4,4-Dimethyl-5-methylene-1,3-dioxolan-2-one

Base Information

• Chemical Name: 4,4-Dimethyl-5-methylene-1,3-dioxolan-2-one
• CAS No.: 4437-80-3
• Molecular Formula: C6H8O3
• Molecular Weight: 128.128
• Hs Code.: 2932999099
• European Community (EC) Number: 224-653-8
• DSSTox Substance ID: DTXSID8063466
• Nikkaji Number: J205.820K
• Wikidata: Q81990759
• Mol file: 4437-80-3.mol

Synonyms:4,4-dimethyl-5-methylidene-1,3-dioxolan-2-one;4437-80-3;4,4-Dimethyl-5-methylene-1,3-dioxolan-2-one;1,3-Dioxolan-2-one, 4,4-dimethyl-5-methylene-;4,4-DIMETHYL-5-METHYLEN-1,3-DIOXOLANE-2-ONE;EINECS 224-653-8;5,5-dimethyl-4-methylene-1,3-dioxolan-2-one;SCHEMBL47839;DTXSID8063466;MFCD00276115;STK664289;AKOS003237047;CS-0236030;FT-0707711;4,4-Dimethyl-5-methylene[1,3]dioxolan-2-one;4,4-dimethyl-5-methylene-[1,3]dioxolan-2-one;EN300-1666321;W-109972;Z1201620090;Carbonic acid, cyclic 1,1-dimethyl-2-methyleneethylene ester

Chemical Property of 4,4-Dimethyl-5-methylene-1,3-dioxolan-2-one

Chemical Property:

• Vapor Pressure: 14.8mmHg at 25°C
• Melting Point: 26oC
• Boiling Point: 121.1°Cat760mmHg
• Flash Point: 48.6°C
• PSA: 35.53000
• Density: 1.11g/cm³
• LogP: 1.44550
• XLogP3: 1.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 128.047344113
• Heavy Atom Count: 9
• Complexity: 169

Purity/Quality:

99%, ^*data from raw suppliers

4,4-Dimethyl-5-methylidene-1,3-dioxolan-2-one ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1(C(=C)OC(=O)O1)C

Technology Process of 4,4-Dimethyl-5-methylene-1,3-dioxolan-2-one

There total 10 articles about 4,4-Dimethyl-5-methylene-1,3-dioxolan-2-one 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: 99.5%

carbon dioxide (124-38-9,18923-20-1) + 2-methyl-but-3-yn-2-ol (115-19-5) → 4,4-dimethyl-5-methylene-1,3-dioxolan-2-one (4437-80-3)

Guidance literature:

With tributylphosphine; at 100 ℃; for 15h; under 75006 Torr;

DOI:10.1021/jo062094m

Reference yield: 97.0%

carbon dioxide (124-38-9,18923-20-1) + 2-methyl-but-3-yn-2-ol (115-19-5) → 4,4-dimethyl-5-methylene-1,3-dioxolan-2-one (4437-80-3) + 3-Hydroxy-3-methyl-2-butanone (115-22-0)

Guidance literature:

With copper(l) chloride; 1-butyl-3-methylimidazolium benzenesulfonate; at 120 ℃; for 8h; under 7600 Torr;

DOI:10.1021/jo0351365

Reference yield: 87.0%

→ 4,4-dimethyl-5-methylene-1,3-dioxolan-2-one (4437-80-3)

Guidance literature:

With silver(I) acetate; DavePhos; In acetonitrile; at 20 ℃; for 18h; under 15001.5 Torr;

upstream raw materials:

carbon dioxide

2-methyl-but-3-yn-2-ol

2-methylbut-3-yn-2-yl carbamate

Downstream raw materials:

4,5-dihydro-2,2-dimethyl-5-phenyl-3(2H)-furanone

4-hydroxy-4-methyl-1-phenyl-1-penten-3-one

2,2-Dimethyl-5-phenyl-4-[1-phenyl-meth-(E)-ylidene]-dihydro-furan-3-one

N-benzoyl-4-hydroxy-4,5,5-trimethyl-1,3-oxazolidin-2-one

Refernces

• 1、 Kim, Hak-Soo,Kim, Jeong-Won,Kwon, Soon-Chul,Shim, Sang-Chul,Kim, Tae-Jeong. "Catalytic formation of carbamates and cyclic carbonates by copper complex of 2,5,19,22-tetraaza[6,6](1,1′)ferrocenophane-1,5-diene X-ray crystal structure of [Cu(1)]PF6". . p. 337 - 344. Retrieved 1997.
• 2、 Qiu, Jikuan,Zhao, Yue,Zhao, Yuling,Wang, Huiyong,Li, Zhiyong,Wang, Jianji,Jiao, Tiantian. "Cu(I)/ionic liquids promote the conversion of carbon dioxide into oxazolidinones at room temperature". . . Retrieved 2019.
• 3、 Gennen, Sandro,Grignard, Bruno,Tassaing, Thierry,Jér?me, Christine,Detrembleur, Christophe. "CO2-Sourced α-Alkylidene Cyclic Carbonates: A Step Forward in the Quest for Functional Regioregular Poly(urethane)s and Poly(carbonate)s". . p. 10394 - 10398. Retrieved 2017.
• 4、 Han, Qiuxia,Huang, Laikuan,Jiao, Jiachen,Li, Mingxue,Shi, Zhuolin,Xiao, Yang. "Synthesis Cu(I)–CN-based MOF with in-situ generated cyanogroup by cleavage of acetonitrile: Highly efficient for catalytic cyclization of propargylic alcohols with CO2". . . Retrieved 2020.
• 5、 Cervantes-Reyes, Alejandro,Farshadfar, Kaveh,Rudolph, Matthias,Rominger, Frank,Schaub, Thomas,Ariafard, Alireza,Hashmi. "Copper-catalysed synthesis of α-alkylidene cyclic carbonates from propargylic alcohols and CO2". supporting information. p. 889 - 897. Retrieved 2021/02/09.
• 6、 Bresciani, Giulio,Bortoluzzi, Marco,Ghelarducci, Claudia,Marchetti, Fabio,Pampaloni, Guido. "Synthesis of α-alkylidene cyclic carbonatesviaCO2fixation under ambient conditions promoted by an easily available silver carbamate". . p. 4340 - 4346. Retrieved 2021/03/15.