3102-33-8

Basic information

• Product Name: trans-3-Penten-2-one
• Synonyms: trans-3-Penten-2-one;3-PENTEN-2-ONE,(E)-;(E)-3-Penten-2-one;3-Penten-2-one, (3E)-;4-methyl-3-buten-2-one
• CAS NO: 3102-33-8
• Molecular Formula: C₅H₈O
• Molecular Weight: 84.11642
• Mol File: 3102-33-8.mol
• Article Data: 10

Chemical Properties

• Melting Point: -54.55°C
• Boiling Point: 109.43°C (estimate)
• Flash Point: 19.8°C
• Appearance: /
• Density: 0.8624
• Refractive Index: 1.4350
• CAS DataBase Reference: trans-3-Penten-2-one(CAS DataBase Reference)
• NIST Chemistry Reference: trans-3-Penten-2-one(3102-33-8)
• EPA Substance Registry System: trans-3-Penten-2-one(3102-33-8)

Safety Data

• Hazardous Substances Data: 3102-33-8(Hazardous Substances Data)

Usage

General Description

Trans-3-penten-2-one, also known as 3-penten-2-one, is an organic compound with the molecular formula C5H8O. It is a colorless liquid with a sharp, fruity odor and is commonly used as a flavoring agent in food and beverages. Trans-3-penten-2-one is also used in the production of perfumes and fragrances due to its pleasant aroma. It is a key intermediate in the synthesis of various organic compounds and is commonly employed in the pharmaceutical and cosmetic industries. Additionally, trans-3-penten-2-one exhibits moderate toxicity and irritation to the eyes and respiratory system, and proper handling and protective measures should be taken when working with this chemical.

Upstream product

• 67-56-1 methanol 
• 78-79-5 isoprene 
• 1825-14-5 pentane-1,3-diol 
• 4401-12-1 trans-1-(3-methyloxiranyl)-ethanone 
• 111957-98-3 Pent-4-en-2-ol 
• 1569-50-2 3-penten-2-ol 
• 872427-96-8 (+/-)-(E)-1-hydroxy-1-(4-methoxyphenyl)hex-4-en-3-one 
• 625-35-4 trans-chrotonyl chloride 
• 917-65-7 methylaluminum dichloride 
• 57362-50-2 4-Hydroxy-1-(triphenyl-λ⁵-phosphanylidene)-pentan-2-one 
• 1487-15-6 2-Methyl-4,5-dihydrofuran 
• 27611-32-1 4-(3-nitro-benzenesulfonyloxy)-pent-1-yne 

Downstream Products

• 104115-29-9 4-[1,3]Dithian-2-yl-pentan-2-one 
• 104115-37-9 Trimethyl-((1Z,3E)-1-phenylsulfanyl-penta-1,3-dienyl)-silane 
• 71097-53-5 2-(1-methyl-3-oxobutyl)-5-methylfuran 
• 106368-54-1 2-(1-propenyl)-1-cyclopentanone 
• 83542-41-0 (E)-3-methyl-5-phenyl-4-pentene-2-one 
• 72189-24-3 3-methyl-4-hexene-2-one 
• 69657-28-9 4-(4-methoxyphenyl)-2-pentanone 
• 17913-10-9 1-methyl-3-phenyl-butanal 
• 451-25-2 4-(4-methylphenyl)pentan-2-one 
• 74395-07-6 4-(4-chlorophenyl)pentane-2-one 
• 26386-83-4 4-Chlor-pentan-2-on 
• 143392-15-8 (3R,4S)-4-Acetyl-3-methyl-cyclohexanone 

Relevant articles and documents

Isomerization of 2-Methyl-4,5-dihydrofuran. Studies with a Single-Pulse Shock Tube

The isomerization of 2-methyl-4,5-dihydrofuran was studied behind reflected shock waves in a pressurized driver single-pulse shock tube over the temperature range 805-1030 K and densities of approximately ca 3*10-5 mol/cm3.Two isomerization products, acetylcyclopropane and 3-penten-2-one, are obtained in the isomerization.Acetylcyclopropane is formed in an irreversible process from 2-methyl-4,5-dihydrofuran.It further isomerizes, at higher temperatures, to cis- and trans-3-penten-2-one.At high temperatures where the conversion of 2-methyl-4,5-dihydrofuran is high, the main source for 3-penten-2-one is acetylcyclopropane.At lower temperatures 3-penten-2-one is formed mainly by a direct isomerization of 2-methyl-4,5-dihydrofuran.A small concentration of decomposition products, mainly methane and ethane, are also found in shock mixtures of 2-methyl-4,5-dihydrofuran, particularly at high temperatures.The Arrhenius relations for the tree aforementioned processes are as follows: 2-methyl-4,5-dihydrofuran -> acetylcyclopropane, k1=1015.4 exp(-56.8*103/RT) s-1; 2-methyl-4,5-dihydrofuran -> 3-penten 2-one, k2=1015.7 exp(-63.6*103/RT) s-1; acetylcyclopropane -> 3-penten-2-one, k3=1014.4 exp(-58.3*103/RT) s-1, where R is expressed in units of cal/(K mol).

A catalytic asymmetric bioorganic route to enantioenriched tetrahydro- and dihydropyranones

A conceptually novel approach to hetero Diels-Alder adducts of carbonyl compounds is described using as the key steps an antibody-mediated kinetic resolution of hydroxyenones followed by a ring-closure process. Various β-hydroxyenones proved to be very good substrates for antibodies 84G3- and 93F3-catalyzed retro-aldol reactions, allowing the preparation of highly enantiomerically enriched (up to 99% ee) precursors of pyranones. An attractive feature of this methodology is the possibility to convert these acyclicenantioenriched β-hydroxyenones into tetrahydropyranones by a conventional Michael-type addition procedure or into the corresponding dihydropyranones using an alternative palladium-catalyzed oxidative ring closure. For the palladium-mediated cyclization, a biphasic system has been implemented that allows the direct preparation of enantiopure dihydropyranones from the corresponding racemic aldol precursors using a sequential antibody-resolution/palladium-cyclization strategy, without isolation of the intermediate enantioenriched hydroxyenones. This bioorganic route is best applied to the preparation of hetero Diels-Alder adducts otherwise derived from less nucleophilic dienes and unactivated dienophiles.

Lewis Acid-Promoted Coupling Reactions of Acid Chlorides with Organoaluminum and Organozinc Reagents

An efficient synthesis of α,α-unsaturated ketones by the reaction of acid chlorides with trialkyl-aluminum (1/3 mole equiv) in the presence of AlCl3 (1 mol equiv) is described. Dialkylzincs were also useful and are easier to prepare than trialkylaluminum. Reaction of RCOCl with R′AlCl3 or R′2AlCl gave R′COR, without AlCl3, in high yield.