CAS 106018-85-3 2-(Trimethylsilyl)ethane-1-sulfonyl chloride (HCID 9837086)

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Basic information

CAS: 106018-85-3
Standard SMILES: C[Si](C)(C)CCS(=O)(=O)Cl
InChIKey: BLPMCIWDCRGIJV-UHFFFAOYSA-N
Molecular formula: C5H13ClO2SSi
Average molar mass: 200.76 g/mol
Monoisotopic mass: 200.00940487

Names & identifiers

Preferred name: 2-(Trimethylsilyl)ethane-1-sulfonyl chloride
IUPAC: 2-trimethylsilylethanesulfonyl chloride
English name: 2-(Trimethylsilyl)ethanesulfonyl chlori&
Molecular formula: C5H13ClO2SSi
Molecular weight: 200.76

Names & synonyms

2-(trimethylsilyl)ethane-1-sulfonyl chlorideRefChem:462634628-168-62-(Trimethylsilyl)ethanesulfonyl chloride106018-85-32-trimethylsilylethanesulfonyl ChlorideMFCD092651532-Trimethylsilanyl-ethanesulfonyl Chloride2-(TRIMETHYLSILYL)ETHANESULFONYL CHLORI2-(TRIMETHYLSILYL)ETHANESULFONYL CHLORI&SES-ClEthanesulfonylchloride, 2-(trimethylsilyl)-

Show more names

06018-85-32-(trimethylsilyl)ethylsulfonylchloro2-(TRISMETHYLSILYL)ETHANESULPHONYLCHLORIDE2-Trimethylsilylethylsulfonyl chloride, SES-Cl

Ethanesulfonyl chloride, 2-(trimethylsilyl)-C5H13ClO2SSiSCHEMBL1115359DTXSID20431554BLPMCIWDCRGIJV-UHFFFAOYSA-N2-(trimethylsilyl)ethylsulfonylchlorideAKOS0063362392-trimethylsilanylethanesulfonyl chloride

Database identifiers

CAS: 106018-85-3
PubChem CID: 9837086
DTXSID: DTXSID20431554

Properties

Computed structural properties

Topological polar surface area: 42.5 Å²
Hydrogen bond donors: 0
Hydrogen bond acceptors: 2
Rotatable bonds: 3
Heavy atoms: 10
Formal charge: 0
Complexity: 187

Physicochemical properties

Boiling point: 146.8 °C/760 · 146.8 °C/760 mmHg
Density: 1.059 g/mL · 1.059 g/mL at 25 °C
refractive index: 20 · n20/D 1.4444
Flash point: 21 °C · 21 °C
storage temp.: 2 · 2-8°C
solubility: Sol most common organic solvents.
InChI: 1S/C5H13ClO2SSi/c1-10(2,3)5-4-9(6,7)8/h4-5H2,1-3H3
InChIKey: BLPMCIWDCRGIJV-UHFFFAOYSA-N
SMILES: C[Si](C)(C)CCS(Cl)(=O)=O
UNSPSC Code: 12352101 · 12352101
NACRES: 22 · NA.22
Symbol(GHS): 2 · GHS02,GHS07
Signal word: Danger
Hazard statements: 225 · H225-H315-H319-H335
Precautionary statements: 210 · P210-P302+P352-P305+P351+P338
target organs: Respiratory system

Safety & regulation

GHS classification

GHS Classification · 4 items

Danger

H225 (100%): Highly Flammable liquid and vapor [Danger Flammable liquids]

P210, P233, P240, P241, P242, P243, P261, P264, P264+P265, P271, P280, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P370+P378, P403+P233, P403+P235, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 42 reports by companies from 5 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Hazard information

Hazard Classes and CategoriesFlam. Liq. 2 (100%)

Safety data

PPE: Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter
wgk: 3
ridadr: UN 1993 3/PG 2
hs_code: 2931900090
risk_code: 11-36/37/38
Signal word: Danger
Symbol(GHS): GHS02,GHS07
hazard_code: F,Xi
safety_code: 26
Storage Class: 3 - Flammable liquids
target organs: Respiratory system
Hazard statements: H225-H315-H319-H335
Hazard Classifications: Eye Irrit. 2Flam. Liq. 2Skin Irrit. 2STOT SE 3
Precautionary statements: P210-P302+P352-P305+P351+P338

Chemistry & industry

Applications · 2 items

Usesβ-Trimethylsilylethanesulfonyl Chloride is used in the protection of primary and secondary amines as their sulfonamides, which are cleaved by fluoride ion. It participates in the reations of Protection of Amines, SESCl in Synthesis, N-Alkylation, Deprotection Conditions, Formation of 2-Trimethylsilylethanesulfonylimines, the (N-SES-Imino) Phenyliodinane or SESN=IPh Reagent, SES-N3, etc.

Uses2-(Trimethylsilyl)ethanesulfonyl Chloride can be prepared to used to treat cancer and other diseases.

Preparation methods · 1 item

Preparation|-Trimethylsilylethanesulfonyl Chloride can be most conveniently synthesized from commercially available vinyltrimethylsilane (eq 1). Radical addition of sodium bisulfite to the vinyl group catalyzed by t-butyl perbenzoate yields the sulfonate salt which can be directly converted to SESCl with phosphorus(V) chloride. The chloride can then be purified by distillation. The intermediate sulfonate salt is commercially available. The chloride can also be prepared in 62% yield from the salt using sulfuryl chloride and triphenylphosphine (eq 2). A less convenient procedure to synthesize SESCl using |-trimethylsilylethylmagnesium chloride and sulfuryl chloride has also been developed (eq 3).