Dimethyl bicyclo[2.2.2]octane-1,4-dicarboxylate

Base Information

• Chemical Name: Dimethyl bicyclo[2.2.2]octane-1,4-dicarboxylate
• CAS No.: 1459-96-7
• Molecular Formula: C12H18O4
• Molecular Weight: 226.273
• Hs Code.: 2917209090
• European Community (EC) Number: 810-235-8
• DSSTox Substance ID: DTXSID20384379
• Nikkaji Number: J2.481.549H
• Wikidata: Q72469522
• Mol file: 1459-96-7.mol

Synonyms:dimethyl bicyclo[2.2.2]octane-1,4-dicarboxylate;1459-96-7;1,4-dimethyl bicyclo[2.2.2]octane-1,4-dicarboxylate;MFCD01312167;Bicyclo[2.2.2]octane-1,4-dicarboxylic acid, dimethyl ester;SCHEMBL2445606;bicyclo[2.2.2]octane-1,4-dicarboxylic acid dimethyl ester;DTXSID20384379;HDOVTVDGSLEUSK-UHFFFAOYSA-N;Bicyclo[2.2.2]octane-1,4-dicarboxylicacid, 1,4-dimethyl ester;AKOS015950741;AM84419;CS-W001269;MB01765;1,4-dicarbomethoxybicyclo[2.2.2]octane;AC-25477;AS-41599;SY041256;FT-0654826;EN300-109771;dimethylbicyclo[2.2.2]octane-1,4-dicarboxylate;A808437;Bicyclo[2.2.2]-1,4-dicarboxylic acid dimethyl ester;Z1427941564;Bicyclo[2.2.2]octane-1,4-dicarboxylic acid, 1,4-dimethyl ester

Chemical Property of Dimethyl bicyclo[2.2.2]octane-1,4-dicarboxylate

Chemical Property:

• Appearance/Colour: white crystal
• Vapor Pressure: 0.00568mmHg at 25°C
• Refractive Index: 1.515
• Boiling Point: 273.6 °C at 760 mmHg
• Flash Point: 126.968 °C
• PSA: 52.60000
• Density: 1.206 g/cm³
• LogP: 1.67300
• Storage Temp.: Sealed in dry,Room Temperature
• XLogP3: 1.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 226.12050905
• Heavy Atom Count: 16
• Complexity: 265

Purity/Quality:

99% ^*data from raw suppliers

Dimethylbicyclo[2.2.2]octane-1,4-dicarboxylate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(=O)C12CCC(CC1)(CC2)C(=O)OC
• Uses: Dimethyl Bicyclo[2.2.2]octane-1,4-dicarboxylate is used in preparation of cycloalkanecarboxamides and related compounds as modulators of the integrated stress pathway.

Technology Process of Dimethyl bicyclo[2.2.2]octane-1,4-dicarboxylate

There total 22 articles about Dimethyl bicyclo[2.2.2]octane-1,4-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: 89.2%

dimethyl 1'H,4'H-dispiro[1,3-dithiolane-2,2'-bicyclo[2.2.2]octane-5',2''-[1,3]dithiolane]-1',4'-dicarboxylate (174685-35-9) → dimethyl bicyclo[2.2.2]octane-1,4-dicarboxylate (1459-96-7)

Guidance literature:

With ethanol; Raney nickel-W₂; for 96h; Heating;

DOI:10.1055/s-1996-4152

Reference yield: 72.0%

dimethyl 1,4-cyclohexane dicarboxylate (94-60-0) + 1-Bromo-2-chloroethane (107-04-0) → dimethyl bicyclo[2.2.2]octane-1,4-dicarboxylate (1459-96-7)

Guidance literature:

With N,N,N,N,N,N-hexamethylphosphoric triamide; lithium diisopropyl amide; In tetrahydrofuran; -78 deg C to RT;

DOI:10.1016/S0040-4039(98)02411-3

Reference yield: 57.0%

dimethyl 1-(2'-chloroethyl)cyclohexane-1,4-dicarboxylate (106004-06-2) → dimethyl bicyclo[2.2.2]octane-1,4-dicarboxylate (1459-96-7)

Guidance literature:

With N,N,N,N,N,N-hexamethylphosphoric triamide; lithium diisopropyl amide; In tetrahydrofuran;

upstream raw materials:

dimethyl bicyclo[2.2.2]oct-2-ene-1,4-dicarboxylate

dimethyl 1-(2'-chloroethyl)cyclohexane-1,4-dicarboxylate

dimethyl 1'H,4'H-dispiro[1,3-dithiolane-2,2'-bicyclo[2.2.2]octane-5',2''-[1,3]dithiolane]-1',4'-dicarboxylate

dimethyl 1,4-cyclohexane dicarboxylate

Downstream raw materials:

benzyl 4-hydroxybicyclo[2.2.2]octan-1-ylcarbamate

Bicyclo<2.2.2>octane-1,4-dimethanol

4-hydroxymethyl-bicyclo[2.2.2]octane-1-carboxylic acid methyl ester

Refernces

• 1、 Bandak, Dmytro,Babii, Oleg,Vasiuta, Roman,Komarov, Igor V.,Mykhailiuk, Pavel K.. "Design and synthesis of novel 19F-amino acid: A promising 19F NMR label for peptide studies". . p. 226 - 229. Retrieved 2015.
• 2、 -. "SYNTHESIS OF BICYCLO[2.2.2]OCTANE DERIVATIVES". Paragraph 0092. . Retrieved 2019/05/02.
• 3、 -. "Bicyclo [2.2.2] octane - 1, 4 - dicarboxylic acid mono methyl ester synthesis method". . . Retrieved 2017/07/07.