Cubane

Base Information

• Chemical Name: Cubane
• CAS No.: 277-10-1
• Molecular Formula: C8H8
• Molecular Weight: 104.152
• UNII: Z5HM0Q7DK1
• DSSTox Substance ID: DTXSID50182062
• Nikkaji Number: J5.449F
• Wikipedia: Cubane
• Wikidata: Q413624
• Metabolomics Workbench ID: 54777
• Mol file: 277-10-1.mol

Synonyms:Cubane;277-10-1;Cuban;UNII-Z5HM0Q7DK1;Z5HM0Q7DK1;Pentacyclo[4.2.0.02,5.03,8.04,7]octane;pentacyclo[4.2.0.0(2,5).0(3,8).0(4,7)]octane;PENTACYCLO(4.2.0.02,5.03,8.04,7)OCTANE;QUADRIPRISMANE;(4)PRISMANE;CUBANE [MI];CHEBI:33014;DTXSID50182062;AKOS024436889;Q413624;Pentacyclo[4.2.0.02,5.03,8.-nu-04,7]octane;pentacyclo[4.2.0.0~2,5~.0~3,8~.0~4,7~]octane;pentacyclo-[4.2.0.0(2,5).0(3,8)-.0,(4,7)]octane, (cubane)

Chemical Property of Cubane

Chemical Property:

• Appearance/Colour: solid
• Melting Point: 125 - 126 C
• Refractive Index: 1.4770 (estimate)
• Boiling Point: 130.31°C (rough estimate)
• Flash Point: 7.6oC
• PSA: 0.00000
• Density: 0.9155 (estimate)
• LogP: 0.98400
• XLogP3: 1.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 0
• Exact Mass: 104.062600255
• Heavy Atom Count: 8
• Complexity: 110

Purity/Quality:

99%, ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C12C3C4C1C5C2C3C45

Technology Process of Cubane

There total 12 articles about Cubane 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: 77.0%

1,4-cubanedicarboxylic acid dichloride (60462-24-0) → cubane (277-10-1)

Guidance literature:

With dmap; 2-mercaptopyridine-1-oxide sodium salt; 2-methylpropan-2-thiol; In tetrahydrofuran; for 1.5h; Heating; Irradiation;

DOI:10.1055/s-1995-3961

Reference yield: 13.0%

cubyllithium → cubane (277-10-1) + p-<2>cubyl (116503-50-5)

Guidance literature:

With dinitrogen tetraoxide; In tetrahydrofuran; -190 deg C -> room temperature;

DOI:10.1021/ja963658e

Reference yield:

cubane-1,4-dicarboxylic acid dimethyl ester (29412-62-2) → cubane (277-10-1)

Guidance literature:

Multi-step reaction with 3 steps

1.1: sodium hydroxide / methanol; water

2.1: thionyl chloride

3.1: 2-mercaptopyridine-1-oxide sodium salt / Irradiation

3.2: Irradiation

With thionyl chloride; 2-mercaptopyridine-1-oxide sodium salt; sodium hydroxide; In methanol; water;

DOI:10.1021/acs.jpca.6b04323

upstream raw materials:

Cuban-1,4-dicarbonsaeure-di-tert-butylperester

1,4-cubanedicarboxylic acid dichloride

n-butyllithium

cubane-1,4-dicarboxylic acid dimethyl ester

Downstream raw materials:

Iodocubane

1,3,5,7-cyclooctatetraene

syn-tricyclo{4.2.0.0(2.5)}octa-3,7-diene

bicyclo<2.2.2>octane

Refernces

• 1、 Della,Patney. "". . p. 251. Retrieved 1976.
• 2、 Houston, Sevan D.,Chalmers, Benjamin A.,Savage, G. Paul,Williams, Craig M.. "Enantioselective synthesis of (: R)-2-cubylglycine including unprecedented rhodium mediated C-H insertion of cubane". supporting information. p. 1067 - 1070. Retrieved 2019/02/07.
• 3、 Eaton,Nodari,Tsanaktsidis,Upadhyaya. "Barton decarboxylation of cubane-1,4-dicarboxylic acid: Optimized procedures for cubanecarboxylic acid and cubane". . p. 501 - 502. Retrieved 2007/10/02.