2,5-DICHLORO-4-FORMYLPYRIDINE Chemical Properties

Melting point:

73-74°

Boiling point:

256.3±35.0 °C(Predicted)

Density 

1.488±0.06 g/cm3(Predicted)

storage temp. 

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

solubility 

DMSO (Slightly), Methanol (Slightly)

form 

Solid

pka

-3.62±0.10(Predicted)

color 

White to Off-White

InChI

InChI=1S/C6H3Cl2NO/c7-5-2-9-6(8)1-4(5)3-10/h1-3H

InChIKey

UIPSRNHDSBVXHY-UHFFFAOYSA-N

SMILES

C1(Cl)=NC=C(Cl)C(C=O)=C1

Safety Information

HazardClass 

IRRITANT

HS Code 

2933399990

2,5-DICHLORO-4-FORMYLPYRIDINE Usage And Synthesis

Uses

2,5-Dichloro-4-pyridinecarboxaldehyde, is an intermediate in the preparation of various pharmaceutical compounds. It is used in the synthesis of 2-Amino-5-aryl-pyridines as selective CB2 agonists.

Synthesis

General procedure for the synthesis of 2,5-dichloropyridine-4-carbaldehyde from 2,5-dichloropyridine and N,N-dimethylformamide: First, 2,5-dichloropyridine (27.0 g, 180 mmol) was dissolved in THF (65 mL), which was added via cannulae to a pre-cooled LDA solution at -78°C (100 mL of a 1.8 M solution of 180 mmol, dissolved in THF (80 mL)). After stirring the mixture at -78 °C for 30 min, a solution of DMF (21.1 mL, 271 mmol) in THF (25 mL) was added slowly via syringe. The reaction was kept at -78 °C for 3 h of continued stirring, followed by slow warming to room temperature. The reaction solution was slowly poured into a mixture of ice (800 mL) and hydrochloric acid (150 mL) and stirred for 20 minutes. The pH was adjusted to 9-10 with 3.0 M NaOH solution, followed by extraction with ether (2 x 500 mL). The organic layers were combined, dried and concentrated with MgSO4 to give the crude product as a light yellow solid. This solid was suspended in n-hexane with a small amount of EtOAc and boiled for 5 min before decanting the liquid and evaporating the solvent to give a yellow solid. Finally, purification by Biotage fast chromatography (using a 65i silica gel column loaded with DCM/EtOAc followed by heptane elution with an elution gradient of 20% EtOAc/heptane, 8 column volumes, and then kept at 5 column volumes) afforded the target compound, 2,5-dichloro pyridine-4-carboxaldehyde (17.9 g, 56% yield), as a light yellow solid.1H NMR ( 400 MHz, DMSO-d6) δ 7.85 (s, 1H), 8.76 (s, 1H), 10.22 (s, 1H).

References

[1] Patent: WO2011/27249, 2011, A2. Location in patent: Page/Page column 58
[2] Bioorganic and Medicinal Chemistry Letters, 2009, vol. 19, # 23, p. 6578 - 6581
[3] Patent: WO2006/50506, 2006, A1. Location in patent: Page/Page column 132
[4] Patent: WO2005/73232, 2005, A1. Location in patent: Page/Page column 34

2,5-DICHLORO-4-FORMYLPYRIDINE(102645-33-0)Related Product Information

• 2,6-Dichloropyridine-4-carboxaldehyde
• 2,3-DICHLORO-4-FORMYLPYRIDINE
• 2,3-DICHLORO-5-FORMYLPYRIDINE
• 2,6-DICHLORO-3-FORMYLPYRIDINE
• ethyl 2,5-dichloroisonicotinate
• 2,3,5-Trichloropyridine-4-carboxylic acid
• ETHYL 2,3,5-TRICHLORO-6-{[(DIMETHYLAMINO)CARBONOTHIOYL]THIO}ISONICOTINATE
• 2,3,5,6-Tetrachloropyridine-4-carboxylic acid
• ETHYL 2-(TERT-BUTYL)-3,6-DICHLORO-5-CYANOISONICOTINATE
• 2,5-Dichloroisonicotinic acid
• RARECHEM AL BW 2014
• methyl 2,5-dichloroisonicotinate
• 2,5-DICHLORO-4-FORMYLPYRIDINE
• 2,3,5,6-TETRACHLOROPYRIDINE-4-CARBOXALDEHYDE
• 2,3,5-Trichloropyridine-4-carboxaldehyde
• 2,3,5,6-TETRACHLOROISONICOTINOYL CHLORIDE