trimethyl pyridine-2,4,6-tricarboxylate

trimethyl pyridine-2,4,6-tricarboxylate Property

Melting point:

148-150 °C

Boiling point:

385.0±37.0 °C(Predicted)

Density 

1.289±0.06 g/cm3(Predicted)

storage temp. 

Inert atmosphere,Room Temperature

pka

-3.11±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..…

trimethyl pyridine-2,4,6-tricarboxylate Chemical Properties,Usage,Production

Synthesis

The general procedure for the synthesis of trimethyl pyridine-2,4,6-tricarboxylate from methanol and pyridine-2,4,6-tricarboxylic acid was as follows: the target compound pyridine-2,4,6-tricarboxylic acid trimethyl ester 2 was prepared according to the literature methodology [44].This was carried out as follows: pyridine-2,4,6-tricarboxylic acid 1 (10 g, 47 mmol) was dissolved in methanol (70 mL), added concentrated sulfuric acid ( 98%, 5 mL) and heated under reflux conditions for 6 h until the complete disappearance of raw material 1 was shown by thin layer chromatography (TLC) monitoring. Upon completion of the reaction, the reaction solution was neutralized with calcium carbonate (CaCO3), the insoluble material was removed by filtration and the filtrate was concentrated under reduced pressure to remove the solvent. The crude product was purified by recrystallization from toluene to give the white crystalline target product 2. Yield: 95%; melting point: 161 °C. Infrared spectrum (IR, KBr, cm?1): 3462, 3304 (NH stretching vibration), 2976, 1737 (C=O stretching vibration), 1644 (C=N stretching vibration), 1488 (C-N stretching vibration). Nuclear magnetic resonance hydrogen spectrum (1H NMR, DMSO-d6) δH: 8.54 (2H, apparent single peak), 3.95 (9H, apparent single peak).

References

[1] Bioorganic Chemistry, 2014, vol. 57, p. 148 - 154
[2] Tetrahedron, 1980, vol. 36, # 1, p. 123 - 129
[3] Monatshefte fuer Chemie, 1917, vol. 38, p. 239
[4] Helvetica Chimica Acta, 2004, vol. 87, # 1, p. 156 - 166