2-CHLORO-PYRIMIDINE-5-SULFONYL CHLORIDE

2-CHLORO-PYRIMIDINE-5-SULFONYL CHLORIDE Property

Melting point:

66-67 °C

Boiling point:

383.2±15.0 °C(Predicted)

Density 

1.711±0.06 g/cm3(Predicted)

storage temp. 

2-8°C, stored under nitrogen

pka

-5.59±0.22(Predicted)

form 

Crystalline Powder or Powder

color 

White to cream

InChI

InChI=1S/C4H2Cl2N2O2S/c5-4-7-1-3(2-8-4)11(6,9)10/h1-2H

InChIKey

DMAOAJYJIATWJS-UHFFFAOYSA-N

SMILES

C1(Cl)=NC=C(S(Cl)(=O)=O)C=N1

Safety

Hazard Codes 

Xi

Risk Statements 

36

Safety Statements 

26

HazardClass 

IRRITANT

HS Code 

2933599590

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Danger

Hazard statements

H302Harmful if swallowed

H312Harmful in contact with skin

H314Causes severe skin burns and eye damage

H332Harmful if inhaled

Precautionary statements

P280Wear protective gloves/protective clothing/eye protection/face protection.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P310Immediately call a POISON CENTER or doctor/physician.

2-CHLORO-PYRIMIDINE-5-SULFONYL CHLORIDE Chemical Properties,Usage,Production

Uses

2-Chloro-pyrimidine-5-sulfonyl chloride is a pyrimidine heterocyclic compound mainly used in organic synthesis and pharmaceutical research and development.

Synthesis

The general procedure for synthesizing 2-chloropyrimidine-5-sulfonyl chloride using 2-hydroxypyrimidine-5-sulfonic acid as a starting material was as follows: referring to the method of Example 26, 2-hydroxypyrimidine-5-sulfonic acid (12.8 g) was mixed with phosphorus pentachloride (37.8 g) and the reaction was stirred for 4 hrs at 180°C. Upon completion of the reaction, the mixture was cooled to room temperature and toluene (200 mL) was added to dissolve the product, followed by filtration to remove insoluble impurities. The filtrate was washed with ice water and dried over anhydrous magnesium sulfate. After removal of the solvent by evaporation under reduced pressure, the residue was allowed to stand in a refrigerator for one day to give 2-chloropyrimidine-5-sulfonyl chloride in the form of a light yellow solid (yield 14.8 g, 96% yield). The product was characterized by 1H-NMR (CDCl3) with chemical shift δ: 9.19 (2H, s).

References

[1] Patent: US2007/60623, 2007, A1. Location in patent: Page/Page column 23
[2] Patent: WO2006/36024, 2006, A1. Location in patent: Page/Page column 159
[3] Patent: EP2336107, 2015, B1. Location in patent: Paragraph 0303
[4] Patent: WO2004/74283, 2004, A1. Location in patent: Page 87
[5] Patent: EP1803709, 2007, A1