4-Cyclohexene-1,1,2,2-tetracarbonitrile

Base Information

• Chemical Name: 4-Cyclohexene-1,1,2,2-tetracarbonitrile
• CAS No.: 13358-22-0
• Molecular Formula: C₁₀H₆N₄
• Molecular Weight: 182.184
• NSC Number: 191887
• UNII: 623BR41J34
• DSSTox Substance ID: DTXSID90158185
• Nikkaji Number: J48.242K
• Wikidata: Q83026357
• Mol file: 13358-22-0.mol

Synonyms:4-Cyclohexene-1,1,2,2-tetracarbonitrile;13358-22-0;4,4,5,5-Tetracyano-1-cyclohexene;623BR41J34;NSC-191887;cyclohex-4-ene-1,1,2,2-tetracarbonitrile;NSC 191887;BRN 2579851;NSC191887;4-09-00-03794 (Beilstein Handbook Reference);SCHEMBL23900361;UNII-623BR41J34;DTXSID90158185;4-Cyclohexene-1,2,2-tetracarbonitrile

Chemical Property of 4-Cyclohexene-1,1,2,2-tetracarbonitrile

Chemical Property:

• Vapor Pressure: 6.11E-11mmHg at 25°C
• Boiling Point: 520.7°Cat760mmHg
• Flash Point: 277.7°C
• Density: 1.25g/cm³
• XLogP3: 0.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 0
• Exact Mass: 182.059246208
• Heavy Atom Count: 14
• Complexity: 397

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C=CCC(C1(C#N)C#N)(C#N)C#N

Technology Process of 4-Cyclohexene-1,1,2,2-tetracarbonitrile

There total 3 articles about 4-Cyclohexene-1,1,2,2-tetracarbonitrile 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%

ethenetetracarbonitrile (670-54-2) + buta-1,3-diene (106-99-0,130983-70-9,29406-96-0,9003-17-2) → 4-Cyclohexen-1,1,2,2-tetracarbonitril (13358-22-0)

Guidance literature:

In benzene; Ambient temperature;

Reference yield:

C20H10N4 → 4-Cyclohexen-1,1,2,2-tetracarbonitril (13358-22-0)

Guidance literature:

Multi-step reaction with 2 steps

1: acetonitrile / 25 °C

2: benzene

In acetonitrile; benzene; 2: Diels-Alder reaction;

DOI:10.1002/kin.20462

Reference yield:

C20H9ClN4 → 4-Cyclohexen-1,1,2,2-tetracarbonitril (13358-22-0)

Guidance literature:

Multi-step reaction with 2 steps

1: acetonitrile / 20 °C / 750.08 Torr

2: benzene

In acetonitrile; benzene; 2: Diels-Alder reaction;

DOI:10.1002/kin.20462

upstream raw materials:

ethenetetracarbonitrile

buta-1,3-diene

Refernces

• 1、 Kiselev, Vladimir D.. "Why can the activation volume of the cycloadduct decomposition in isopolar retro-diels-alder reactions be negative?". experimental part. p. 117 - 125. Retrieved 2011/05/19.
• 2、 Konovalov, A. I.,Kiselev, V. D.. "THE EFFECT OF THE STABILIZATION AND LOCALIZATION ENERGY ON THE REACTIVITY OF THE REAGENTS IN THE DIELS-ALDER REACTION". . p. 1018 - 1028. Retrieved 2007/10/02.