Bicyclo[2.2.1]hept-5-ene-2-carbonitrile

Name: Bicyclo[2.2.1]hept-5-ene-2-carbonitrile
Brand: ChemScene
Availability: InStock
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CAS No. 95-11-4
Cat. No. CS-W013582
Purity≥98%
MDL No.None

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Excepted Quantity	$0.00
FedEx Limited Quantities Ground	$0.00
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Accessible (Haz class 3, 4, 5 or 8), Domestic	$158.00+
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Bicyclo[2.2.1]hept-5-ene-2-carbonitrile|CS-W013582

Structure of 95-11-4

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General Information

CAS No. 95-11-4
Cat. No. CS-W013582
Purity ≥98%
MDL No. None
Storage 4°C
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₈H₉N
Molecular Weight 119.17
Synonym(s) Bicyclo[2.2.1]hept-5-ene-2-carbonitrile (mixture of isomers)
SMILES N#CC1C(C2)C=CC2C1

Description

Bicyclo[2.2.1]hept-5-ene-2-carbonitrile features a strained bicyclic framework with a conjugated nitrile group, enabling participation in Diels-Alder reactions and serving as a rigid scaffold for synthetic intermediates. The electron-deficient alkene facilitates cycloadditions under mild conditions, while the nitrile moiety offers versatility in further functionalization.

Application

Bicyclo[2.2.1]hept-5-ene-2-carbonitrile serves as a versatile bicyclic building block in synthetic organic chemistry, leveraging its strained cyclohexene framework and pendant nitrile group for functionalization. The rigid, hydrophobic scaffold enables stereocontrolled transformations, while the carbonitrile moiety facilitates nucleophilic additions, reductions, or amidation reactions. Its bench-stable nature and compatibility with standard reaction conditions make it well-suited for applications in medicinal chemistry and natural product synthesis.

Synthesis

Route1
- 5453-80-5
- ~93%
- In-stock
  
  95-11-4
References
- Sridhar, Madabhushi; Reddy, Mallu Kishore Kumar; Sairam, Vangipuram Venkata; Raveendra, Jillella; Godala, Kondal Reddy; Narsaiah, Chinthala; Ramanaiah, Beeram China; Reddy, Cirandur Suresh Tetrahedron Letters, 2012 , vol. 53, # 27 p. 3421 - 3424
Route2
- 542-92-7
- 107-13-1
- ~93%
- In-stock
  
  95-11-4
References
- Hall Jnr.; Padlas; Li; Clever; Wang Journal of the Chemical Society - Series Chemical Communications, 1991 , # 18 p. 1279 - 1281
Route3
- 90086-80-9
- ~38%
- In-stock
  
  95-11-4
References
- Zuidema, Daniel R.; Dennison, Ami L.; Park, Elizabeth Y.; Mebane, Robert C. Synthetic Communications, 2008 , vol. 38, # 21 p. 3810 - 3815

Safety Information

Download SDS

GHS Pictogram :	GHS No : GHS07
Signal Word : Warning	UN#: N/A
Class : N/A	Packing Group : N/A
Hazard Statements : H302-H315-H319-H335
Precautionary Statements : P261-P264-P270-P271-P280-P302+P352-P304+P340-P305+P351+P338-P330-P362+P364-P403+P233-P405-P501

Quality Control

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Computational Chemistry Data

TPSA 23.79
LogP 1.72218
H_Acceptors 1
H_Donors 0
Rotatable_Bonds 0

Other Classifications

Material Science Polymer Materials Macromolecular Monomer

Building Blocks Skeleton Bridge Rings compounds Other bridge ring compounds

Building Blocks Skeleton Fatty ring compounds Cyclohexane compounds

Material Science Polymer/Macromolecule Reagents Monomers Cyclic Olefin Monomers

Key Words

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Bicyclo[2.2.1]hept-5-ene-2-carbonitrile

CAS No. 95-11-4

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