5-Bromopyridine-2-carbaldehyde Chemical Properties

Melting point:

91-96 °C

Boiling point:

70°C/26mmHg(lit.)

Density 

1.683±0.06 g/cm3(Predicted)

storage temp. 

2-8°C

pka

1.36±0.10(Predicted)

form 

powder to crystal

color 

White to Light yellow to Light orange

Water Solubility 

Insoluble in water.

Sensitive 

Air Sensitive

InChI

InChI=1S/C6H4BrNO/c7-5-1-2-6(4-9)8-3-5/h1-4H

InChIKey

ZQVLPMNLLKGGIU-UHFFFAOYSA-N

SMILES

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

CAS DataBase Reference

31181-90-5(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38-20/21/22

Safety Statements 

22-26-36/37/39-36

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

29333990

MSDS

• Language:English Provider:ALFA

5-Bromopyridine-2-carbaldehyde Usage And Synthesis

Chemical Properties

Light yellow Cryst

Uses

5-Bromopyridine-2-carboxaldehyde is used as organic chemical synthesis intermediate.

Synthesis

5-Bromo-2-pyridinecarboxaldehyde was synthesized according to General Method C using 2,5-dibromopyridine and N,N-dimethylformamide (DMF) as raw materials. The specific operation was as follows: 2,5-dibromopyridine (237 mg, 1 mmol) was mixed with DMF (115 μL, 1.5 mmol) for the reaction. After completion of the reaction, the crude product was purified by fast column chromatography (eluent: hexane/ethyl acetate = 10:1) to afford the target compound 5-bromo-2-pyridinecarboxaldehyde (27b) as a brown solid (149 mg, 80% yield). Thin layer chromatography (TLC) analysis showed an Rf value of 0.45 (Expander: hexane/ethyl acetate = 8:1). Nuclear magnetic resonance hydrogen spectroscopy (1H NMR, 400 MHz, CDCl3) data were as follows: δ 10.03 (1H, s), 8.85 (1H, dd, J = 0.8, 2.0 Hz), 8.02 (1H, ddd, J = 0.8, 2.0, 8.0 Hz), 7.85 (1H, dd, J = 0.8, 8.0 Hz). The nuclear magnetic resonance carbon spectrum (13C NMR, 100 MHz, CDCl3) data were as follows: δ 192.4, 151.7, 151.3, 140.0, 126.3, 122.8. The spectral data obtained were in agreement with literature reports.

References

[1] Bioorganic and Medicinal Chemistry, 2018, vol. 26, # 22, p. 5852 - 5869
[2] Patent: WO2007/15744, 2007, A1. Location in patent: Page/Page column 58-59
[3] Chemistry - A European Journal, 2006, vol. 12, # 13, p. 3472 - 3483
[4] Patent: WO2006/22794, 2006, A1. Location in patent: Page/Page column 49
[5] Tetrahedron Letters, 2000, vol. 41, # 22, p. 4335 - 4338

5-Bromopyridine-2-carbaldehyde(31181-90-5)Related Product Information

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• 5-BROMOPYRIDINE-2-CARBONYL CHLORIDE