2-METHYL-5-NITRONICOTINIC ACID

2-METHYL-5-NITRONICOTINIC ACID Property

Melting point:

215-215.5 °C

Boiling point:

370.1±42.0 °C(Predicted)

Density 

1.477±0.06 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

pka

2.47±0.10(Predicted)

Appearance

Light brown to brown Solid

Safety

Hazard Codes 

Xi

HazardClass 

IRRITANT

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-METHYL-5-NITRONICOTINIC ACID Chemical Properties,Usage,Production

Synthesis

General procedure for the synthesis of 2-methyl-5-nitronicotinic acid from ethyl 2-methyl-5-nitronicotinate: compound D4 (300 g, 1.4 mol) was dissolved in a mixture of 800 mL hydrochloric acid and 800 mL water. The reaction mixture was heated under reflux conditions for 1 hour. Upon completion of the reaction, it was cooled to room temperature, the reaction solution was diluted with 2.0 L of water and slowly neutralized with the addition of solid sodium bicarbonate to pH=5.0. During this process, a precipitate was gradually formed. The mixture was further cooled and the precipitate was collected by filtration. After drying, brown solid D5 (223 g, 85.7% yield) was obtained. The product was characterized by 1H NMR (DMSO-d6, 300 MHz): δ = 2.84 (s, 3H), 8.74-8.75 (d, 1H), 9.35-9.36 (d, 1H), 13.90 (s, 1H).LC-MS analysis showed that the [M-1]+ peak was located at 180.9.

References

[1] Patent: WO2008/88881, 2008, A1. Location in patent: Page/Page column 33-34
[2] Journal of the American Chemical Society, 1953, vol. 75, p. 737
[3] Patent: WO2007/56016, 2007, A2. Location in patent: Page/Page column 105