Pentacyclo[4.2.0.02,5.03,8.04,7]octanecarbonyl chloride (9CI)

Base Information

• Chemical Name: Pentacyclo[4.2.0.02,5.03,8.04,7]octanecarbonyl chloride (9CI)
• CAS No.: 60462-14-8
• Molecular Formula: C₉H₇ClO
• Molecular Weight: 166.607
• Hs Code.: 2915900090
• Mol file: 60462-14-8.mol

Synonyms:Pentacyclo[4.2.0.02,5.03,8.04,7]octanecarbonyl chloride (9CI)

Chemical Property of Pentacyclo[4.2.0.02,5.03,8.04,7]octanecarbonyl chloride (9CI)

Chemical Property:

• PSA: 17.07000
• LogP: 1.11960

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of Pentacyclo[4.2.0.02,5.03,8.04,7]octanecarbonyl chloride (9CI)

There total 3 articles about Pentacyclo[4.2.0.02,5.03,8.04,7]octanecarbonyl chloride (9CI) 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: 94.0%

cubane-1-carboxylic acid (53578-15-7) → Cubancarbonsaeurechlorid (60462-14-8)

Guidance literature:

With oxalyl dichloride; N,N-dimethyl-formamide; In dichloromethane; for 1h; Inert atmosphere;

DOI:10.1002/chem.201805124

Reference yield:

monocarbomethoxycubane (29412-63-3) → Cubancarbonsaeurechlorid (60462-14-8)

Guidance literature:

Multi-step reaction with 2 steps

1: NaOH / methanol / 4 h / Heating

2: SOCl₂ / 0.25 h / Heating

With sodium hydroxide; thionyl chloride; In methanol;

DOI:10.1248/cpb.41.1760

Reference yield:

4-methoxycarbonylcubane-1-carbonyl chloride (60462-18-2) → Cubancarbonsaeurechlorid (60462-14-8)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.) sodium salt of N-hydroxypyridine-2(1H)-thione, DMAP, 2.) tert-butylmercaptan, AIBN / 1.) benzene, reflux, 1 h, 2.) benzene, reflux, 2 h

2: NaOH / methanol / 4 h / Heating

3: SOCl₂ / 0.25 h / Heating

With dmap; sodium hydroxide; thionyl chloride; 2,2'-azobis(isobutyronitrile); 2-mercaptopyridine-1-oxide sodium salt; 2-methylpropan-2-thiol; In methanol;

DOI:10.1248/cpb.41.1760

upstream raw materials:

cubane-1-carboxylic acid

monocarbomethoxycubane

4-methoxycarbonylcubane-1-carbonyl chloride

Downstream raw materials:

(cubyl)(methyl)methanone

pentacyclo[4.2.0.0^2,5.0^3,8.0^4,7]octane-1-methanamine

1-cubanecarboxamide

Iodocubane

Refernces

• 1、 Lukin, Kirill A.,Li, Jianchang,Eaton, Philip E.,Kanomata, Nobuhiro,Hain, Jürgen,Punzalan, Eric,Gilardi, Richard. "Synthesis and chemistry of 1,3,5,7-tetranitrocubane including measurement of its acidity, formation of o-nitro anions, and the first preparations of pentanitrocubane and hexanitrocubane". . p. 9591 - 9602. Retrieved 1997.
• 2、 Xing, Hui,Houston, Sevan D.,Chen, Xuejie,Ghassabian, Sussan,Fahrenhorst-Jones, Tyler,Kuo, Andy,Murray, Cody-Ellen P.,Conn, Kyna-Anne,Jaeschke, Kara N.,Jin, Da-Yun,Pasay, Cielo,Bernhardt, Paul V.,Burns, Jed M.,Tsanaktsidis, John,Savage, G. Paul,Boyle, Glen M.,De Voss, James J.,McCarthy, James,Walter, Gimme H.,Burne, Thomas H. J.,Smith, Maree T.,Tie, Jian-Ke,Williams, Craig M.. "Cyclooctatetraene: A Bioactive Cubane Paradigm Complement". supporting information. p. 2729 - 2734. Retrieved 2019/02/03.
• 3、 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.