2(3H)-Furanone, dihydro-4-methylene-

Base Information

• Chemical Name: 2(3H)-Furanone, dihydro-4-methylene-
• CAS No.: 22195-18-2
• Molecular Formula: C5H6O2
• Molecular Weight: 98.09990
• DSSTox Substance ID: DTXSID20486665
• Nikkaji Number: J2.741.754J
• Mol file: 22195-18-2.mol

Synonyms:2(3H)-Furanone, dihydro-4-methylene-;22195-18-2;4-methylenedihydro-2(3H)-furanone;4-METHYLIDENEOXOLAN-2-ONE;4-methylene-tetrahydro-furan-2-one;3-methylene-gamma-butyrolactone;DTXSID20486665;HXJRZYGDAMTOOL-UHFFFAOYSA-N;AKOS015908182

Chemical Property of 2(3H)-Furanone, dihydro-4-methylene-

Chemical Property:

• PSA: 26.30000
• LogP: 0.48950
• XLogP3: 0.1
• 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:

dihydro-4-methylene-2(3H)-Furanone 97.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C=C1CC(=O)OC1

Technology Process of 2(3H)-Furanone, dihydro-4-methylene-

There total 3 articles about 2(3H)-Furanone, dihydro-4-methylene- 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: 80.0%

ethyl 4-hydroxy-3-methylenebutyrate (155342-55-5) → β-methylene butyrolactone (22195-18-2)

Guidance literature:

With trifluoroacetic acid; In dichloromethane; Ambient temperature;

DOI:10.1016/S0040-4020(01)81120-0

Reference yield:

itaconic acid anhydride (2170-03-8) → β-methylene butyrolactone (22195-18-2)

Guidance literature:

Multi-step reaction with 3 steps

1: 60 percent / Pseudomonas fluorescens lipase / benzene / 24 h

2: 1.) ethyl chloroformate, triethylamine; 2.) NaBH₄ / 1.) THF, 0 deg C, 0.5 h; 2.) THF, water, 2 h, 10 deg C

3: 80 percent / CF₃COOH / CH₂Cl₂ / Ambient temperature

With sodium tetrahydroborate; chloroformic acid ethyl ester; triethylamine; trifluoroacetic acid; pseudomonas fluorescens lipase; In dichloromethane; benzene;

DOI:10.1016/S0040-4020(01)81120-0

Reference yield:

2-methylene-succinic acid 4-ethyl ester (57718-07-7) → β-methylene butyrolactone (22195-18-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) ethyl chloroformate, triethylamine; 2.) NaBH₄ / 1.) THF, 0 deg C, 0.5 h; 2.) THF, water, 2 h, 10 deg C

2: 80 percent / CF₃COOH / CH₂Cl₂ / Ambient temperature

With sodium tetrahydroborate; chloroformic acid ethyl ester; triethylamine; trifluoroacetic acid; In dichloromethane;

DOI:10.1016/S0040-4020(01)81120-0

upstream raw materials:

ethyl 4-hydroxy-3-methylenebutyrate

2-methylene-succinic acid 4-ethyl ester

itaconic acid anhydride

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