18402-82-9

Basic information

• Product Name: 3-OCTEN-2-ONE
• Synonyms: 3-OCTEN-2-ONE;FEMA 3416;TRANS-3-OCTEN-2-ONE;(E)-Oct-3-en-2-one;3-Octen-2-one, (E)-;TRANS TRANS - 2 4-UNDECADIENAL 90+%;(E)-1-Hexenylmethyl ketone;(E)-3-Octen-2-one
• CAS NO: 18402-82-9
• Molecular Formula: C₈H₁₄O
• Molecular Weight: 126.2
• EINECS: 216-793-3
• Product Categories: Alphabetical Listings;Flavors and Fragrances;O-P
• Mol File: 18402-82-9.mol
• Article Data: 33

Chemical Properties

• Boiling Point: 100 °C18 mm Hg(lit.)
• Flash Point: 130 °F
• Appearance: /
• Density: 0.857 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.897mmHg at 25°C
• Refractive Index: n20/D 1.448(lit.)
• CAS DataBase Reference: 3-OCTEN-2-ONE(CAS DataBase Reference)
• NIST Chemistry Reference: 3-OCTEN-2-ONE(18402-82-9)
• EPA Substance Registry System: 3-OCTEN-2-ONE(18402-82-9)

Safety Data

• Statements: 10
• Safety Statements: 16
• RIDADR: UN 1224 3/PG 3
• WGK Germany: 3
• Hazardous Substances Data: 18402-82-9(Hazardous Substances Data)

Usage

General Description

3-Octen-2-one, also known as ethyl vinyl ketone, is a chemical compound with the molecular formula C8H14O. It is a colorless liquid with a strong, fruity odor and is commonly used as a flavor and fragrance ingredient. It is naturally present in various fruits and has been identified as one of the odor-active components in the aroma of several types of wine. In addition to its use in the food and beverage industry, 3-octen-2-one is also used in organic synthesis and as a solvent in chemical reactions. It is considered to be a volatile organic compound and may have potential health hazards if inhaled or ingested in large quantities.

InChI:InChI=1/C8H14O/c1-3-4-5-6-7-8(2)9/h6-7H,3-5H2,1-2H3/b7-6+

Upstream product

• 57648-55-2 (E)-oct-3-en-2-ol 
• 1119-58-0 oct-3-yn-2-one 
• 109-72-8 n-butyllithium 
• 1423-60-5 methyl ethynyl ketone 
• 16029-98-4 trimethylsilyl iodide 
• 51731-17-0 trans-4-methoxy-3-buten-2-one 
• 41746-22-9 oct-3-yn-2-ol 
• 110-62-3 pentanal 
• 598-31-2 1-bromoacetone 
• 67-64-1 acetone 
• 592-41-6 1-hexene 
• 78-94-4 methyl vinyl ketone 
• 2351-88-4 ethyl 2-heptenoate 
• 75-16-1 methylmagnesium bromide 

Downstream Products

• 420849-79-2 (2R,3S)-1-(3-butyl-oxiranyl)-ethanone 
• 420849-79-2 (2S,3R)-1-(3-butyl-oxiranyl)-ethanone 
• 1449281-65-5 (E)-4-methyl-N-(2-oxooct-3-en-1-yl)-N-tosylbenzenesulfonamide 
• 51134-60-2 3-bromooctan-2-one 
• 821-55-6 2-Nonanone 
• 21454-42-2 oct-3t-en-2-one-(2,4-dinitro-phenylhydrazone) 

Relevant articles and documents

Low catalyst loading in the cross metathesis of olefins with methyl vinyl ketone

An olefin-metathesis catalyst featuring a 1,3-bis(2,6-diisopropylphenyl)-4, 5-dihydroimidazol-2-ylidene N-heterocyclic carbene and an ester-chelating carbene ligand efficiently promoted the cross metathesis of olefins with 3-buten-2-one in the presence of copper iodide as cocatalyst. At optimized reaction conditions a 10-20 times lower catalyst loading compared to the state of the art could be achieved. Georg Thieme Verlag Stuttgart New York.

A rapid and simple cleanup procedure for metathesis reactions

Figure presented A new method for easy removal of ruthenium from metathesis reactions by using a polar isocyanide is reported. This protocol removed most ruthenium byproducts from a variety of synthetically useful metatheses. Moreover, the isocyanide-promoted carbene insertion results in rapid destruction of carbene reactivity, demonstrated in the commonly used first- and second-generation Grubbs' carbenes.

Biocatalytic Enantioselective Oxidation of Sec-Allylic Alcohols with Flavin-Dependent Oxidases

The oxidation of allylic alcohols is challenging to perform in a chemo- as well as stereo-selective fashion at the expense of molecular oxygen using conventional chemical protocols. Here, we report the identification of a library of flavin-dependent oxidases including variants of the berberine bridge enzyme (BBE) analogue from Arabidopsis thaliana (AtBBE15) and the 5-(hydroxymethyl)furfural oxidase (HMFO) and its variants (V465T, V465S, V465T/W466H and V367R/W466F) for the enantioselective oxidation of sec-allylic alcohols. While primary and benzylic alcohols as well as certain sugars are well known to be transformed by flavin-dependent oxidases, sec-allylic alcohols have not been studied yet except in a single report. The model substrates investigated were oxidized enantioselectively in a kinetic resolution with an E-value of up to >200. For instance HMFO V465S/T oxidized the (S)-enantiomer of (E)-oct-3-en-2-ol (1 a) and (E)-4-phenylbut-3-en-2-ol with E>200 giving the remaining (R)-alcohol with ee>99% at 50% conversion. The enantioselectivity could be decreased if required by medium engineering by the addition of cosolvents (e. g. dimethyl sulfoxide).

Iron-catalyzed aerobic oxidation of allylic alcohols: The issue of C=C bond isomerization

An aerobic oxidation of allylic alcohols using Fe(NO3) 3·9H2O/TEMPO/NaCl as catalysts under atmospheric pressure of oxygen at room temperature was developed. This eco-friendly and mild protocol provides a convenient pathway to the synthesis of stereodefined α,β-unsaturated enals or enones with the retention of the C-C double-bond configuration.