2,6,6-Trimethyl-2-vinyltetrahydropyran

Base Information

• Chemical Name: 2,6,6-Trimethyl-2-vinyltetrahydropyran
• CAS No.: 7392-19-0
• Deprecated CAS: 13837-56-4
• Molecular Formula: C₁₀H₁₈O
• Molecular Weight: 154.252
• European Community (EC) Number: 230-983-3,237-550-8
• UNII: V3824Q785M
• DSSTox Substance ID: DTXSID8051338
• Nikkaji Number: J100.127B
• Wikidata: Q27291478
• Metabolomics Workbench ID: 47624
• Mol file: 7392-19-0.mol

Synonyms:7392-19-0;2,6,6-Trimethyl-2-vinyltetrahydropyran;2-ethenyl-2,6,6-trimethyloxane;Linaloyl oxide;LIMETOL;2,2,6-Trimethyl-6-vinyltetrahydropyran;Bois de rose oxide;2H-Pyran, 2-ethenyltetrahydro-2,6,6-trimethyl-;2,2,6-Trimethyl-6-vinyltetrahydro-2H-pyran;2H-Pyran, tetrahydro-2,2,6-trimethyl-6-vinyl-;FEMA No. 3735;13837-56-4;2-Ethenyltetrahydro-2,6,6-trimethyl-2H-pyran;Tetrahydro-2,2,6-trimethyl-6-vinyl-2H-pyran;2,6,6-Trimethyl-2-ethenyltetrahydropyran;UNII-V3824Q785M;2,6,6-Trimethyl-2-ethenyltetrahydro-2H-pyran;2H-Pyran,2-ethenyltetrahydro-2,6,6-trimethyl-;EINECS 230-983-3;EINECS 237-550-8;2-VINYLTETRAHYDRO-2,6,6-TRIMETHYL-2H-PYRAN;V3824Q785M;2,6,6-Trimethoxy-2-vinyltetrahydropyran;2,6,6-Trimethyl-2-vinyl-tetrahydropyrane;2,2,6-Trimethyl-6-ethenyl-tetrahydropyran;Dehydroxylinalool oxide A;Geranic_oxide;GERANIC OXIDE;2,2,6-Trimethyl-6-vinyl-tetrahydropyran;SCHEMBL583643;DTXSID8051338;FEMA 3735;CHEBI:132848;AKOS006281378;2-vinyl-2,6,6-trimethyl tetrahydropyran;2,6,6-Trimethyl-2-ethenyltetrahydro-2-pyran;2h-piran, 2-eteniltetrahidro-2,6,6-trimetil-;2,2,6-TRIMETHYL-6-VINYLTETRAHYDROPYRANE;2,6,6 - trimethoxy - 2 - vinyltetrahydropyran;2-Ethenyltetrahydro-2,6,6-trimethylpyran, 9CI;(1)-Tetrahydro-2,6,6-trimethyl-2-vinyl-2H-pyran;2,6,6-TRIMETHYL-2-VINYLTETRAHYDRO-2H-PYRAN;(+-)-tetrahydro-2,6,6-trimethyl-2-vinyl-2H-pyran;PYRAN, TETRAHYDRO-2,2,6-TRIMETHYL-6-VINYL-;Q27291478;(+/-)-2,6,6-TRIMETHYL-2-VINYLTETRAHYDROPYRAN;(.+-.)-Tetrahydro-2,6,6-trimethyl-2-vinyl-2H-pyrane;2,6,6-TRIMETHYL-6-VINYLTETRAHYDROPYRAN [FHFI];2,6,6-TRIMETHYL-2-VINYLTETRAHYDROPYRAN, (+/-)-;( .PLUS/MINUS.) - tetrahydro - 2,6,6 - trimethyl - 2 - vinyl - 2H - pyran

Chemical Property of 2,6,6-Trimethyl-2-vinyltetrahydropyran

Chemical Property:

• Vapor Pressure: 4.89hPa at 25℃
• Boiling Point: 171 °C at 760 mmHg
• Flash Point: 49.4 °C
• PSA: 9.23000
• Density: 0.88 g/cm³
• LogP: 2.91020
• Storage Temp.: Amber Vial, Refrigerator, Under inert atmosphere
• Solubility.: Chloroform (Sparingly), Ethyl Acetate (Slightly)
• Water Solubility.: 449mg/L at 20℃
• XLogP3: 2.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 1
• Exact Mass: 154.135765193
• Heavy Atom Count: 11
• Complexity: 160

Purity/Quality:

99.9% ^*data from raw suppliers

Limetol ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1(CCCC(O1)(C)C=C)C
• Uses: Limetol, is the cyclized derivative of linalool (L465950), melanol, and other unsaturated alcohols, that was shown to give a product mixture that can be used in fragrance and perfumery industry.

Technology Process of 2,6,6-Trimethyl-2-vinyltetrahydropyran

There total 16 articles about 2,6,6-Trimethyl-2-vinyltetrahydropyran which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 90.0%

2-ethynyl-2,6,6-trimethyl-3,4,5,6-tetrahydro-(2H)-pyran (13837-60-0) → 2-vinyl-2,6,6-trimethyl-3,4,5,6-tetrahydro-2H-pyran (7392-19-0,13226-34-1,13837-56-4)

Guidance literature:

With Lindlar's catalyst; hydrogen; for 4h;

DOI:10.1080/00397910902945345

Reference yield: 81.0%

2,6-dimethyloct-7-ene-2,6-diol (29210-77-3,57784-11-9) → 2-vinyl-2,6,6-trimethyl-3,4,5,6-tetrahydro-2H-pyran (7392-19-0,13226-34-1,13837-56-4)

Guidance literature:

With ammonium cerium(IV) nitrate; In acetonitrile; at 20 ℃; for 9h;

DOI:10.1055/s-2006-947356

Reference yield: 53.0%

dimethyl-2,6 octadiene-6,7 ol-2 (56072-48-1) → 2-vinyl-2,6,6-trimethyl-3,4,5,6-tetrahydro-2H-pyran (7392-19-0,13226-34-1,13837-56-4)

Guidance literature:

With silver nitrate; In water; acetone; at 60 ℃; for 20h; exclusion of light;

upstream raw materials:

2-ethynyl-2,6,6-trimethyl-3,4,5,6-tetrahydro-(2H)-pyran

dimethyl-2,6 octadiene-6,7 ol-2

(Z)-N,N-diethyl-7-hydroxy-3,7-octenylamine

Dithiocarbonic acid S-methyl ester O-[1-(2,6,6-trimethyl-tetrahydro-pyran-2-yl)-ethyl] ester

Downstream raw materials:

2-ethynyl-2,6,6-trimethyl-3,4,5,6-tetrahydro-(2H)-pyran

Refernces

• 1、 Alvarez-Manzaneda,Chaboun,Alvarez,Cabrera,Alvarez-Manzaneda,Haidour,Ramos. "Cerium(IV) ammonium nitrate (CAN): A very efficient reagent for the synthesis of tertiary ethers". . p. 1829 - 1834. Retrieved 2008/02/08.
• 2、 Morin, Ph.,Gunther, C.,Peyron, L.,Richard, H.. "Etude des phenomenes physico-chimiques intervenant lors du procede d'hydrodistillation". . p. 921 - 930. Retrieved 2007/10/02.