2396-77-2

Basic information

• Product Name: Methyl 2-hexenoate
• Synonyms: FEMA 2709;METHYL TRANS-2-HEXENOATE;METHYL T2 HEXENOATE;METHYL 2-HEXENOATE;Methyl hex-2-enoate;2-Hexenoic acid methyl;Methyl-2-Furaote
• CAS NO: 2396-77-2
• Molecular Formula: C₇H₁₂O₂
• Molecular Weight: 128.17
• EINECS: 607-296-6
• Mol File: 2396-77-2.mol
• Article Data: 2

Chemical Properties

• Melting Point: 32 °C
• Boiling Point: 149.3 °C at 760 mmHg
• Flash Point: 45.4 °C
• Appearance: /
• Density: 0.908 g/cm³
• Vapor Pressure: 4.06mmHg at 25°C
• Refractive Index: 1.427
• Storage Temp.: 2-8°C
• CAS DataBase Reference: Methyl 2-hexenoate(CAS DataBase Reference)
• NIST Chemistry Reference: Methyl 2-hexenoate(2396-77-2)
• EPA Substance Registry System: Methyl 2-hexenoate(2396-77-2)

Safety Data

• Hazardous Substances Data: 2396-77-2(Hazardous Substances Data)

Usage

Description

Methyl 2-hexenoate is an organic compound with a green, musty, earthy, sweet, and fruity odor, along with a very powerful, sharp, green-fruity flavor. It can be synthesized by various methods, such as boiling the corresponding acid with methanol in the presence of concentrated H2SO4 in chloroform and subsequent elimination of water from the vapors using MgSO4, or from 3-chloropropionic acid methyl ester and anhydrous sodium acetate in acetic acid.

Uses

1. Used in Flavor Industry:
Methyl 2-hexenoate is used as a flavoring agent for its unique green-fruity flavor and aroma. It is particularly suitable for enhancing the taste and smell of various food products, making it a valuable addition to the flavor industry.
2. Used in Fragrance Industry:
Due to its green, musty, earthy, sweet, and fruity odor, Methyl 2-hexenoate is also used as a component in the fragrance industry. It can be incorporated into perfumes, colognes, and other scented products to provide a distinct and appealing fragrance.
3. Used in Chemical Synthesis:
Methyl 2-hexenoate can be utilized as a starting material or intermediate in the synthesis of various chemicals and compounds. Its unique chemical properties make it a versatile building block for creating new molecules with potential applications in different industries.
4. Used in Research and Development:
The distinct chemical properties and odor profile of Methyl 2-hexenoate make it an interesting compound for research and development purposes. Scientists and researchers can study its properties and potential applications in various fields, such as pharmaceuticals, materials science, and environmental science.

Preparation

By boiling the corresponding acid with methanol in the presence of concentrated H2SO4 in chloroform and subsequent elimination of water from the vapors using MgSO4; also from 3-chloropropionic acid methyl ester and anhydrous sodium acetate in acetic acid

InChI:InChI=1/C7H12O2/c1-3-4-5-6-7(8)9-2/h5-6H,3-4H2,1-2H3

Upstream product

• 592-41-6 1-hexene 
• 2396-78-3 methyl 3-hexenoate 

Downstream Products

• 133269-38-2 (2R,3R)-3-Propyl-oxirane-2-carboxylic acid methyl ester 
• 30414-54-1 methyl 3-oxohexanoate 
• 21188-58-9 methyl 3-hydroxyhexanoate 
• 68756-64-9 2-hydroxyhexanoic acid methyl ester 
• 1425667-40-8 (R,E)-ethyl [8-(4-nitrophenyl)-6-oxo-oct-7-en-4-yl]carbamate 
• 1425667-38-4 (R,E)-ethyl [6-oxo-8-phenyl-oct-7-en-4-yl]carbamate 

Relevant articles and documents

Linear Selective Isomerization/Hydroformylation of Unsaturated Fatty Acid Methyl Esters: A Bimetallic Approach

Herein, we report about the development of an isomerization/hydroformylation tandem reaction to selectively convert fatty acid methyl esters into asymmetric α,ω-functionalized aldehyde esters. An orthogonal tandem catalytic system consisting of a palladium-based isomerization catalyst and a rhodium-based hydroformylation catalyst was developed, using methyl 3-hexenoate as a model substrate. Using this catalyst, high yields (81% at 99% conversion) and regioselectivities (l/b-ratio of 98/2) toward the desired terminal hydroformylation product are obtained in the conversion of methyl 3-hexenoate under mild conditions. Ethyl 4-decenoate was subsequently applied as a second model substrate to identify challenges associated with the longer chain length of the unsaturated ester. Finally, methyl oleate was converted using the developed catalyst system. High aldehyde yields of 74% (at 99% conversion) with an l/b-ratio of 91/9 are obtained.