Dimethyl cyclohexane-1,2-dicarboxylate

Base Information

• Chemical Name: Dimethyl cyclohexane-1,2-dicarboxylate
• CAS No.: 1687-29-2
• Molecular Formula: C10H16O4
• Molecular Weight: 200.235
• Hs Code.: 2917209090
• European Community (EC) Number: 605-528-0
• Nikkaji Number: J45.871F
• Wikidata: Q63391620
• Mol file: 1687-29-2.mol

Synonyms:1,2-Cyclohexanedicarboxylicacid, dimethyl ester, (1R,2S)-rel- (9CI);1,2-Cyclohexanedicarboxylic acid,dimethyl ester, cis- (8CI);Dimethyl cis-1,2-cyclohexanedicarboxylate;NSC144650;cis-1,2-Cyclohexanedicarboxylic acid dimethyl ester;

Chemical Property of Dimethyl cyclohexane-1,2-dicarboxylate

Chemical Property:

• Vapor Pressure: 0.0133mmHg at 25°C
• Refractive Index: 1.457
• Boiling Point: 259 °C at 760 mmHg
• Flash Point: 121.3 °C
• PSA: 52.60000
• Density: 1.102 g/cm³
• LogP: 1.13880
• Storage Temp.: Sealed in dry,Room Temperature
• XLogP3: 1.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 200.10485899
• Heavy Atom Count: 14
• Complexity: 200

Purity/Quality:

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

Dimethyl cis-1,2-Cyclohexanedicarboxylate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(=O)C1CCCCC1C(=O)OC
• Isomeric SMILES: COC(=O)[C@@H]1CCCC[C@@H]1C(=O)OC

Technology Process of Dimethyl cyclohexane-1,2-dicarboxylate

There total 15 articles about Dimethyl cyclohexane-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: 100.0%

methanol (67-56-1) + 1,2-cis-cyclohexanedicarboxylic anhydride (13149-00-3) → dimethyl cis-1,2-cyclohexanedicarboxylate (1687-29-2)

Guidance literature:

With sulfuric acid; at 20 - 60 ℃;

DOI:10.1021/jacs.7b03539

Reference yield: 85.0%

methanol (67-56-1) + carbon monoxide (201230-82-2) + cyclohexene (110-83-8) → dimethyl cis-1,2-cyclohexanedicarboxylate (1687-29-2)

Guidance literature:

methanol; cyclohexene; With (bis(2,6-dimethylphenyl) butane-2,3-diimine)palladium(II)bis(trifluoroacetate); toluene-4-sulfonic acid; p-benzoquinone; In tetrahydrofuran; at 20 ℃; for 0.166667h; Autoclave; Inert atmosphere;

carbon monoxide; In tetrahydrofuran; at 20 ℃; for 66h; under 3000.3 Torr; diastereospecific reaction; Autoclave;

DOI:10.1002/adsc.201701597

Reference yield:

phthalic acid dimethyl ester (131-11-3,64441-70-9) → dimethyl cis-1,2-cyclohexanedicarboxylate (1687-29-2)

Guidance literature:

With methanol; ruthenium; at 200 ℃; under 102971 Torr; Hydrogenation;

upstream raw materials:

diazomethane

(1R,2S)-cyclohexane-1,2-dicarboxylic acid

methanol

phthalic acid dimethyl ester

Downstream raw materials:

dimethyl (1S,2R)-4-oxocyclohexane-1,2-dicarboxylate

(1RS,2SR)-dimethyl 4-oxocyclohexane-1,2-dicarboxylate

(1R,2R)-(-)-trans-cyclohexane-1,2-dicarboxylic acid

(1S,2S)-cyclohexane-1,2-dicarboxylic acid

Refernces

• 1、 Ravi Ganesh,Pachore, Sharad S.,Pratap,Umesh,Basaveswara Rao,Murthy,Suresh Babu. "Enantioselective Synthesis of ((1 R,2 R)-Cyclohexane-1,2-diyl)bis(methylene)dimethanesulfonate, a Lurasidone Hydrochloride Intermediate". . p. 2676 - 2682. Retrieved 2015.
• 2、 Cope,Herrick. "-". . . Retrieved 1950.
• 3、 Wang, Yaxin,Hu, Xiafei,Morales-Rivera, Cristian A.,Li, Guo-Xing,Huang, Xin,He, Gang,Liu, Peng,Chen, Gong. "Epimerization of Tertiary Carbon Centers via Reversible Radical Cleavage of Unactivated C(sp3)-H Bonds". supporting information. p. 9678 - 9684. Retrieved 2018/07/21.
• 4、 Phan-Vu, Duc-Ha,Tan, Chung-Sung. "Synthesis of phthalate-free plasticizers by hydrogenation in water using RhNi bimetallic catalyst on aluminated SBA-15". . p. 18178 - 18188. Retrieved 2017/04/04.