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Sigma-Aldrich

2-(Trimethylsilyl)ethanesulfonyl chloride

Synonym(s):

2-Trimethylsilylethylsulfonyl chloride, SES-Cl

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About This Item

Linear Formula:
(CH3)3SiCH2CH2SO2Cl
CAS Number:
106018-85-3
Molecular Weight:
200.76
MDL number:
MFCD09265153
UNSPSC Code:
12352101
PubChem Substance ID:
24885632
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

Related Categories

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
GHS02,GHS07

Signal Word

Danger

Hazard Statements

H225,H315,H319,H335

Hazard Classifications

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

Target Organs

Respiratory system

Storage Class Code

3 - Flammable liquids

WGK

WGK 3

Flash Point(F)

70.0 °F - closed cup

Flash Point(C)

21.1 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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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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