2-Chloro-4-iodopyridine-3-carboxaldehyde Chemical Properties

Melting point:

87-92 °C

Boiling point:

326.6±42.0 °C(Predicted)

Density 

2.083±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

form 

solid

pka

-1.53±0.10(Predicted)

Appearance

Light yellow to yellow Solid

Sensitive 

Air & Light Sensitive

InChI

InChI=1S/C6H3ClINO/c7-6-4(3-10)5(8)1-2-9-6/h1-3H

InChIKey

OPZCXONVRBYGHX-UHFFFAOYSA-N

SMILES

C1(Cl)=NC=CC(I)=C1C=O

CAS DataBase Reference

153034-90-3(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi,Xn

Risk Statements 

36/37/38-22

Safety Statements 

26-36/37/39-37

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

29333990

MSDS

• Language:English Provider:ALFA

2-Chloro-4-iodopyridine-3-carboxaldehyde Usage And Synthesis

Uses

2-Chloro-4-iodopyridine-3-carboxaldehyde is an organic heterocyclic compound that can be used as a pharmaceutical intermediate.

Chemical Properties

Yellow-green solid

Synthesis

Example 1: Synthesis of N-(2-(2,6-dichlorophenyl)-2H-pyrazolo[4,3-c]pyridin-4-yl)cyclopropanecarboxamide Step 1: Preparation of 2-chloro-4-iodonicotinaldehyde A solution of 2-chloro-3-iodopyridine (5.0 g, 21 mmol) in anhydrous THF (30 mL) was slowly added dropwise to a solution of lithium diisopropylammonium (15 mL, 30 mmol) in anhydrous THF (50 mL) that was pre-cooled to -78 °C. The reaction mixture was stirred continuously at -78 °C for 3 hours. Subsequently, ethyl formate (4.0 g, 54 mmol) was added to the reaction system and stirring was continued at the same temperature for 1.5 hours. Upon completion of the reaction, the reaction was quenched by the addition of water (10 mL), after which the mixture was slowly warmed to room temperature. THF was removed by distillation under reduced pressure after addition of 2 M HCl (50 mL).The aqueous phase was extracted with ethyl acetate (2 x 50 mL). The organic phases were combined, washed with brine, dried over anhydrous Na2SO4 and concentrated under reduced pressure. The crude product was purified by silica gel column chromatography (eluent: ether/petroleum ether=1:4) to afford the target compound 2-chloro-4-iodonicotinaldehyde as a yellow solid (3.0 g, 54% yield). NMR (500MHz, CDCl3): δ10.22 (s, 1H), 8.09 (d, J=5.0Hz, 1H), 7.95 (d, J=5.0Hz, 1H).

References

[1] Synthetic Communications, 1996, vol. 26, # 23, p. 4421 - 4436
[2] Journal of Organic Chemistry, 1993, vol. 58, # 27, p. 7832 - 7838
[3] Journal of Heterocyclic Chemistry, 2001, vol. 38, # 5, p. 1039 - 1044
[4] Patent: WO2012/66061, 2012, A1. Location in patent: Page/Page column 76-77

2-Chloro-4-iodopyridine-3-carboxaldehyde(153034-90-3)Related Product Information

• Clopidol
• 2-Bromopyridine-5-carbaldehyde
• 2-Bromo-3-iodopyridine
• 2-Bromo-4-iodopyridine
• 2-BROMO-3-FORMYLPYRIDINE
• 2-Chloro-4-iodopyridine
• 2-Chloro-5-chloromethylpyridine
• Difluorochloromethane
• 2-CHLORO-4-IODO-3-METHYLPYRIDINE
• 2-CHLORO-4-IODO-NICOTINIC ACID METHYL ESTER
• 2-CHLORO-4-IODO-NICOTINIC ACID
• 4-Iodopyridine
• 2-CHLORO-4-IODO-NICOTINIC ACID ETHYL ESTER
• 4-Iodo-3-methylpyridine
• 2-Chloro-4-iodopyridine-3-carboxaldehyde
• pyridylaldehyde