2-(trifluoroMethoxy)isonicotinic acid

2-(trifluoroMethoxy)isonicotinic acid Property

Melting point:

149-152 °C(Solv: chloroform (67-66-3))

Boiling point:

315.3±37.0 °C(Predicted)

Density 

1.527±0.06 g/cm3(Predicted)

storage temp. 

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

pka

2.99±0.10(Predicted)

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P270Do not eat, drink or smoke when using this product.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P301+P312IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P321Specific treatment (see … on this label).

P330Rinse mouth.

P332+P313IF SKIN irritation occurs: Get medical advice/attention.

P362Take off contaminated clothing and wash before reuse.

P501Dispose of contents/container to..…

2-(trifluoroMethoxy)isonicotinic acid Chemical Properties,Usage,Production

Synthesis

Palladium catalyst (10% loaded on charcoal, 330 mg) was added to a solution of 2-chloro-6-trifluoromethoxyisonicotinic acid (43, 1.1 g, 4.55 mmol) and ammonium formate (574 mg, 9.1 mmol, 2 eq.) in methanol (8 mL) at 25 °C and mixed by stirring. The reaction mixture was stirred continuously at 55 °C for 16 hours. After completion of the reaction, filtration was carried out and the filtrate was concentrated by evaporation. The residue was partitioned between ethyl acetate (2 x 15 mL) and 2.0 M hydrochloric acid (20 mL) for extraction. The organic layers were combined, dried over sodium sulfate and evaporated to give the pure product 2-trifluoromethoxyisonicotinic acid (44,760 mg, 3.7 mmol, 81% yield) as a white powder with a melting point of 149-152°C. 1H NMR (CD3OD, 300 MHz): δ=8.39 (d, J=5.1 Hz, 1H), 7.77 (dd, J=5.1,1.0 Hz, 1H), 7.51 (d, J=1.0 Hz, 1H).19F NMR ((CD3)2CO, 282 MHz): δ=-57.6.13C NMR (CD3OD, 75 MHz): δ=164.9,157.2,148.4,143.3,121.8,120.3 (q, J=260 Hz). 112.5. Elemental analysis (C7H4F3NO3, Mr=207): calculated values C 40.59%, H 1.95%, N 6.76%; measured values C 40.28%, H 2.21%, N 6.67%.

References

[1] Patent: WO2010/40461, 2010, A1. Location in patent: Page/Page column 45
[2] European Journal of Organic Chemistry, 2010, # 31, p. 6043 - 6066