4712-51-0

Basic information

• Product Name: BIS(TRIMETHYLSILYLMETHYL) SULFIDE
• Synonyms: TRIMETHYLSILYLMETHYLSULPHIDE;THIOBIS(METHYLENE)BIS(TRIMETHYLSILANE);BIS(TRIMETHYLSILYLMETHYL) SULFIDE;BIS(TRIMETHYLSILYLMETHYL) SULPHIDE;Bis(trimethylsilylmethyl) sulfide >=98.0%;trimethyl(trimethylsilylmethylsulfanylmethyl)silane
• CAS NO: 4712-51-0
• Molecular Formula: C8H22SSi2
• Molecular Weight: 206.5
• Mol File: 4712-51-0.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 88 °C21 mm Hg(lit.)
• Flash Point: 65-66°C/5mm
• Appearance: /
• Density: 0.844 g/mL at 20 °C(lit.)
• Vapor Pressure: 0.392mmHg at 25°C
• Refractive Index: n20/D 1.455
• BRN: 1740046
• CAS DataBase Reference: BIS(TRIMETHYLSILYLMETHYL) SULFIDE(CAS DataBase Reference)
• NIST Chemistry Reference: BIS(TRIMETHYLSILYLMETHYL) SULFIDE(4712-51-0)
• EPA Substance Registry System: BIS(TRIMETHYLSILYLMETHYL) SULFIDE(4712-51-0)

Safety Data

• Statements: 36/37/38
• Safety Statements: 23-24/25
• RIDADR: UN 3334
• WGK Germany: 3
• F: 10-13
• TSCA: No
• Hazardous Substances Data: 4712-51-0(Hazardous Substances Data)

Usage

General Description

Bis(trimethylsilylmethyl) sulfide, also known as BTMS, is a chemical compound primarily used in organic synthesis. This particular organosilicon compound has a unique structure, containing a sulfur atom bonded to two silicon atoms, each of which is surrounded by three methyl groups. Therefore, it is a sulfur derivative of trimethylsilanes. BTMS is a versatile reagent known for its powerful nucleophilic property, utilized in several chemical reactions including those involving ketones and aldehydes. While it can prove quite useful in laboratory settings, it should be handled with care due to its reactive nature.

InChI:InChI=1/C8H22SSi2/c1-10(2,3)7-9-8-11(4,5)6/h7-8H2,1-6H3

Upstream product

• 2344-80-1 Chloromethyltrimethylsilane 
• 18165-76-9 trimethylsilanyl-methanethiol 
• 18243-41-9 (bromomethyl)trimethylsilane 

Downstream Products

• 100005-02-5 2-trimethylsilyltetrahydrothiophene-3,4-(N-phenyl)dicarboxyimide 

Relevant articles and documents

Photoelectron spectra and molecular properties CXXII. The low first ionization energies of the β-trimethylsilyl substituted sulfides (H3C)3SiH2CSCH2Si(CH3)3 and ((H3C)3Si)3CSCH3 and their rationalization

The rather low first vertical ionization energies of bis(trimethylsilylmethyl)sulfide, IE1 V = 8.04 eV, and tris(trimethylsilyl)methylmethyl sulfide, IE1 V = 7.66 eV, are compared with those of other alkyl, silylalkyl and silylsulfides and shown further to confirm the small influence of α-trimethylsilyl groups and of the very large donor effect of β-trimethylsilyl substituents in the ground state of radical cations.The overall 2.8 eV (!) lowering of the sulfur ? lone pair ionization and of the individual, mostly non-additive, substituent effects, are rationalized in terms of a qualitative approach based on the electron distribution in the ground state of the neutral molecules.

COMMERCIALLY VIABLE SYNTHESIS OF CANTHARIDIN AND BIOACTIVE CANTHARIDIN DERIVATIVES

The present disclosure provides methods for synthesizing cantharidin and cantharidin derivatives.

Thiocarbonyl Ylides. VI. New Generation of Thiocarbonyl Ylides from Organosilicon Compounds Containing Sulfur and Their 1,3-Cycloadditions

Thermolysis of bromo(trimethylsilyl)methyltrimethylsilylmethyl sulfide was found to give a thiocarbonyl ylide, the 1,3-cycloaddition of which proved a new method for the synthesis of tetrahydrothiophenes.The effect of the silyl group of the ylide on the regio- and stereoselectivity in these 1,3-dipolar cycloaddtions is discussed.Keywords---thiocarbonyl ylide; 1,3-cycloaddition; organosilicon compound; thermolysis; tetrahydrothiophene; regioselectivity