5935-15-9

Usage

Chemical Class

Fatty alcohols

Physical State

Colorless liquid

Odor

Mild, sweet

Solubility

Insoluble in water

Uses

a. Solvent in manufacturing perfumes, cosmetics, and cleaning agents
b. Intermediate in the synthesis of other chemicals
c. Production of fragrance and flavor compounds

Additional Properties

Antimicrobial

Applications

a. Formulation of antimicrobial products
b. Personal care items

Safety Precautions

Potential irritant effects on skin, eyes, and respiratory system; handle with caution

Upstream product

• 2404-44-6 1,2-Epoxydecane 
• 67-56-1 methanol 
• 69814-30-8 2-hydroxydecylphenyl selenide 
• 69814-31-9 2-(phenylseleno)decan-1-ol 

Relevant academic research and scientific papers

Aniline-terephthalaldehyde resin p-toluenesulfonate (ATRT) as a highly efficient and reusable catalyst for alcoholysis, hydrolysis, and acetolysis of epoxides

Alcoholysis, hydrolysis, and acetolysis of epoxides were carried out in the presence of a catalytic amount of aniline-terephthalaldehyde resin p-toluenesulfonate (ATRT) to give the corresponding β-substituted alcohols in good yields. Alcoholysis and hydrolysis of epoxides catalyzed by ATRT proceeded faster than those by pyridinium p-toluenesulfonate (PPTS).

Alcoholysis of Epoxides Catalyzed by Tetracyanoethylene and Dicyanoketene Acetals

A typical π-acid tetracyanoethylene and capto-dative olefin dicyanoketene acetals were found to catalyze stereospecific alcoholysis of epoxides at the ambient temperature to 50°C in good yields. Mildness and significant chemoselectivity of the catalysts were demonstrated by intactness of tetrahydropyranyl ether and ethylene acetal groups. A novel regioselectivity associated with anchimeric assistance of the ethereal group on the side chain was observed in the ring opening reaction of the 1,2-disubstituted epoxides.

Catalytic activities of dicyanoketene acetals in alcoholysis of epoxides

The catalytic activity of various types of capto-dative ethylenes has been investigated on alcoholysis of epoxides, and dicyanoketene dimethyl acetal (DCKDMA) and dicyanoketene ethylene acetal (DCKEA) are found to be efficient and mild catalysts.

A synthetically useful regioselective epoxide ring-opening procedure

The reaction of alcohols with epoxides in the presence of boron trifluoride etherate has been investigated and found to proceed with variable regioselectivity depending on the substituents attached to the oxirane ring.

A New Route to Epoxides and Ketones by m-Chloroperbenzoic Acid Oxidation of β-Hydroxyalkyl Phenyl Selenides and Tellurides

Treatment of primary (β-hydroxy)alkyl phenyl selenides with m-chloroperbenzoic acid (3-5 mol equiv.) in tetrahydrofuran or methanol gives the corresponding epoxides in high yield. cis-1-Methylene-4-t-butylcyclohexane oxide is obtained stereospecifically from 4-t-butyl-1-(phenylselenomethyl)cyclohexanol prepared by the addition of α-(phenylseleno)methyl anion to 4-t-butylcyclohexanone.On the other hand, similar oxidation of secondary (β-hydroxy)alkyl phenyl selenides affords the unexpected carboxylic acids or their esters.When a phenyl group is present on the carbon bearing the OH moiety in β-hydroxyselenides and tellurides , the oxidation is accompanied by phenyl migration to afford ketones.The reaction can be applied to one-carbon-homologated ring expansion of the benzene-ring-fused cyclic ketones by combining with the addition of an α-(phenylseleno)methyl or α-(phenyltelluro)methyl moiety to the ketones.