Pyridine, 5-(chloromethyl)-2-(trifluoromethyl)- (9CI) Chemical Properties

Boiling point:

110°C/19mm

storage temp. 

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

Appearance

Colorless to light yellow Solid-liquid mixture

InChI

InChI=1S/C7H5ClF3N/c8-3-5-1-2-6(12-4-5)7(9,10)11/h1-2,4H,3H2

InChIKey

PRPAYPBERKUDKO-UHFFFAOYSA-N

SMILES

C1(C(F)(F)F)=NC=C(CCl)C=C1

Safety Information

RIDADR 

3265

HazardClass 

8

PackingGroup 

Ⅲ

HS Code 

2933399990

Pyridine, 5-(chloromethyl)-2-(trifluoromethyl)- (9CI) Usage And Synthesis

Synthesis

General procedure for the synthesis of 5-chloromethyl-2-trifluoromethylpyridine from 6-trifluoromethyl-3-pyridine methanol: At room temperature and under nitrogen protection, [6-(trifluoromethyl)pyridin-3-yl]methanol (4.41 g, 24.9 mmol) was dissolved in anhydrous dichloromethane (82.5 ml) and triethylamine (4.2 ml, 30.1 mmol) and 4-dimethylamino pyridine (21.5 mg, 0.176 mmol). The reaction mixture was cooled to 0 °C, methanesulfonyl chloride (3.0 ml, 38.8 mmol) was added slowly dropwise and stirred at 0 °C for 1 h. The mixture was gradually warmed up to room temperature and continued to be stirred for 22 h. After the reaction was completed, the reaction was carried out at room temperature. After completion of the reaction, the mixture was concentrated under reduced pressure to give the crude product. The crude product was purified by silica gel column chromatography with the eluent ratio of hexane:ethyl acetate=9:1→1:1 to afford 5-(chloromethyl)-2-trifluoromethylpyridine. The yield was 3.99 g, 84%, as yellow liquid.

References

[1] Patent: JP2017/178911, 2017, A. Location in patent: Paragraph 0133; 0134
[2] Patent: US2013/131036, 2013, A1. Location in patent: Paragraph 1574; 1575
[3] Patent: WO2013/62966, 2013, A2. Location in patent: Paragraph 101; 102
[4] Patent: US2014/107340, 2014, A1. Location in patent: Paragraph 0116
[5] Organic Letters, 2017, vol. 19, # 14, p. 3895 - 3898

Pyridine, 5-(chloromethyl)-2-(trifluoromethyl)- (9CI)(386715-33-9)Related Product Information

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