2-Chloro-6-trifluoromethylnicotinic acid Chemical Properties

Melting point:

120 °C

Boiling point:

271.3±40.0 °C(Predicted)

Density 

1.603±0.06 g/cm3(Predicted)

storage temp. 

under inert gas (nitrogen or Argon) at 2-8°C

form 

powder to crystal

pka

1.42±0.28(Predicted)

color 

White to Light yellow

InChI

InChI=1S/C7H3ClF3NO2/c8-5-3(6(13)14)1-2-4(12-5)7(9,10)11/h1-2H,(H,13,14)

InChIKey

DXRBTBMFFGEVCX-UHFFFAOYSA-N

SMILES

C1(Cl)=NC(C(F)(F)F)=CC=C1C(O)=O

CAS DataBase Reference

280566-45-2(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi,Xn

Risk Statements 

36/37/38-22

Safety Statements 

26-36/37/39

RIDADR 

UN 2811 6.1 / PGIII

WGK Germany 

3

Hazard Note 

Irritant

HS Code 

2933399990

2-Chloro-6-trifluoromethylnicotinic acid Usage And Synthesis

Chemical Properties

White to Light yellow powder to crystal

Uses

2-Chloro-6-trifluoromethylnicotinic acid is used as an intermediate in organic synthesis.

Synthesis

Lithium diisopropylammonium (LDA) (44.2 g, 1.5 eq.) was added slowly and dropwise to a stirred tetrahydrofuran (1.0 L) solution of 2-chloro-6-(trifluoromethyl)pyridine (50.0 g, 1.0 eq.) at -78 °C. The reaction temperature was maintained at -78°C and after 2 hours of reaction, carbon dioxide (500 g) was passed into the reaction mixture. The reaction mixture was gradually warmed to room temperature and stirring was continued for 10 minutes. The reaction progress was monitored by thin layer chromatography (TLC). Upon completion of the reaction, the reaction mixture was acidified to pH 2 with 1N hydrochloric acid and then extracted with ethyl acetate (2 x 500 mL). The organic layers were combined, washed sequentially with water (500 mL) and brine (500 mL), dried with anhydrous sodium sulfate, and concentrated under reduced pressure to obtain the crude product. The crude product was co-milled with petroleum ether to obtain pure 2-chloro-6-(trifluoromethyl)nicotinic acid (Int-15) (40.0 g, yield 64.6%).

References

[1] European Journal of Organic Chemistry, 2004, # 18, p. 3793 - 3798
[2] Patent: WO2013/64460, 2013, A1. Location in patent: Page/Page column 125; 126

2-Chloro-6-trifluoromethylnicotinic acid(280566-45-2)Related Product Information

• Trifluoromethanesulfonic acid
• 2-Chloro-6-(trifluoromethyl)pyridine
• Epichlorohydrin
• 2-(Trifluoromethyl)benzyl chloride
• 6-(Trifluoromethyl)nicotinic acid
• 2-Chloro-6-methylnicotinic acid
• 5-(Trifluoromethyl)nicotinic acid
• 3-(Trifluoromethyl)benzaldehyde
• 2-Methylbenzotrifluoride
• 2-(Trifluoromethyl)benzoic acid
• 4-(Trifluoromethyl)nicotinic acid
• Chloromethyltrimethylsilane
• 2-Aminobenzotrifluoride
• 2-chloro-6-(trifluoroMethyl)isonicotinic acid
• methyl 2-chloro-6-(trifluoromethyl)pyridine-4-carboxylate
• 2-chloro-6-(trifluoromethyl)isonicotinonitrile
• 2-chloro-6-(trifluoroMethoxy)pyridine
• Chloroacetic acid