3,5-Dibromopyridine-4-carboxaldehyde Chemical Properties

Melting point:

118-122 °C (lit.)

Boiling point:

278.1±35.0 °C(Predicted)

Density 

2.090±0.06 g/cm3(Predicted)

storage temp. 

under inert gas (nitrogen or Argon) at 2–8 °C

solubility 

Choroform (Slightly), Methanol (Slightly, Sonicated)

form 

Solid

pka

-1.47±0.28(Predicted)

color 

Pale Yellow to Light Yellow

InChI

InChI=1S/C6H3Br2NO/c7-5-1-9-2-6(8)4(5)3-10/h1-3H

InChIKey

WPBYVMDYYFWYAY-UHFFFAOYSA-N

SMILES

C1=NC=C(Br)C(C=O)=C1Br

Safety Information

Hazard Codes 

Xn

Risk Statements 

22-36/37/38-43

Safety Statements 

26-36/37

RIDADR 

UN 2811 6.1/PG 3

WGK Germany 

3

HazardClass 

6.1

PackingGroup 

Ⅲ

HS Code 

2933399990

3,5-Dibromopyridine-4-carboxaldehyde Usage And Synthesis

Uses

3,5-Dibromo-4-pyridinecarboxaldehyde is easily soluble in water and miscible with organic solvents. It is used as an intermediate for synthesising the insecticide pyrazinone and in textiles to improve the stiffness of cotton fabrics.

Synthesis

Step 1: Diisopropylamine (2.4 g, 24.0 mmol) was dissolved in anhydrous tetrahydrofuran (20 mL) under nitrogen protection and cooled to 0 °C. A n-butyllithium solution (9.6 mL, 24.0 mmol) in hexane was slowly added dropwise and stirred continuously for 30 min at this temperature. Subsequently, additional anhydrous tetrahydrofuran (30 mL) was added and the reaction mixture was further cooled to -78 °C. To this low-temperature solution, dry 3,5-dibromopyridine (4.7 g, 20 mmol) was added, diluted dropwise with tetrahydrofuran (50 mL), and stirring was continued for 30 minutes. Next, methyl formate (2.4 g, 40 mmol) was added and the reaction mixture was continued stirring at -78 °C for 30 min. After slowly warming to room temperature, the reaction was quenched with saturated sodium bicarbonate solution (100 mL) and extracted with ethyl acetate (50 mL × 3). The organic phases were combined, dried over anhydrous sodium sulfate, concentrated and purified by column chromatography to afford the target product 3,5-dibromopyridine-4-carbaldehyde (26-b) as a light yellow solid (4.0 g, 75% yield).1H NMR (300 MHz, DMSO-d6) δ: 10.06 (s, 1H), 8.87 (s, 2H).

References

[1] Patent: US2017/158680, 2017, A1. Location in patent: Paragraph 0418; 0419; 0420
[2] Bioorganic and Medicinal Chemistry Letters, 2007, vol. 17, # 10, p. 2789 - 2794
[3] Journal of Fluorine Chemistry, 2006, vol. 127, # 6, p. 755 - 759
[4] Patent: US6232320, 2001, B1

3,5-Dibromopyridine-4-carboxaldehyde(70201-42-2)Related Product Information

• 2,5-Dibromopyrazine
• meso-2,3-Dibromosuccinic acid
• 2,3-Dibromopropionic acid
• 1,2-Dibromopropane
• 2,2-Bis(bromomethyl)propane-1,3-diol
• 3,5-Dibromopyridine
• 4-Pyridinecarboxaldehyde
• 2,5-Dibromopyridine
• 1,3-Dibromo-5,5-dimethylhydantoin
• 5-Bromo-2-chloroisonicotinic acid
• 3-Bromoisonicotinic acid
• 5-BROMO-2-HYDROXY-4-PYRIDINECARBOXYLIC ACID
• 1-(3-BROMOPYRIDIN-4-YL)ETHANONE
• 2-ACETAMIDO-5-BROMOISONICOTINIC ACID
• 3-BROMO-5-METHYLPYRIDINE-4-CARBOXALDEHYDE
• Methyl 5-bromo-2-chloroisonicotinate
• 2,6-DIBROMOPYRIDINE-4-CARBOXALDEHYDE
• 2,6-Dibromopyridine-3-carboxaldehyde