1,3-Dehydroadamantane

Base Information

• Chemical Name: 1,3-Dehydroadamantane
• CAS No.: 24569-89-9
• Molecular Formula: C10H14
• Molecular Weight: 134.221
• DSSTox Substance ID: DTXSID40179305
• Nikkaji Number: J1.009.117I,J570.620C
• Wikipedia: 1,3-Dehydroadamantane
• Wikidata: Q4545676
• Mol file: 24569-89-9.mol

Synonyms:1,3-Dehydroadamantane;24569-89-9;DTXSID40179305;Q4545676

Chemical Property of 1,3-Dehydroadamantane

Chemical Property:

• Vapor Pressure: 0.466mmHg at 25°C
• Boiling Point: 200.2°Cat760mmHg
• Flash Point: 52.5°C
• Density: 1.11g/cm³
• XLogP3: 3.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 0
• Exact Mass: 134.109550447
• Heavy Atom Count: 10
• Complexity: 182

Purity/Quality:

99%, ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C2CC34CC1CC3(C2)C4

Technology Process of 1,3-Dehydroadamantane

There total 11 articles about 1,3-Dehydroadamantane 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: 81.0%

1,3-dibromoadamantane (876-53-9) → 1,3-dehydroadamantane (24569-89-9)

Guidance literature:

With lithium; In tetrahydrofuran; at 20 ℃; for 24h;

DOI:10.1021/ja062157i

Reference yield:

1-Chloro-3-iodoadamantane (60389-53-9) → 1-chloroadamantane (935-56-8) + adamantane (281-23-2) + 1,3-dehydroadamantane (24569-89-9)

Guidance literature:

With trimethylstannylsodium; In tetrahydrofuran; for 0.5h; Ambient temperature;

DOI:10.1021/jo00078a009

Reference yield:

1-Bromo-3-iodoadamantane (152580-96-6) → 1-Adamantyl bromide (768-90-1) + adamantane (281-23-2) + 1,3-dehydroadamantane (24569-89-9)

Guidance literature:

With trimethylstannylsodium; In tetrahydrofuran; for 0.5h; Ambient temperature;

DOI:10.1021/jo00078a009

upstream raw materials:

1-bromo-3-chloroadamantane

1,3-dibromoadamantane

1,3-Diiodoadamantane

1-Chloro-3-iodoadamantane

Downstream raw materials:

1-tosylaminoadamantane

1-adamantyl-O,O-diphenylphosphonate

2-(adamantan-1-yl)isoindoline-1,3-dione

1-chloroadamantane

Refernces

• 1、 Adcock, William,Clark, Christopher I.. "Mechanistic Definition of Trimethylstannylation of 1,3-Dihaloadamantanes: Delocalized Radical Anions as Possible Intermediates". . p. 7341 - 7349. Retrieved 1993.
• 2、 Inomata, Sotaro,Harada, Yusuke,Nakamura, Yuya,Nakamura, Taisuke,Ishizone, Takashi. "Synthesis of 1,3-dehydroadamantanes possessing alkyl, phenyl, and alkoxy substituents by intramolecular wurtz-type coupling reaction of 1,3-dibromoadamantanes". . p. 3332 - 3340. Retrieved 2014/01/06.