1120-06-5

Usage

Uses

Used in Chemical Research:
2-Decanol is used as a reactant in the development of miniature catalytic reactors for the oxidation of alcohols with O2 in supercritical CO2. This application is significant for studying the efficiency and selectivity of catalytic reactions in a controlled environment.
Used in Enzyme Substrate Studies:
In the field of biochemistry, 2-Decanol is utilized to investigate the substrate spectrum of phytanoyl-CoA hydroxylase, focusing on the length of the acyl chain and the branch at the second position. This research contributes to the understanding of enzyme specificity and its role in various metabolic pathways.
Used in the Chemical Industry:
2-Decanol can be employed as an intermediate in the synthesis of various chemicals, such as surfactants, detergents, and lubricants, due to its alcohol functional group and linear structure. Its properties make it suitable for use in the formulation of industrial products that require specific characteristics, such as solubility and reactivity.

Synthesis Reference(s)

The Journal of Organic Chemistry, 60, p. 5963, 1995 DOI: 10.1021/jo00123a039

InChI:InChI=1/C10H22O/c1-3-4-5-6-7-8-9-10(2)11/h10-11H,3-9H2,1-2H3/t10-/m0/s1

Upstream product

• 2404-44-6 1,2-Epoxydecane 
• 64-17-5 ethanol 
• 111-66-0 oct-1-ene 
• 110-05-4 di-tert-butyl peroxide 
• 693-54-9 Decan-2-one 
• 1825-62-3 ethyl trimethylsilyl ether 
• 39563-53-6 2-bromodecane 
• 124-19-6 nonan-1-al 
• 2004-70-8 1-methylbuta-1,3-diene 
• 1184-58-3 dimethylaluminum chloride 
• 124-18-5 decane 
• 71532-52-0 4,7,9-decatrien-2-ol 
• 64154-07-0 2-Decyltosylat 
• 84988-03-4 C₁₆H₂₆Br₂Te 

Downstream Products

• 55193-10-7 Valeriansaeure-2-decanester 
• 53690-77-0 2-Trimethylsilyloxy-decan 
• 55194-65-5 1-methylnonyl stearate 
• 135213-22-8 (3,5-Dinitro-phenyl)-carbamic acid (R)-1-methyl-nonyl ester 
• 135213-23-9 (3,5-Dinitro-phenyl)-carbamic acid (S)-1-methyl-nonyl ester 
• 124-18-5 decane 
• 1002-56-8 2-chlorodecane 
• 20063-97-2 2-decene 
• 4336-70-3 (cyanomethyl)triphenylphosphonium chloride 
• 33758-16-6 (S)-decan-2-ol 
• 1120-06-5 (R)-decan-2-ol 
• 693-54-9 Decan-2-one 
• 92565-91-8 2-Methoxymethoxy-decane 
• 32687-84-6 sulfuric acid mono-(1-methyl-nonylester); sodium-salt 

Relevant academic research and scientific papers

Catalytic enantioselective addition of alkyl grignard reagents to aliphatic aldehydes

Herein, we report an efficient catalytic system for the enantioselective addition of alkyl Grignard reagents to a broad range of aliphatic aldehydes with good yields and enantioselectivities. Remarkably, the challenging methylmagnesium bromide (MeMgBr) can also be added to a variety of aliphatic aldehydes, providing versatile chiral methyl carbinol units with unprecedented yields and enantioselectivities in a simple one-pot procedure under mild conditions. Copyright

Deracemization of secondary alcohols through a concurrent tandem biocatalytic oxidation and reduction

(Chemical Equation Presented) Breaking the mirror: A purified alcohol dehydrogenase (ADH) for stereoselective reduction and whole cells of a microorganism for enantioselective oxidation operated concurrently to effect the stereoinversion of one enantiomer of a racemic secondary alcohol and provide the optically pure alcohol in >99% yield (see scheme). R,R′ = alkyl.

Regio- And stereoselective subterminal hydroxylations of n-decane by fungi in a liquid-liquid interface bioreactor (L-L IBR)

This article may be the first report to describe the excellent regio- and stereoselective subterminal hydroxylations of n-alkane with microorganisms. Approximately 2000 fungal strains were screened for the regioselective hydroxylation of n-decane with a s

Novel Pd/C-catalyzed redox reactions between aliphatic secondary alcohols and ketones under hydrogenation conditions: Application to H-D exchange reaction and the mechanistic study

A liquid-phase redox system between secondary alcohols and ketones is described. Deuteration of either secondary alcohols or ketones using the Pd/C-H2-D2O system gave a mixture of deuterium-labeled secondary alcohols and ketones. The results indicated that the secondary alcohol was oxidized to the corresponding ketone without oxidants under the hydrogenation conditions and the hydrogenation of the aliphatic ketone to the corresponding secondary alcohol simultaneously proceeded. Detailed mechanistic studies on the redox system as well as the H-D exchange reaction are discussed.

