2-CHLORO-6-PHENYLPYRAZINE

2-CHLORO-6-PHENYLPYRAZINE Property

Melting point:

34-35 °C(Solv: hexane (110-54-3))

Boiling point:

111-112 °C(Press: 1 Torr)

Density 

1.245±0.06 g/cm3(Predicted)

storage temp. 

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

pka

-1.48±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-CHLORO-6-PHENYLPYRAZINE Chemical Properties,Usage,Production

Synthesis

General procedure for the synthesis of 2-chloro-6-phenylpyrazine: to a solvent mixture of 2,6-dichloropyrazine (2.0 eq.) dissolved in a 3:1 ratio of aqueous DME with 2M sodium carbonate (0.125 M), phenylboronic acid (1.0 eq.) was added, followed by the addition of PdCl2(dppf)-DCM adduct (0.1 eq.). The reaction mixture was placed in a microwave reactor and heated at 120 °C for 15 min. After completion of the reaction, the crude product was diluted with ethyl acetate and washed with saturated aqueous NaHCO3 solution. After the aqueous phase was saturated with sodium chloride, the organic phase was dried with magnesium sulfate, filtered and concentrated. The crude product was purified by silica gel column chromatography with the eluent being heptane to a heptane solution containing 30% ethyl acetate, resulting in 2-chloro-6-phenylpyrazine in 75% yield.LC/MS analysis showed a m/z of 191.0 (MH+) and a retention time (Rt) of 1.00 min.

References

[1] Patent: WO2012/4217, 2012, A1. Location in patent: Page/Page column 63
[2] Patent: US2012/225061, 2012, A1. Location in patent: Page/Page column 24
[3] Organic Letters, 2016, vol. 18, # 13, p. 3082 - 3085
[4] Patent: WO2009/89042, 2009, A1. Location in patent: Page/Page column 108