818-57-5

Basic information

• Product Name: METHYL 4-PENTENOATE
• Synonyms: 4-Pentenoic acid methyl ester, Allylacetic acid methyl ester, Methyl allylacetate;Allylacetic acid methyl ester;Methyl 4-pentenoate >=95.0% (GC);methyl pent-4-enoate
• CAS NO: 818-57-5
• Molecular Formula: C₆H₁₀O₂
• Molecular Weight: 114.14
• Mol File: 818-57-5.mol
• Article Data: 20

Chemical Properties

• Boiling Point: 96.2°C at 760 mmHg
• Flash Point: 29 °C
• Appearance: /
• Density: 0.904g/cm³
• Vapor Pressure: 44mmHg at 25°C
• Refractive Index: n20/D 1.415
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• CAS DataBase Reference: METHYL 4-PENTENOATE(CAS DataBase Reference)
• NIST Chemistry Reference: METHYL 4-PENTENOATE(818-57-5)
• EPA Substance Registry System: METHYL 4-PENTENOATE(818-57-5)

Safety Data

• Hazard Codes: Xi
• Statements: 10-36
• Safety Statements: 26
• RIDADR: UN 3272 3/PG 3
• WGK Germany: 3
• F: 10-23
• Hazardous Substances Data: 818-57-5(Hazardous Substances Data)

Usage

Description

METHYL 4-PENTENOATE is an unsaturated methyl ester that is synthesized through the esterification of 1-pentenoic acid with methanol. It is known for its medium strength odor and is recommended to be smelled in a 10.00% solution or less. METHYL 4-PENTENOATE has unique chemical properties, such as undergoing amidation with formamide via an acetone-initiated photochemical reaction to form a 1:1 adduct. Additionally, it has been reported to participate in the metathesis with different Mo(VI)alkylidene complexes and acts as a chain transfer agent during the polymerization of exo,exo-5,6-bis(methoxymethyl)-7-oxabicyclo[2.2.1]hept-2-ene using RuII(H20)6(tos)2 (tos = p-toluenesulfonate) as a catalyst.

Uses

Used in Chemical Synthesis:
METHYL 4-PENTENOATE is used as a chemical intermediate for the synthesis of various organic compounds. Its reactivity in amidation and metathesis reactions makes it a valuable component in the creation of complex molecules and materials.
Used in Polymerization Processes:
As a chain transfer agent, METHYL 4-PENTENOATE plays a crucial role in the polymerization of specific compounds, such as exo,exo-5,6-bis(methoxymethyl)-7-oxabicyclo[2.2.1]hept-2-ene. Its use in this capacity can influence the molecular weight and architecture of the resulting polymers, which can be tailored for specific applications.
Used in Fragrance Industry:
Given its medium strength odor, METHYL 4-PENTENOATE can be utilized in the fragrance industry as a component in creating various scent profiles. Its unique aroma can contribute to the development of distinct and appealing fragrances for a range of products.
Used in Research and Development:
Due to its unique chemical properties and reactivity, METHYL 4-PENTENOATE is also used in research and development settings. Scientists and chemists can explore its potential applications in new chemical reactions, material development, and other innovative uses that have yet to be discovered.

InChI:InChI=1/C6H10O2/c1-3-4-5-6(7)8-2/h3H,1,4-5H2,2H3

Upstream product

• 74785-94-7 methyl 4-phenylselenylpentanoate 
• 67-56-1 methanol 
• 124-38-9 carbon dioxide 
• 25055-86-1 3-(3-methyl-3H-diazirine-3-yl)propionic acid 
• 25055-91-8 methyl 3-(3-methyldiazirin-3-yl)propanoate 
• 123-76-2 levulinic acid 
• 108-29-2 5-methyl-dihydro-furan-2-one 
• 818-58-6 methyl (E)-pent-3-enoate 
• 106-99-0 buta-1,3-diene 
• 74-85-1 ethene 
• 627-91-8 adipic acid monomethyl ester 
• 5454-83-1 5-bromovaleric acid methyl ester 
• 21035-54-1 crotylamine 
• 201230-82-2 carbon monoxide 

Downstream Products

• 6654-36-0 methyl 6-oxohexanoate 
• 170726-04-2 4-{4-[5-(2-Carboxy-ethyl)-4,5-dihydro-isoxazol-3-yl]-phenoxymethyl}-piperidine-1-carboxylic acid tert-butyl ester 
• 185682-31-9 4-(2-{4-[5-(2-Carboxy-ethyl)-4,5-dihydro-isoxazol-3-yl]-phenoxy}-ethyl)-piperidine-1-carboxylic acid tert-butyl ester 
• 526-55-6 2-(3-indole)-ethanol 
• 106-79-6 dimethyl sebacate 
• 1731-84-6 nonanoic acid methyl ester 
• 7433-56-9 (E)-5-decene 
• 35329-51-2 methyl (E)-non-4-enoate 
• 20731-19-5 methyl non-4-enoate 
• 72719-14-3 5-(3,4-dimethoxybenzyl)dihydrofuran-2(3H)-one 
• 21618-92-8 5-(3′,4′-dihydroxyphenyl)-γ-valerolactone 
• 21876-11-9 6-oxo-6-phenyl-hexanoic acid methyl ester 
• 15591-70-5 methyl 4-(1H-indol-3-yl)butanoate 

Relevant articles and documents

Probing the Mechanism of Photoaffinity Labeling by Dialkyldiazirines through Bioorthogonal Capture of Diazoalkanes

Dialkyldiazirines have emerged as reagents of choice for biological photoaffinity labeling studies. The mechanism of crosslinking has dramatic consequences for biological applications where instantaneous labeling is desirable, as carbene insertions display different chemoselectivity and are much faster than competing mechanisms involving diazo or ylide intermediates. Here, deuterium labeling and diazo compound trapping experiments are employed to demonstrate that both carbene and diazo mechanisms operate in the reactions of a dialkyldiazirine motif that is commonly utilized for biological applications. For the fraction of intermolecular labeling that does involve a carbene mechanism, direct insertion is not necessarily involved, as products derived from a carbonyl ylide are also observed. We demonstrate that a strained cycloalkyne can intercept diazo compound intermediates and serve as a bioorthogonal probe for studying the contribution of the diazonium mechanism of photoaffinity labeling on a model protein under aqueous conditions.

METHOD FOR PRODUCING PENTENOIC ACID ESTER

PROBLEM TO BE SOLVED: To provide a production method capable of obtaining a pentenoic acid ester in high yield even without using a large amount of alcohol while suppressing by-production of an ether. SOLUTION: There is provided a method for producing a pentenoic acid ester, which comprises a step of synthesizing a pentenoic acid ester containing at least one selected from the group consisting of formulas (2), (3) and (4) by bringing γ-valerolactone and an alcohol of the formula (1) into contact with each other in the presence of a catalyst containing X type zeolite. [In the formula (1), R represents an alkyl group having 1 to 6 carbon atoms. In the formulas (2), (3) and (4), R represents an alkyl group having 1 to 6 carbon atoms]. SELECTED DRAWING: None COPYRIGHT: (C)2019,JPOandINPIT

Efficient and sustainable transformation of gamma-valerolactone into nylon monomers

Herein, we reported the facile synthesis of dicarboxylic esters from biomass derived gamma-valerolactone (GVL) aiming for nylon monomer preparation via a novel synthetic route which improved the efficiency and overcame the need for toxic carbon monoxide for the synthesis of dicarboxylic esters from GVL.