4-(PYRIMIDIN-5-YL)BENZALDEHYDE Chemical Properties

Melting point:

145-149 °C (lit.)

Boiling point:

369.1±35.0 °C(Predicted)

Density 

1.205±0.06 g/cm3(Predicted)

storage temp. 

2-8°C, stored under nitrogen

pka

1.52±0.10(Predicted)

form 

solid

Appearance

Off-white to light brown Solid

InChI

InChI=1S/C11H8N2O/c14-7-9-1-3-10(4-2-9)11-5-12-8-13-6-11/h1-8H

InChIKey

BXNXTOLXLPQMHS-UHFFFAOYSA-N

SMILES

C(=O)C1=CC=C(C2=CN=CN=C2)C=C1

CAS DataBase Reference

198084-12-7(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xn,Xi

Risk Statements 

22-36

Safety Statements 

26

WGK Germany 

3

Hazard Note 

Irritant

HS Code 

2913000090

MSDS

• Language:English Provider:SigmaAldrich

4-(PYRIMIDIN-5-YL)BENZALDEHYDE Usage And Synthesis

Uses

4-(Pyrimidin-5-yl)benzaldehyde is a useful reactant and reagent in organic reactions such as the synthesis of 1,?2-?difluorination of alkenes, and β-?Cyanoacrylamides.

Synthesis

To a stirred solution of 5-bromopyrimidine (1 eq.), 4-formylphenylboronic acid (1.3-3.0 eq.), and sodium carbonate monohydrate (1.3-3.0 eq.) in a mixed solvent of dimethoxyethane/water (4:1, v/v) (concentration of about 0.05-0.2 M) was added tetrakis(triphenylphosphine)palladium (Pd(PPh3)4, 0.1 eq.). The reaction mixture was stirred at 90 °C for about 18 h and subsequently quenched with water. The mixture was extracted with dichloromethane (CH2Cl2) according to standard post-treatment steps and the organic layer was dried over anhydrous sodium sulfate (Na2SO4) or anhydrous magnesium sulfate (MgSO4), filtered and concentrated under reduced pressure. The crude product was purified by fast column chromatography or silica gel radial chromatography. According to the above general method, 4-(5-pyrimidinyl)benzaldehyde (162 mg, 99% yield) was obtained from 5-bromopyrimidine (199 mg, 1.25 mmol) and 4-formylphenylboronic acid (469 mg, 3.13 mmol).

References

[1] Patent: WO2007/22371, 2007, A2. Location in patent: Page/Page column 25; 71
[2] Journal of Medicinal Chemistry, 2013, vol. 56, # 20, p. 8049 - 8065

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