565-00-4

Basic information

• Product Name: Comphene
• Synonyms: 2-dimethyl-3-methylene-(+/-)-bicyclo[2.2.1]heptan;FEMA 2229;D,L-CAMPHENE;CAMPHENE 90;CAMPHENE 46;AKOS NCG1-0107;Camphene (contains ca 20% trycyclene);containsca20%richcyclene
• CAS NO: 565-00-4
• Molecular Formula: C₁₀H₁₆
• Molecular Weight: 136.23
• EINECS: 201-234-8
• Mol File: 565-00-4.mol

Chemical Properties

• Melting Point: 48-52 °C(lit.)
• Boiling Point: 159-160 °C(lit.)
• Flash Point: 94 °F
• Appearance: /
• Density: 0.85 g/mL at 25 °C(lit.)
• Vapor Pressure: 3.38mmHg at 25°C
• Refractive Index: 1.483
• Water Solubility: practically insoluble
• CAS DataBase Reference: Comphene(CAS DataBase Reference)
• NIST Chemistry Reference: Comphene(565-00-4)
• EPA Substance Registry System: Comphene(565-00-4)

Safety Data

• Hazard Codes: F
• Statements: 11
• Safety Statements: 16-33
• RIDADR: UN 1325 4.1/PG 2
• WGK Germany: 2
• RTECS: EX1055000
• Hazardous Substances Data: 565-00-4(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Comphene is used as an active ingredient in the pharmaceutical industry for its various medicinal properties. It is known to possess anti-inflammatory, analgesic, and antipyretic effects, making it a valuable component in the formulation of drugs for treating pain, inflammation, and fever.
Used in Flavor and Fragrance Industry:
Comphene is used as a key component in the flavor and fragrance industry due to its strong camphor or turpentine odor. It is commonly used in the production of perfumes, colognes, and other scented products to provide a unique and distinct aroma.
Used in Agrochemical Industry:
In the agrochemical industry, Comphene is utilized as a component in the synthesis of various pesticides and insecticides. Its natural properties make it an effective ingredient in controlling pests and protecting crops.
Used in Cosmetics Industry:
Comphene is used as an additive in the cosmetics industry for its antimicrobial and antifungal properties. It is often found in products such as soaps, lotions, and creams to help maintain a clean and healthy environment for the skin.
Used in Biodegradable Plastics:
Comphene is used as a component in the development of biodegradable plastics. Its natural origin and ability to degrade over time make it an environmentally friendly option for the production of sustainable plastic materials.
Used in Chemical Synthesis:
Comphene is used as a starting material in the chemical synthesis of various compounds, including pharmaceuticals, agrochemicals, and other specialty chemicals. Its versatile chemical properties allow for a wide range of synthetic applications.

Potential Exposure

Camphene is used to manufacture synthetic camphor; for making moth-proofing and in the cosmetics, perfume, and food flavoring industries.

Shipping

UN1325 Flammable solids, organic, n.o.s., Hazard Class: 4.1; Labels: 4.1-Flammable solid. UN2319 Terpene hydrocarbons, n.o.s., Hazard Class: 3; Labels: 3- Flammable liquid

Purification Methods

Crystallise it twice from EtOH, then repeatedly melted and frozen at 30mm pressure. [Williams & Smyth J Am Chem Soc 84 1808 1962.] Alternatively it is dissolved in Et2O, dried over CaCl2 and Na, filtered, evaporated and the residue is sublimed in a vacuum [NMR: Hana & Koch Chem Ber 111 2527 1978].

Incompatibilities

Forms explosive mixture with air. Emulsions in xylene may violently decompose on contact with iron or aluminum above 70C. Incompatible with oxidizers (chlorates, nitrates, peroxides, permanganates, perchlorates, chlorine, bromine, fluorine, etc.); contact may cause fires or explosions. Keep away from alkaline materials, strong bases, strong acids, oxoacids, epoxides. Contact with reducing agents may cause exothermic reaction, releasing flammable hydrogen gas

Waste Disposal

Dissolve or mix the material with a combustible solvent and burn in a chemical incinerator equipped with an afterburner and scrubber. All federal, state, and local environmental regulations must be observed.

InChI:InChI=1/C10H16/c1-7-8-4-5-9(6-8)10(7,2)3/h8-9H,1,4-6H2,2-3H3

Upstream product

• 80-56-8 Pinene 
• 64-17-5 ethanol 
• 92281-96-4 5,5-dimethyl-6-methylene-norbornan-2-one semicarbazone 
• 141-52-6 sodium ethanolate 
• 1071684-68-8 4-chloro-2-isopropyl-5-methyl-benzenesulfonic acid bornyl ester 
• 4443-48-5 bornan-exo-2-yl bromide 
• 37487-17-5 rac O-isoborneol S-methyl carbonodithioate 
• 137634-60-7 oxalic acid monoisobornyl ester 
• 137634-60-7 oxalic acid monoisobornyl ester 
• 861624-39-7 ethyl-(2,3,3-trimethyl-[2]norbornyl)-ether 
• 464-41-5 bornyl chloride 
• 557-34-6 zinc diacetate 
• 64-19-7 acetic acid 
• 127-09-3 sodium acetate 

