3-BROMO-1-METHYLPYRIDIN-2(1H)-ONE

3-BROMO-1-METHYLPYRIDIN-2(1H)-ONE Property

Boiling point:

120-125 °C(Press: 0.5 Torr)

Density 

1.664±0.06 g/cm3(Predicted)

storage temp. 

Inert atmosphere,Room Temperature

pka

-2.77±0.62(Predicted)

Appearance

Off-white to gray Solid

InChI

InChI=1S/C6H6BrNO/c1-8-4-2-3-5(7)6(8)9/h2-4H,1H3

InChIKey

HKLQWLOMEUJSOR-UHFFFAOYSA-N

SMILES

C1(=O)N(C)C=CC=C1Br

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

H315Causes skin irritation

H320Causes eye irritation

H335May cause respiratory irritation

Precautionary statements

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

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.

3-BROMO-1-METHYLPYRIDIN-2(1H)-ONE Chemical Properties,Usage,Production

Synthesis

Example 19: A mixture of 3-bromo-2-hydroxypyridine (740 mg, 4.25 mmol), potassium carbonate (1.18 g, 8.5 mmol), and iodomethane (2.65 mL, 42.5 mmol) in 1,2-dimethoxyethane (DME, 10 mL) was heated to reflux, and the reaction was carried out overnight. Upon completion of the reaction, the mixture was filtered and the solids were washed with ethyl acetate. The filtrate and washings were combined and concentrated to dryness under reduced pressure. The resulting crude product was purified by dry column chromatography on silica gel (27 g) to afford the target compound 3-bromo-1-methyl-2-pyridinone (0.63 g, 79% yield) using ethyl acetate as eluent. The product was detected by low resolution mass spectrometry (LRMS, electrospray ionization, positive ion mode) and showed a molecular ion peak m/z 188 ([M + H]+).

References

[1] Synlett, 2015, vol. 26, # 11, p. 1557 - 1562
[2] Bioorganic and Medicinal Chemistry Letters, 2011, vol. 21, # 23, p. 7076 - 7080
[3] Journal of Medicinal Chemistry, 2017, vol. 60, # 12, p. 4840 - 4860
[4] Patent: US6388084, 2002, B1
[5] Patent: WO2017/197046, 2017, A1. Location in patent: Page/Page column 344; 345