Dimethyl difluoromalonate

Base Information

• Chemical Name: Dimethyl difluoromalonate
• CAS No.: 379-95-3
• Molecular Formula: C₅H₆F₂O₄
• Molecular Weight: 168.097
• Hs Code.: 2917190090
• DSSTox Substance ID: DTXSID9073175
• Nikkaji Number: J1.558.743A
• Wikidata: Q82001573
• Mol file: 379-95-3.mol

Synonyms:Dimethyl difluoromalonate;379-95-3;Dimethyl difluoropropanedioate;dimethyl 2,2-difluoropropanedioate;PROPANEDIOIC ACID, DIFLUORO-, DIMETHYL ESTER;1,3-dimethyl 2,2-difluoropropanedioate;C5H6F2O4;MFCD00516931;Malonic acid, difluoro-, dimethyl ester;dimethyl 2,2-difluoromalonate;Dimethyldifluoromalonate;SCHEMBL2580230;DTXSID9073175;AMY3267;BBL101694;STL555490;AKOS006272801;Difluoropropanedioic acid dimethyl ester;MS-20264;SY039128;LS-120074;CS-0121280;FT-0677596;D82219;EN300-109111

Chemical Property of Dimethyl difluoromalonate

Chemical Property:

• Vapor Pressure: 8.09mmHg at 25°C
• Melting Point: -35℃ (approx)
• Refractive Index: 1.3721 (589.3 nm 20℃)
• Boiling Point: 134.4°C at 760 mmHg
• Flash Point: 35°C
• PSA: 52.60000
• Density: 1.303g/cm³
• LogP: -0.03230
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• XLogP3: 0.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 4
• Exact Mass: 168.02341499
• Heavy Atom Count: 11
• Complexity: 159

Purity/Quality:

98%, ^*data from raw suppliers

Dimethyl difluoromalonate ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xi

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(=O)C(C(=O)OC)(F)F
• Uses: Diethyl difluoromalonate is an important raw material and intermediate used in organic synthesis, pharmaceuticals and agrochemicals.

Technology Process of Dimethyl difluoromalonate

There total 10 articles about Dimethyl 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: 77.0%

malonic acid dimethyl ester (108-59-8) → dimethyl 2,2-difluoro-malonate (379-95-3)

Guidance literature:

With tetra(n-butyl)ammonium hydroxide; Selectfluor; In methanol; acetonitrile; at 82 ℃; for 0.166667h; microwave irradiation;

DOI:10.1016/j.jfluchem.2004.10.043

Reference yield: 73.2%

methanol (67-56-1) + 1,3-bis(fluorosulfonyloxy)hexafluoropropane (75668-21-2) → dimethyl 2,2-difluoro-malonate (379-95-3)

Guidance literature:

With potassium fluoride; for 10h; Heating;

DOI:10.1007/BF00953623

Reference yield: 62.0%

methyl Pentafluorobut-3-enoate (20562-79-2) → dimethyl 2,2-difluoro-malonate (379-95-3) + Methyl pentafluoro-3,4-epoxybutanate (268226-88-6)

Guidance literature:

With oxygen; UV-irradiation;

upstream raw materials:

diazomethane

2,2-difluoromalonic acid

methanol

1-chloroheptafluoro-2,5-cyclohexadiene

Downstream raw materials:

Difluor-malonsaeure-diamid

Refernces

• 1、 -. "PROCESSES FOR MAKING SERD TRICYCLIC COMPOUNDS HAVING A SUBSTITUTED PHENYL OR PYRIDINYL MOIETY". Paragraph 0330-0331. . Retrieved 2022/01/12.
• 2、 Xiao, Ji-Chang,Shreeve, Jean'ne M.. "Microwave-assisted rapid electrophilic fluorination of 1,3-dicarbonyl derivatives with Selectfluor". . p. 475 - 478. Retrieved 2007/10/03.