Downstream Products

• 86351-88-4 (+/-)-N-(2,3,3-trimethyl-[2exo]norbornyl)-formamide 
• 98-82-8 Isopropylbenzene 
• 99-87-6 4-methylisopropylbenzene 
• 13211-15-9 (+-)-camphenilone 
• 124-76-5 isoborneol 
• 464-41-5 bornyl chloride 
• 50705-16-3 3,3-dimethylbicyclo[2.2.1]heptane-2-carbaldehyde 
• 466-12-6 2-endo-hydroxymethyl-3,3-dimethylbicyclo[2.2.1]heptane-2-exo-ol 
• 464-78-8 ketopinic acid 
• 2792-42-9 (R,R)-camphor oxime 
• 473-35-8 2-(3-carboxy-cyclopentyl)-2-methyl-propionic acid 
• 4017-70-3 2-endo,10-Dichlor-bornan 
• 25570-91-6 (+/-)-2exo-hydroxy-bornane-10-nitrile 
• 76-22-2 Camphor 

Relevant articles and documents

ZrO2-SiO2 mixed oxides xerogel and aerogel as solid acid catalysts for solvent free isomerization of α-pinene and dehydration of 4-methyl-2-pentanol

Sulfated and non-sulfated ZrO2-SiO2 mixed oxide xerogel and aerogel samples having varied Zr/Si molar ratio were evaluated as solid acid catalysts for the isomerization of α-pinene and dehydration of 4-methyl-2-pentanol. Sulfation resulted into enhancement in the catalytic activity of both xerogel and aerogel samples towards the studied reactions. For example, sulfated catalysts showed 86-98% conversion of α-pinene and 8-35% conversion of 4-methyl-2-pentanol. The selectivity data for camphene and limonene indicated the requirement of moderate acidity. The correlation with cyclohexanol dehydration showed that isomerization of α-pinene is a Bronsted acid catalyzed reaction. The relationship of 4-methyl-2-pentanol conversion with acid site density and sulfur per unit area was found to be linear.

NOVEL PRODUCTS FROM BECKMANN FRAGMENTATION OF CAMPHOR OXIME IN POLYPHOSPHORIC ACID

Heating camphor oxime with PPA affords, besides the known fragmentation products isoaminocamphor (4) and β-campholenonitrile (13), four isomeric ketones C10H14O resulting from intramolecular acylation of the intermediate α-campholenonitrile (3).The ketones have been identified as 5-ketocamphene (6), 6-ketocamphene (8), tricyclenone (9), and endo-2,4-dimethylbicyclooct-2-ene-7-one (14).The latter results from a novel ring expansion, probably by way of a protonated cyclopropane.

Liquid Crystalline Catalysis, 3, Monomolecular Rearrangements of Terpene Derivatives in Liquid Crystalline Solvents

The ability of limonene and linalool to rearrange in mesomorphic media is apparently determined by the constraints exerted by the solvent structure on the translational diffusions of the reactant solute molecules.Selective conversions seem to be promoted by the different media.Alkylcyclohexyl- and alkylbicyclohexyl-carboxylic acids and their mixtures with toluic acid have been used as solvents.The B structure of their smectic phases has been demonstrated by X-ray diffraction studies.

Dehydrogenation of β-Pinene to p-Cymene over Platinum-Alumina Catalyst in the Presence of Nitrogen, Hydrogen and Pyridine

Dehydrogenation of β-pinene has been carried out over platinum-alumina (0.6percent Pt) catalyst at 300 deg C in the presence of nitrogen, hydrogen and pyridine.Nitrogen acts as a diluent while hydrogen acts both as a diulent and as a promoter.Pyridine on the other hand functions as a diluent and as a poison.As a result, it affects the formation of different products to different extent.The optimum conditions such as platinum concentration, temperature and contact time for dehydrogenation, hydrogenation and disproportionation reactions were established using cyclohexane, p-cymene and cyclohexene, respectively before actually studying the d ehydrogenation of β-pinene.

Effect of Sulfate Ions on Activity of TiO2, Fe2O3 and ZrO2 for the 2-Pinene Isomerization Reaction

Treatment of titanium oxide, Fe2O3 and ZrO2 with (NH4)2SO4 brought high catalytic activity for isomerization of 2-pinene.The selectivities of the catalysts for formation of camphene and 1,7,7-trimethyltricyclo2.6>heptane(tricyclene) were high (60-70 percent).The effect of sulfate ions has been interpreted in terms of surface acid strenght.Key words: Oxides / Sulphate ion / Isomerization / 2-Pinene

Isomerization of β-pinene in the Vapour Phase over Alumina Catalyst: Influence of Partial Pressure of Nitrogen and Pyridine

The isomerization of β-pinene in the vapour phase over alumina catalyst has been studied in the presence of nitrogen and pyridine.The isomerization proceeds via two parallel paths, one giving bicyclic products such as α-pinene and camphene and the other giving rise to monocyclic menthadienes such as dipentene, terpinolene, α-terpinene and γ-terpinene.Nitrogen acts as a diluent while pyridine functions as a diluent and as a poison.As a result, it affects the formation of different products to different extent.The isomerization of β-pinene over alumina follows a second order kinetics.Based on the experimental facts a tentative mechanism, in terms of carbonium ion intermediates, has been proposed.