2-Chloropyridine-5-sulfonyl chloride Chemical Properties

Melting point:

51 °C

Boiling point:

132 °C(Press: 8 Torr)

Density 

1.615±0.06 g/cm3(Predicted)

storage temp. 

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

form 

solid

pka

-5.29±0.10(Predicted)

Appearance

White to light yellow Solid

InChI

InChI=1S/C5H3Cl2NO2S/c6-5-2-1-4(3-8-5)11(7,9)10/h1-3H

InChIKey

QXZKKHONVQGXAK-UHFFFAOYSA-N

SMILES

C1=NC(Cl)=CC=C1S(Cl)(=O)=O

CAS DataBase Reference

6684-39-5(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36

Safety Statements 

26

RIDADR 

UN3261

HazardClass 

8

HS Code 

2933399990

2-Chloropyridine-5-sulfonyl chloride Usage And Synthesis

Uses

6-Chloro-3-pyridinesulfonyl Chloride, is a heterocylic building block used for chemical synthesis. It is also an intermediate in the synthesis of 6-Aminopyridine-3-sulfonamide (A628835), that can be used as anticoccidial agents.

Synthesis

General procedure for the synthesis of 2-chloropyridine-5-sulfonyl chloride from 2-chloro-5-aminopyridine: 10 g (79.2 mmol) of 2-chloro-5-aminopyridine was dissolved in a mixture of concentrated hydrochloric acid (16 mL) and glacial acetic acid (89 mL), and cooled to 10 °C in an ice bath. 5.46 g (79.2 mmol) of sodium nitrite was added in batches and the reaction temperature was controlled to be below 15 °C. After stirring the reaction mixture for 1 hour, it was slowly added dropwise to a solution containing sulfur dioxide (carrier 27 mL), 2.77 g (16.2 mmol) of sulfur dioxide, copper(II) chloride dihydrate, and a solution consisting of acetic acid (59 mL) and water (11 mL), with the dropwise addition time being controlled to be between 5 and 10 minutes. The reaction mixture was gradually warmed to room temperature and subsequently poured into an ice-water mixture (300 mL) and stirring was continued for 15 minutes. The precipitate was isolated by filtration, washed with water (2 x 100 mL) and dried under reduced pressure to give 12.99 g of 2-chloropyridine-5-sulfonyl chloride. The product was characterized by 1H NMR (400 MHz, chloroform-d): δ 7.62 (1H, d, J = 8.31 Hz), 8.26 (1H, dd, J = 8.56,2.69 Hz), 9.04 (1H, d, J = 2.69 Hz).

References

[1] Patent: US2008/39464, 2008, A1. Location in patent: Page/Page column 30-31
[2] Organic Process Research and Development, 2009, vol. 13, # 5, p. 875 - 879
[3] Bioorganic and Medicinal Chemistry Letters, 2013, vol. 23, # 13, p. 3947 - 3953
[4] Patent: WO2009/39328, 2009, A1. Location in patent: Page/Page column 54
[5] Patent: EP1144368, 2004, B1. Location in patent: Page 64

2-Chloropyridine-5-sulfonyl chloride(6684-39-5)Related Product Information

• 2-Chloro-3-cyanopyridine
• Sulfuryl chloride
• Pivaloyl chloride
• Tosyl chloride
• Clopidol
• Ammonium chloride
• Calcium chloride
• Polyvinyl chloride
• Choline chloride
• 2-Chloro-5-chloromethylpyridine
• Sodium chloride
• 4-Nitrobenzenesulfonyl chloride
• Benzenesulfonyl chloride
• 2-Amino-6-chloropyridine
• 6-Chloropicolinic acid
• Potassium chloride
• 2-Chloropyridine
• Methanesulfonyl chloride