2-Butenedioic acid, 2-fluoro-, dimethyl ester, (Z)-

Base Information

• Chemical Name: 2-Butenedioic acid, 2-fluoro-, dimethyl ester, (Z)-
• CAS No.: 18414-17-0
• Molecular Formula: C6H7FO4
• Molecular Weight: 162.118
• European Community (EC) Number: 877-522-8
• ChEMBL ID: CHEMBL3247956
• Nikkaji Number: J1.553.398F
• Mol file: 18414-17-0.mol

Synonyms:18414-17-0;2-Butenedioic acid, 2-fluoro-, dimethyl ester, (Z)-;Dimethyl 2-fluorofumarate;dimethyl (Z)-2-fluorobut-2-enedioate;starbld0042006;CHEMBL3247956;dimethyl erythro-3-fluoromaloate;EN300-726448;1,4-DIMETHYL (2Z)-2-FLUOROBUT-2-ENEDIOATE;2-Butenedioic acid, 2-fluoro-, dimethyl ester, (2Z)-

Chemical Property of 2-Butenedioic acid, 2-fluoro-, dimethyl ester, (Z)-

Chemical Property:

• PSA: 52.60000
• LogP: 0.18580
• XLogP3: 0.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 4
• Exact Mass: 162.03283686
• Heavy Atom Count: 11
• Complexity: 197

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(=O)C=C(C(=O)OC)F
• Isomeric SMILES: COC(=O)/C=C(/C(=O)OC)\F

Technology Process of 2-Butenedioic acid, 2-fluoro-, dimethyl ester, (Z)-

There total 3 articles about 2-Butenedioic acid, 2-fluoro-, dimethyl ester, (Z)- 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: 21.0%

(R)-2,3-dihydro-3-iso-propyl-2-(toluene-4-sulfonyl)benzo[d]isothiazole (1148114-80-0) + dimethyl acetylenedicarboxylate (762-42-5) → 2-{2-[2-methyl-1-(toluene-4-sulfonylamino)-propyl]-phenylsulfanyl}-but-2-en-dioic acid dimethyl ester (1148114-91-3) + (R)-4,5-dihydro-2,3-dimethyldicarboxylate-4-(toluene-4-sulfonyl)-5-iso-propyl-1,4-benzo[f]thiazepine (1148114-83-3) + (Z)-dimethyl 2-fluoro 2-butene dioate (18414-17-0)

Guidance literature:

With 1,3-bis-(diphenylphosphino)propane; In dichloromethane; at 40 ℃; for 14h; optical yield given as %de; Inert atmosphere;

DOI:10.1021/jo900449a

Reference yield:

diazomethane (186581-53-3,908094-01-9,334-88-3) + fluorofumaric acid (672-18-4) → (Z)-dimethyl 2-fluoro 2-butene dioate (18414-17-0)

Guidance literature:

DOI:10.1039/j39680001232

Reference yield:

maleic anhydride (108-31-6) + methanol (67-56-1) → (Z)-dimethyl 2-fluoro 2-butene dioate (18414-17-0) + dimethyl meso-α,α'-difluorosuccinate (74398-81-5,222312-03-0) + dimetyl D,L-2,3-difluorosuccinate (222312-03-0) + dimetyl threo-2-chloro-3-fluorosuccinate

Guidance literature:

Yield given. Multistep reaction. Further byproducts given. Yields of byproduct given;

DOI:10.1016/0022-1139(93)02975-K

upstream raw materials:

diazomethane

fluorofumaric acid

maleic anhydride

methanol

Downstream raw materials:

fluorofumaric acid

Dimethyl succinate

Refernces

• 1、 Syvret, Robert G.,Vassilaros, Daniel L.,Parees, David M.,Pez, Guido P.. "The formation of halogenated succinates by liquid-phase direct fluorination with elemental fluorine". . p. 277 - 282. Retrieved 2007/10/02.