Dimethyl trans-1,2-cyclopropanedicarboxylate

Base Information

• Chemical Name: Dimethyl trans-1,2-cyclopropanedicarboxylate
• CAS No.: 826-35-7
• Molecular Formula: C7H10 O4
• Molecular Weight: 158.154
• Hs Code.: 29172000
• European Community (EC) Number: 692-727-0
• DSSTox Substance ID: DTXSID10423928
• Nikkaji Number: J305.228A
• Wikidata: Q82236270
• Mol file: 826-35-7.mol

Synonyms:826-35-7;DIMETHYL TRANS-1,2-CYCLOPROPANEDICARBOXYLATE;dimethyl (1R,2R)-cyclopropane-1,2-dicarboxylate;(1R,2R)-rel-Dimethyl cyclopropane-1,2-dicarboxylate;dimethyl trans-cyclopropane-1,2-dicarboxylate;Cyclopropane-1,2-dicarboxylic acid dimethyl ester, E;Dimethyltrans-1,2-cyclopropanedicarboxylate;SCHEMBL974400;AMY3257;DTXSID10423928;1,2-Cyclopropanedicarboxylic acid, dimethyl ester, (1R,2R)-rel-;MFCD00062806;AKOS016346730;AS-50384;CS-0028052;dimethyl-trans-1,2-cyclopropanedicarboxylate;P10056;(1R,2R)-dimethyl cyclopropane-1,2-dicarboxylate;dimethyl (+/-)-trans-cyclopropane-1,2-dicarboxylate;trans-cyclopropane-1,2-dicarboxylic acid dimethylester;1beta,2alpha-Cyclopropanedicarboxylic acid dimethyl ester;cyclopropane-trans-1,2-dicarboxylic acid dimethyl ester

Chemical Property of Dimethyl trans-1,2-cyclopropanedicarboxylate

Chemical Property:

• Vapor Pressure: 0.121mmHg at 25°C
• Melting Point: 173 °C
• Refractive Index: 1.4425-1.4445
• Boiling Point: 101 °C (18 mmHg)
• Flash Point: 99°C
• PSA: 52.60000
• Density: 1.12
• LogP: -0.03150
• Storage Temp.: 2-8°C(protect from light)
• Solubility.: Chloroform, Dichloromethane, Methanol (Slightly)
• 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

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

Safty Information:

• Hazard Codes: Xn
• Statements: 22
• Safety Statements: 36/37/39-26

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(=O)C1CC1C(=O)OC
• Isomeric SMILES: COC(=O)[C@@H]1C[C@H]1C(=O)OC

Technology Process of Dimethyl trans-1,2-cyclopropanedicarboxylate

There total 9 articles about Dimethyl trans-1,2-cyclopropanedicarboxylate 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: 66.0%

methyl chloroacetate (96-34-4) + acrylic acid methyl ester (292638-85-8,9003-21-8,96-33-3) → dimethyl cis-cyclopropane-1,2-dicarboxylate (826-34-6) + dimethyl trans-1,2-cyclopropanedicarboxylate (826-35-7)

Guidance literature:

With sodium methylate; 1.) RT, 16 h, 2.) methanol, 75-80 deg C, 14 h;

Reference yield: 20.0%

crotonic acid methyl ester (623-43-8) + (Dimethylsulfuranyliden)essigsaeure-methylester (103548-67-0) → dimethyl 3β-methylcyclopropane-1α,2α-dicarboxylate (14661-79-1) + methyl 3-methylcyclopropane-1α,2β-dicarboxylate (28363-79-3) + dimethyl trans-1,2-cyclopropanedicarboxylate (826-35-7) + dimethylfumarate (624-49-7)

Guidance literature:

In dichloromethane; for 22h; Heating;

Reference yield:

dimethyl 2,4-dibromopentanedioate (31358-13-1,31448-67-6,149198-10-7,869-09-0) → dimethyl cis-cyclopropane-1,2-dicarboxylate (826-34-6) + dimethyl trans-1,2-cyclopropanedicarboxylate (826-35-7)

Guidance literature:

With (PPh₃)2N⁽¹⁺⁾*Cr(CO)4NO^(1-); In acetonitrile; at -40 ℃; Mechanism; other solvents and temperatures; same reaction with meso isomer;

upstream raw materials:

dimethyl 2,4-dibromopentanedioate

crotonic acid methyl ester

(Dimethylsulfuranyliden)essigsaeure-methylester

diiodomethane

Refernces

• 1、 Budnikova,Petrukhina,Kargin. "Coordination Catalysis in Organic Electrosynthesis. Stoichiometry and Products of Reduction of Dibromomethane by Ni(0) Complexes with π-Acceptor Ligands". . p. 257 - 259. Retrieved 2007/10/03.
• 2、 Liu, Yingchun,Sorensen, Ted S.,Sun, Fang. "Stereoselective 1,3-debromination reactions". . p. 258 - 262. Retrieved 2007/10/02.