1135-66-6

Basic information

• Product Name: Isolongifolene
• Synonyms: C15 H24, 2H-2,4a-Methanonaphthalene, 1,3,4,5,6,7-hexahydro-1,1,5,5-tetramethyl-, (2S)-;ISOLONGIFOLENE(SG);(2s)-2h-1,3,4,5,6,7-hexahydro-1,1,5,5-tetramethyl-4a-methanonaphthalen;1,3,4,5,6,7-Hexahydro-1,1,5,5-tetramethyl-2H-2,4a-methanonaphthalene;ISOLONGIFOLENE WITH GC;(2S,4aR)-1,2,3,4,4a,5,6,7-Octahydro-1,1,5,5-tetramethyl-2,4a-methanonaphthalene;(2S,4aR)-1,3,4,5,6,7-Hexahydro-1,1,5,5-tetramethyl-2H-2,4a-methanonaphthalene;(2S,4aR)-1,3,4,5,6,7-Hexahydro-1,1,5,5-tetramethyl-2H-2α,4aα-methanonaphthalene
• CAS NO: 1135-66-6
• Molecular Formula: C₁₅H₂₄
• Molecular Weight: 204.35
• EINECS: 214-494-2
• Mol File: 1135-66-6.mol
• Article Data: 15

Chemical Properties

• Boiling Point: 255-256 °C
• Flash Point: 49°C
• Appearance: COA
• Density: 0.930 g/mL at 20 °C(lit.)
• Vapor Pressure: 5.49Pa at 25℃
• Refractive Index: n20/D 1.499
• Storage Temp.: 2-8°C
• Water Solubility: 59.998μg/L at 25℃
• BRN: 2207559
• CAS DataBase Reference: Isolongifolene(CAS DataBase Reference)
• NIST Chemistry Reference: Isolongifolene(1135-66-6)
• EPA Substance Registry System: Isolongifolene(1135-66-6)

Safety Data

• Statements: 10
• RIDADR: UN 2319 3/PG 3
• WGK Germany: 3
• HazardClass: 3.2
• PackingGroup: III
• Hazardous Substances Data: 1135-66-6(Hazardous Substances Data)

Usage

Uses

(-)-Isolongifolene may be used in the preparation of (-)-isolongifolenone, a potent insect repellent.

General Description

(-)-Isolongifolene is a sesquiterpene that can be found in pine cone and Japanese cedar essential oils.

Flammability and Explosibility

Flammable

Purification Methods

Reflux it over, and distil it from Na. [Zeiss & Arakawa J Am Chem Soc 76 1653 1954, IR: Reinaecker & Graafe Angew Chem, Int Ed Engl 97 348 1985, UV and NMR: Ranganathan et al. Tetrahedron 26 621 1970, Beilstein 5 IV 1191.]

InChI:InChI=1/C15H24/c1-13(2)8-5-6-12-14(3,4)11-7-9-15(12,13)10-11/h6,11H,5,7-10H2,1-4H3/t11-,15?/m0/s1

Upstream product

• 475-20-7 longifolene 
• 475-20-7 decahydro-4,8,8-trimethyl-9-methylene-1,4-methanoazulene 
• 1139-17-9 (-)-Isolongifolol 
• 103873-45-6 7βH-8-oxoisolongifol-9-ene 
• 26839-51-0 7αH-8-oxoisolongifolane 
• 26839-72-5 7βH-8-oxoisolongifolane 
• 91482-03-0 8,11-dibromolongibornane 
• 108643-00-1 11-acetoxylongicyclene 
• 108643-04-5 4-Keto-pseudoneolongifolene 
• 108643-01-2 4-hydroxy-pseudoneolongifolene 
• 7664-93-9 sulfuric acid 
• 64-19-7 acetic acid 
• 16846-09-6 (-)-longifolene 
• 106540-16-3 7βH-8-Oxoisolongifolane tosylhydrazone 

Downstream Products

• 26839-52-1 1,2,3,4,5,6-hexahydro-1,1,5,5-tetramethyl-7H-2,4a-methanonaphthalen-7-one 
• 41746-30-9 isolongifolan-10-one 
• 26619-69-2 Isolongifolene β-epoxide 
• 1396021-22-9 (2R,4aR)-N-[N-(S)-(p-toluenesulfonyl)-p-toluenesulfonimidoyl]-1,1,5,5-tetramethyl-2,3,4,5,6,7-hexahydro-1H-2,4a-methanonaphthalen-7-amine 
• 59056-72-3 1-(octahydro-7,7,8,8-tetramethyl-2,3b-methano-3bH-cyclopenta[1,3]cyclopropa[1,2]benzen-4-yl)ethanone 
• 26839-51-0 7αH-8-oxoisolongifolane 

Relevant articles and documents

Pore-engineered silica-alumina: Texture, acidity, and activity for conversion of longifolene to isolongifolene

Pore-engineered silica-alumina was synthesized for the conversion of longifolene to isolongifolene, and the effects of texture and surface properties on the activity were examined. The acidity and texture of the modified silica-alumina play a vital role in governing the catalytic isomerization of longifolene to isolongifolene. A conversion of 97% of longifolene with 95% selectivity has been achieved. Springer-Verlag 2011.

STUDIES IN SESQUITERPENES--LVI ISOLONGIFOLENE (Part 7): MECHANISM OF REARRANGEMENT OF LONGIFOLENE TO ISOLONGIFOLENE--II

The question of possible neutral intermediates which may lie on the reaction pathway in going from longifolene to isolongifolene has been investigated using BF3*Et2O-AcOD and D3PO4-dioxane, as reagents.It has been found that longicyclene is not an obligat

Isomerization of longifolene to isolongifolene catalyzed by montmorillonite clay

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Alkylation of Benzene with Camphene over Zeolite

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