3,5-dichloro-2-iodopyrazine

3,5-dichloro-2-iodopyrazine Property

Melting point:

101.3-103.0 °C

Boiling point:

278.7±35.0 °C(Predicted)

Density 

2?+-.0.06 g/cm3(Predicted)

storage temp. 

2-8°C(protect from light)

pka

-6.27±0.10(Predicted)

Appearance

Off-white to light brown Solid

Safety

Hazard Codes 

T

Risk Statements 

25

Safety Statements 

45

RIDADR 

UN2811

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

H312Harmful in contact with skin

H332Harmful if inhaled

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.

P330Rinse mouth.

P363Wash contaminated clothing before reuse.

P501Dispose of contents/container to..…

3,5-dichloro-2-iodopyrazine Chemical Properties,Usage,Production

Synthesis

Synthesis of 3,5-dichloro-2-iodopyrazine (11a): 2,6-dichloropyrazine (9) (149 mg, 1.0 mmol) was dissolved in THF (2 mL) at 25 °C, then TMPZnCl-LiCl (1.3 M in THF, 0.85 mL, 1.1 mmol) was added. The reaction mixture was stirred at this temperature for 30 min. Subsequently, iodine (I2, 381 mg, 1.5 mmol) was dissolved in anhydrous THF (2 mL) and slowly added dropwise to the reaction system and stirring was continued for 0.5 hr. Upon completion of the reaction, the reaction was quenched with saturated aqueous NaHCO3 (10 mL) and saturated aqueous Na2S2O3 (10 mL) and extracted with ether (3 × 50 mL). The organic phases were combined, dried with anhydrous Na2SO4, filtered and concentrated under reduced pressure. Purification by fast column chromatography (CH2Cl2/n-pentane, 1:2) afforded the target product 11a (251 mg, 90%) as a colorless solid with a melting point: 101.3-103.0 °C. 1H-NMR (300 MHz, CDCl3) δ: 8.30 (s, 1H). 13C-NMR (75 MHz, CDCl3) δ: 153.1, 146.9, 142.9, 142.1. 146.9, 142.4, 115.7. m/z (%) MS (70 eV, EI): 274 (100) [M+], 147 (75), 127 (18), 86 (32), 57 (21), 44 (94). ν/cm-1 IR (ATR): 2969, 2633, 2281, 1784, 1738, 1510, 1491, 1379, 1353. 1491, 1379, 1353, 1323, 1274, 1230, 1217, 1205, 1175, 1162, 1143, 1018, 893, 843, 655, 634, 618, 611, 604. HRMS (EI) calculated value of C4HCl2IN2 (M+): 273.8561, measured value: 273.8555.

References

[1] Organic Letters, 2009, vol. 11, # 8, p. 1837 - 1840
[2] Patent: US2011/288296, 2011, A1. Location in patent: Page/Page column 11
[3] Synthesis (Germany), 2016, vol. 48, # 19, p. 3155 - 3164
[4] Tetrahedron Letters, 2011, vol. 52, # 36, p. 4590 - 4594
[5] Organic Letters, 2013, vol. 15, # 9, p. 2156 - 2159