4-METHOXYCARBONYLCUBANECARBOXYLIC ACID

Base Information

• Chemical Name: 4-METHOXYCARBONYLCUBANECARBOXYLIC ACID
• CAS No.: 24539-28-4
• Molecular Formula: C11H10 O4
• Molecular Weight: 206.198
• Hs Code.: 29172090
• Mol file: 24539-28-4.mol

Synonyms:Pentacyclo[4.2.0.02,5.03,8.04,7]octane-1,4-dicarboxylicacid, monomethyl ester (8CI,9CI); NSC 640885

Chemical Property of 4-METHOXYCARBONYLCUBANECARBOXYLIC ACID

Chemical Property:

• Vapor Pressure: 1.46E-05mmHg at 25°C
• Melting Point: 181°C
• Refractive Index: 1.822
• Boiling Point: 341.5°Cat760mmHg
• PKA: 4.24±0.40(Predicted)
• Flash Point: 141.4°C
• PSA: 63.60000
• Density: 1.956g/cm³
• LogP: -0.01800

Purity/Quality:

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

4-Methoxycarbonylcubanecarboxylic acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: 4-Methoxycarbonylcubanecarboxylic Acid is a cubane derivative being studied for its potential to act as a benzene bioisostere. 4-Methoxycarbonylcubanecarboxylic acid is a tertiary carboxylic acid that can undergo iododecarboxylation using 1,3-diiodo-5,5-dimethylhydantoin (DIH) as both reaction initiator and iodine source under irradiative conditions. This product was previously listed as BML00136.

Technology Process of 4-METHOXYCARBONYLCUBANECARBOXYLIC ACID

There total 2 articles about 4-METHOXYCARBONYLCUBANECARBOXYLIC ACID 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: 99.0%

cubane-1,4-dicarboxylic acid dimethyl ester (29412-62-2) → 4-(methoxycarbonyl)-1-cubanecarboxylic acid (24539-28-4)

Guidance literature:

With sodium hydroxide; In tetrahydrofuran; at 20 ℃; for 18h;

DOI:10.1016/j.tet.2017.10.075

Reference yield: 3.0%

cubane-1,4-dicarboxylic acid dimethyl ester (29412-62-2) → 4-(methoxycarbonyl)-1-cubanecarboxylic acid (24539-28-4) + cubane-1,4-dicarboxylic acid (32846-66-5)

Guidance literature:

With sodium hydroxide; In tetrahydrofuran; methanol; Ambient temperature;

DOI:10.1055/s-1995-3961

Reference yield: 91.0%

4-(methoxycarbonyl)-1-cubanecarboxylic acid (24539-28-4) → cubane-1,4-dicarboxylic acid (32846-66-5)

Guidance literature:

With water; sodium hydroxide; In methanol; for 4.5h; Reflux;

DOI:10.1002/adsc.201100145

upstream raw materials:

cubane-1,4-dicarboxylic acid dimethyl ester

Downstream raw materials:

4-(4-Bromo-phenyl)-cubane-1-carboxylic acid methyl ester

4-(2-Bromo-phenyl)-cubane-1-carboxylic acid methyl ester

4-(4-Trifluoromethyl-phenyl)-cubane-1-carboxylic acid methyl ester

4-(3-Trifluoromethyl-phenyl)-cubane-1-carboxylic acid methyl ester

Refernces

• 1、 McGonagle, Alison E.,Savage, G. Paul. "Free-radical polymerization and ring-expansion of a cubane acrylate: A unique low-shrink polymer". . p. 145 - 149. Retrieved 2009.
• 2、 Eaton,Nodari,Tsanaktsidis,Upadhyaya. "Barton decarboxylation of cubane-1,4-dicarboxylic acid: Optimized procedures for cubanecarboxylic acid and cubane". . p. 501 - 502. Retrieved 1995.
• 3、 Zhang,Zhu,Anh,Song. "Highly efficient, selective and ultrasound-assisted monohydrolysis of polyhedral diesters in co-solvent". . p. 7351 - 7354. Retrieved 2013.
• 4、 Dallaston, Madeleine A.,Brusnahan, Jason S.,Wall, Craig,Williams, Craig M.. "Thermal and Sensitiveness Determination of Cubanes: Towards Cubane-Based Fuels for Infrared Countermeasures". supporting information. p. 8344 - 8352. Retrieved 2019/06/04.
• 5、 Houston, Sevan D.,Xing, Hui,Bernhardt, Paul V.,Vanden Berg, Timothy J.,Tsanaktsidis, John,Savage, G. Paul,Williams, Craig M.. "Cyclooctatetraenes through Valence Isomerization of Cubanes: Scope and Limitations". supporting information. p. 2735 - 2739. Retrieved 2019/02/07.