4-(2-HYDROXYETHYL)THIOMORPHOLINE 1,1-DIOXIDE Chemical Properties

Melting point:

74 °C

Boiling point:

197 °C / 1mmHg

Density 

1.287±0.06 g/cm3(Predicted)

storage temp. 

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

solubility 

soluble in Methanol

form 

powder to crystal

pka

14.80±0.10(Predicted)

color 

White to Light yellow to Light orange

InChI

InChI=1S/C6H13NO3S/c8-4-1-7-2-5-11(9,10)6-3-7/h8H,1-6H2

InChIKey

GILLKIJFJOBJCD-UHFFFAOYSA-N

SMILES

N1(CCO)CCS(=O)(=O)CC1

CAS DataBase Reference

26475-62-7(CAS DataBase Reference)

Safety Information

HS Code 

2934999090

4-(2-HYDROXYETHYL)THIOMORPHOLINE 1,1-DIOXIDE Usage And Synthesis

Synthesis

To a stirred solution of 2-bromoethanol (11.78 mL, 165.92 mmol, 7.0 equiv) in acetonitrile (68 mL) was added potassium carbonate (9.8 g, 71.10 mmol, 3.0 equiv). The reaction mixture was stirred at room temperature for 30 minutes before thiomorpholine-1,1 -dioxide (3.2 g, 23.70 mmol, 1.0 eq.) was added. The reaction mixture was heated to reflux and stirred overnight. The progress of the reaction was monitored by thin layer chromatography (TLC) to confirm that the feedstock was completely consumed and the target product was generated. Upon completion of the reaction, the mixture was cooled to room temperature and filtered. The filtrate was concentrated to obtain the crude product, which was subsequently purified by column chromatography using a mixture of dichloromethane and 3% methanol as eluent, resulting in 4-(2-hydroxyethyl)thiomorpholine-1,1-dioxide (2.5 g, 60.0% yield) as a brown liquid. The product was characterized by 1H NMR (DMSO-d6, 300 MHz): δ 4.50 (t, 1H), 3.51 (q, 2H), 3.07 (m, 4H), 2.95 (m, 4H), 2.58 (t, 2H); Mass Spectrometry (MS): [M + H]+ m/z 180.19 (10%).

References

[1] Patent: WO2017/149518, 2017, A1. Location in patent: Page/Page column 24; 25

4-(2-HYDROXYETHYL)THIOMORPHOLINE 1,1-DIOXIDE(26475-62-7)Related Product Information

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