35234-87-8

Basic information

• Product Name: dimethyl 2,3-dicyanobut-2-enedioate
• CAS NO: 35234-87-8
• Molecular Formula: C₈H₆N₂O₄
• Molecular Weight: 194.1442
• Mol File: 35234-87-8.mol
• Article Data: 9

Chemical Properties

• Boiling Point: 310.4°C at 760 mmHg
• Flash Point: 134.7°C
• Density: 1.315g/cm³
• Vapor Pressure: 0.0006mmHg at 25°C
• Refractive Index: 1.484
• CAS DataBase Reference: dimethyl 2,3-dicyanobut-2-enedioate(CAS DataBase Reference)
• NIST Chemistry Reference: dimethyl 2,3-dicyanobut-2-enedioate(35234-87-8)
• EPA Substance Registry System: dimethyl 2,3-dicyanobut-2-enedioate(35234-87-8)

Safety Data

• Hazardous Substances Data: 35234-87-8(Hazardous Substances Data)

Upstream product

• 670-54-2 ethenetetracarbonitrile 
• 105-34-0 methyl 2-cyanoacetate 
• 101342-44-3 dimethyl 2,3-dicyanomaleate 
• 23604-61-7 1,1,3,3-tetramethyl-8-thia-5,6-diazaspiro[3.4]oct-5-en-2-one 
• 89976-96-5 cyanoacetic acid 2-(2-cyanoacetoxy) ethyl ester 
• 115668-29-6 2,3-bis(trimethylsilyloximinomethyl)but-2E,Z-en-1,4-dicarboxylic acid dimethyl ester 
• 115668-28-5 (E)-2,3-Bis-(hydroxyimino-methyl)-but-2-enedioic acid dimethyl ester 
• 31253-11-9 methyl 2-bromo-2-cyanoacetate 
• 74894-01-2 cis,trans-1,4-bis(dimethylamino)buta-1,3-diene 

Downstream Products

• 105020-45-9 4-Cyano-1H-pyrazole-3-carboxylic acid methyl ester 
• 105020-37-9 4-Cyan-1-methyl-3-pyrazolcarbonsaeure-methylester 
• 33090-69-6 methyl 3-cyano-1H-pyrazole-4-carboxylate 
• 70910-18-8 4-Cyan-1-methyl-5-pyrazolcarbonsaeure-methylester 
• 105020-38-0 methyl 1-methyl-1H-1,2,3-triazole-5-carboxylate 
• 105020-39-1 2-Methyl-1,2,3-triazol-4-carbonsaeure-methylester 
• 57362-82-0 1-Methyl-1,2,3-triazol-4-carbonsaeure-methylester 
• 110569-30-7 (1R,2R,3R,4R)-2,3-Dicyano-1,4-diphenyl-1,2,3,4-tetrahydro-naphthalene-2,3-dicarboxylic acid dimethyl ester 
• 110569-29-4 (1S,2R,3R,4S)-2,3-Dicyano-1,4-diphenyl-1,2,3,4-tetrahydro-naphthalene-2,3-dicarboxylic acid dimethyl ester 
• 110569-28-3 trans-2,3-dicyano-trans-2,3-bis(methoxycarbonyl)-cis-1,4-diphenyltetralin 
• 88692-09-5 dimethyl 3,4-trans-dicyano-2,2-diphenylthiolane-3,4-dicarboxylate 
• 88692-09-5 cis-3,4-dicyano-2,2-diphenyltetrahydrothiophene-3,4-dicarboxylate 
• 139943-17-2 (1R,2S,3S)-1,2-Dicyano-3-dimethylamino-cyclohex-4-ene-1,2-dicarboxylic acid dimethyl ester 
• 1226855-16-8 dimethyl (Z)-3-cyano-2-[(4-trifluoromethylphenyl)amino]butanedioate 

Relevant articles and documents

β,β'-Functionalized N,N-divinyl-N-trimethylsilyloxyamines via silylation of β-substituted aliphatic nitro compounds. The investigation of the mechanism of the process using selective trapping reagents

Hitherto unknown N,N-divinyl-N-trimethylsilyloxyamines of the general formula |XC(R)=CH|2NOSiMe3 (X = CO2Me, CN, 5-methyloxycarbonylisoxazolin-3-yl; R = H, Me, CH(Me)CO2Me) were obtained with moderate to good yields by silylation of nitro compounds XCH(R)CH2NO2 with N,O-bis(trimethylsilyl)acetamide. The mechanism of this reaction was studied by the example of silylation of methyl-3-nitropropionate using selective trapping reagents. Trimethylsilyl ester of the starting aci-nitro compound and methyl 2-nitroso acrylate were intercepted as consecutive intermediates. Thus, the silylation of β-functionalized nitro compounds could be presented as a convenient route to practically unknown β-substituted nitroso-alkenes XC(R)=CHNO which behave as active 1,3-heterodienes towards ethyl vinyl ether used as trapping reagent.

1,3-CYCLOADDITIONS OF ALIPHATIC THIONE S-METHYLIDES TO DIMETHYL 2,3-DICYANOFUMARATE AND 2,3-DICYANOMALEATE; A TEST CASE FOR STERIC COURSE AND MECHANISM

The 1,3-cycloadditions of thione S-methylides 2 and 9 to dimethyl 2,3-dicyanofumarate and 2,3-dicyanomaleate are nonstereospecific.A preceding cis,trans isomerization of the unsaturated dipolarophiles catalyzed by the thiadiazolines (precursors of the thione S-methylides) had to be suppressed in order to clarify the stereochemical leakage during the cycloaddition.

Room temperature dynamic polymers based on Diels-Alder chemistry

Dynamers based on reversible Diels-Alder chemistry have been obtained and shown to undergo dynamic exchange at room temperature. Their study in solution by small-angle neutron scattering indicated the formation of long and highly flexible chains. Polydispersed molecules gave Tg values below room temperature, permitting the generation of a dynamic elastomer upon introduction of a dynamic cross-linking agent. The use of a system with a low equilibrium constant gives access to materials with interesting self-healing properties.