Cyclopropane-1,2-dicarboxylic acid dimethyl ester

Base Information

• Chemical Name: Cyclopropane-1,2-dicarboxylic acid dimethyl ester
• CAS No.: 702-28-3
• Molecular Formula: C₇H₁₀O₄
• Molecular Weight: 158.154
• Hs Code.: 2917209090
• European Community (EC) Number: 861-639-6
• DSSTox Substance ID: DTXSID10369155
• Nikkaji Number: J387.708F
• Mol file: 702-28-3.mol

Synonyms:1,2-Cyclopropanedicarboxylic acid, dimethyl ester;dimethyl cis-1,2-cyclopropanedicarboxylate;2S)-cyclopropane-1,2-dicarboxylate;1,2-Cyclopropanedicarboxylic acid,dimethyl ester;

Chemical Property of Cyclopropane-1,2-dicarboxylic acid dimethyl ester

Chemical Property:

• Refractive Index: 1.4472 (estimate)
• Boiling Point: 219°C (estimate)
• PSA: 52.60000
• Density: 1.1584
• LogP: -0.03150
• Storage Temp.: 2-8°C
• XLogP3: 0.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 158.05790880
• Heavy Atom Count: 11
• Complexity: 167

Purity/Quality:

98%,99%, ^*data from raw suppliers

Dimethylcyclopropane-1,2-dicarboxylate 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(=O)C1CC1C(=O)OC

Technology Process of Cyclopropane-1,2-dicarboxylic acid dimethyl ester

There total 4 articles about Cyclopropane-1,2-dicarboxylic acid dimethyl ester 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: 94.0%

Dimethyl glutarate (1119-40-0) → 1,2-cyclopropane dicarboxylic acid diester (702-28-3)

Guidance literature:

With hydrogenchloride; copper(ll) bromide; lithium diisopropyl amide; In tetrahydrofuran; hexane; at -78 ℃; Product distribution; var. temp., var. metal salt, var. molar equiv., var. solvent additive;

DOI:10.1021/jo00155a047

Reference yield: 65.0%

methyl chloroacetate (96-34-4) + acrylic acid methyl ester (292638-85-8,9003-21-8,96-33-3) → 1,2-cyclopropane dicarboxylic acid diester (702-28-3)

Guidance literature:

With sodium hydride;

DOI:10.1016/S0040-4039(00)95703-4

Reference yield:

C17H19O4S(1+)*BF4(1-) (89363-76-8) + acrylic acid methyl ester (292638-85-8,9003-21-8,96-33-3) → 1,2-cyclopropane dicarboxylic acid diester (702-28-3)

Guidance literature:

With potassium carbonate; Yield given. Multistep reaction; 1.)CHCl₃, H₂O, 0 deg C, 2.) 24h, ambient temp.;

DOI:10.1021/jo00184a030

upstream raw materials:

Dimethyl glutarate

methyl chloroacetate

acrylic acid methyl ester

C₁₇H₁₉O₄S⁽¹⁺⁾*BF₄^(1-)

Downstream raw materials:

trans-1,2-cyclopropanedicarboxylic acid

(1RS,2RS)-1,2-cyclopropanedicarboxylic acid monomethyl ester

(1aR,1bS,3S,5aS)-3-Phenyl-hexahydro-4-oxa-4a-aza-cyclopropa[a]pentalene

(1aR,1bS,3R,5aS)-3-Phenyl-hexahydro-4-oxa-4a-aza-cyclopropa[a]pentalene

Refernces

• 1、 Tufariello, Joseph J.,Milowsky, Arnold S.,Al-Nuri, Mohammed,Goldstein, Steven. "The Synthesis and Cycloaddition Reactions of 3-Azabicyclohex-2-ene 3-oxide and 3-Azabicyclohept-2-ene 3-oxide. Highly Strained Bicyclic Nitrones". . p. 267 - 270. Retrieved 2007/10/02.
• 2、 Chung, Sung Kee,Dunn, Larson B.. "Oxidative Cyclization of Dicarboxylate Dienolates as a New Cyclization Method". . p. 1125 - 1127. Retrieved 2007/10/02.