22515-25-9

Basic information

• Product Name: 4-TRIMETHYLSILYL-THIOANISOLE
• Synonyms: 4-TRIMETHYLSILYL-THIOANISOLE;Silane,trimethyl[4-(methylthio)phenyl]-;1-(Trimethylsilyl)-4-thioanisole
• CAS NO: 22515-25-9
• Molecular Formula: C₁₀H₁₆SSi
• Molecular Weight: 196.38454
• Mol File: 22515-25-9.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 249 °C at 760 mmHg
• Flash Point: 104.4 °C
• Appearance: /
• Density: 0.95 g/cm³
• CAS DataBase Reference: 4-TRIMETHYLSILYL-THIOANISOLE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-TRIMETHYLSILYL-THIOANISOLE(22515-25-9)
• EPA Substance Registry System: 4-TRIMETHYLSILYL-THIOANISOLE(22515-25-9)

Safety Data

• Hazardous Substances Data: 22515-25-9(Hazardous Substances Data)

Upstream product

• 75-77-4 chloro-trimethyl-silane 
• 17882-12-1 4-trimethylsilylbenzenethiol 
• 74-88-4 methyl iodide 
• 1450-14-2 1,1,1,2,2,2-hexamethyldisilane 
• 123-09-1 4-chlorophenyl methyl sulfide 
• 104-95-0 (4-bromophenyl)thioanisole 

Downstream Products

• 1186026-67-4 1-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-4-(trimethylsilyl)benzene 
• 1295631-11-6 C₁₀H₁₅FSSi 
• 54560-64-4 Methyl-4-trimethylsilylphenylsulfoxid 
• 1295631-13-8 C₁₀H₁₅FOSSi 
• 1295631-14-9 C₂₀H₃₀S₂Si₂ 
• 18546-89-9 bis-[(4-trimethylsilyl)phenyl]disulfide 
• 100-68-5 methyl-phenyl-thioether 

Relevant articles and documents

Palladium-Catalyzed ipso-Borylation of Aryl Sulfides with Diborons

A catalytic Miyaura-type ipso-borylation of aryl sulfides with diboron reagents has been achieved, providing arylboronate esters of synthetic use. The key conditions to transform inherently reluctant C-S bonds into C-B bonds include a palladium-NHC (N-heterocyclic carbene) precatalyst, bis(pinacolato)diboron, and lithium hexamethyldisilazide. This protocol is applicable to a reasonable range of aryl alkyl sulfides. Twofold borylation was observed in the reaction of diphenyl sulfide.

Palladium-catalyzed silylation of aryl chlorides with hexamethyldisilane

A method for the palladium-catalyzed silylation of aryl chlorides has been developed. The method affords desired product in good yield, is tolerant of a variety of functional groups, and provides access to a wide variety of aryltrimethylsilanes from commercially available aryl chlorides. Additionally, a one-pot procedure that converts aryl chlorides into aryl iodides has been developed.

Arylcalcium hydrides as precursors to alkoxides and aryloxides of calcium

Calcium atoms react with +I-substituted benzene derivatives under cocondensation conditions to yield arylcalcium hydrides. With toluene, tert-butylbenzene, and trimethyl(phenyl)silane the reaction showed no selectivity for C-H activation, resulting in the formation of each of the three possible isomers, while with m-xylene the reaction resulted in selective activation of the bond meta to the CH3 groups. Treatment of (tert-butylphenyl)calcium hydride with di- and trisubstituted phenols such as 2,6-di-tert-butylphenol, 2,6-di-tert-butyl-4-methylphenol, and 2,4,6-tri-tert-butylphenol resulted in the formation of calcium aryloxides in yields > 95%. [Ca(2,4,6-tBu3C6H2O)2 (THF)3] crystallises from a THF solution as a distorted trigonal bipyramid, with two THF ligands in the trans-axial positions and the third THF ligand and both aryloxide groups in equatorial positions. The Ca-OAryl bond length was found to average at 2.181(3). A. The Ca-O-CAryl angles are almost linear, with Cal-O1-C1 and Ca1-O2-C19 being 173.9(3)° and 178.8(3)°, respectively, while the O1-Cal-O2 angle was determined as 157.04(12)°. A reaction between (tert-butylphenyl)calcium hydride and triphenylmethanol resulted in the formation of the corresponding monomeric calcium bis(alkoxide) Ca(OCPh3)2(THF)4 in 95% yield. The structure was determined as a distorted octahedron with the alkoxide ligands in a cis-equatorial arrangement. The Ca-O bond length was determined at 2.1609(17) A. The Ca-O-CAryl angle of 177.46(16)° is almost linear, while the O1-Cal-O1A angle was determined at 110.12(19)°. ( Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003).