1968-40-7

Basic information

• Product Name: ETHYL 4-PENTENOATE
• Synonyms: ETHYL PENT-4-ENOATE;ETHYL 4-PENTENOATE;4-Ethoxycarbonylbut-1-ene;Ethyl pent-4-enoate, (Ethyl allylacetate;Ethyl allylacetate~4-Pentenoic acid ethyl ester;Pent-4-enoic aci;ethyl pent-4-en-1-oate;Ethyl pent-4-enoate, 98+%
• CAS NO: 1968-40-7
• Molecular Formula: C₇H₁₂O₂
• Molecular Weight: 128.17
• EINECS: 217-818-0
• Mol File: 1968-40-7.mol
• Article Data: 36

Chemical Properties

• Boiling Point: 40°C 25mm
• Flash Point: 37°C
• Appearance: /
• Density: 0,9 g/cm3
• Vapor Pressure: 13.7mmHg at 25°C
• Refractive Index: 1.4170
• Water Solubility: Miscible with alcohol. Immiscible with water.
• BRN: 1751643
• CAS DataBase Reference: ETHYL 4-PENTENOATE(CAS DataBase Reference)
• NIST Chemistry Reference: ETHYL 4-PENTENOATE(1968-40-7)
• EPA Substance Registry System: ETHYL 4-PENTENOATE(1968-40-7)

Safety Data

• Statements: 10-36
• Safety Statements: 16-26-60-43-33-7
• RIDADR: 3272
• TSCA: Yes
• HazardClass: 3
• PackingGroup: III
• Hazardous Substances Data: 1968-40-7(Hazardous Substances Data)

Usage

Chemical Properties

Colorless liquid; green fruity aroma.

Uses

Ethyl 4-pentenoate is found in leaf oil of Prunus phaeosticta phaeosticta from Taiwan. It is also used in the preparation of 5-iodomethyl-dihydro-furan-2-one by reacting with iodine.

Aroma threshold values

Ethereal type, medium strength odor.

Synthesis Reference(s)

The Journal of Organic Chemistry, 40, p. 2556, 1975 DOI: 10.1021/jo00905a041Synthetic Communications, 16, p. 1529, 1986 DOI: 10.1080/00397918608056406

InChI:InChI=1/C7H12O2/c1-3-5-6-7(8)9-4-2/h3H,1,4-6H2,2H3

Upstream product

• 141-52-6 sodium ethanolate 
• 610-89-9 2-acetyl-pent-4-enoic acid ethyl ester 
• 74-86-2 acetylene 
• 141-78-6 ethyl acetate 
• 623-73-4 diazoacetic acid ethyl ester 
• 24850-33-7 allyltributylstanane 
• 2678-54-8 ketene diethyl acetal 
• 106-95-6 allyl bromide 
• 591-80-0 pent-4-enoic acid 
• 64-17-5 ethanol 
• 50-00-0 formaldehyd 
• 1173997-10-8 ethyl 4-((1-phenyl-1H-tetrazol-5-yl)sulfonyl)butanoate 
• 623-48-3 ethyl iodoacetae 
• 78-39-7 Triethyl orthoacetate 

Downstream Products

• 16744-89-1 2-methylhex-5-en-2-ol 
• 132106-12-8 4-(4-isopropyl-phenyl)-valeric acid ethyl ester 
• 857482-81-6 4-m-tolyl-valeric acid ethyl ester 
• 14660-52-7 ethyl 5-bromovalerate 
• 36873-45-7 ethyl 2-formylpent-4-enoate 
• 2100-17-6 4-pentenal 
• 923002-01-1 1-(2,5-dimethylphenylsulfonyl)-5-hexen-2-one 
• 909565-10-2 1-(2,4-dimethylphenylsulfonyl)-5-hexen-2-one 
• 923001-98-3 1-(3-methylphenylsulfonyl)-5-hexen-2-one 
• 923002-03-3 1-(3,4-dimethylphenylsulfonyl)-5-hexen-2-one 
• 923001-97-2 1-(2-methylphenylsulfonyl)-5-hexen-2-one 
• 923002-04-4 1-(3,5-dimethylphenylsulfonyl)-5-hexen-2-one 
• 923002-02-2 1-(2,6-dimethylphenylsulfonyl)hex-5-en-2-one 
• 923002-00-0 1-(2,3-dimethylphenylsulfonyl)-5-hexen-2-one 

Relevant articles and documents

Coupling Reactions of α-Halo Esters with Allyl- and Acetonyltin Reagents. An Improved Synthesis of α-Acetonyl-γ-butyrolactone

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β-Lactam synthesis using organoiron intermediates. Preparation of 3-carbomethoxycarbapenam

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Allyltris(trimethylsilyl)silane as Radical Allylating Agent for Organic Halides

Reaction of allyltris(trimethylsilyl)silane with organic halides under the free radical conditions resulted in allylation of the halides in moderate to good yields.The presence of three trimethylsilyl groups on the silicon could enhance the homolytic dissociation of a Si-C bond in the β-silylalkyl radical.

A New Route to the Prostaglandin Skeleton via Radical Alkylation. Synthesis of 6-Oxoprostaglandin E1

A new, mild, and efficient method for the construction of the prostanoid skeleton involving cuprate addition to α-(phenylseleno)cyclopentenones followed by radical-based coupling to the resulting products with allylstannane derivatives is described.The method is applied to the synthesis of 6-oxoprostaglandin E1, a biologically active and naturally occurring compound.

Diastereoselective and Stereodivergent Synthesis of 2-Cinnamylpyrrolines Enabled by Photoredox-Catalyzed Iminoalkenylation of Alkenes

A photoredox-catalyzed iminoalkenylation of γ-alkenyl O-acyl oximes has been developed. Readily available alkenylboronic acids serve as alkenylation reagents, leading to densely functionalized pyrrolines. Both (E)- and (Z)-cinnamylpyrrolines are accessible depending on the reaction solvent. In dichloromethane, (E)-cinnamylpyrrolines are produced through a photoredox-mediated single-electron-transfer process. In tetrahydrofuran, (Z)-cinnamylpyrrolines are generated by photocatalytic contra-thermodynamic E-to-Z isomerization of (E)-cinnamylpyrrolines though an energy-transfer pathway. Two stereocenters are established with complete diastereoselectivity and only one diastereomer is isolated.

Palladium-Catalyzed Electrochemical Allylic Alkylation between Alkyl and Allylic Halides in Aqueous Solution

A new route for the direct cross-coupling of alkyl and allylic halides using electrochemical technique has been developed in aqueous media under air. Catalyzed by Pd(OAc)2, the Zn-mediated allylic alkylations proceed smoothly between a full range of alkyl halides (primary, secondary, and tertiary) and substituted allylic halides. Protection-deprotection of acidic hydrogen in the substrates is avoided.