680-42-2

Basic information

• Product Name: diethyl fluoro(nitro)propanedioate
• CAS NO: 680-42-2
• Molecular Formula: C₇H₁₀FNO₆
• Molecular Weight: 223.1558
• Mol File: 680-42-2.mol

Chemical Properties

• Boiling Point: 244.5°C at 760 mmHg
• Flash Point: 101.7°C
• Density: 1.317g/cm³
• Vapor Pressure: 0.0303mmHg at 25°C
• Refractive Index: 1.434
• CAS DataBase Reference: diethyl fluoro(nitro)propanedioate(CAS DataBase Reference)
• NIST Chemistry Reference: diethyl fluoro(nitro)propanedioate(680-42-2)
• EPA Substance Registry System: diethyl fluoro(nitro)propanedioate(680-42-2)

Safety Data

• Hazardous Substances Data: 680-42-2(Hazardous Substances Data)

Upstream product

• 603-67-8 diethyl nitromalonate 
• 86884-38-0 diethyl 2-nitromalonate 2-sodium salt 

Downstream Products

• 3620-16-4 ethyl 2-fluoro-2-nitroacetate 

Relevant articles and documents

Catalyzed fluorination of carbonyl compounds

The present invention provides a method of substituting a carbonyl compound with fluorine at the α-position, comprising reaching the carbonyl compound with a fluorinating present of a metal-containing catalyst. The reaction results in replacement of a hydrogen atom by fluorine. The catalyst, which is used in a catalytically effective amount, is preferably a transition metal. In one class of methods the catalyst is a transition metal compound. In another class of methods, the catalyst is an elemental metal, in which case the carbonyl compound has an activating group attached to the carbon atom which is substituted by fluorine.

Process for the preparation of esters

A process for the preparation of an ester, especially fluorinated esters R1 O.OC--CHR2 --CO.OR3, R1 and R3 are each independently selected from alkyl, cycloalkyl and aryl. R2 is selected from hydrogen, alkyl, cycloalkyl. The method includes the steps of covering a corresponding compound of formula 2: R1 O.OC--CHR2 --CO.OR3 in the presence of a base, of salt of a compound of formula 2, into corresponding compound of formula 1 by the reaction of elemental fluorine.

Elemental fluorine. Part 9 : Catalysis of the direct fluorination of 2-substituted carbonyl compounds

Catalysis of the reaction between fluorine and a range of 2-substituted carbonyl compounds has been investigated. Most notably, the preparation of diethyl-2-fluoromalonate has been achieved in high yield by fluorination of diethylmalonate in the presence of hydrated copper nitrate. Reactions between fluorine and carbanions derived from 2-substituted carbonyl compounds, including phosphonates, sulphones and nitriles, are also discussed.

Elemental fluorine. Part 3 [1]. The preparation of dialkyl fluoromalonates by direct fluorination

Dialkyl fluoromalonates have been prepared by treating the sodium derivatives of the parent dialkyl malonates with elemental fluorine.

N-Fluorobisimide: An Efficient Reagent for the α-Fluorination of Functionalized Carbonyl Compounds

The N-fluorobisimide (1) has been used in the electrophilic fluorination of the lithium enolate of esters, amides, and ketones.The corresponding α-fluorocarbonyl compounds have been obtained in good yields.The α-fluorination of β-diesters, β-diamides, β-keto esters, and β-diketones has been performed either on the neutral compounds or on the metal enolates.In this way some geminal azafluoro, chlorofluoro, fluorooxy compounds have been prepared in nearly quantitative yields.Also some α-keto esters and acids have been selectively monofluorinated in the β-position by simple treatment of the neutral compound with 1.