2-(6-bromopyridin-2-yl)acetic acid

2-(6-bromopyridin-2-yl)acetic acid Property

Boiling point:

347.2±27.0 °C(Predicted)

Density 

1.710±0.06 g/cm3(Predicted)

storage temp. 

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

pka

3.76±0.10(Predicted)

Appearance

Off-white to light brown Solid

InChI

InChI=1S/C7H6BrNO2/c8-6-3-1-2-5(9-6)4-7(10)11/h1-3H,4H2,(H,10,11)

InChIKey

XZQWPHKCEJPCDK-UHFFFAOYSA-N

SMILES

C1(CC(O)=O)=NC(Br)=CC=C1

Safety

HazardClass 

IRRITANT

HS Code 

2933399990

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

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

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P271Use only outdoors or in a well-ventilated area.

P280Wear protective gloves/protective clothing/eye protection/face protection.

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.

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

P312Call a POISON CENTER or doctor/physician if you feel unwell.

P321Specific treatment (see … on this label).

P332+P313IF SKIN irritation occurs: Get medical advice/attention.

P337+P313IF eye irritation persists: Get medical advice/attention.

P362Take off contaminated clothing and wash before reuse.

P403+P233Store in a well-ventilated place. Keep container tightly closed.

P405Store locked up.

P501Dispose of contents/container to..…

2-(6-bromopyridin-2-yl)acetic acid Chemical Properties,Usage,Production

Uses

6-Bromo-2-pyridineacetic Acid is used in preparation of pyrimidine derivatives as RORγ modulators.

Synthesis

The general procedure for the synthesis of 2-bromo-6-pyridylacetic acid from ethyl (6-bromopyridin-2-yl)acetate was as follows: to a mixed solution of THF (10 mL), water (10 mL), and MeOH (20 mL) containing ethyl 2-(6-bromo-2-pyridinyl)acetate (2.00 g, 8.19 mmol) was added LiOH-H2O (1.03 g, 24.5 mmol). Subsequently, the reaction mixture was stirred at 20 °C for 2 hours. After completion of the reaction, the mixture was concentrated in vacuum. The residue was acidified with 1.0 N HCl to pH=3.0, washed with water (150 mL) and extracted with ethyl acetate (3 x 150 mL). The organic layers were combined, dried with Na2SO4, filtered and concentrated in vacuum to give 2-bromo-6-pyridineacetic acid (1.70 g, 96% yield) as a light yellow solid. The product was characterized by 1H NMR (400 MHz, DMSO-d6): δ=12.63 (br.s, 1H), 7.86-7.71 (m, 1H), 7.59 (d, J=8.0 Hz, 1H), 7.46 (d, J=7.6 Hz, 1H), 3.81 (s, 2H).

References

[1] Patent: WO2018/106636, 2018, A1. Location in patent: Paragraph 00239
[2] Journal of Organic Chemistry, 2018, vol. 83, # 16, p. 9088 - 9095