106018-85-3 Usage
Description
2-(TRIMETHYLSILYL)ETHANESULFONYL CHLORI&, also known as β-Trimethylsilylethanesulfonyl Chloride, is a chemical compound with the formula (CH3)3SiCH2CH2SO2Cl. It is a yellow oil with a boiling point of 60 °C at 0.1 mmHg. 2-(TRIMETHYLSILYL)ETHANESULFONYL CHLORI& is widely used in organic synthesis and pharmaceutical applications due to its unique reactivity and properties.
Uses
Used in Organic Synthesis:
2-(TRIMETHYLSILYL)ETHANESULFONYL CHLORI& is used as a protecting group for primary and secondary amines in the form of sulfonamides. These protected amines can be selectively cleaved by fluoride ion, making it a valuable tool in the synthesis of complex organic molecules.
Used in Pharmaceutical Applications:
In the pharmaceutical industry, 2-(TRIMETHYLSILYL)ETHANESULFONYL CHLORI& is used to treat cancer and other diseases. Its reactivity allows for the development of novel drug candidates with potential therapeutic benefits.
Used in Protection of Amines:
2-(TRIMETHYLSILYL)ETHANESULFONYL CHLORI& is used as a protecting agent for amines during organic synthesis. It helps prevent unwanted reactions and allows for selective deprotection under specific conditions.
Used in Synthesis:
The compound is utilized in the synthesis of various organic molecules, including the formation of 2-Trimethylsilylethanesulfonylimines and the (N-SES-Imino) Phenyliodinane or SESN=IPh reagent.
Used in N-Alkylation:
2-(TRIMETHYLSILYL)ETHANESULFONYL CHLORI& is employed in N-alkylation reactions, which are crucial for the synthesis of various pharmaceutical compounds.
Used in Deprotection Conditions:
The compound is used to create deprotection conditions in organic synthesis, allowing for the controlled removal of protecting groups to reveal the desired functional groups.
Used in Formation of SES-N3:
2-(TRIMETHYLSILYL)ETHANESULFONYL CHLORI& is used in the formation of SES-N3, a compound that has potential applications in the synthesis of various organic molecules and pharmaceuticals.
Preparation
β-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 β-trimethylsilylethylmagnesium chloride and sulfuryl
chloride has also been developed (eq 3).
Purification Methods
Check IR; if the bands at ~3200 (OH) cm-1 are strong, then much of the SES-Cl had hydrolysed, and it should be treated with POCl3 (with cooling) and stirred at ~25o for about 1hour, poured into ice cold H2O, extracted with CH2Cl2, washed with NaHCO3, dried (Na2SO4), evaporated , and it distils as a yellow oil in a vacuum. This procedure is used for converting the Na salt to SES-Cl. It reacts with amines to form amides, e.g. SES-NRR’, which on heating with CsF (i.e. F-ions) in DMF at 95o provide the amine (NHRR’), SO2 and CH2=CH2 [Weinreb et al. Tetrahedron Lett 27 2099 1986]. [Ribiere et al. Chem Rev 106 2249 2006.]
Check Digit Verification of cas no
The CAS Registry Mumber 106018-85-3 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 1,0,6,0,1 and 8 respectively; the second part has 2 digits, 8 and 5 respectively.
Calculate Digit Verification of CAS Registry Number 106018-85:
(8*1)+(7*0)+(6*6)+(5*0)+(4*1)+(3*8)+(2*8)+(1*5)=93
93 % 10 = 3
So 106018-85-3 is a valid CAS Registry Number.
