2-bromo-6-ethyl-pyridine

2-bromo-6-ethyl-pyridine Property

Boiling point:

110-115 °C(Press: 20 Torr)

Density 

1.413±0.06 g/cm3(Predicted)

storage temp. 

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

pka

1.46±0.10(Predicted)

Appearance

Colorless to light yellow Liquid

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

H315Causes skin irritation

H319Causes serious eye irritation

H332Harmful if inhaled

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

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

P271Use only outdoors or in a well-ventilated area.

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.

P304+P340IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.

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

P312Call a POISON CENTER or doctor/physician if you feel unwell.

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-bromo-6-ethyl-pyridine Chemical Properties,Usage,Production

Synthesis

At -80 °C, 2-bromo-6-methylpyridine (CAS 5315-25-3) (2.0 g, 11.7 mmol, 1.0 eq.) was dissolved in THF (10 mL) and LDA (12.3 mL, 12.3 mmol, 1.05 eq.) was added slowly. The reaction mixture was kept stirred at -78 °C for 1 hour. Subsequently, iodomethane (1.8 g, 12.3 mmol, 1.05 eq.) was added to the reaction system and the mixture was gradually warmed up to room temperature and stirring was continued for 3 hours. Upon completion of the reaction, the reaction was quenched with saturated NaHCO3 solution (2 mL), diluted with water (50 mL) and extracted with ethyl acetate (2 x 100 mL). The organic phases were combined, washed with brine and dried over anhydrous Na2SO4. After concentration under reduced pressure, the residue was purified by silica gel column chromatography with petroleum ether/ethyl acetate (20/1) as eluent to afford 2-bromo-6-ethylpyridine (1.0 g, yellow solid, 46% yield). The product was detected by ESI-MS and showed (M + H)+ peaks located at 185.9 and 187.9.

References

[1] Patent: US2009/253750, 2009, A1. Location in patent: Page/Page column 9
[2] Patent: WO2016/11390, 2016, A1. Location in patent: Page/Page column 194
[3] Patent: WO2017/127430, 2017, A1. Location in patent: Page/Page column 52
[4] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1991, # 3, p. 501 - 507