50373-56-3

Basic information

• Product Name: 3-octyl acetate
• Synonyms: 3-Octanol, 3-acetate; 1-Ethyl hexyl acetate; 3-Octanol acetate; Amyl ethyl carbinyl acetate; EINECS 225-471-1; FEMA No. 3583; Oct-3-yl ethanoate; 3-Octanol, acetate
• CAS NO: 50373-56-3
• Molecular Formula: C₁₀H₂₀O₂
• Molecular Weight: 172.26
• EINECS: 225-471-1
• Mol File: 50373-56-3.mol

Chemical Properties

• CAS DataBase Reference: 3-octyl acetate(CAS DataBase Reference)
• NIST Chemistry Reference: 3-octyl acetate(50373-56-3)
• EPA Substance Registry System: 3-octyl acetate(50373-56-3)

Safety Data

• Hazardous Substances Data: 50373-56-3(Hazardous Substances Data)

Upstream product

• 343940-00-1 C₁₀H₂₀N₂O₂ 
• 107-92-6 butyric acid 
• 111-86-4 n-Octylamine 
• 64-19-7 acetic acid 
• 111-65-9 octane 
• 546-67-8 lead(IV) tetraacetate 
• 106-99-0 buta-1,3-diene 
• 557-20-0 diethylzinc 
• 66-25-1 hexanal 
• 108-22-5 Isopropenyl acetate 
• 106-68-3 3-octanone 
• 589-98-0 rac-3-octanol 
• 108-05-4 vinyl acetate 
• 79-03-8 propionyl chloride 

Relevant articles and documents

Consecutive addition esterification and hydrolysis of cyclic olefins catalyzed by multi-SO3H functionalized multi heteropolyanion-based ionic hybrids undersolvent-free conditions

An efficient protocol for the synthesis of cycloalkyl carboxylates and alcohols from cyclic olefins is described. The cyclic olefins were converted to corresponding target molecules under solvent-free conditions catalyzed by two novel multi-SO3H functionalized multi heteropolyanion-based ionic hybrids through one-pot consecutive addition esterification and hydrolysis reactions. This approach has several advantages, including high yield, simple workup and simple purification.

Fractional distribution of graphene oxide and its potential as an efficient and reusable solid catalyst for esterification reactions

Graphene oxide (GrO) prepared by the Hummers method was separated into three different fractions (GrO5000, GrO2000, and GrOres) on the basis of their dispersion stability in the water. Infrared, nuclear magnetic resonance, X-ray photoelectron spectroscopy, and elemental analyses revealed that GrO5000 possesses a high degree of oxygen functionalities including phenolic, carboxylic, and -OSO2H groups, compared with the other fractions. The GrO5000 was found to be a highly efficient and reusable solid catalyst for the esterification of various carboxylic acids with a variety of alcohols to furnish corresponding esters in high to excellent yields. The catalytic activity of the GrO5000 was attributed to the ability of highly polar GrO5000 scaffold to adsorb/attract reactants, where the acid functionalities of GrO5000 facilitated the esterification process efficiently. The chemical and structural features of GrO5000 were discussed to understand the improved catalytic activity compared with GrO2000 and conventional solid acid catalysts.

Stabilization of long-chain intermediates in solution. octyl radicals and cations

The rearrangements of 1-octyl, 1-decyl and 1-tridecyl intermediates obtained from thermal lead(IV) acetate (LTA) decarboxylation of nonanoic, undecanoic and tetradecanoic acid were investigated experimentally through analysis and distribution of the products. The relationships between 1,5-, 1,6- and possibly existing 1,7-homolytic hydrogen transfer in 1-octyl-radical, as well as successive 1,2-hydride shift in corresponding cation have been computed via Monte-Carlo method. Taking into account that ratios of 1,5-/1,6-homolytic rearrangements in 1-octyl- and 1-tridecyl radical are approximately the same, the simulation shows very low involvement of 1,7-hydrogen rearrangement (1,5-/1,6-/1,7-hydrogen rearrangement = 85:31:1) in 1-octyl radical.

