35234-88-9

Basic information

• Product Name: DIETHYL DICYANOFUMARATE, 97
• Synonyms: DIETHYL DICYANOFUMARATE, 97;diethyl 2,3-dicyanofumarate;2,3-Dicyanofumaric acid diethyl ester
• CAS NO: 35234-88-9
• Molecular Formula: C₁₀H₁₀N₂O₄
• Molecular Weight: 222.1974
• EINECS: 252-453-0
• Mol File: 35234-88-9.mol
• Article Data: 11

Chemical Properties

• Melting Point: 114-118 °C(lit.)
• Boiling Point: 337.3°Cat760mmHg
• Flash Point: 147.1°C
• Appearance: /
• Density: 1.23g/cm³
• Vapor Pressure: 0.000106mmHg at 25°C
• Refractive Index: 1.482
• CAS DataBase Reference: DIETHYL DICYANOFUMARATE, 97(CAS DataBase Reference)
• NIST Chemistry Reference: DIETHYL DICYANOFUMARATE, 97(35234-88-9)
• EPA Substance Registry System: DIETHYL DICYANOFUMARATE, 97(35234-88-9)

Safety Data

• Hazard Codes: Xn
• Statements: 20/21/22
• Safety Statements: 26-27-36-36/39
• Hazardous Substances Data: 35234-88-9(Hazardous Substances Data)

Usage

Synthesis Reference(s)

Synthetic Communications, 22, p. 3169, 1992 DOI: 10.1080/00397919208021130

InChI:InChI=1/C10H10N2O4/c1-3-15-9(13)7(5-11)8(6-12)10(14)16-4-2/h3-4H2,1-2H3/b8-7+

Upstream product

• 7446-08-4 selenium(IV) oxide 
• 13280-85-8 ethyl 2,2-dibromo-2-cyanoacetate 
• 506-78-5 cyanogen iodide 
• 762-21-0 acetylenedicarboxylic acid diethyl ester 
• 86290-00-8 diethyl 2,3-dicyanomaleate 
• 101342-43-2 methyl tricyanoethylenecarboxylate 
• 81852-22-4 ethyl cyano<thio>acetate 
• 1187-46-8 ethyl bromocyanoacetate 
• 105-56-6 ethyl 2-cyanoacetate 

Downstream Products

• 93996-19-1 4-(α.β-Dicyano-α.β-diethoxycarbonyl-ethyl)-N.N-dimethyl-anilin 
• 93004-40-1 N-<3-Nitro-phenyl>-trans-α,β-dicyano-β-aethoxycarbonyl-vinylamin 
• 219725-32-3 diethyl 5-amino-1-(m-chlorophenyl)pyrazole-3,4-dicarboxylate 
• 1135824-03-1 ethyl 1-benzoyl-4-cyano-5-oxo-2,5-dihydro-1H-pyrazole-3-carboxylate 
• 1135823-95-8 ethyl 2-cyano-2-(6-oxo-2-phenyl-4H-1,3,4-oxadiazin-5(6H)-ylidene)acetate 
• 1192178-69-0 diethyl (E)-2-cyano-3-[2,2-dimethyl-3-(morpholin-4-yl)-3-phenylazetidin-1-yl]but-2-enedioate 
• 1192178-67-8 diethyl (E)-2-cyano-3-[3-(morpholin-4-yl)-3-phenylazetidin-1-yl]but-2-enedioate 
• 1192178-81-6 diethyl (Z)-2-cyano-3-(cyclohexylamino)but-2-enedioate 
• 97833-91-5 N-<4-Methoxy-phenyl>-trans-α.β-diethoxycarbonyl-β-cyano-vinylamin 
• 92166-59-1 N-<4-Methoxy-phenyl>-trans-α.β-dicyano-β-ethoxycarbonyl-vinylamin 
• 55260-59-8 2,3-Dicyano-2-(4,4-dimethyl-2,6-dioxo-cyclohexyl)-succinic acid diethyl ester 
• 97525-68-3 (Z)-4-chloro-N-<2-cyano-1,2-bis(ethoxycarbonyl)vinyl>aniline 
• 92044-65-0 (E)-4-chloro-N-<1,2-dicyano-2-(ethoxycarbonyl)vinyl>aniline 
• 97834-81-6 (Z)-N-<2-cyano-1,2-bis(ethoxycarbonyl)vinyl>-4-methylaniline 

Relevant articles and documents

Ester-Substituted Electron-Poor Alkenes for Cycloaddition-Retroelectrocyclization (CA-RE) and Related Reactions

We report the reactions of electron-deficient alkenes, tetrasubstituted by carboxylic ester and cyano groups, with electron-rich (dimethylamino)phenyl-substituted alkynes. Mono- or diester-substituted alkenes exclusively undergo the [2+2] cycloaddition-retroelectrocyclization (CA-RE) reaction, well established for multicyanated ethenes, whereas tri- and tetraester-substituted alkenes also undergo a [4+2] hetero-Diels-Alder (HDA) reaction with a third product being formed, presumably by a [3+2] cycloaddition reaction followed by rearrangement. Electrochemical studies revealed cathodic shifts of the first reduction potential of the buta-1,3-dienes obtained from the CA-RE reaction as cyano groups are substituted for ester moieties. Post-CA-RE functionalization of the ester-substituted buta-1,3-dienes by transesterification, diazonium chemistry, and cross-coupling is described. The formation of a pharmacologically interesting pyrazolopyran illustrates the synthetic utility of ester-substituted CA-RE products.

An unexpected reaction of diethyl phosphite with electron-deficient dialkyl dicyanofumarates

Diethyl phosphite reacts with both dimethyl dicyanofumarate and dicyanomaleate in boiling 1,2-dichloroethane to yield, after chromatographic workup, a 1:1-mixture of the corresponding meso- and dl-dicyanosuccinates. The analogous transformation was observed in the cases of diethyl and diisopropyl dicyanofumarates. A reaction pathway via initial formation of a P-C bond followed by its hydrolytic cleavage is proposed.

Remote-control photoswitching using NIR light

(Chemical Equation Presented) Near-infrared (NIR) light is used to toggle photoswitches back and forth between their two isomers even though the chromophores do not significantly absorb this type of light. The reactions are achieved through a "remote control" process by using photon up-converting hexagonal NaYF4 nanocrystals doped with lanthanide ions. These nanoparticles absorb 980 nm light and convert it to wavelengths that can be used to trigger the photoswitches offering a practical means to potentially achieve 3D-data storage, drug-delivery, and photolithography.