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

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

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

• 591-78-6 n-hexan-2-one 
• 24850-33-7 allyltributylstanane 
• 2622-05-1 allylmagnesium bromide 
• 911482-75-2 allylboronic acid 2,2-dimethyl-1,3-propanediol ester 
• 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 
• 36219-40-6 1-bromo-2-hydroxy-2-methyl-3-butene 
• 693-03-8 n-butyl magnesium bromide 

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.

Efficient synthesis of homoallylic alcohols/amines from allyltributylstannane and carbonyl compounds/imines using iodine as catalyst under acetic acid-water medium

This paper describes a general method for the synthesis of homoallylic alcohols and amines by nucleophilic addition reaction of allyltributylstannane to carbonyl compounds and aldimines where iodine acts as a catalyst in H2O/acetic acid (1:1) medium. Only 10 mol% of I2 is required for various organic transformations. By using this process, various homoallylic alcohols and amines are produced in good to excellent yields.

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.

Catalytic use of zinc amide for transmetalation with allylboronates: General and efficient catalytic allylation of carbonyl compounds, imines, and hydrazones

The efficient catalytic allylation of ketones, imines, and hydrazones with allylboronates using a catalytic amount of zinc amide is reported. In this reaction, the boron-to-zinc exchange process occurred smoothly to afford the corresponding allylzinc amides, and the desired allylation reactions proceeded in high efficiency (～0.1mol%). A mechanistic study revealed that transmetalation was a rate-determining step in the catalytic cycle, and also that the amide ligand on the zinc center played a key role in preparing reactive allylzinc species. Catalytic asymmetric allylations were also investigated, and high enantioselectivities were obtained using chiral diamine ligands. Copyright

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.

SnCl2·2H2O-mediated Barbier-type allylation: A comparative evaluation of the catalytic performance of CuI and Pd(OAc) 2

A systematic investigation has been carried out for the allylation of carbonyl compounds under SnCl2·2H2O-mediated Barbier-type conditions, using CuI and Pd(OAc)2 as catalysts. Ketones, which are not reactive under the influence of CuI, however, could be activated by using Pd(OAc)2 as a catalyst.

Facile preparation of allylzinc species from allylboronates and zinc amide via a boron-to-zinc exchange process and their reactions with carbonyl compounds, imines and hydrazones

Facile formation of allylzinc species from allylboronate and zinc amide was discovered. The boron-to-zinc exchange process occurred smoothly to afford the corresponding allylzinc amides, which were successfully employed in catalytic allylation reactions with electrophiles. Asymmetric catalysis using a chiral zinc amide is also reported.

Utility of neodymium diiodide as a reductant in ketone coupling reactions

Matrix presented The viability of Ndl2 as a one-electron reducing agent in organic synthesis has been examined by studying coupling reactions between alkyl chlorides and ketones and aldehydes.

An efficient and highly selective deprotecting method for β-(trimethylsilyl)ethoxymethyl ethers

A series of β-(trimethylsilyl)ethoxymethyl ethers were hydrolyzed to their corresponding alcohols in high yields by using a catalytic amount of CBr4 (15%) in MeOH under refluxing reaction conditions. The chemoselective deprotection between trialkylsilyl and β-(trimethylsilyl)-ethoxymethyl-protected alcohols can be achieved by using an alcohol with steric hindrance such as iPrOH. The selectivity also can be achieved in the CBr4/MeOH reaction mixture under ultrasonic reaction conditions.

A simple and highly efficient deprotecting method for methoxymethyl and methoxyethoxymethyl ethers and methoxyethoxymethyl esters

A series of methoxyethoxymethyl (MEM)- and methoxymethyl (MOM)-ethers and MEM-esters were hydrolyzed to their corresponding alcohols and carboxylic acids by a catalytic amount of CBr4 (10%) in iPrOH under refluxing reaction condition. The chemoselective hydrolysis between R3Si- and MEM-protected alcohols can be achieved by using different steric bulkness solvents such as MeOH or iPrOH.