4948-28-1

Basic information

• Product Name: (1RS,2RS,5RS)-2,6,6-TRIMETHYLBICYCLO[3.1.1]HEPTAN-2-OL
• Synonyms: 2,6,6-Trimethylbicyclo(3.1.1)heptan-2-ol, (1alpha,2alpha,5alpha)-;2-Pinanol, cis-;2-Pinanol, cis- (8ci);Caswell no. 663l;(1-alpha,2-alpha,5-alpha)-2,6,6-trimethylbicyclo(3.1.1)heptan-2-ol;2,6,6-trimethyl-,(1.alpha.,2.alpha.,5.alpha.)-Bicyclo[3.1.1]heptan-2-ol;2,6,6-trimethyl-,(1-alpha,2-alpha,5-alpha)-bicyclo(3.1.1)heptan-2-o;2,6,6-trimethyl-,(1alpha,2alpha,5alpha)-bicyclo[3.1.1]heptan-2-o
• CAS NO: 4948-28-1
• Molecular Formula: C₁₀H₁₈O
• Molecular Weight: 154.25
• EINECS: 225-591-4
• Mol File: 4948-28-1.mol
• Article Data: 3

Chemical Properties

• Melting Point: 68-71 °C
• Boiling Point: 205 °C(lit.)
• Flash Point: 79 °C
• Appearance: /
• Density: 0.8389 (rough estimate)
• Vapor Pressure: 0.0684mmHg at 25°C
• Refractive Index: 1.4666 (estimate)
• CAS DataBase Reference: (1RS,2RS,5RS)-2,6,6-TRIMETHYLBICYCLO[3.1.1]HEPTAN-2-OL(CAS DataBase Reference)
• NIST Chemistry Reference: (1RS,2RS,5RS)-2,6,6-TRIMETHYLBICYCLO[3.1.1]HEPTAN-2-OL(4948-28-1)
• EPA Substance Registry System: (1RS,2RS,5RS)-2,6,6-TRIMETHYLBICYCLO[3.1.1]HEPTAN-2-OL(4948-28-1)

Safety Data

• Hazard Codes: Xn
• Statements: 21/22-36/37/38
• Safety Statements: 26-36/37
• RIDADR: UN 1325 4.1/PG 2
• WGK Germany: 2
• RTECS: DT5080000
• Hazardous Substances Data: 4948-28-1(Hazardous Substances Data)

Usage

Description

(1RS,2RS,5RS)-2,6,6-TRIMETHYLBICYCLO[3.1.1]HEPTAN-2-OL, also known as bornyl alcohol, is a bicyclic monoterpene alcohol that is commonly found in the essential oils of various plants, such as pine and fir trees. It has a distinctive piney, woody aroma and is frequently used in perfumery and flavoring. Bornyl alcohol has also demonstrated potential for various biological activities, including antiviral, antibacterial, anti-inflammatory, and analgesic properties. It is also commonly used in traditional medicine for its medicinal properties, particularly in the treatment of respiratory and bronchial problems. Additionally, bornyl alcohol has been studied for its potential as an insect repellent and in the development of environmentally friendly pesticides.

Uses

Used in Perfumery and Flavoring Industry:
(1RS,2RS,5RS)-2,6,6-TRIMETHYLBICYCLO[3.1.1]HEPTAN-2-OL is used as a fragrance ingredient for its characteristic piney, woody aroma, adding depth and complexity to perfumes and colognes.
Used in Traditional Medicine:
(1RS,2RS,5RS)-2,6,6-TRIMETHYLBICYCLO[3.1.1]HEPTAN-2-OL is used as a medicinal agent for its antiviral, antibacterial, anti-inflammatory, and analgesic properties, particularly in the treatment of respiratory and bronchial problems.
Used in Insect Repellent and Pesticide Development:
(1RS,2RS,5RS)-2,6,6-TRIMETHYLBICYCLO[3.1.1]HEPTAN-2-OL is used as an active ingredient in insect repellents and environmentally friendly pesticides due to its potential as a natural insect deterrent.

InChI:InChI=1/C10H18O/c1-9(2)7-4-5-10(3,11)8(9)6-7/h7-8,11H,4-6H2,1-3H3/t7-,8+,10-/m0/s1

Upstream product

• 5813-49-0 nitrosyl acetate 
• 13293-47-5 2αH-pinan-3α-ylamine 
• 4952-03-8 1-methylcyclohexane hydroperoxide 
• 473-55-2 2,6,6-trimethylbicyclo[3.1.1]heptane 
• 766-07-4 cyclohexyl hydroperoxide 
• 80-15-9 Cumene hydroperoxide 

Relevant articles and documents

Studies on the Oxidation of cis- and trans-Pinane with Molecular Oxygen

The pinanes are preferably attacked at the tertiary C-H bond in 2-position, but products of the oxidative attack at the secondary C-H-bonds in 3- and 4-position are also found.At 100 deg C cis-pinane is attacked more easily than trans-pinane (kcis : ktrans = 6.4), the relative rates of attack at the secondary C-H bonds in positions 3 and 4 with respect to the tertiary C-H bond in 2-position were also determined (in cis-pinane ksec : ktert = 0.027; in trans-pinane ksec : ktert = 0.20).After the attack at the 2-C-H bond the radical formed can either react with oxygen to form the corresponding cis- and trans-peroxy radicals and further to give cis- and trans-2-hydroperoxy pinane or fragmentate to the monocyclic radical derived from α-terpinene, giving as a final products α-terpinene hydroperoxide and the bicyclic 8-hydroperoxy 4,4,8-trimethyl 2,3-dioxabicyclononane.The corresponding alcohols were found after reduction with sodium sulphite.The oxidation at position 2 of the pinanes delivers not only the cis- and trans-hydroperoxide but also, as short-lived intermediates, the corresponding 2-pinanyloxy radicals.These radicals fragmentate forming a carbon radical with cyclobutane structure whose oxidation products were identified.Besides fragmentation of the 2-pinanyloxy radical also an intramolecular H-transfer from the methyl group in 9-position to the oxygen of the trans-pinanyloxy radical takes place leading to 9-hydroperoxy trans-pinane-2-ol.

Rearrangement of Pinane Derivatives. Part 8. Deamination of 2αH-Pinan-3α-ylamine

Solvolysis of 2αH-pinan-3α-yl toluene-p-sulphonate has been shown to proceed with concomitant 1,2-hydride shift to give the pinan-2-yl carbocation.Contrary to earlier reports, this species reacts normally to give, in good yield, pinan-2-yl substitution products.In contrast the pinan-3-ylamines react via a similar route, but give much smaller amounts of pinan-2-yl products.The usual reasons for differences between solvolysis and deamination (i.e. the intermediacy of diazonium ions and/or high-energy ions) can be discounted, and possible reasons for the differences in behaviour are discussed.