4643-27-0

Basic information

• Product Name: 2-OCTEN-4-ONE
• Synonyms: FEMA 3603;2-OCTEN-4-ONE;(2E)-2-Octen-4-one;Oct-2-en-4-one;octene-2-one-4;2-Octen-4-one,97%;2-OCTENE-4-ONE;2-Octen-one
• CAS NO: 4643-27-0
• Molecular Formula: C₈H₁₄O
• Molecular Weight: 126.2
• EINECS: 225-071-7
• Mol File: 4643-27-0.mol

Chemical Properties

• Boiling Point: 65°C/15mm
• Flash Point: 65°C/15mm
• Appearance: /
• Density: 0.850
• Vapor Pressure: 0.897mmHg at 25°C
• Refractive Index: 1.4450
• Storage Temp.: Refrigerator
• Water Solubility: Insoluble in water.
• CAS DataBase Reference: 2-OCTEN-4-ONE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-OCTEN-4-ONE(4643-27-0)
• EPA Substance Registry System: 2-OCTEN-4-ONE(4643-27-0)

Safety Data

• Hazard Codes: Xi
• Statements: 10-36/37/38-36
• Safety Statements: 16-26-36
• RIDADR: 1993
• TSCA: Yes
• HazardClass: 3
• PackingGroup: III
• Hazardous Substances Data: 4643-27-0(Hazardous Substances Data)

Usage

Uses

Used in Flavor and Fragrance Industry:
2-Octen-4-one is used as a flavoring agent for its sweet, fruity, and tropical taste characteristics, particularly resembling pineapple and strawberry. It is valued for its ability to enhance the aroma of various food products, contributing to a more appealing and authentic taste experience.
Used in Perfumery:
In the perfumery industry, 2-Octen-4-one is utilized as a fragrance ingredient due to its unique and pleasant aroma. It helps to create complex and long-lasting scents by adding depth and a tropical nuance to perfume compositions.
Used in Chemical Synthesis:
2-Octen-4-one serves as a reactant in the rhodium-catalyzed asymmetric ring opening of oxabicyclic alkenes with organoboronic acids. This application highlights its utility in the synthesis of complex organic molecules, which can be further used in various chemical and pharmaceutical processes.
Used in Food Industry:
2-Octen-4-one is found in various food products, such as roasted hazelnuts, wheaten bread, and white bread, where it contributes to their distinct and appetizing flavors. Its presence in these foods is a result of natural processes during cooking or baking, enhancing the overall taste and aroma.

Synthesis Reference(s)

Journal of the American Chemical Society, 107, p. 7179, 1985 DOI: 10.1021/ja00310a073The Journal of Organic Chemistry, 52, p. 1885, 1987 DOI: 10.1021/jo00386a001Synthesis, p. 49, 1988

InChI:InChI=1/C8H14O/c1-3-5-7-8(9)6-4-2/h4,6H,3,5,7H2,1-2H3/b6-4+

Upstream product

• 3724-65-0 2-butenoic acid 
• 65807-62-7 oct-1-en-4-one 
• 749860-75-1 1-methylhept-2-ynyl acetate 
• 98-80-6 phenylboronic acid 
• 24388-23-6 2-phenyl-4,4,5,5-tetramethyl-1,3,2-dioxoborole 
• 4406-77-3 2-Phenyl-1,3,2-dioxaborinane 
• 638-29-9 n-valeryl chloride 
• 762-72-1 allyl-trimethyl-silane 
• 67-56-1 methanol 
• 111-67-1 2-octene 

Downstream Products

• 119163-22-3 1-(3-Methyl-oxiranyl)-pentan-1-one 
• 1037806-86-2 C₁₇H₂₆O₃ 
• 1353719-62-6 (S)-5-ethyl-5-((S)-4-oxooctan-2-yl)-2-phenyloxazol-4(5H)-one 
• 1266679-38-2 (5S,6R)-3-butyl-5-methyl-6-(phenylsulfonyl)cyclohex-2-enone 
• 1266679-24-6 R-2-methyl-1,1-bis(phenylsulfonyl)octan-4-one 
• 1226808-32-7 (2R,6R,E)-benzyl 2-(3-oxohept-1-enyl)-6-propylpiperidine-1-carboxylate 
• 1088640-14-5 tert-butyl benzyloxy(4-oxooctan-2-yl)carbamate 

