Methyl 3-butenoate

Base Information

• Chemical Name: Methyl 3-butenoate
• CAS No.: 3724-55-8
• Molecular Formula: C5H8O2
• Molecular Weight: 100.117
• Hs Code.: 2916190090
• European Community (EC) Number: 223-076-9
• NSC Number: 250983
• DSSTox Substance ID: DTXSID5063150
• Nikkaji Number: J191.424C
• Wikidata: Q72488930
• Mol file: 3724-55-8.mol

Synonyms:Methyl 3-butenoate;3724-55-8;Methyl But-3-enoate;3-Butenoic acid, methyl ester;methyl-3-butenoate;methylbut-3-enoate;but-3-enoic acid methyl ester;CH2=CHCH2C(O)OCH3;EINECS 223-076-9;MFCD00082587;NSC 250983;methyl 3-buteneoate;Methyl 3-butenoate, 95%;SCHEMBL183554;DTXSID5063150;SCHEMBL13123537;BCP21651;NSC250983;AKOS017276233;NSC-250983;BS-22316;SY025883;CS-0158011;FT-0716102;M3405;EN300-113971;F15018;Methyl But-3-enoate pound>>3-Butenoic acid, methyl ester

Chemical Property of Methyl 3-butenoate

Chemical Property:

• Vapor Pressure: 57.3mmHg at 25°C
• Melting Point: -78.42°C (estimate)
• Refractive Index: n20/D 1.409(lit.)
• Boiling Point: 90 °C at 760 mmHg
• Flash Point: 16.3 °C
• PSA: 26.30000
• Density: 0.939 g/cm³
• LogP: 0.73550
• XLogP3: 0.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 3
• Exact Mass: 100.052429494
• Heavy Atom Count: 7
• Complexity: 76.1

Purity/Quality:

99% ^*data from raw suppliers

Methyl 3-butenoate 95% ^*data from reagent suppliers

Safty Information:

• Pictogram(s): F
• Hazard Codes: F
• Statements: 11
• Safety Statements: 16

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Other Classes -> Esters, Other
• Canonical SMILES: COC(=O)CC=C
• Uses: Methyl 3-butenoate may be employed for the synthesis of dipeptide olefin isosteres using intermolecular olefin cross-metathesis.

Technology Process of Methyl 3-butenoate

There total 38 articles about Methyl 3-butenoate 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: 100.0%

allyl methyl carbonate (35466-83-2) → methyl but-3-enoate (3724-55-8)

Guidance literature:

With carbon monoxide; triphenylphosphine; palladium diacetate;

Reference yield: 99.0%

π-allyl-palladium chloride + Methyl formate (107-31-3) → methyl but-3-enoate (3724-55-8) + palladium (7440-05-3)

Guidance literature:

With carbon monoxide; sodium butyrate; In neat (no solvent); mixt. of PdCl(C3H5), HCO2Me and NaC4H9O (as nucleophile) stirred at room temp. for 30 min, addn. of CO, react. time 2 h; react. mixt. filtered, colourless liquid analysed by GLC;

DOI:10.1016/0304-5102(89)80136-1

Reference yield: 98.0%

1-(diphenylphosphinoyl)-1,1-dimethoxy-3-butene → methyl but-3-enoate (3724-55-8) + Diphenylphosphine oxide (4559-70-0)

Guidance literature:

With hydrogenchloride; In dichloromethane;

DOI:10.1002/ejoc.200300631

upstream raw materials:

diazomethane

but-3-enoic acid

methanol

but-3-enoyl chloride

Downstream raw materials:

ethyl 2-cyclopropyl acetate

4-hydroxy-4-(2-propenyl)-hepta-1,6-diene

[3-(4-Cyano-phenyl)-4,5-dihydro-isoxazol-5-yl]-acetic acid methyl ester

4-[4-(5-Methoxycarbonylmethyl-4,5-dihydro-isoxazol-3-yl)-phenoxymethyl]-piperidine-1-carboxylic acid tert-butyl ester

Refernces

• 1、 Falck,Kumar, P. Srinagesh,Reddy, Y. Krishna,Zou, Gang,Capdevila, Jorge H.. "Stereospecific synthesis of EET metabolites via Suzuki-Miyaura coupling". . p. 7211 - 7212. Retrieved 2001.
• 2、 Iwakura et al.. "". . p. 841. Retrieved 1969.
• 3、 Obuah, Collins,Darkwa, James. "(Ferrocenylpyrazolyl)palladium(II) complexes: Syntheses, characterization and rearrangement in solution". . p. 39 - 48. Retrieved 2016.
• 4、 Chen, Pan-Pan,Hong, Xin,Jarvo, Elizabeth R.,McGinnis, Tristan M.,Sanford, Amberly B.,Thane, Taylor A.. "Nickel-Catalyzed Alkyl-Alkyl Cross-Electrophile Coupling Reaction of 1,3-Dimesylates for the Synthesis of Alkylcyclopropanes". supporting information. . Retrieved 2020/03/23.
• 5、 Mattingly, Stephanie J.,Wuest, Frank,Schirrmacher, Ralf. "Synthesis of 2-Fluoroacetoacetic Acid and 4-Fluoro-3-hydroxybutyric Acid". supporting information. p. 2351 - 2358. Retrieved 2019/05/24.