2-BROMO-3-FORMYLPYRIDINE Chemical Properties

Melting point:

73 °C

Boiling point:

100 °C / 3mmHg

Density 

1.683±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

form 

powder to crystal

pka

-1.01±0.10(Predicted)

color 

White to Orange to Green

InChI

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

InChIKey

GNFWMEFWZWXLIN-UHFFFAOYSA-N

SMILES

C1(Br)=NC=CC=C1C=O

CAS DataBase Reference

128071-75-0(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xn,Xi

Risk Statements 

22-36-43

Safety Statements 

26-36/37

WGK Germany 

3

Hazard Note 

Irritant

HS Code 

29333990

MSDS

• Language:English Provider:SigmaAldrich

2-BROMO-3-FORMYLPYRIDINE Usage And Synthesis

Uses

2-Bromo-3-pyridinecarboxaldehyde is a pyridine heterocyclic compound mainly used in laboratory organic synthesis processes.

Chemical Properties

Yellow solid

Synthesis

To a cooled solution of diisopropylamine (20.4 g, 28.0 mL, 0.202 mol) in anhydrous THF (400 mL) at -78 °C was slowly added n-BuLi (0.192 mol, 58.0 mL, 3.3 M hexane solution). The reaction mixture was stirred at -78 °C for 1 h, followed by the dropwise addition of anhydrous THF (150 mL) solution of 2-bromopyridine (25.3 g, 0.160 mol) over 20 min. After keeping the reaction at -78 °C for 90 min, an anhydrous THF (25 mL) solution of DMF (35.0 g, 0.480 mol) cooled to -78 °C was quickly added. Stirring was continued at -78 °C for 80 min, and upon completion of the reaction, the reaction was quenched with NaH2PO4 (27.6 g, 0.230 mol, dissolved in H2O (120 mL)), slowly warmed to room temperature, and diluted with MeOt-Bu (500 mL). The organic phase was separated, washed with brine (2100 mL), dried over anhydrous Na2SO4 and concentrated under reduced pressure. The crude product was ground with pentane and after decantation, the remaining solid was recrystallized from hexane to give 16.7 g of 2-bromo-3-pyridinecarboxaldehyde as a pale yellow solid in 56% yield, melting point 67-69 °C. 1H NMR (400 MHz, CDCl3) δ: 10.35 (s, 1H), 8.57 (dd, J=4.7,2.1 Hz, 1H), 8.17 (dd, J= 7.6,2.1Hz, 1H), 7.44 (dd, J=7.6,4.7,0.6Hz, 1H).13C NMR (101MHz, CDCl3) δ: 190.4,154.0,144.9,137.5,130.1,123.0. Calculated values for elemental analyses (C6H4BrNO): C, 38.74; H. 2.17; N, 7.53; Br, 42.96. Measured values: C, 38.58; H, 2.08; N, 7.57; Br, 42.69.

References

[1] Tetrahedron Letters, 2008, vol. 49, # 17, p. 2839 - 2843
[2] Chemical Communications, 2011, vol. 47, # 23, p. 6635 - 6637
[3] Organic Letters, 2007, vol. 9, # 5, p. 891 - 894
[4] Tetrahedron Letters, 2017, vol. 58, # 20, p. 1989 - 1991
[5] Synthesis (Germany), 2018, vol. 50, # 1, p. 155 - 169

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