Diethyl cis-cyclopropane-1,2-dicarboxylate

Base Information

• Chemical Name: Diethyl cis-cyclopropane-1,2-dicarboxylate
• CAS No.: 710-43-0
• Molecular Formula: C₉H₁₄O₄
• Molecular Weight: 186.208
• Hs Code.: 2917209090
• Mol file: 710-43-0.mol

Synonyms:1,2-Cyclopropanedicarboxylic acid, diethyl ester, cis-;cis-cyclopropane-1,2-dicarboxylic acid diethyl ester;cis-Cyclopropan-1,2-dicarbonsaeure-diaethylester;Diethylcis-cyclopropane-1,2-dicarboxylate;cis-Diethyl cyclopropane-1,2-dicarboxylate;

Chemical Property of Diethyl cis-cyclopropane-1,2-dicarboxylate

Chemical Property:

• Refractive Index: 1.4450 (estimate)
• Boiling Point: 280.69°C (rough estimate)
• PSA: 52.60000
• Density: 1.0620
• LogP: 0.74870
• Storage Temp.: Sealed in dry,Room Temperature

Purity/Quality:

98%min ^*data from raw suppliers

Diethylcis-1,2-Cyclopropanedicarboxylate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: Diethyl cis-1,2-Cyclopropanedicarboxylate is used in the synthetic preparation of intermolecular metal-catalyzed carbenoid cyclopropanations.

Technology Process of Diethyl cis-cyclopropane-1,2-dicarboxylate

There total 12 articles about Diethyl cis-cyclopropane-1,2-dicarboxylate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 70.0%

3-oxabicyclo[3.1.0]hexane-2,4-dione (5617-74-3) + ethanol (64-17-5) → cis-cyclopropane-1,2-dicarboxylic acid diethyl ester (710-43-0)

Guidance literature:

With sulfuric acid; for 5h; Heating;

DOI:10.1055/s-1983-30385

Reference yield: 43.0%

chloroacetic acid ethyl ester (105-39-5) + ethyl acrylate (140-88-5,9003-32-1) → cis-cyclopropane-1,2-dicarboxylic acid diethyl ester (710-43-0) + diethyl trans-cyclopropane-1,2-dicarboxylate (3999-55-1)

Guidance literature:

With sodium hydride; In toluene; at 60 ℃; for 1h; to initiate the reaction MeOH;

DOI:10.1016/S0040-4020(01)89583-1

Reference yield:

trimethylsulfoxonium iodide (1774-47-6) + Diethyl maleate (141-05-9) → cis-cyclopropane-1,2-dicarboxylic acid diethyl ester (710-43-0) + diethyl trans-cyclopropane-1,2-dicarboxylate (3999-55-1)

Guidance literature:

With sodium hydride; Multistep reaction. Yields of byproduct given; 1.) DMSO, 20 min, 2.) 1 h;

upstream raw materials:

ethanol

cis-1,2-cyclopropanedicarboxylic acid

cyclopropane-1,1,2-tricarboxylic acid triethyl ester

chloroacetic acid ethyl ester

Downstream raw materials:

ethyl cis-2-chlorocarbonylcyclopropanecarboxylate

3-benzyl-4-hydroxy-4-methyl-3-azabicyclo[3.1.0]hexane-2-one

3-benzyl-3-aza-bicyclo[3.1.0]hexane-2,4-dione

3-benzyl-3-aza-bicyclo[3.1.0]hexane

Refernces

• 1、 Kaur, Kirandeep,Aeron, Shelly,Bruhaspathy, Miriyala,Shetty, Shankar J.,Gupta, Suman,Hegde, Laxminarayan H.,Silamkoti, Arun D. V.,Mehta, Anita,Chugh, Anita,Gupta, Jang B.,Sarma,Kumar, Naresh. "Design, synthesis and activity of novel derivatives of Oxybutynin and Tolterodine". . p. 2093 - 2096. Retrieved 2007/10/03.
• 2、 Ashton,Canning Meurer,Cantone,Field,Hannah,Karkas,Liou,Patel,Perry,Wagner,Walton,Tolman. "Synthesis and antiherpetic activity of (±)-9-[[(Z)-2-(hydroxymethyl)cyclopropyl]methyl]guanine and related compounds". . p. 2304 - 2315. Retrieved 2007/10/02.