2-(5-bromopyridin-2-yl)acetic acid Chemical Properties

Melting point:

120-123℃

Boiling point:

326.2±27.0 °C(Predicted)

Density 

1.710±0.06 g/cm3(Predicted)

storage temp. 

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

form 

powder

pka

3.81±0.10(Predicted)

Appearance

Light yellow to yellow Solid

InChI

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

InChIKey

ATKULCGQSLCGEK-UHFFFAOYSA-N

SMILES

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

CAS DataBase Reference

192642-85-6

Safety Information

Hazard Codes 

Xn

Risk Statements 

22-41

Safety Statements 

26-39

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

2933399990

2-(5-bromopyridin-2-yl)acetic acid Usage And Synthesis

Synthesis

General procedure for the synthesis of 2-(5-bromopyridin-2-yl)acetic acid from diethyl malonate: In Example 40, diethyl 2-(5-bromopyridin-2-yl)-malonate (16.6 g, 52.5 mmol) was dissolved in methanol (200 mL) followed by addition of 2N aqueous sodium hydroxide solution (105 mL, 210 mmol). The reaction mixture was stirred at room temperature for 3 h, after which the solvent was removed by vacuum concentration. The residue was dissolved in water and neutralized with 2N hydrochloric acid to pH 3-4. Subsequently, the solid formed was collected by filtration, washed sequentially with water and ether, and dried to give a white solid product that did not require further purification (9.0 g, 80% yield). Results of mass spectrometry analysis: calculated value 215 (MH+), measured value 215 (MH+).

References

[1] Patent: US2010/69328, 2010, A1. Location in patent: Page/Page column 36
[2] Patent: WO2016/34673, 2016, A1. Location in patent: Page/Page column 100
[3] Patent: WO2014/53967, 2014, A1. Location in patent: Page/Page column 160; 161

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