Cyclooctyne

Base Information

• Chemical Name: Cyclooctyne
• CAS No.: 1781-78-8
• Molecular Formula: C15H16 N4 . Cl H
• Molecular Weight: 108.183
• Hs Code.: 2902199090
• UNII: 35MR2L5G3W
• DSSTox Substance ID: DTXSID50170424
• Nikkaji Number: J80.315D
• Wikipedia: Cyclooctyne
• Wikidata: Q3676516
• Metabolomics Workbench ID: 55685
• Mol file: 1781-78-8.mol

Synonyms:Cyclooctyne;1781-78-8;UNII-35MR2L5G3W;35MR2L5G3W;1-Cyclooctyne;1-Cyclooctyne #;CYCLOOCTYNE [MI];CHEBI:37815;DTXSID50170424;Q3676516

Chemical Property of Cyclooctyne

Chemical Property:

• Vapor Pressure: 3.91mmHg at 25°C
• Melting Point: -34° to-32°
• Refractive Index: nD20 1.4876
• Boiling Point: 155.4°Cat760mmHg
• Flash Point: 34.7°C
• PSA: 0.00000
• Density: 0.86g/cm³
• LogP: 2.34400
• XLogP3: 3.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 0
• Exact Mass: 108.093900383
• Heavy Atom Count: 8
• Complexity: 98.5

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CCCC#CCC1
• Uses: Building block in cycloaddition reactions.

Technology Process of Cyclooctyne

There total 20 articles about Cyclooctyne 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: 87.0%

1-bromocyclooctene (4103-11-1,38440-26-5) → cyclooctyne (1781-78-8)

Guidance literature:

With lithium diisopropylamide; at 0 ℃; Kinetics;

DOI:10.1021/acs.joc.6b0228

Reference yield: 86.0%

(E)-1-Bromo-cyclooctene (61815-42-7,38440-26-5) → cyclooctyne (1781-78-8)

Guidance literature:

With 18-crown-6 ether; potassium tert-butylate; In Petroleum ether; at 80 ℃; for 4h;

Reference yield: 83.0%

1,2-dibromocyclooctane (29974-69-4) → cyclooctyne (1781-78-8)

Guidance literature:

With 18-crown-6 ether; potassium tert-butylate; In Petroleum ether; at 80 ℃; for 4h;

upstream raw materials:

cyclooctane-1,2-dione-dihydrazone

4,5,6,7,8,9-hexahydro-cycloocta[1,2,3]selenadiazole

4,5,6,7,8,9-hexahydro-cycloocta[1,2,3]triazol-1-ylamine

(E)-1-Bromo-cyclooctene

Downstream raw materials:

9-Phenyl-tricyclo[8.6.0.0^2,6]hexadeca-1⁽¹⁰⁾,2,4,6,8-pentaene

2.4.12-Tri-tert-butyl-5.6.7.8.9.10-hexahydrocyclooctaazulen

14-phenyl-6,8,9,10,11,12-hexahydro-7H-5,12-etheno-benzo[b]cycloocta[e]phosphinine

2,4,12-triphenyl-5,6,7,8,9,10-hexahydro-4H-1,4-etheno-cycloocta[b]phosphinine

Refernces

• 1、 Meier,H.,Menzel,I.. "-". . p. 215 - 216. Retrieved 1971.
• 2、 Blomquist,Liu. "-". . p. 2153. Retrieved 1953.
• 3、 Meier,H.,Menzel,I.. "". . p. 1059. Retrieved 1971.
• 4、 Ma, Yun,Woltornist, Ryan A.,Algera, Russell F.,Collum, David B.. "Reactions of Sodium Diisopropylamide: Liquid-Phase and Solid-Liquid Phase-Transfer Catalysis by N, N, N′, N″, N″-Pentamethyldiethylenetriamine". supporting information. p. 13370 - 13381. Retrieved 2021/09/03.
• 5、 Ma, Yun,Algera, Russell F.,Collum, David B.. "Sodium Diisopropylamide in N,N-Dimethylethylamine: Reactivity, Selectivity, and Synthetic Utility". . p. 11312 - 11315. Retrieved 2016/11/29.