Bicyclo[2.2.1]heptane-2-carbonitrile

Base Information

• Chemical Name: Bicyclo[2.2.1]heptane-2-carbonitrile
• CAS No.: 2234-26-6
• Molecular Formula: C8H11N
• Molecular Weight: 121.182
• Hs Code.: 2926909090
• European Community (EC) Number: 218-782-9
• UNII: 57U33ASF4X
• DSSTox Substance ID: DTXSID90870431
• Nikkaji Number: J42.492G
• Wikipedia: Bicyclo(2.2.1)heptane-2-carbonitrile
• Wikidata: Q4903816
• Mol file: 2234-26-6.mol

Synonyms:2-Norbornanecarbonitrile;2234-26-6;Bicyclo[2.2.1]heptane-2-carbonitrile;Norbornane-2-carbonitrile;2-cyanonorbornane;Bicyclo(2.2.1)heptane-2-carbonitrile;EINECS 218-782-9;57U33ASF4X;exo-Bicyclo(2.2.1)heptane-2-carbonitrile;endo-Bicyclo(2.2.1)heptane-2-carbonitrile;3211-90-3;exo-Bicyclo[2.2.1]heptane-2-carbonitrile;endo-Bicyclo[2.2.1]heptane-2-carbonitrile;2-Norbornanecarbonitrile, endo-;endo-2-Cyanobicyclo(2.2.1)heptane;3211-87-8;UNII-57U33ASF4X;SCHEMBL74890;2-Norbornanecarbonitrile, exo-;DTXSID90870431;2-Cyano-bicyclo[2,2,1]heptane;NSC 46412;AKOS009159496;LS-97077;FT-0622955;EN300-131202;J-014649;J-800478;Q4903816;Z1079179250

Chemical Property of Bicyclo[2.2.1]heptane-2-carbonitrile

Chemical Property:

• Appearance/Colour: white to beige-brown adhering crystalline solid
• Vapor Pressure: 0.49mmHg at 25°C
• Melting Point: 43-45 ºC
• Refractive Index: 1.498
• Boiling Point: 192.4 °C at 760 mmHg
• Flash Point: 78.9 °C
• PSA: 23.79000
• Density: 1.01 g/cm³
• LogP: 1.94618
• XLogP3: 2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 121.089149355
• Heavy Atom Count: 9
• Complexity: 165

Purity/Quality:

98%Min ^*data from raw suppliers

bicyclo[2.2.1]heptane-2-carbonitrile ^*data from reagent suppliers

Safty Information:

• Pictogram(s): F,Xn
• Hazard Codes: F,Xn
• Statements: 11-20/21/22-36/37/38
• Safety Statements: 16-26-27-36/37/39

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1CC2CC1CC2C#N
• Uses: Bicyclo[2.2.1]heptane-2-carbonitrile is a useful reagent in the preparation of cyanoboranes and polynorbornenes.

Technology Process of Bicyclo[2.2.1]heptane-2-carbonitrile

There total 31 articles about Bicyclo[2.2.1]heptane-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: 100.0%

norborn-2-ene (498-66-8) + 2-hydroxy-2-methylpropanenitrile (75-86-5) → 2-norbornanecarbonitrile (2234-26-6)

Guidance literature:

With nickel(II) acetate tetrahydrate; triphenylphosphine; zinc; In N,N-dimethyl-formamide; at 90 ℃; for 15h; Reagent/catalyst; Solvent; Autoclave;

Reference yield: 91.0%

bicyclo[2.2.1]hept-5-ene-2-carbonitrile (95-11-4) → 2-norbornanecarbonitrile (2234-26-6)

Guidance literature:

With magnesium; palladium on activated charcoal; In methanol; Ambient temperature;

Reference yield: 86.0%

1-<2-(2-Cyanonorbornyl)>-2-carbomethoxyhydrazine (124243-30-7) → 2-norbornanecarbonitrile (2234-26-6)

Guidance literature:

With sodium cyanide; In methanol; at 17 ℃; for 4.7h; electrolysis;

DOI:10.1021/jo00290a048

upstream raw materials:

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

2-Norbornanone carbomethoxyhydrazone

sodium cyanide

1-<2-(2-Cyanonorbornyl)>-2-carbomethoxyhydrazine

Downstream raw materials:

endo-bicyclo[2.2.1]heptane-2-carboxamide

C₁₉H₂₈N₂

2-Aminomethylbicyclo<2.2.1>heptane hydrochloride

norbornane-2-carboxylic acid

Refernces

• 1、 Brown,Rick. "". . p. 112. Retrieved 1969.
• 2、 Bhunia, Anup,Bergander, Klaus,Studer, Armido. "Cooperative Palladium/Lewis Acid-Catalyzed Transfer Hydrocyanation of Alkenes and Alkynes Using 1-Methylcyclohexa-2,5-diene-1-carbonitrile". supporting information. p. 16353 - 16359. Retrieved 2018/11/25.
• 3、 Nemoto, Koji,Nagafuchi, Tsuyoshi,Tominaga, Ken-ichi,Sato, Kazuhiko. "Efficient nickel-catalyzed hydrocyanation of alkenes using acetone cyanohydrin as a safer cyano source". . p. 3199 - 3203. Retrieved 2016/07/06.