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2-(Trimethylsilyl)ethanesulfonyl chloride

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Synonym(s):
2-Trimethylsilylethylsulfonyl chloride, SES-Cl
Linear Formula:
(CH3)3SiCH2CH2SO2Cl
CAS Number:
Molecular Weight:
200.76
MDL number:
PubChem Substance ID:
NACRES:
NA.22

refractive index

n20/D 1.4444

bp

146.8 °C/760 mmHg

density

1.059 g/mL at 25 °C

storage temp.

2-8°C

SMILES string

C[Si](C)(C)CCS(Cl)(=O)=O

InChI

1S/C5H13ClO2SSi/c1-10(2,3)5-4-9(6,7)8/h4-5H2,1-3H3

InChI key

BLPMCIWDCRGIJV-UHFFFAOYSA-N

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This Item
927492389028.20281
2-Chlorobutane for synthesis

8.20281

2-Chlorobutane

density

1.059 g/mL at 25 °C

density

0.942 g/mL at 25 °C (lit.)

density

0.942 g/mL at 25 °C (lit.)

density

0.87 g/cm3 at 20 °C

storage temp.

2-8°C

storage temp.

−20°C

storage temp.

−20°C

storage temp.

2-30°C

refractive index

n20/D 1.4444

refractive index

n20/D 1.435 (lit.), n20/D 1.436

refractive index

n20/D 1.435 (lit.)

refractive index

-

Application

Reactant involved in:
  • Nucleophilic substitution for synthesis of nicotinamine and its analogs
  • Regioselective metal-free oxidative cyclization of sulfonamides
  • Annulation reactions
  • Tin-free radical carbonylation of alkylsulfonyl derivatives
  • Asymmetric aziridination
Reagent used for protection of an amino group as a SES-amide. The SES group can be conveniently removed by fluoride ion.

pictograms

FlameExclamation mark

signalword

Danger

Hazard Classifications

Eye Irrit. 2 - Flam. Liq. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

3 - Flammable liquids

wgk_germany

WGK 3

flash_point_f

70.0 °F - closed cup

flash_point_c

21.1 °C - closed cup

ppe

Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter


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2-(Trimethylsilyl)ethanesulfonyl (or SES) group in amine protection and activation.
Patrice Ribière et al.
Chemical reviews, 106(6), 2249-2269 (2006-06-15)

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