pinene catalyzed by metalloporphyrins

Metallodeuteroporphyrins (MDPs) were employed as the catalysts for aerobic oxidation of β-pinene in absence of solvents and additives. Allylic hydroxylation products were found to be the main products from this protocol. The catalytic activity of MDPs with different metal nuclei and the influences of technological conditions on this reaction were investigated. This catalytic system has bright application prospect since only eco-friendly and readily available dioxygen were needed.

Synthesis of bimetallic Zr(Ti)-naphthalendicarboxylate MOFs and their properties as Lewis acid catalysis

Bimetallic Zr(Ti)-NDC based metal-organic frameworks (MOFs) have been prepared by incorporation of titanium(iv) into zirconium(iv)-NDC-MOFs (UiO family). The resulting materials maintain thermal (up to 500 °C), chemical and structural stability with respect to parent Zr-MOFs as can be deduced from XRD, N2 adsorption, FTIR and thermal analysis. The materials have been studied in Lewis acid catalyzed reactions, such as, domino Meerwein-Ponndorf-Verley (MPV) reduction-etherification of p-methoxybenzaldehyde with butanol, isomerization of α-pinene oxide and cyclization of citronellal.