3-Pyridineacrylic acid Chemical Properties

Melting point:

232-235 °C (dec.)(lit.)

Boiling point:

270.21°C (rough estimate)

Density 

1.2517 (rough estimate)

refractive index 

1.5320 (estimate)

storage temp. 

Inert atmosphere,Room Temperature

solubility 

DMSO (Slightly), Methanol (Slightly, Heated)

pka

3.13±0.10(Predicted)

form 

Solid

color 

White

InChI

InChI=1S/C8H7NO2/c10-8(11)4-3-7-2-1-5-9-6-7/h1-6H,(H,10,11)

InChIKey

VUVORVXMOLQFMO-UHFFFAOYSA-N

SMILES

C(O)(=O)C=CC1=CC=CN=C1

CAS DataBase Reference

1126-74-5(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi,Xn

Risk Statements 

36/37/38-22

Safety Statements 

26-36-37/39-36/37/39

WGK Germany 

3

F 

10

HazardClass 

IRRITANT

HS Code 

29333990

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

3-Pyridineacrylic acid Usage And Synthesis

Chemical Properties

white to light yellow crystal powder

Uses

3-Pyridineacrylic Acid is an inhibitor of peptidylglycine amidating monooxygenase.

Synthesis

To a solution of butyl 3-(pyridin-3-yl)prop-2-enoate (70 g, 341 mmol, 1.00 equiv) in ethanol (150 mL) was added a solution of potassium hydroxide (40 g, 712.94 mmol, 2.09 equiv) in water (150 mL). The reaction mixture was stirred at room temperature for 20 hours. Upon completion of the reaction, the pH of the solution was adjusted to 6 with 12 M hydrochloric acid.The precipitate was collected by filtration to give 50 g (98% yield) of trans-3-(3-pyridyl)acrylic acid as an off-white solid.LCMS analysis (Method C, electrospray ionization, m/z): retention time = 0.78 min, m/z = 149.9 [M+H]+.

References

[1] Patent: WO2014/74715, 2014, A1. Location in patent: Paragraph 0170
[2] Journal of Medicinal Chemistry, 2014, vol. 57, # 3, p. 770 - 792

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