4-(PYRIDIN-4-YL)ANILINE Chemical Properties

Melting point:

232-234℃

Boiling point:

319.1±17.0 °C(Predicted)

Density 

1.133

storage temp. 

Keep in dark place,Inert atmosphere,Room temperature

pka

6.55±0.10(Predicted)

Appearance

Off-white to light brown Solid

InChI

InChI=1S/C11H10N2/c12-11-3-1-9(2-4-11)10-5-7-13-8-6-10/h1-8H,12H2

InChIKey

GKVYVZSNXXTOMQ-UHFFFAOYSA-N

SMILES

C1(N)=CC=C(C2C=CN=CC=2)C=C1

Safety Information

Hazard Codes 

Xi

Risk Statements 

20/21/22-36/37/38-38

Safety Statements 

26-36/37/39

HS Code 

2933399990

4-(PYRIDIN-4-YL)ANILINE Usage And Synthesis

Uses

4-(4-Pyridinyl)aniline is diazotized, its product is nitrated and reduced to form 2-Amino-4-(4-pyridyl)phenol, which can increase cardiac contractility; Also, it is derived from 4-Pyridineboronic Acid (P991355), which is boronic acid derivative and their binding affinities with diols.

Synthesis

Tert-butyl 4-(pyridin-4-yl)phenylcarbamate (600 mg, 2.2 mmol) was treated with a mixture of dichloromethane (DCM) and trifluoroacetic acid (TFA) (1:1, 1 mL) for 2 hr at room temperature, and upon completion of the reaction, 4-(pyridin-4-yl)aniline (20) (380 mg, 99%) was obtained. Subsequently, the solvent was removed by distillation under reduced pressure. The structure of the product 4-(pyridin-4-yl)aniline (20) was 1H NMR (400 MHz, d6-DMSO) δ 8.81 (s, 2H), 8.25 (s, 2H), 7.76 (d, J = 8.7 Hz, 2H), 6.87 (m, 2H), 2.09 (s, 2H) and mass spectrometry (ESI) m/z 171 [M + H]+ for Confirmation. High resolution mass spectrometry (HRMS) calculated value of CnHn2 171.0917 and measured value of 171.0938 further verified the structure of the product.

References

[1] Journal of Medicinal Chemistry, 2012, vol. 55, # 5, p. 2474 - 2478
[2] Patent: WO2013/112722, 2013, A1. Location in patent: Page/Page column 45
[3] Dyes and Pigments, 2017, vol. 137, p. 229 - 235
[4] Journal of Medicinal Chemistry, 1997, vol. 40, # 22, p. 3542 - 3550

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