Diethyl 2,2-difluoromalonate

Base Information

• Chemical Name: Diethyl 2,2-difluoromalonate
• CAS No.: 680-65-9
• Molecular Formula: C7H10F2O4
• Molecular Weight: 196.151
• Hs Code.: 29171900
• European Community (EC) Number: 676-755-0
• NSC Number: 92219
• UNII: 6JC4XD98WS
• DSSTox Substance ID: DTXSID90218192
• Nikkaji Number: J802.656D
• Wikidata: Q72461807
• Mol file: 680-65-9.mol

Synonyms:Diethyl 2,2-difluoromalonate;680-65-9;diethyl difluoromalonate;diethyl 2,2-difluoropropanedioate;2,2-Difluoro-malonic acid diethyl ester;MFCD00221617;1,3-diethyl 2,2-difluoropropanedioate;Difluoromalonic acid diethyl ester;6JC4XD98WS;Propanedioic acid, difluoro-, diethyl ester;NSC92219;NSC-92219;Diethyl2,2-difluoromalonate;C7H10F2O4;NSC 92219;diethyldifluoromalonate;UNII-6JC4XD98WS;diethyl difluoropropanedioate;NCIOpen2_001498;Propanedioic acid, 2,2-difluoro-, 1,3-diethyl ester;SCHEMBL1979744;Diethyl 2,2-difluoromalonate #;diethyl2,2-difluoropropanedioatev;DTXSID90218192;Difluoromalonic acid,diethyl ester;BBL104146;FD2014;STL557961;AKOS005063388;PB29047;AS-48911;SY009606;AM20100629;CS-0043634;FT-0624923;EN300-92173;A835999;J-520279

Chemical Property of Diethyl 2,2-difluoromalonate

Chemical Property:

• Vapor Pressure: 20.6mmHg at 25°C
• Refractive Index: 1.38
• Boiling Point: 181.2 °C at 760 mmHg
• Flash Point: 62.1 °C
• PSA: 52.60000
• Density: 1.21 g/cm³
• LogP: 0.74790
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Water Solubility.: Not miscible or difficult to mix in water.
• XLogP3: 1.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 6
• Exact Mass: 196.05471512
• Heavy Atom Count: 13
• Complexity: 183

Purity/Quality:

99% ^*data from raw suppliers

Diethyldifluoromalonate ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36/37/39-45-36-37

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)C(C(=O)OCC)(F)F

Technology Process of Diethyl 2,2-difluoromalonate

There total 3 articles about Diethyl 2,2-difluoromalonate 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: 73.0%

sodium diethylmalonate (996-82-7) → fluoromalonic acid diethyl ester (685-88-1) + diethyl 2,2-difluoromalonate (680-65-9)

Guidance literature:

With 1-fluoro-2,4,6-trimethylpyridinium trifluoromethanesulfonate; In tetrahydrofuran; at 0 ℃; for 0.1h;

DOI:10.1021/ja00179a047

Reference yield: 59.0%

ethoxycarbonylketene ethyltrimethylsilyl acetal (17906-37-5) → fluoromalonic acid diethyl ester (685-88-1) + diethyl 2,2-difluoromalonate (680-65-9)

Guidance literature:

With fluorine; In trichlorofluoromethane; at -78 ℃;

DOI:10.1021/jo00297a090

Reference yield:

diethyl malonate (105-53-3) → fluoromalonic acid diethyl ester (685-88-1) + diethyl 2,2-difluoromalonate (680-65-9)

Guidance literature:

With sodium hydride; fluorine; In acetonitrile; Title compound not separated from byproducts; 1.) r.t., 1 h, 2.) -15 deg C, 1 h;

DOI:10.1016/0022-1139(96)03422-7

upstream raw materials:

ethoxycarbonylketene ethyltrimethylsilyl acetal

sodium diethylmalonate

diethyl malonate

Downstream raw materials:

2,2-Difluoro-N,N'-bis-[2-(trityl-amino)-ethyl]-malonamide

Difluor-malonsaeure-diamid

2-fluoropropanediamide

C₄₅H₆₃F₂NO₅

Refernces

• 1、 Chambers,Hutchinson,Thomson. "Elemental fluorine. Part 3 [1]. The preparation of dialkyl fluoromalonates by direct fluorination". . p. 165 - 166. Retrieved 2007/10/03.
• 2、 Umemoto, Teruo,Fukami, Shinji,Tomizawa, Ginjiro,Harasawa, Kikuko,Kawada, Kosuke,Tomita, Kyoichi. "Power and structure-variable fluorinating agents. The N-fluoropyridinium salt system". . p. 8563 - 8575. Retrieved 2007/10/02.