Relevant articles and documents

β-Borylation of conjugated carbonyl compounds with silylborane or bis(pinacolato)diboron catalyzed by Au nanoparticles

Conjugated aldehydes and ketones undergo reaction with Me2PhSiBpin (pin: pinacolato) catalyzed by Au nanoparticles supported on TiO2 forming exclusively the β-borylation products, via the intermediate formation of the labile silaboration adducts. This chemoselectivity pathway is complementary to the so far known analogous reaction catalyzed by other metals, where β-silylation occurs instead. β-Borylation also occurs with pinBBpin under identical reaction conditions in a variety of conjugated carbonyl compounds, including esters and amides which are unreactive in their attempted Au-catalyzed silaboration. This journal is

Environment-friendly method for synthesizing propenyl ketone compound

The invention discloses an environment-friendly method for synthesizing a propenyl ketone compound. The method comprises the following steps: subjecting an aldehyde compound and allyl bromide to a Barbier reaction in the presence of metal powder, so as to obtain an allyl alcohol compound; and subjecting the allyl alcohol compound to a structural isomerization reaction in the presence of a catalyst, thereby obtaining the propenyl ketone compound. The method disclosed by the invention has the advantages of short synthesis route, mild reaction conditions, simplicity in operation, readily available raw materials, and the like and has relatively high academic research value and market economy significance.

A mild isomerization reaction for β,γ-unsaturated ketone to α,β-unsaturated ketone

A series of β,γ-unsaturated ketones were isomerized to their corresponding α,β-unsaturated ketones by the introduction of DABCO in iPrOH at room temperature. The endo-cyclic double bond (β,γ-position) on ketone was rearranged to exo-cyclic double bond (α,β-position) under the reaction conditions.

Synthesis of β-Amino and β-Methoxy Ketones by Lewis Acids Promoted β-Substitution Reactions of βγ,-Unsaturated Ketones

A reaction mixture of β,γ-unsaturated ketone and BF 3·OEt2 in CH3OH was stirred at room temperature and β-methoxy ketone was produced in high yield. The β-amino ketone was obtained as the major product from a reaction mixture of β,γ-unsaturated ketone, AlCl3 and Ts-NH2 in CH2Cl2 at room temperature. This Lewis acid promoted β-substitution reaction mechanism was proposed as that the process occurred via in situ isomerization of β,γ-unsaturated ketone to α,β-unsaturated ketone followed by the 1,4-addition reaction.

Serine carbonates

Serine carbonates of formula I are precursors for organoleptic compounds, masking agents and antimicrobial agents. Further they are alternative substrates for malodor producing enzymes. The symbols in formula I are defined in claim 1.

InBr3-Catalyzed Alkynylation and Allylation of Acid Chlorides: A Facile Synthesis of Alkynyl and Allyl Ketones

Alkynylsilanes and allyltrimethylsilane undergo smooth coupling with acid chlorides in the presence of 5 mol% of indium tribromide under mild conditions to afford the corresponding α,β-acetylenic ketones and β,γ-unsaturated ketones in excellent yields in a short reaction time with high selectivity.

Compounds having protected hydroxy groups

The present invention relates to compounds with protected hydroxy groups of formula (I) These compounds are precursors for organoleptic agents, such as fragrances, and masking agents and for antimicrobial agents. When activated, the compounds of formula (I) are cleaved and form one or more organoleptic and/or antimicrobial compounds.

Compounds having protected hydroxy groups

The present invention relates to compounds with protected hydroxy groups of formula (I) These compounds are precursors for organoleptic agents, such as fragrances, and masking agents and for antimicrobial agents. When activated, the compounds of formula (I) are cleaved and form one or more organoleptic and/or antimicrobial compounds.

High turnover numbers for the catalytic selective epoxidation of alkenes with 1 atm of molecular oxygen

The diiron-substituted silicotungstate γ-SiW10{Fe3+(OH2}2O 386- (schematically shown) is an effective catalyst for the oxygenation of alkenes in homogeneous reaction media with 1 atm of molecular oxygen. For example, a selectivity for cyclooctene oxide of 98% and a turnover number of 10000 were achieved in the epoxidation of cyclooctene. The catalyst is stable under the reaction conditions, and its ability to use molecular oxygen raises the prospect of using it in industrial epoxidation processes.