A stereoselective inverting sec -alkylsulfatase for the deracemization of sec -alcohols

A metallo-β-lactamase-type alkylsulfatase was found to catalyze the enantioselective hydrolysis of sec-alkylsulfates with strict inversion of configuration. This catalytic event, which does not have an analog in chemocatalysis, yields homochiral (S)-configurated alcohols and nonreacted sulfate esters. The latter could be converted into (S)-sec-alcohols as the sole product in up to >99% ee via a chemoenzymatic deracemization protocol on a preparative scale.

Iron-catalysed green synthesis of carboxylic esters by the intermolecular addition of carboxylic acids to alkenes

Iron triflate, in situ-formed from FeCl3 and triflic acid, or FeCl3 and silver triflate efficiently catalyse the intermolecular addition of carboxylic acids to various alkenes to yield carboxylic esters; the reaction is applicable to the synthesis of unstable esters, such as acrylates. The Royal Society of Chemistry.

An algorithm for the deconvolution of mass spectrosopic patterns in isotope labeling studies. Evaluation for the hydrogen-deuterium exchange reaction in ketones

(Graph Presented) An easy to use computerized algorithm for the determination of the amount of each labeled species differing in the number of incorporated isotope labels based on mass spectroscopic data is described and evaluated. Employing this algorithm, the microwave-assisted synthesis of various α-labeled deuterium ketones via hydrogen-deuterium exchange with deuterium oxide was optimized with respect to time, temperature, and degree of labeling. For thermally stable ketones the exchange of α-protons was achieved at 180°C within 40-200 min. Compared to reflux conditions, the microwave-assisted protocol led to a reduction of the required reaction time from 75-94 h to 40-200 min. The α-labeled deuterium ketones were reduced by biocatalytic hydrogen transfer to the corresponding enantiopure chiral alcohols and the deconvolution algorithm validated by regression analysis of a mixture of labeled and unlabeled ketones/alcohols.

Lipase/aluminum-catalyzed dynamic kinetic resolution of secondary alcohols

(Chemical Equation Presented) Racemization wanted: The dynamic kinetic resolution of secondary alcohols can be achieved by a simple and readily available catalyst system. Substrate racemization is effected at room temperature by a combination of (racemic) 1,1′-bi-2-naphthol (binol) or 2,2′-biphenol with AIMe3, and a lipase performs enantiospecific acylation (see scheme).

Practical synthesis of (S)-(+)-3-octanol by lipase-catalyzed enantioselective acetylation

(S)-(+)-3-Octanol (S)-1 was prepared in high enantiomeric excess through catalyzed acetylation of racemic alcohol 1 by using lipase from Candida antarctica (Chirazyme L-2) in the presence of vinyl acetate in toluene at 30°C. The pure (S)-1 was obtained in 73% isolated yield with 62% conversion. Moreover, acetate (R)-2 was converted to (S)-1 via mesylation and followed by hydrolysis using sodium bicarbonate solution in 44% yield. Copyright Taylor & Francis Group, LLC.

Catalysts for asymmetric addition of organozinc regents to aldehydes and method for preparation

Chiral aminoalcohol catalysts and methods for their preparation are provided. The first catalyst is prepared via selective hydrogenation of one of two benzene rings in a precursor. The aminoalcohol promotes the asymmetric addition of organozinc reagents to aldehydes to afford optically active alcohols or their esters. The second catalyst is prepared by selective dialkylation of 3-exo-aminoisoborneol with a 2-haloethyl ether. The aminoalcohol promotes the addition of organozinc reagents to aliphatic aldehydes containing a β-branch with greatly enhanced enantioselectivity relative to DAIB.

An amino alcohol ligand for highly enantioselective addition of organozinc reagents to aldehydes: Serendipity rules

(matrix presented) Amino alcohol 4 (or its enantiomer) is prepared in two simple steps. Commercial (1R,2S)-2-amino-1,2-diphenylethanol is dialkylated with bis(2-bromoethyl) ether. Subsequent hydrogenation over 5% Rh on alumina in the presence of morpholine unexpectedly stops at the hexahydro derivative 4. Amino alcohol 4 promotes the enantioselective addition of diethylzinc to aldehydes at room temperature in up to 99% enantiomeric excess.