DIMETHYL CIS-1,2-CYCLOPROPANEDICARBOXYLATE

Base Information

• Chemical Name: DIMETHYL CIS-1,2-CYCLOPROPANEDICARBOXYLATE
• CAS No.: 826-34-6
• Molecular Formula: C7H10O4
• Molecular Weight: 158.154
• Hs Code.: 29172090
• Mol file: 826-34-6.mol

Synonyms:1,2-Cyclopropanedicarboxylicacid, dimethyl ester, (1R,2S)-rel- (9CI);1,2-Cyclopropanedicarboxylic acid,dimethyl ester, cis- (8CI);(cis)-1,2-Bis(methoxycarbonyl)cyclopropane;Dimethyl cis-1,2-cyclopropanedicarboxylate;Dimethylcis-1,2-cyclopropanedicarboxylate;

Chemical Property of DIMETHYL CIS-1,2-CYCLOPROPANEDICARBOXYLATE

Chemical Property:

• Appearance/Colour: clear colourless liquid
• Vapor Pressure: 0.121mmHg at 25°C
• Refractive Index: 1.4445-1.4465
• Boiling Point: 219.2 °C at 760 mmHg
• Flash Point: 99 °C
• PSA: 52.60000
• Density: 1.231 g/cm₃
• LogP: -0.03150
• Storage Temp.: 2-8°C

Purity/Quality:

99%, ^*data from raw suppliers

DIMETHYL CIS-1,2-CYCLOPROPANEDICARBOXYLATE 98.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22
• Safety Statements: 36/37/39-26

MSDS Files:

SDS file from LookChem

Useful:

• 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.

Technology Process of DIMETHYL CIS-1,2-CYCLOPROPANEDICARBOXYLATE

There total 17 articles about DIMETHYL CIS-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: 55.0%

diazomethane (186581-53-3,908094-01-9,334-88-3) → dimethyl cis-cyclopropane-1,2-dicarboxylate (826-34-6)

Guidance literature:

With hydrogenchloride; sodium hydroxide; dihydrogen peroxide; In methanol; 1.) -70 deg C, 2) -30 deg C, 3.) 0 deg C, several hours;

DOI:10.1021/jo00327a004

Reference yield:

diazomethane (186581-53-3,908094-01-9,334-88-3) + (R)-Cyclopropane-1,2-dicarboxylic acid monomethyl ester → dimethyl cis-cyclopropane-1,2-dicarboxylate (826-34-6) + dimethyl (-)-trans-1,2-cyclopropanedicarboxylate

Guidance literature:

In diethyl ether; at 0 ℃;

DOI:10.1021/ja0305961

upstream raw materials:

diazomethane

(±)-2-(methoxycarbonyl)cyclopropanecarboxylic acid

methanol

cis-1,2-cyclopropanedicarboxylic acid anhydride

Downstream raw materials:

Dimethyl glutarate

(±)-2-(methoxycarbonyl)cyclopropanecarboxylic acid

((1R,2S)-2-Hydroxymethyl-cyclopropyl)-methanol

cis-1,2-Cyclopropandicarbonsaeuredihydrazid

Refernces

• 1、 Doering, William Von E.,Barsa, Edward Albert. "Fate of diradicals in the caldera: Stereochemistry of thermal stereomutation and ring enlargement in cis- and trans-1-cyano-2(E)- propenylcyclopropanes". . p. 12353 - 12362. Retrieved 2007/10/03.
• 2、 Martin-Vila, Marta,Muray, Elena,Aguado, Gemma P.,Alvarez-Larena, Angel,Branchadell, Vicenc,Minguillon, Cristina,Giralt, Ernest,Ortuo, Rosa M.. "Enantioselective synthetic approaches to cyclopropane and cyclobutane β-amino acids: Synthesis and structural study of a conformationally constrained β-dipeptide". . p. 3569 - 3584. Retrieved 2007/10/03.