62108-06-9

Basic information

• Product Name: 2-Allyl-2-hexanol
• Synonyms: 2-Allyl-2-hexanol;4-Methyl-1-octen-4-ol;4-methyloct-1-en-4-ol
• CAS NO: 62108-06-9
• Molecular Formula: C9H18O
• Molecular Weight: 142.23862
• Product Categories: Aliphatics, Pharmaceuticals, Intermediates & Fine Chemicals
• Mol File: 62108-06-9.mol
• Article Data: 20

Chemical Properties

• Melting Point: -7°C (estimate)
• Boiling Point: 224.85°C (estimate)
• Appearance: /
• Density: 0.8660 (estimate)
• Refractive Index: 1.4391 (estimate)
• Storage Temp.: -20°C Freezer
• Solubility: DCM, Ethyl Acetate
• CAS DataBase Reference: 2-Allyl-2-hexanol(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Allyl-2-hexanol(62108-06-9)
• EPA Substance Registry System: 2-Allyl-2-hexanol(62108-06-9)

Safety Data

• Hazardous Substances Data: 62108-06-9(Hazardous Substances Data)

Usage

Description

2-Allyl-2-hexanol is an organic compound with the molecular formula C10H20O. It is a colorless liquid with a distinctive odor and is commonly used as an intermediate in the synthesis of various chemicals and pharmaceuticals.

Uses

Used in Pharmaceutical Industry:
2-Allyl-2-hexanol is used as an intermediate in the synthesis of Misoprostol (M368755), a cytoprotective prostaglandin PGE analogue. It plays a crucial role in the development of this medication, which is used to prevent gastric ulcers and treat conditions like gastric acid-related disorders.
Used in Chemical Synthesis:
2-Allyl-2-hexanol is also used as a building block in the synthesis of various organic compounds, including fragrances, flavors, and other specialty chemicals. Its unique structure allows for versatile chemical reactions, making it a valuable component in the creation of a wide range of products.

Synthesis Reference(s)

Tetrahedron Letters, 30, p. 7149, 1989 DOI: 10.1016/S0040-4039(01)93920-6

Upstream product

• 693-03-8 n-butyl magnesium bromide 
• 36219-40-6 1-bromo-2-hydroxy-2-methyl-3-butene 
• 911482-75-2 allylboronic acid 2,2-dimethyl-1,3-propanediol ester 
• 591-78-6 n-hexan-2-one 
• 24850-33-7 allyltributylstanane 
• 2622-05-1 allylmagnesium bromide 
• 107-05-1 3-chloroprop-1-ene 
• 191732-48-6 (E)-(3-bromoprop-1-en-1-yl)tributylstannane 
• 106-95-6 allyl bromide 
• 127700-08-7 [2-(1-Allyl-1-methyl-pentyloxymethoxy)-ethyl]-trimethyl-silane 
• 556-56-9 allyl iodid 
• 75-97-8 3,3-dimethyl-butan-2-one 
• 64549-05-9 allyldibutyltin chloride 
• 109-72-8 n-butyllithium 

Downstream Products

• 29839-53-0 5-butyl-5-methyl-tetrahydro-furan-3-ol 

Relevant articles and documents

ALLYL BUTYLTIN HALIDES (CH2=CHCH2)SnBu3-nCln(n=0, 1, 2, 3). PREPARATION, CARBON-13NMR CHARACTERISATION AND ALLYLSTANNYLATION ABILITY TOWARDS KETONES AND ALDEHYDES

Mixed allylbutyltin halides (CH2=CHCH2)SnBu3-nCln (n=0-3) have been prepared, and characterized by carbon-13 NMR spectroscopy.Their ability to bring about allylstannylation of ketones and aldehydes, to form organostannoxy compounds, Bu3-nSnClnOC(R')(R'')CH2CH=CH2, has been shown to increase on increasing the value of n, that is on increasing the acceptor ability of the tin centre.

Lewis acid catalyzed synthesis of cyclic carbonates, precursors of 1,2- and 1,3-diols

An eco-friendly synthesis of cyclic carbonates through a Lewis acid catalyzed cyclization of tert-butyl carbonates is described. These cyclic carbonates are precursors of 1,2- and 1,3-diols, and the developed method was applied to a short synthesis of a diarylheptanoid, (3S,5S)-alpinikatin.

Rapid access to homoallylic alcohols via Pd(OAc)2 catalyzed Barbier type allylation in presence of DMAP

DMAP was found to accelerate significantly the rate of Pd(OAc)2 catalyzed Barbier type allylation of carbonyl compounds by allylbromide using SnCl2·2H2O as reducing agent. Both aldehyde as well as ketones produced excellent yields within a short reaction time in the presence of 3 mol % of Pd(OAc)2 and 12 mol % of DMAP at room temperature. Aldehydes could be allylated within 5-10 min whereas, in case of ketones, the reaction completes in 45-120 min.