Bicyclo[2.2.2]octane-2-methanol

Base Information

• Chemical Name: Bicyclo[2.2.2]octane-2-methanol
• CAS No.: 5019-91-0
• Molecular Formula: C9H16O
• Molecular Weight: 140.2227
• NSC Number: 167506
• DSSTox Substance ID: DTXSID10304829
• Mol file: 5019-91-0.mol

Synonyms:{bicyclo[2.2.2]octan-2-yl}methanol;5019-91-0;Bicyclo[2.2.2]octane-2-methanol;2-bicyclo[2.2.2]octanylmethanol;Bicyclo(2.2.2)octane-2-methanol;NSC167506;C(O)C1CC2CCC1CC2;SCHEMBL4995408;DTXSID10304829;bicyclo[2,2,2]oct-3-yl methanol;NSC 167506;NSC-167506;EN300-268005

Chemical Property of Bicyclo[2.2.2]octane-2-methanol

Chemical Property:

• Vapor Pressure: 0.0143mmHg at 25°C
• Boiling Point: 228.4°Cat760mmHg
• Flash Point: 103.8°C
• Density: 0.99g/cm³
• XLogP3: 2.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 1
• Exact Mass: 140.120115130
• Heavy Atom Count: 10
• Complexity: 114

Purity/Quality:

99%min ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: C1CC2CCC1CC2CO

Technology Process of Bicyclo[2.2.2]octane-2-methanol

There total 5 articles about Bicyclo[2.2.2]octane-2-methanol 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: 50.0%

methyl bicyclo[2.2.2]octane-2-carboxylate (81425-81-2) → (bicyclo[2.2.2]octan-2-yl)methanol (5019-91-0)

Guidance literature:

With lithium aluminium tetrahydride; In tetrahydrofuran; at 0 - 20 ℃; Inert atmosphere;

DOI:10.1021/jacs.9b05932 DOI:10.1021/jacs.9b05932

Reference yield:

bicyclo<2.2.2>oct-5-ene-2-carboxaldehyde (38259-00-6) → (bicyclo[2.2.2]octan-2-yl)methanol (5019-91-0)

Guidance literature:

With 1,4-dioxane; copper oxide-chromium oxide; at 150 ℃; under 117681 Torr; Hydrogenation;

Reference yield:

cyclohexa-1,3-diene (1165952-91-9) → (bicyclo[2.2.2]octan-2-yl)methanol (5019-91-0)

Guidance literature:

Multi-step reaction with 3 steps

1: bis(trifluoromethanesulfonyl)amide; allyl-trimethyl-silane / toluene / 1 h / 0 - 20 °C / Inert atmosphere

2: hydrogen; palladium on activated charcoal / ethyl acetate; dichloromethane / 2.5 h

3: lithium aluminium tetrahydride / tetrahydrofuran / 0 - 20 °C / Inert atmosphere

With lithium aluminium tetrahydride; palladium on activated charcoal; hydrogen; bis(trifluoromethanesulfonyl)amide; allyl-trimethyl-silane; In tetrahydrofuran; dichloromethane; ethyl acetate; toluene;

DOI:10.1021/jacs.9b05932 DOI:10.1021/jacs.9b05932

upstream raw materials:

bicyclo<2.2.2>oct-5-ene-2-carboxaldehyde

cyclohexa-1,3-diene

5-methoxycarbonylbicyclo<2.2.2>oct-2-ene

methyl bicyclo[2.2.2]octane-2-carboxylate

Downstream raw materials:

bicyclo[3.3.1]non-2-ene

Refernces

• 1、 Zhang, Kaining,Chang, Liang,An, Qing,Wang, Xin,Zuo, Zhiwei. "Dehydroxymethylation of Alcohols Enabled by Cerium Photocatalysis". . p. 10556 - 10564. Retrieved 2019/08/28.
• 2、 -. "Secondary and tertiary-2-phenylbicyclo[2,2,2]oct-3-yl alkylamines and composition thereof". . . Retrieved 2008/06/13.