4,6-Dichloro-2-(methylsulfonyl)pyrimidine Chemical Properties

Melting point:

117-118°C

Boiling point:

402.3±48.0 °C(Predicted)

Density 

1.604

storage temp. 

Keep in dark place,Inert atmosphere,Room temperature

solubility 

soluble in Methanol

form 

powder to crystal

pka

-9.08±0.30(Predicted)

color 

White to Yellow to Orange

InChI

InChI=1S/C5H4Cl2N2O2S/c1-12(10,11)5-8-3(6)2-4(7)9-5/h2H,1H3

InChIKey

DROUVIKCNOHKBA-UHFFFAOYSA-N

SMILES

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

CAS DataBase Reference

4489-34-3(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xn

Risk Statements 

22-36

Safety Statements 

26-24/25

HS Code 

29335990

4,6-Dichloro-2-(methylsulfonyl)pyrimidine Usage And Synthesis

Chemical Properties

White solid

Synthesis

The general procedure for the synthesis of 4,6-dichloro-2-(methylsulfonyl)pyrimidines from 4,6-dichloro-2-methylthioalkylpyrimidines is as follows: Example 27: Synthesis of 4,6-dichloro-2-(methylsulfonyl)pyrimidine Commercially available 4,6-dichloro-2-methylsulfanylpyrimidine (Aldrich, 21.0 g, 107.0 mmol, 1 eq.) was dissolved in dichloromethane and cooled in an ice bath. Subsequently, 3-chloroperoxybenzoic acid (60.0 g, 77% wt, 268.0 mmol, 2.5 eq.) was added in batches. The resulting white suspension was stirred at room temperature for 4 hours. Upon completion of the reaction, it was washed sequentially with a mixture of 1 M sodium thiosulfate solution and saturated sodium bicarbonate solution (1:1, v/v, 200 mL x 3), saturated sodium bicarbonate solution (100 mL x 3) and brine (100 mL x 1). The organic phase was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The product was dried under high vacuum overnight to give the title compound EPO27 as a white solid (22.0 g, 91% yield). Thin layer chromatography Rf value was 0.20 (unfolding agent: 20% ethyl acetate/hexane); mass spectrum m/z 227 (calculated value 227, corresponding to molecular formula C5H4Cl2N2O2S+).

References

[1] Patent: WO2007/14250, 2007, A2. Location in patent: Page/Page column 17-18
[2] Patent: WO2007/87245, 2007, A2. Location in patent: Page/Page column 27
[3] Patent: WO2007/87246, 2007, A2. Location in patent: Page/Page column 27
[4] Patent: WO2008/13807, 2008, A2. Location in patent: Page/Page column 6
[5] Angewandte Chemie - International Edition, 2017, vol. 56, # 28, p. 8153 - 8157

4,6-Dichloro-2-(methylsulfonyl)pyrimidine(4489-34-3)Related Product Information

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• Sodium dichloroisocyanurate
• Dichloroethane
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• 2-Amino-4-methoxypyrimidine
• 2-METHANESULFONYL-PYRIMIDINE
• 4,6-Dimethyl-2-methylsulfonylpyrimidine
• Pyrimidine
• 4-Chloro-2-(methylsulfonyl)pyrimidine
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• PYRIMIDINE, 4,6-DICHLORO-5-METHYL-2-(METHYLSULFONYL)-
• 4,6-Dichloro-2-(methylsulfonyl)pyrimidine