Methyl 4-pentenoate

Base Information

• Chemical Name: Methyl 4-pentenoate
• CAS No.: 818-57-5
• Molecular Formula: C6H10O2
• Molecular Weight: 114.144
• Hs Code.: 2916199590
• European Community (EC) Number: 627-166-2
• UNII: G48IPZ8O71
• DSSTox Substance ID: DTXSID60231373
• Nikkaji Number: J436.466J
• Wikidata: Q27278732
• Metabolomics Workbench ID: 48991
• Mol file: 818-57-5.mol

Synonyms:methyl pent-4-enoate;Methyl 4-pentenoate;818-57-5;4-Pentenoic acid, methyl ester;Methyl allylacetate;4-Pentenoic acid methyl ester;Allylacetic acid methyl ester;Methyl 4-pentenoate [FHFI];FEMA No. 4353;UNII-G48IPZ8O71;G48IPZ8O71;methyl-4-pentenoate;methylpent-4-enoate;Methyl 4-pentenoate #;SCHEMBL514725;pent-4-enoic acid methyl ester;SCHEMBL13123544;DTXSID60231373;CHEBI:173394;LMFA07010954;AKOS017326482;AB16906;AT23749;Methyl 4-pentenoate, >=95.0% (GC);BS-23625;CS-0187527;FT-0747351;EN300-100649;Q27278732

Chemical Property of Methyl 4-pentenoate

Chemical Property:

• Vapor Pressure: 44mmHg at 25°C
• Refractive Index: n20/D 1.415
• Boiling Point: 96.2oC at 760 mmHg
• Flash Point: 29oC
• PSA: 26.30000
• Density: 0.904g/cm3
• LogP: 1.12560
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• XLogP3: 1.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 4
• Exact Mass: 114.068079557
• Heavy Atom Count: 8
• Complexity: 86.5

Purity/Quality:

99% ^*data from raw suppliers

4-PentenoicAcidMethylEster ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 10-36
• Safety Statements: 26

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(=O)CCC=C

Technology Process of Methyl 4-pentenoate

There total 24 articles about Methyl 4-pentenoate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 6.0%

methanol (67-56-1) + 5-methyl-dihydro-furan-2-one (108-29-2) → Methyl 4-pentenoate (818-57-5) + methyl 2-pentenoate (15790-87-1,15790-88-2,818-59-7) + methyl 3-pentenoate (20515-19-9,36781-66-5,818-58-6)

Guidance literature:

With sodium X zeolite; at 215 ℃; for 1h; Inert atmosphere;

Reference yield:

5-bromovaleric acid methyl ester (5454-83-1) → 3,4,5,6-tetrahydro-2H-pyran-2-one (542-28-9,26354-94-9) + Methyl 4-pentenoate (818-57-5) + methyl bromide (74-83-9) + methyl 2-pentenoate (15790-87-1,15790-88-2,818-59-7) + methyl 3-pentenoate (20515-19-9,36781-66-5,818-58-6)

Guidance literature:

at 405.2 - 418.8 ℃; Product distribution; Kinetics; Thermodynamic data; pyrolysis, Ea;

DOI:10.1021/j100291a041

Reference yield:

methanol (67-56-1) + 5-methyl-dihydro-furan-2-one (108-29-2) → Methyl 4-pentenoate (818-57-5) + methyl valerate (624-24-8) + methyl 3-pentenoate (20515-19-9,36781-66-5,818-58-6) + 4-methoxy pentanoic acid methyl ester (818-68-8)

Guidance literature:

With SO₄^2-/USY ; at 250 ℃; for 4h; under 22502.3 Torr; Reagent/catalyst; Catalytic behavior; Inert atmosphere; Green chemistry;

DOI:10.1039/c4ra13682a

upstream raw materials:

methanol

crotylamine

carbon monoxide

5-bromovaleric acid methyl ester

Downstream raw materials:

5-Azido-4-phenylselanyl-pentanoic acid methyl ester

5-phenylselanylmethyl-dihydro-furan-2-one

pent-4-enoic acid

5-(3-acetoxy-4-methoxy-phenyl)-4-hydroxy-pentanoic acid methyl ester

Refernces

• 1、 Marckwordt, Annemarie,El Ouahabi, Fatima,Amani, Hadis,Tin, Sergey,Kalevaru, Narayana V.,Kamer, Paul C. J.,Wohlrab, Sebastian,de Vries, Johannes G.. "Nylon Intermediates from Bio-Based Levulinic Acid". supporting information. p. 3486 - 3490. Retrieved 2019/02/13.
• 2、 Brentzel, Zachary J.,Ball, Madelyn R.,Dumesic, James A.. "Selective Production of Terminally Unsaturated Methyl Esters from Lactones Over Metal Oxide Catalysts". . p. 3072 - 3081. Retrieved 2018/08/22.