4-(Trifluoromethyl)nicotinonitrile Chemical Properties

Boiling point:

75-77°C 15mm

Density 

1.37±0.1 g/cm3(Predicted)

storage temp. 

Store at room temperature

solubility 

Chloroform (Sparingly), Methanol (Slightly)

form 

Oil

pka

-0.57±0.18(Predicted)

color 

Colourless

InChI

InChI=1S/C7H3F3N2/c8-7(9,10)6-1-2-12-4-5(6)3-11/h1-2,4H

InChIKey

DHIRCRHQLUNYDS-UHFFFAOYSA-N

SMILES

C1=NC=CC(C(F)(F)F)=C1C#N

CAS DataBase Reference

13600-43-6(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi,Xn,T

Risk Statements 

36/37/38-20/21/22-25

Safety Statements 

26-36-36/37-45

HazardClass 

IRRITANT

HS Code 

2933399990

4-(Trifluoromethyl)nicotinonitrile Usage And Synthesis

Chemical Properties

Pale yellow solid

Definition

ChEBI: 4-(Trifluoromethyl)nicotinonitrile is a member of pyridines and a nitrile.

Synthesis

The general procedure for the synthesis of 3-cyano-4-trifluoromethylpyridine (Compound VIIb) from Compound (CAS:533932-97-7) and Compound (CAS:533932-96-6) is as follows (refer to Example 5): Step F: To a solution of 28% sodium methanol (580 mg, 3.0 mmol) in methanol (5 mL) was added a methanol solution of 3-[(4,4,4-trifluoro-3-oxo-1-butenyl)amino]-2-propenenenitrile (a mixture of IIa and IIb; 380 mg, 2.0 mmol), and the reaction mixture was stirred and then refluxed for 2 hours at room temperature. After completion of the reaction, the reaction solution was poured into water and extracted with ethyl acetate. The organic layers were combined, washed with brine, dried over magnesium sulfate and then concentrated. The resulting residue was purified by silica gel column chromatography (elution solvent: hexane/ethyl acetate = 3/1) to give 195 mg (56.5% yield) of the target compound 3-cyano-4-trifluoromethylpyridine. 1H-NMR spectrum (200 MHz, CD3OD) δ (ppm): 9.11 (1H, s), 9.03 (1H, d, J=5.1 Hz), 7.72 (1H, d, J=5.1 Hz).

References

[1] Patent: EP1460071, 2004, A1. Location in patent: Page 39
[2] Patent: EP1460071, 2004, A1. Location in patent: Page 40

4-(Trifluoromethyl)nicotinonitrile(13600-43-6)Related Product Information

• 4-(Trifluoromethyl)pyridine
• (Trifluoromethyl)trimethylsilane
• 4-Aminobenzotrifluoride
• Benzotrifluoride
• 4-(Trifluoromethyl)nicotinic acid
• 2,6-Lutidine
• 2,4,6-Collidine
• 3-Cyanopyridine
• 2-Methylbenzotrifluoride
• 4-Methylpyridine
• 4-Bromobenzotrifluoride
• Azamethiphos
• 3-Trifluoromethylpyridine
• Pyridine
• Lithium trifluoromethanesulfonate
• 2-(Trifluoromethyl)pyridine
• 4-(Trifluoromethyl)benzaldehyde
• 3-Cyano-4-methylpyridine