Bicyclo[2.2.2]oct-5-ene-2-carbonitrile

Base Information

• Chemical Name: Bicyclo[2.2.2]oct-5-ene-2-carbonitrile
• CAS No.: 3008-14-8
• Molecular Formula: C₉H₁₁N
• Molecular Weight: 133.193
• NSC Number: 42840
• DSSTox Substance ID: DTXSID50952489
• Nikkaji Number: J1.520.745K
• Mol file: 3008-14-8.mol

Synonyms:Bicyclo[2.2.2]oct-5-ene-2-carbonitrile;38258-93-4;3008-13-7;NSC42840;SCHEMBL678190;DTXSID50952489;5-cyanobicyclo[2,2,2]oct-2-ene;5-cyanobicyclo[2.2.2]oct-2-ene;Bicyclo(2.2.2)oct-5-ene-2-carbonitrile, (1alpha,2alpha,4alpha)-;Bicyclo(2.2.2)oct-5-ene-2-carbonitrile, (1alpha,2beta,4alpha)-;NSC-42840;3008-14-8;bicyclo[2.2.2]oct-7-ene-6-carbonitrile;Bicyclo[2.2.2]oct-5-ene-2-carbonitrile, (1.alpha.,2.alpha.,4.alpha.)-;Bicyclo[2.2.2]oct-5-ene-2-carbonitrile, (1.alpha.,2.beta.,4.alpha.)-

Chemical Property of Bicyclo[2.2.2]oct-5-ene-2-carbonitrile

Chemical Property:

• Vapor Pressure: 0.03mmHg at 25°C
• Boiling Point: 244.6°C at 760 mmHg
• Flash Point: 85.9°C
• Density: 1.03g/cm³
• XLogP3: 1.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 133.089149355
• Heavy Atom Count: 10
• Complexity: 208

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: C1CC2C=CC1CC2C#N

Technology Process of Bicyclo[2.2.2]oct-5-ene-2-carbonitrile

There total 11 articles about Bicyclo[2.2.2]oct-5-ene-2-carbonitrile 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: 83.0%

bicyclo<2.2.2>oct-5-ene-2-exo-carboxamide (94991-41-0,99032-21-0) → 5-exo-cyanobicyclo<2.2.2>oct-2-ene (3008-13-7,3008-14-8,38258-93-4)

Guidance literature:

With p-toluenesulfonyl chloride; In pyridine;

DOI:10.1002/hlca.19840670723

Reference yield:

(+/-)-bicyclo[2.2.2]oct-5-ene-2endo-carboxamide (94991-41-0,99032-21-0) → 5-endo-cyanobicyclo<2.2.2>oct-2-ene (3008-13-7,3008-14-8,38258-93-4)

Guidance literature:

With phosphorus pentoxide; Erhitzen unter vermindertem Druck;

DOI:10.1021/ja01553a044

Reference yield:

bicyclo[2.2.2]oct-5-ene-2-carbonyl chloride (50845-86-8,51372-02-2,99094-77-6) → 5-endo-cyanobicyclo<2.2.2>oct-2-ene (3008-13-7,3008-14-8,38258-93-4)

Guidance literature:

Multi-step reaction with 2 steps

1: NH₃

2: P₂O₅ / Erhitzen unter vermindertem Druck

With ammonia; phosphorus pentoxide;

DOI:10.1021/ja01553a044

upstream raw materials:

(+/-)-bicyclo[2.2.2]oct-5-ene-2endo-carboxamide

cyclohexa-1,3-diene

acrylonitrile

bicyclo[2.2.2]oct-5-ene-2-carbonyl chloride

Downstream raw materials:

(2-endo)-bicyclo<2.2.2>oct-5-ene-2-carboxylic acid

Refernces

• 1、 Li, Yufei,Padias, Anne Buyle,Hall, H. K.. "Evidence for 2-Hexene-1,6-diyl Diradicals Accompanying the Concerted Diels-Alder Cycloaddition of Acrylonitrile with Nonpolar 1,3-Dienes". . p. 7049 - 7058. Retrieved 2007/10/02.
• 2、 Grob, Cyril A.,Sawlewicz, Pawel. "216. Bicyclooctanes. Syntheses and Hydrolyses of 6-exo-substituted 2-exo- and 2-endo-Bicyclooctyl p-Toluenesulfonates. Part 9". . p. 1859 - 1867. Retrieved 2007/10/02.