514-99-8

Basic information

• Product Name: 6,6-dimethylbicyclo[3.1.1]heptane-2-methanol
• Synonyms: 6,6-dimethylbicyclo[3.1.1]heptane-2-methanol;Bicyclo3.1.1heptane-2-methanol, 6,6-dimethyl-;MYRTANOL;Benihiol;Pinane-10-ol
• CAS NO: 514-99-8
• Molecular Formula: C₁₀H₁₈O
• Molecular Weight: 154.24932
• EINECS: 208-191-4
• Mol File: 514-99-8.mol
• Article Data: 20

Chemical Properties

• Boiling Point: 219.5°Cat760mmHg
• Flash Point: 96°C
• Appearance: /
• Density: 0.95g/cm³
• PKA: 14.99±0.10(Predicted)
• CAS DataBase Reference: 6,6-dimethylbicyclo[3.1.1]heptane-2-methanol(CAS DataBase Reference)
• NIST Chemistry Reference: 6,6-dimethylbicyclo[3.1.1]heptane-2-methanol(514-99-8)
• EPA Substance Registry System: 6,6-dimethylbicyclo[3.1.1]heptane-2-methanol(514-99-8)

Safety Data

• Hazardous Substances Data: 514-99-8(Hazardous Substances Data)

Usage

InChI:InChI=1S/C10H18O/c1-10(2)8-4-3-7(6-11)9(10)5-8/h7-9,11H,3-6H2,1-2H3

Upstream product

• 23727-16-4 myrtenal 
• 6712-78-3 myrtenol 
• 127-91-3 (1R,5R)-(+)-β-pinene 
• 64-19-7 acetic acid 
• 177698-19-0 Beta-pinene 
• 127-91-3 (1R/S,5R/S)-6,6-dimethyl-2-methylenebicyclo[3.1.1]heptane 
• 515-00-4 (+/-)-myrtenol 
• 601-74-1 (1R,5S)-6,6-dimethylbicyclo[3.1.1]hept-2-ene-2-carboxylic acid 
• 64-17-5 ethanol 
• 33741-31-0 (1R,2S)-pinan-10-oic acid methyl ester 
• 33741-30-9 methyl (1S,5R)-6,6-dimethylbicyclo[3.1.1]hept-2-ene-2-carboxylate 
• 18172-67-3 beta-pinene 
• 1118071-19-4 2-chloromethyl-6,6-dimethylbicyclo[3.1.1]heptane 
• 62-53-3 aniline 

Downstream Products

• 4764-14-1 (+/-)-Myrtanal 
• 4764-14-1 (+/-)-Isomyrtanal 
• 4764-14-1 cis-myrtanal 
• 81510-31-8 [2-((1R,2R,5R)-6,6-Dimethyl-bicyclo[3.1.1]hept-2-ylmethoxy)-ethyl]-diphenyl-phosphane 
• 590410-99-4 (1R,2R,5R)-trans-myrtanyl tosylate 
• 16750-96-2 trans-Myrtanyl-tosylat 
• 4764-14-1 (-)-cis-myrtanal 
• 127-92-4 6,6-Dimethyl-bicyclo<3.1.1>heptan 
• 81510-28-3 (1R,2R,5R)-2-[2-(Diphenyl-phosphinoyl)-ethoxymethyl]-6,6-dimethyl-bicyclo[3.1.1]heptane 
• 4764-14-1 6,6-dimethylbicyclo<3.3.1>heptane-2-carboxaldehyde 
• 29021-36-1 (1R)-10-Acetoxy-cis-pinan 

Relevant articles and documents

HYDROALUMINATION OF CYCLOOLEFINS BY DIISOBUTYLALUMINUM HYDRIDE CATALYZED BY ZIRCONIUM COMPOUNDS

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One-Pot Myrtenol Amination over Au, Au–Pd and Pd Nanoparticles Supported on Alumina

Abstract: One-pot bio-based myrtenol amination was studied in the presence of alumina supported Au, Au–Pd and Pd nanoparticles subjected to the thermal treatment under oxidizing or reducing atmosphere. Myrtenol amination with aniline was carried out under nitrogen atmosphere (9?bar) at 453?K using toluene as a solvent. The effect of the active metal along with the influence of redox pre-treatment on the catalytic behavior in the hydrogen borrowing reaction was explored. The catalyst characterization was done by transmission electron microscopy, X-ray photoelectron spectroscopy, inductively coupled plasma optical emission spectroscopy, nitrogen adsorption. The active metal and the catalysts redox pretreatment affected more noticeably selectivity to the reaction products rather than myrtenol conversion. Monometallic Au/Al2O3 catalyst promoted predominantly formation of the target secondary amine and the corresponding imine without a significant impact of the side reaction of C=C bond hydrogenation in myrtenol, whereas monometallic Pd catalyst activated C=C bond resulting in its hydrogenation. At the same time in the presence of Au–Pd simultaneous hydrogenation of both C=C and C=N bond occurred. Au–Pd catalysts activated in oxygen and hydrogen showed different catalytic activity determined by the composition of surface active sites. Monometallic gold catalyst was more effective in the hydrogen transfer in the case of substrates with competitive unsaturated functional groups. Graphic Abstract: [Figure not available: see fulltext.].

A preparation method of Myrtle myristic aldehyde

The invention discloses a preparation method of myrtanal. The method sequentially comprises the following steps: 1, carrying out a hydroboration-oxidation reaction on beta-pinene to generate myrtanol; and 2, carrying out a selective oxidation reaction on myrtanol and active dimethyl sulphoxide to generate myrtanal. Myrtanol is synthesized in a high efficiency manner through hydroboration-oxidation of beta-pinene as a raw material, and the yield is greater than 90%; myrtanal is prepared through selective oxidation of the active dimethyl sulphoxide at room temperature, and the yield is greater than 80%, so the total yield of conversion from the initial raw material beta-pinene to myrtanal is greater than 72%. Compared with present methods, the method disclosed in the invention has the advantages of cheap and easily available reaction raw materials, mild reaction conditions, high purity and high yield of the above obtained product, and great reduction of the preparation cost of myrtanal.