3-Methyl-2(5H)-furanone

Base Information

• Chemical Name: 3-Methyl-2(5H)-furanone
• CAS No.: 22122-36-7
• Molecular Formula: C5H6O2
• Molecular Weight: 98.1014
• Hs Code.: 2932209090
• European Community (EC) Number: 627-982-9
• UNII: N9KXQ3851K
• DSSTox Substance ID: DTXSID50176643
• Nikkaji Number: J376.241F
• Wikidata: Q27284743
• Mol file: 22122-36-7.mol

Synonyms:3-Methyl-2(5H)-furanone;22122-36-7;3-Methylfuran-2(5H)-one;4-methyl-2H-furan-5-one;2(5H)-Furanone, 3-methyl-;2(5H)-Furanone, methyl-;2-Methyl-2-butenolide;UNII-N9KXQ3851K;N9KXQ3851K;.alpha.-Methyl-.gamma.-crotonolactone;3-methyl-5H-furan-2-one;2-Methyl-2-buten-4-olide;FEMA NO. 4902;VGHBEMPMIVEGJP-UHFFFAOYSA-;DTXSID50176643;GEO-01823;MFCD00191545;AKOS015916280;CS-0204540;FT-0692218;M1078;T72100;3-Methyl-2(5H)-furanone, technical grade, 90%;4-Hydroxy-2-methyl-2-butenoic Acid gamma-Lactone;W-200229;Q27284743;InChI=1/C5H6O2/c1-4-2-3-7-5(4)6/h2H,3H2,1H3

Chemical Property of 3-Methyl-2(5H)-furanone

Chemical Property:

• Vapor Pressure: 0.102mmHg at 25°C
• Melting Point: 72-73 °C(Solv: ethyl ether (60-29-7))
• Refractive Index: n20/D 1.467(lit.)
• Boiling Point: 222.4 °C at 760 mmHg
• Flash Point: 83.3 °C
• PSA: 26.30000
• Density: 1.12 g/cm³
• LogP: 0.48950
• 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: 124

Purity/Quality:

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

3-Methyl-2(5H)-furanone ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CCOC1=O
• Uses: 3-Methyl-2(5H)-furanone is the suitable model compound used to investigate the fragmentation mechanism of five membered lactones by electrospray ionisation tandem mass spectrometry and also to study the airway irritation of isoprene, isoprene/ozone, and isoprene/ozone/nitrogen dioxide mixture.

Technology Process of 3-Methyl-2(5H)-furanone

There total 56 articles about 3-Methyl-2(5H)-furanone 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%

carbon monoxide (201230-82-2) + 3-iodo-but-2-ene-1-ol (35761-83-2) → 3-methyl-5H-furan-2-one (22122-36-7)

Guidance literature:

With potassium carbonate; hydrazine; bis-triphenylphosphine-palladium(II) chloride; In tetrahydrofuran; at 25 ℃; for 72h; under 760 Torr;

DOI:10.1021/ja00532a034

Reference yield: 98.0%

2,3-butadien-1-ol (18913-31-0) + carbon monoxide (201230-82-2) → 3-methyl-5H-furan-2-one (22122-36-7)

Guidance literature:

With dodecacarbonyl-triangulo-triruthenium; triethylamine; In 1,4-dioxane; at 100 ℃; for 8h; under 7600 Torr;

DOI:10.1021/jo0350615

Reference yield: 96.0%

3-methyl-3-(4-trimethylsilylphenylselenyl)-3H-dihydrofuran-2-one (850185-98-7) → 3-methyl-5H-furan-2-one (22122-36-7)

Guidance literature:

With dihydrogen peroxide; In dichloromethane; at 0 - 20 ℃; for 0.75h;

DOI:10.1055/s-2004-837289

upstream raw materials:

4,5-dihydro-3-hydroxy-3-methyl-2(3H)-furanone

α-methylene-γ-butyrolactone

α-bromo-α-methyl-γ-butyrolactone

citraconic acid anhydride

Downstream raw materials:

triisopropyl((3-methylfuran-2-yl)oxy)silane

1,4-diacetoxy-2-methyl-butane

2-methyl-2-butene-1,4-diyl (Z)-diacetate

2-methyl-1,4-butandiol

Refernces

• 1、 Smith,Stevens. "-". . p. 1931. Retrieved 1978.
• 2、 Trost,B.M.,Salzmann,T.N.. "-". . p. 6840 - 6842. Retrieved 1973.
• 3、 Wyss, Heinz,Voegeli, Ulrich,Scheffold, Rolf. "Stereoselective Hydride Reduction of Tetronic Acid Derivatives. Synthesis of Branched-Chain Tetrofuranoses". . p. 775 - 786. Retrieved 1981.
• 4、 Alexander, Taylor S.,Clay, Travis J.,Maldonado, Bryan,Nguyen, Johny M.,Martin, David B.C.. "Comparative studies of palladium and copper-catalysed γ-arylation of silyloxy furans with diaryliodonium salts". . p. 2229 - 2238. Retrieved 2019/03/06.
• 5、 -. "Α-hydroxycarboxylic acid or its oligomer by treatment with hydrogen at high temperature and high pressure water or hydroxy butyrolactone derivative γ - furanone derivative". Paragraph 0027; 0055. . Retrieved 2017/11/11.