672-18-4

Basic information

• Product Name: 2-fluorofumarate
• Synonyms: 2-fluorofumarate
• CAS NO: 672-18-4
• Molecular Formula: C₄H₃FO₄
• Molecular Weight: 134.06
• Mol File: 672-18-4.mol
• Article Data: 5

Chemical Properties

• Melting Point: 236-237 °C
• Boiling Point: 317.8°C at 760 mmHg
• Flash Point: 146°C
• Appearance: /
• Density: 1.621g/cm³
• Vapor Pressure: 7.96E-05mmHg at 25°C
• Refractive Index: 1.486
• PKA: 1.62±0.19(Predicted)
• CAS DataBase Reference: 2-fluorofumarate(CAS DataBase Reference)
• NIST Chemistry Reference: 2-fluorofumarate(672-18-4)
• EPA Substance Registry System: 2-fluorofumarate(672-18-4)

Safety Data

• Hazardous Substances Data: 672-18-4(Hazardous Substances Data)

Usage

General Description

2-fluorofumarate is a chemical compound that is derived from fumaric acid, an intermediate in the citric acid cycle. It is a fluorinated derivative of fumarate, with a fluorine atom substituted for one of the hydrogen atoms in the molecule. This modification alters the chemical and biological properties of fumarate, making 2-fluorofumarate a potent inhibitor of fumarase, an enzyme involved in the citric acid cycle and other metabolic pathways. As a result, 2-fluorofumarate has potential applications in cancer therapy, as it has been shown to inhibit tumor growth by disrupting cellular metabolism. Additionally, it has been studied for its potential as a tool in metabolic imaging and as a probe for studying fumarate metabolism in various biological systems.

InChI:InChI=1/C4H3FO4/c5-2(4(8)9)1-3(6)7/h1H,(H,6,7)(H,8,9)/b2-1-

Upstream product

• 18414-17-0 (Z)-dimethyl 2-fluoro 2-butene dioate 
• 392-46-1 meso-2,3-difluorosuccinic acid 
• 665-31-6 2,2-difluorosuccinic acid 
• 868-24-6 diethyl 2,3-difluorosuccinate 
• 760-91-8 Fluorfumarsaeure-butylethylester 

Downstream Products

• 18414-17-0 (Z)-dimethyl 2-fluoro 2-butene dioate 
• 2714-23-0 3-fluorofuran-2,5-dione 
• 106138-31-2 (2R,3S)-3-fluoroaspartic acid 
• 110-15-6 succinic acid 
• 687-50-3 2-Fluorosuccinic acid 
• 67191-71-3 n-Butyl-fluorfumarat 
• 4495-77-6 diethyl 2-fluorofumarate 
• 67191-70-2 Dipropyl-2-fluorfumarat 

Relevant articles and documents

Synthesis of the first fluorinated cantharidin analogues

Fluorinated cantharidin analogues (4-7) have been synthesized for the first time. The key step in each synthesis is an exo-selective Diels-Alder reaction of furan with the appropriate fluorinated maleic anhydride. 17O NMR measurements of 5-7 an

ELIMINATION OF HYDROGEN FLUORIDE FROM FLUORINATED SUCCINIC ACIDS.(II) KINETICS OF DEHYDROFLUORINATION OF FLUORO-, 2,2-DIFLUORO-, MESO- AND DL-2,3-DIFLUORO-, AND TRIFLUOROSUCCINIC ACIDS

Elimination of hydrogen fluoride from fluorosuccinic acid gave fumaric acid, from 2,2-difluorosuccinic acid, meso- and DL-2,3-difluorosuccinic acid fluorofumaric acid, and dehydrofluorination of trifluorosuccinic acid afforded difluoromaleic acid.Kinetic data based on 1H NMR measurements are presented for temperatures of 60 deg C, 75 deg C and 90 deg C.All the dehydrofluorinations follow second order kinetics.Activation energies for the dehydrofluorination of the above acids were found to be: 19.3, 17.3, 18.8, 17.9 and 18.3 kcal, respectively.Since both diastereomeric 2,3-difluorosuccinic acids give fluorofumaric acid as the only product of dehydrofluorination, one of them (DL) undergoes trans elimination while the other (meso) must undergo cis elimination.