2-Bromothieno[3,2-c]pyridin-4(5H)-one

2-Bromothieno[3,2-c]pyridin-4(5H)-one Property

Boiling point:

461.7±45.0 °C(Predicted)

Density 

1.801±0.06 g/cm3(Predicted)

storage temp. 

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

pka

12.12±0.20(Predicted)

Appearance

Brown to black Solid

InChI

InChI=1S/C7H4BrNOS/c8-6-3-4-5(11-6)1-2-9-7(4)10/h1-3H,(H,9,10)

InChIKey

ZDUWCUXIWRAXLF-UHFFFAOYSA-N

SMILES

C1(=O)NC=CC2SC(Br)=CC1=2

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

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

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

2-Bromothieno[3,2-c]pyridin-4(5H)-one Chemical Properties,Usage,Production

Synthesis

General procedure for the synthesis of 2-bromo-4-hydroxythieno[3,2-C]pyridine from the compound (CAS: 636999-00-3): intermediate 49 2-bromothieno[3,2-C]pyridin-4(5H)-one [(2E)-3-(5-bromothiophene-2-yl)]acryloyl azide (18.00 g, 69.7 mmol) was dissolved in dichloromethane (100 mL) and the resulting solution was slowly added dropwise to diphenyl ether (90 mL) at 150 °C. The reaction temperature was then raised to 220 °C and maintained for 1 hour. Upon completion of the reaction, the mixture was cooled to room temperature and ether was added to precipitate the solid. The solid product was separated by filtration to give 13.58 g (84.6% yield). The product was characterized by 1H NMR (270 MHz, DMSO-d6): δ 6.82 (d, J = 7.13 Hz, 1H), 7.27 (d, J = 6.86 Hz, 1H), 7.54 (s, 1H), 11.55 (s, 1H); the mass spectrum (MS) showed m/z 230.1 ([M-H]+); and the purity of the HPLC analysis was 92%.

References

[1] Patent: WO2004/828, 2003, A1