gamma-Methylene-gamma-butyrolactone

Base Information

• Chemical Name: gamma-Methylene-gamma-butyrolactone
• CAS No.: 10008-73-8
• Molecular Formula: C5H6O2
• Molecular Weight: 98.1014
• Hs Code.: 2932209090
• European Community (EC) Number: 233-004-8
• UNII: B6FM50XSNZ
• DSSTox Substance ID: DTXSID50142924
• Nikkaji Number: J241.218G
• Wikidata: Q27116832
• Metabolomics Workbench ID: 55368
• ChEMBL ID: CHEMBL93112
• Mol file: 10008-73-8.mol

Synonyms:gamma-Methylene-gamma-butyrolactone;10008-73-8;5-methylideneoxolan-2-one;Dihydro-5-methylenefuran-2(3H)-one;5-methylenedihydrofuran-2(3H)-one;alpha'-angelica lactone;2(3H)-Furanone, dihydro-5-methylene-;4-Hydroxy-4-pentenoic acid gamma-lactone;CHEBI:36439;UNII-B6FM50XSNZ;B6FM50XSNZ;EINECS 233-004-8;.gamma.-Methylene-.gamma.-butyrolactone;5-Methylenedihydro-2(3H)-furanone;4-PENTEN-4-OLIDE;CHEMBL93112;5-Methylenetetrahydrofuran-2-one;DTXSID50142924;5-Methylenedihydro-2(5H)-furanone;MFCD00042762;2(3H)-Furanone,dihydro-5-methylene-;AKOS015905172;.gamma.-methylen-.gamma.-butyrolactone;gamma -Methylene- gamma -butyrolactone;5-METHYLENETETRAHYDRO-2-FURANONE;AS-62676;gamma-Methylene-gamma-butyrolactone, 99%;ANGELICA LACTONE .GAMMA.-FORM [MI];CS-0204399;FT-0693004;M1385;T71516;4-HYDROXY-4-PENTENOIC ACID .GAMMA.-LACTONE;J-000034;Q27116832

Chemical Property of gamma-Methylene-gamma-butyrolactone

Chemical Property:

• Appearance/Colour: clear colourless to light yellow liquid
• Vapor Pressure: 0.654mmHg at 25°C
• Melting Point: 18 °C
• Refractive Index: n20/D 1.466(lit.)
• Boiling Point: 186.7 °C at 760 mmHg
• Flash Point: 76.7 °C
• PSA: 26.30000
• Density: 1.07 g/cm³
• LogP: 0.83710
• XLogP3: 0.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 98.036779430
• Heavy Atom Count: 7
• Complexity: 115

Purity/Quality:

98%,99%, ^*data from raw suppliers

γ-Methylene-γ-butyrolactone ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 42/43
• Safety Statements: 23-36/37-45

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C=C1CCC(=O)O1

Technology Process of gamma-Methylene-gamma-butyrolactone

There total 23 articles about gamma-Methylene-gamma-butyrolactone 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%

4-pentynoic acid (6089-09-4) → 5-methylenedihydrofuran-2-one (10008-73-8)

Guidance literature:

Cl₂Ru[=C=C(H)'But](PCy₃)(N,N'-bis-aryl-imidazoline); In toluene; at 110 ℃; for 2h;

DOI:10.1016/S0040-4039(02)02233-5

Reference yield: 89.5%

formaldehyd (50-00-0,30525-89-4,61233-19-0) + 3-(triphenylphosphoranyliden)dihydro-2(3H)-furanone (34932-07-5) → 5-methylenedihydrofuran-2-one (10008-73-8)

Guidance literature:

DOI:10.1002/hlca.19800630512

Reference yield: 81.0%

4-pentynoic acid (6089-09-4) + tert-butyl alcohol (75-65-0) → 5-methylenedihydrofuran-2-one (10008-73-8)

Guidance literature:

With mercury(II) oxide; for 4h; Heating;

DOI:10.1039/c39830000991

upstream raw materials:

5-methyl-2-furanone

5-iodomethyl-dihydro-furan-2-one

methanol

4-pentynoic acid

Downstream raw materials:

5-[2,2-bis(methoxycarbonyl)ethyl]tetrahydrofuran-2-one

11b-methyl-5,6,11,11b-tetrahydro-1H-indolizino[8,7-b]indol-3(2H)-one

1,6-Dioxa-dispiro[4.1.5.1]trideca-8,11-diene-2,10-dione

1,6,7,14-Tetraoxa-dispiro[4.2.5.2]pentadeca-9,12-diene-2,11-dione

Refernces

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• 6、 Mas-Marza, Elena,Mata, Jose A.,Peris, Eduardo. "Triazolediylidenes: A versatile class of ligands for the preparation of discrete molecules of homo- and hetero-binuclear complexes for improved catalytic applications". . p. 3729 - 3731. Retrieved 2007.
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• 8、 Yuan, Ning,Gudmundsson, Arnar,Gustafson, Karl P. J.,Oschmann, Michael,Tai, Cheuk-Wai,Persson, Ingmar,Zou, Xiaodong,Verho, Oscar,Bajnóczi, éva G.,B?ckvall, Jan-E.. "Investigation of the Deactivation and Reactivation Mechanism of a Heterogeneous Palladium(II) Catalyst in the Cycloisomerization of Acetylenic Acids by in Situ XAS?". . p. 2999 - 3008. Retrieved 2021.
• 9、 Ferré, Meritxell,Catto?n, Xavier,Wong Chi Man, Michel,Pleixats, Roser. "Sol–Gel Immobilized N-Heterocyclic Carbene Gold Complex as a Recyclable Catalyst for the Rearrangement of Allylic Esters and the Cycloisomerization of γ-Alkynoic Acids". . p. 2824 - 2831. Retrieved 2016.
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