A biocatalytic one-pot oxidation/reduction sequence for the deracemisation of a sec-alcohol

Biocatalytic deracemisation via inversion of rac-2-decanol was accomplished by a combined oxidation/reduction sequence using the same 'single' catalyst for both steps. Overall, the (R)-alcohol was inverted to the corresponding (S)-alcohol. Lyophilised cells of various Rhodococci spp. were tested for the unselective oxidation of the racemic sec-alcohol using acetone as the hydrogen acceptor in the first step. For the second step, the stereoselective asymmetric reduction of the corresponding ketone, 2-propanol was employed as the hydrogen donor. Employing lyophilised cells of Rhodococcus sp. CBS 717.73 racemic 2-decanol was transformed to (S)-2-decanol with excellent enantiomeric excess (92% ee) and yield (82% isolated yield) in the combined one-pot oxidation/reduction sequence.

Borane - THF: New solutions with improved thermal properties and stability

A new generation of borane-THF solutions stabilized with 0.005 M of 1,2,2,6,6-pentamethylpiperidine or N-isopropyl-N-methyl-tert-butylamine have been developed. These BTHF solutions show superior stability and reactivity at ambient temperatures when compared to BTHF complex unstabilized or stabilized with 0.005 M NaBH4.

REDUCTION OF ALDEHYDES AND KETONES TO ALCOHOLS WITH HYDROUS ZIRCONIUM OXIDE AND 2-PROPANOL

Reduction of aldehydes and ketones with 2-propanol was found to proceed efficiently in the presence of hydrous zirconium oxide.The reaction is performed simply and the products are easily isolated in the pure state by filtering off the hydrous zirconium oxide, followed by evaporation of solvents.

Highly enantioselective reduction of ketones by chiral diol-modified lithium aluminum hydride reagents

Some readily available chiral diols from indene and d-mannitol were investigated as chiral modifiers in lithium aluminum hydride reduction of ketones, and it was discovered that further modification of these reducing reagents by a simple a-amino alcohol resulted in a remarkable increase in optical yield. Among the investigated chiral modifiers, chiral diol 1 gave the highest enantioselectivities.

Towards the development of a selective ruthenium-catalyzed hydroformylation of olefins

The ruthenium-catalyzed hydroformylation of 1- and 2-octene to give preferentially the corresponding linear aldehyde is reported. The catalyst system comprising of Ru3(CO)12 and an imidazole- substituted monophosphine ligand allows for high chemo- and regioselectivity. The hydroformylation proceeds with unprecedented rates for a ruthenium-based catalyst. Copyright

Molybdenum-catalyzed conversion of diols and biomass-derived polyols to alkenes using isopropyl alcohol as reductant and solvent

Chemical processes capable of reducing the high oxygen content of biomass-derived polyols are in demand in order to produce renewable substitutes for chemicals of fossil origin. Deoxydehydration (DODH) is an attractive reaction that in a single step transforms a vicinal diol into an alkene, but the reaction requires a homogeneous catalyst, a reductant, and a solvent, which are typically expensive, unsustainable, or inefficient. Herein, we present the use of molybdenum(VI)-based compounds, in particular the cheap and commercially available (NH4)6Mo7O24·4H2O, as catalysts for the DODH of vicinal diols in isopropyl alcohol (iPrOH), which serves as both the solvent and reductant. The reaction proceeds at 240-250 °C in a pressurized autoclave, and the alkene yield from simple aliphatic diols can be as high as 77%. The major byproducts are carbonyl compounds - formed by dehydration of the diol - and the alcohols formed by transfer hydrogenation of the carbonyl compounds; the total yield of reduced species (i.e., alkene and alcohols) can be as high as 92%. The DODH of glycerol yields allyl alcohol, which undergoes subsequent Mo-catalyzed deoxygenation to propylene driven by the oxidation of iPrOH; a major byproduct is the homocoupled product 1,5-hexadiene. Further insight in this Mo-catalyzed deoxygenation is gained by an investigation of model compounds: The allylic alcohol 1-hexen-3-ol is deoxygenated to hexene isomers in a yield of 65%, while benzyl alcohol is deoxygenated to toluene in a yield of 93%. The DODH of erythritol yields 39% 2,5-dihydrofuran, while the DODH of the proposed intermediate 1,4-anhydroerythritol yields 75%. The mechanism of the DODH of 1,4-anhydroerythritol was investigated by means of density functional theory (DFT), and the rate-determining step (24.1 kcal/mol) was found to be reduction of a molybdenum(VI) diolate to a molybdenum(IV) diolate.