5-Norbornene-2-carbonitrile Chemical Properties

Melting point:

12-14 °C(lit.)

Boiling point:

82-86 °C10 mm Hg(lit.)

Density 

0.999 g/mL at 25 °C(lit.)

refractive index 

n20/D 1.488(lit.)

Flash point:

150 °F

storage temp. 

Sealed in dry,Room Temperature

form 

clear liquid

color 

Light yellow to Amber to Dark green

InChI

InChI=1S/C8H9N/c9-5-8-4-6-1-2-7(8)3-6/h1-2,6-8H,3-4H2

InChIKey

BMAXQTDMWYDIJX-UHFFFAOYSA-N

SMILES

C12CC(C=C1)CC2C#N

CAS DataBase Reference

95-11-4(CAS DataBase Reference)

NIST Chemistry Reference

Bicyclo[2.2.1]hept-5-ene-2-carbonitrile(95-11-4)

EPA Substance Registry System

Bicyclo[2.2.1]hept-5-ene-2-carbonitrile (95-11-4)

Safety Information

Hazard Codes 

Xn

Risk Statements 

20/21/22-36/37/38

Safety Statements 

26-36/37/39-36/37

WGK Germany 

3

RTECS 

RB7930000

HS Code 

29269090

Toxicity

LD50 ivn-mus: 10 mg/kg CSLNX* NX#00780

MSDS

• Language:English Provider:5-Norbornene-2-carbonitrile
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS

5-Norbornene-2-carbonitrile Usage And Synthesis

Chemical Properties

clear colourless liquid

Uses

Bicyclo[2.2.1]hept-2-ene-5-carbonitrile is used in method for continuously preparing cyanonorbornene by using microchannel reactor.

General Description

The hydrogenation of 5-norbornene-2-carbonitrile was studied using real-time mass spectrometric analysis.

Safety Profile

A poison by intravenous route.When heated to decomposition it emits toxic vapors ofNOx.

Synthesis

The general procedure for the synthesis of 3,7-dimethylocta-1,6-diene and bicyclo[2.2.1]hept-5-ene-2-carbonitrile from the compound (CAS:67403-76-3) and dicycloheptadiene was as follows: to a 4 mL screw-capped vial in an argon-protected glove box were added sequentially the compound 69 (82.6 mg, 0.50 mmol), norepiglottidiene 8 (51 μL, 0.5 mmol), hexane solution of 1.0 M AIMe2Cl (50 μL, 10.0 mol%, 0.05 mmol), Ni(COD)2 (3.45 mg, 2.5 mol%, 12.5 μmol), and DPEphos (6.75 mg, 2.5 mol%, 12.5 μmol) in THF ( 1.0 mL) solution. The vials were removed from the glove box and the reaction temperature was controlled at 28°C. The reaction mixture was stirred at 28 °C for 16 h and then concentrated under reduced pressure. The residue was purified by silica gel fast column chromatography (100% pentane as eluent) to afford product 70 (49.0 mg, 71% yield). The structure of the product was confirmed by 1H NMR (500 MHz, CDCl3) and 13C NMR (125 MHz, CDCl3) as follows: 1H NMR δ 5.74-5.64 (m, 1H), 5.13-5.06 (m, 1H), 4.99-4.88 (m, 2H), 2.12 (p, J=7.0 Hz, 1H ), 2.01-1.89 (m, 2H), 1.68 (s, 3H), 1.60 (s, 3H), 1.35-1.26 (m, 2H), 0.99 (d, J=6.9Hz, 3H); 13C NMR δ 144.91, 131.44, 124.80, 112.61, 37.51, 36.89, 25.88, 20.30, 17.83.

References

[1] Patent: WO2017/93149, 2017, A1. Location in patent: Page/Page column 28

5-Norbornene-2-carbonitrile(95-11-4)Related Product Information

• Methylene dithiocyanate
• 5-Dibenzosuberenone
• 1-HEPTENE
• 5-ETHYLIDENE-2-NORBORNENE
• Norbornene
• 6-Methyl-5-hepten-2-one
• Allyl heptanoate
• Sodium cyanoborohydride
• 2,2'-Azobis(2,4-dimethyl)valeronitrile
• Dicyclopentadiene
• ETHYL 2-CYANOACRYLATE
• 2,5-Norbornadiene
• Bicyclo[1.1.1]pentane-1-carboxamide
• Bicyclo[1.1.1]pentane-1,3-dicarboxamide
• Bicyclo[1.1.1]pentane-1-sulfonamide
• bicyclo[1.1.1]pentane-1,3-dicarbonitrile
• 4-Carboxylbenzocyclobutene
• 4-Hydroxymethylbenzocyclobutene