(6-BroMopyridin-2-yl)acetic acid ethyl ester

(6-BroMopyridin-2-yl)acetic acid ethyl ester Property

Boiling point:

297.4±25.0 °C(Predicted)

Density 

1.451±0.06 g/cm3(Predicted)

storage temp. 

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

pka

-0.03±0.12(Predicted)

Appearance

Colorless to light yellow Liquid

Safety

HS Code 

2933399990

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..…

(6-BroMopyridin-2-yl)acetic acid ethyl ester Chemical Properties,Usage,Production

Synthesis

To a solution of 2-bromo-6-methylpyridine (5.00 g, 29.0 mmol, CAS 5315-25-3) in tetrahydrofuran (THF, 100 mL) was slowly added lithium diisopropylammonium (LDA, 2.0 M, 30.5 mL) at -70 °C. The reaction temperature was maintained at -70 °C and after stirring for 0.5 h, diethyl carbonate (5.26 mL, 43.6 mmol) was added. The reaction mixture was slowly warmed to 20 °C and stirring was continued at this temperature for 4 hours. Upon completion of the reaction, the reaction mixture was washed with deionized water (120 mL) and subsequently extracted with ethyl acetate (3 x 150 mL). The organic layers were combined, dried with anhydrous sodium sulfate (Na2SO4), filtered and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: petroleum ether/ethyl acetate=10:1, v/v) to afford ethyl (6-bromopyridin-2-yl)acetate (5.50 g, 77% yield) as a pale yellow oil.1H NMR (400 MHz, CDCl3) δ=7.50-7.41 (m, 1H), 7.33 (d, J=7.6 Hz, 1H ), 7.21 (d, J=7.6Hz, 1H), 4.11 (q, J=7.2Hz, 2H), 3.75 (s, 2H), 1.20 (t, J=7.2Hz, 3H).

References

[1] Journal of Organic Chemistry, 2018, vol. 83, # 16, p. 9088 - 9095
[2] Patent: WO2018/106636, 2018, A1. Location in patent: Paragraph 00238
[3] Patent: US2016/297762, 2016, A1. Location in patent: Paragraph 0361-0362