7-Bromo-2,3-dihydro-[1,4]dioxino[2,3-b]pyridine

7-Bromo-2,3-dihydro-[1,4]dioxino[2,3-b]pyridine Property

Boiling point:

272.5±40.0 °C(Predicted)

Density 

1.690±0.06 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

form 

solid

pka

2.42±0.20(Predicted)

Appearance

Off-white to light yellow Solid

Safety

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

2934999090

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..…

7-Bromo-2,3-dihydro-[1,4]dioxino[2,3-b]pyridine Chemical Properties,Usage,Production

Synthesis

To a suspension of DMF (150 mL) containing 5-bromo-2,3-dihydroxypyridine (10.0 g, 52.63 mmol, CAS 34206-49-0), K2CO3 (21.78 g, 158 mmol) and 1,2-dibromoethane (11.87 g, 63.2 mmol) were added sequentially. The reaction mixture was heated to 100 °C and the reaction was stirred at this temperature for 5 hours. After completion of the reaction, the mixture was cooled to room temperature and subsequently poured into ice water. The reaction mixture was extracted with EtOAc to separate the organic and aqueous phases. The aqueous phase was further extracted with EtOAc and all organic phases were combined. The organic phase was dried with anhydrous Na2SO4, filtered and concentrated under reduced pressure to give the crude product. The crude product was purified by silica gel column chromatography with the eluent being a petroleum ether solution of 10% ethyl acetate. Finally, 2.2 g (18% yield) of pure 6-bromo-[1,3]dioxolo[4,5-b]pyridine was obtained, and its structure was confirmed by 1H NMR (400 MHz, DMSO): δ 7.85 (d, 1H, J=2Hz), 7.59 (d, 1H, J=2Hz), 4.41 (m, 2H), 4.27 (m, 2H).

References

[1] Patent: US2013/12530, 2013, A1. Location in patent: Paragraph 0186
[2] Zeitschrift fuer Naturforschung, Teil B: Anorganische Chemie, Organische Chemie, 1984, vol. 39, # 11, p. 1598 - 1606
[3] Patent: US2010/280013, 2010, A1. Location in patent: Page/Page column 45