Dimethyl 1,4-cubanedicarboxylate

Base Information

• Chemical Name: Dimethyl 1,4-cubanedicarboxylate
• CAS No.: 29412-62-2
• Molecular Formula: C12H12O4
• Molecular Weight: 220.225
• Hs Code.: 29172090
• European Community (EC) Number: 814-007-9
• NSC Number: 124104
• DSSTox Substance ID: DTXSID50183630
• Nikkaji Number: J88.601G
• Wikidata: Q72469637
• Mol file: 29412-62-2.mol

Synonyms:Dimethyl 1,4-cubanedicarboxylate;29412-62-2;dimethyl cubane-1,4-dicarboxylate;Cubane-1,4-dicarboylic acid dimethyl ester;1,8-DIMETHYL CUBANE-1,8-DICARBOXYLATE;1,4-Bis(methoxycarbonyl)cubane;Cubane-1,4-dicarboxylic acid dimethyl ester;SCHEMBL352325;dimethylcubane-1,4-dicarboxylate;DTXSID50183630;OXBMFCGRQJNAOY-UHFFFAOYSA-N;AMY37355;MFCD29060101;NSC124104;AKOS015851360;CS-W001051;GS-8000;NSC 124104;NSC-124104;D5542;FT-0689544;D-4690;EN300-156445;F19635;A819887;dimethyl pentacyclo [4.2.0.02,5.03,8.04,7]octane-1,4-dicarboxylate;Pentacyclo[4.2.0.02,5.03,8.04,7]octane-1,4-dicarboxylic acid, 1,4-dimethyl ester;Pentacyclo[4.2.0.02,5.03,8.04,7]octane-1,4-dicarboxylicacid, 1,4-dimethyl ester;Dimethyl cubane-1,4-dicarboxylate

Chemical Property of Dimethyl 1,4-cubanedicarboxylate

Chemical Property:

• Vapor Pressure: 0.00702mmHg at 25°C
• Melting Point: 163-165 °C(lit.)
• Refractive Index: 1.704
• Boiling Point: 270 °C at 760 mmHg
• Flash Point: 131.3 °C
• PSA: 52.60000
• Density: 1.684 g/cm³
• LogP: 0.07040
• Storage Temp.: Sealed in dry,Room Temperature
• XLogP3: 0
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 220.07355886
• Heavy Atom Count: 16
• Complexity: 382

Purity/Quality:

99% ^*data from raw suppliers

Dimethyl1,4-cubanedicarboxylate ^*data from reagent suppliers

Safty Information:

• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(=O)C12C3C4C1C5C2C3C45C(=O)OC

Technology Process of Dimethyl 1,4-cubanedicarboxylate

There total 20 articles about Dimethyl 1,4-cubanedicarboxylate 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: 80.5%

methyl bisulfate (75-93-4) + cubane-1,4-dicarboxylic acid → dimethyl pentacyclo[4.2.0.0.2,50.3,804,7]octane-1,4-dicarboxylate (29412-62-2)

Guidance literature:

at 30 ℃; for 1h;

DOI:10.1007/BF00699835

Reference yield: 71.0%

cubane-1,4-dicarboxylic acid (32846-66-5) → cubane-1,4-dicarboxylic acid dimethyl ester (29412-62-2)

Guidance literature:

With Dowex 50W-X₈ resin; In methanol; for 24h; Reflux;

DOI:10.1016/j.bmcl.2013.12.087

Reference yield: 30.0%

methanol (67-56-1) + cubane-1,4-dicarboxylic acid (32846-66-5) → cubane-1,4-dicarboxylic acid dimethyl ester (29412-62-2)

Guidance literature:

With sulfuric acid; for 18h; Inert atmosphere; Reflux;

DOI:10.1021/op400181g

upstream raw materials:

diazomethane

carbon dioxide

tert.-butyl lithium

1,4-diiodocubane

Downstream raw materials:

1,2,4,7-Tetra(carboxymethyl)cubane

1,4-bis(1-hydroxy-1-methylethyl)pentacyclo<4.2.0.0^2,5.0^3,8.0^4,7>octane

methyl 4-(1-hydroxy-1-methylethyl)pentacyclo<4.2.0.0^2,5.0^3,8.0^4,7>octane-1-carboxylate

methyl 4-(α,α-diphenylhydroxymethyl)pentacyclo<4.2.0.0^2,5.0^3,8.0^4,7>octane-1-carboxylate

Refernces

• 1、 Hasegawa, Takeshi,Nigo, Tomohiro,Kuwatani, Yoshiyuki,Ueda, Ikuo. "Mechanistic Study of Base-Promoted Rearrangement of 1,5-Dibromopentacyclo2,5.03,9.04,8>decane-6,10-dione to 10-Oxa-9-oxopentacyclo2,4.03,6.05,8>decane-3-carboxylic Acid". . p. 2676 - 2681. Retrieved 1993.
• 2、 Falkiner, Michael J.,Littler, Stuart W.,McRae, Kenneth J.,Savage, G. Paul,Tsanaktsidis, John. "Pilot-Scale Production of Dimethyl 1,4-Cubanedicarboxylate". . p. 1503 - 1509. Retrieved 2013.
• 3、 Jelínková, Kristyna,Surmová, Heda,Matelová, Alena,Rouchal, Michal,Prucková, Zdeňka,Dastychová, Lenka,Ne?as, Marek,Vícha, Robert. "Cubane Arrives on the Cucurbituril Scene". supporting information. p. 2698 - 2701. Retrieved 2017/05/24.