826-34-6

Basic information

• Product Name: DIMETHYL CIS-1,2-CYCLOPROPANEDICARBOXYLATE
• Synonyms: DIMETHYL CIS-1,2-CYCLOPROPANEDICARBOXYLATE;cis-Dimethylcyclopropane dicarboxylate;Dimethyl cis-1,2-cyclopropanedicarboxylate 98%;(1R)-Cyclopropane-1β,2β-dicarboxylic acid dimethyl ester;(1R,2S)-1,2-Cyclopropanedicarboxylic acid dimethyl ester;Dimethyl cis-1,2-cyclopropanedicarboxylate,98%;DIETHYL CIS-1,2-CYCLOPROPANEDICARBOXYLATE;DiMethyl cis-1,2-clopropanedicarboxylate
• CAS NO: 826-34-6
• Molecular Formula: C₇H₁₀O₄
• Molecular Weight: 158.15
• Product Categories: Cycloalkanes
• Mol File: 826-34-6.mol
• Article Data: 15

Chemical Properties

• Boiling Point: 112 °C (18 mmHg)
• Flash Point: 99 °C
• Appearance: Clear colorless/Liquid
• Density: 1.15
• Vapor Pressure: 0.121mmHg at 25°C
• Refractive Index: 1.4445-1.4465
• Storage Temp.: 2-8°C
• CAS DataBase Reference: DIMETHYL CIS-1,2-CYCLOPROPANEDICARBOXYLATE(CAS DataBase Reference)
• NIST Chemistry Reference: DIMETHYL CIS-1,2-CYCLOPROPANEDICARBOXYLATE(826-34-6)
• EPA Substance Registry System: DIMETHYL CIS-1,2-CYCLOPROPANEDICARBOXYLATE(826-34-6)

Safety Data

• Hazard Codes: Xn
• Statements: 22
• Safety Statements: 36/37/39-26
• Hazardous Substances Data: 826-34-6(Hazardous Substances Data)

Usage

Chemical Properties

CLEAR COLOURLESS LIQUID

Uses

Dimethyl cis-1,2-Cyclopropanedicarboxylate, is used for cis-trans isomerization of cyclopropyl radical trap catalyzed by extradiol catechol dioxygenases with evidence for semiquinone intermediate.

InChI:InChI=1/C7H10O4/c1-10-6(8)4-3-5(4)7(9)11-2/h4-5H,3H2,1-2H3/t4-,5+

Upstream product

• 186581-53-3 diazomethane 
• 13279-88-4 (±)-2-(methoxycarbonyl)cyclopropanecarboxylic acid 
• 67-56-1 methanol 
• 5617-74-3 cis-1,2-cyclopropanedicarboxylic acid anhydride 
• 31358-13-1 dimethyl 2,4-dibromopentanedioate 
• 624-48-6 dimethyl cis-but-2-ene-1,4-dioate 
• 74-95-3 1,1-dibromomethane 
• 3724-55-8 methyl but-3-enoate 
• 6832-16-2 methyl diazoacetate 
• 5617-74-3 3-oxabicyclo[3.1.0]hexane-2,4-dione 
• 20561-09-5 diethyl (cis,trans)-1,2-cyclopropanedicarboxylate 
• 58616-95-8 trans-1,2-cyclopropanedicarboxylic acid 
• 149-73-5 trimethyl orthoformate 
• 96-34-4 methyl chloroacetate 

Downstream Products

• 2345-68-8 ((1R,2S)-2-Hydroxymethyl-cyclopropyl)-methanol 
• 2374-08-5 cis-1,2-Cyclopropandicarbonsaeuredihydrazid 
• 696-74-2 cis-1,2-cyclopropanedicarboxylic acid 
• 13279-88-4 (±)-2-(methoxycarbonyl)cyclopropanecarboxylic acid 
• 88335-87-9 (1S,RS)-cis-2-methoxycarbonyl-cyclopropane-1-carboxylic acid 
• 89395-28-8 (1R,5S)-3-oxabicyclo[3.1.0]hexan-2-one 
• 88335-86-8 (1R,2S)-cis-2-methoxycarbonyl-cyclopropane-1-carboxylic acid 
• 119908-64-4 C₅H₄O₄^(2-)*2K⁽¹⁺⁾ 
• 98516-04-2 Acetic acid (1R,2S)-2-hydroxymethyl-cyclopropylmethyl ester 

Relevant articles and documents

Nickel(0)-Catalyzed Reactions of Bicyclobutanes. Geminal Two-Bond Cleavage Reaction and the Stereospecific Olefin Trapping of the Carbenoid Intermediate.

Zerovalent nickel complexes such as bis(acrylonitrile)nickel(0) or bis(1,5-cyclooctadiene)nickel(0) catalyze the reaction of bicyclobutanes and electron-deficient olefins such as methyl acrylate and acrylonitrile to give the corresponding allylcyclopropane derivatives in excellent yields.The reaction of 3-deuterio-1,2,2-trimethylbicyclobutane indicates that the two-bond cleavage occurs at the central ? bond and one of the four peripheral bonds of bicyclobutanes to generate an allylcarbene-nickel complex as the reactive intermediate.The reactionof bicyclobutane with (Z)-β-deuterioacrylate or a pair of E and Z 1,2-disubstituted olefins proceeded with a high degree of stereospecificity.The mechanism of cycloaddition is discussed.

Cyclopropane formation by nickel-catalysed electroreductive coupling of activated olefins and unactivated gem-dibromo compounds

Cyclopropyl derivatives have been prepared with good yields by transition-metal catalysed electroreductive coupling of activated olefins and unactivated gem-dibromo compounds. This electrolysis is characterized by the use of a Fe/Ni catalyst system, acetonitrile as the solvent and a catalytic amount of triphenylphosphine as ligand. This procedure is a good alternative to the classical preparations of cyclopropyl derivatives from activated olefins (Simmons-Smith reaction, 1,3-dipolar addition of diazomethane, 1,4-addition of phosphorus and sulfur ylides).

Coordination Catalysis in Organic Electrosynthesis. Stoichiometry and Products of Reduction of Dibromomethane by Ni(0) Complexes with π-Acceptor Ligands

Reaction of Ni(0) complexes with dibromomethane gives different final products depending on the nature of the process in the stage of oxidative addition, which proceeds either through the elimination of two bromide ions to give intermediate carbene, or by the elimination of one bromide ion, depending on the ligand enviroment in the metal complex.