Bis(trimethylsilyl)sulfide
Encyclopedia
Bis sulfide is the chemical compound
with the formula ((CH3)3Si)2S. Often abbreviated (tms
)2S, this colourless, vile-smelling liquid is a useful aprotic source of “S2−“ in chemical synthesis.
with anhydrous
sodium sulfide
:
((CH3)3Si)2S must be protected from air because it hydrolyzes
readily:3Si)2S + H2O → ((CH3)3Si)2O
+ H2S
(IV) for oxygen and halides. An idealized reaction is:3Si)2S + MO → ((CH3)3Si)2O + MS
In a similar way, it has been used in the conversion of aldehyde
s and ketone
s to the corresponding thiones.
Chemical compound
A chemical compound is a pure chemical substance consisting of two or more different chemical elements that can be separated into simpler substances by chemical reactions. Chemical compounds have a unique and defined chemical structure; they consist of a fixed ratio of atoms that are held together...
with the formula ((CH3)3Si)2S. Often abbreviated (tms
Trimethylsilyl
A trimethylsilyl group is a functional group in organic chemistry. This group consists of three methyl groups bonded to a silicon atom [−Si3], which is in turn bonded to the rest of a molecule...
)2S, this colourless, vile-smelling liquid is a useful aprotic source of “S2−“ in chemical synthesis.
Synthesis
The reagent is prepared by treating trimethylsilyl chlorideTrimethylsilyl chloride
Trimethylsilyl chloride, also known as chlorotrimethylsilane is a silyl halide, with a variety of different uses in chemistry. It has the formula 3SiCl, and under standard conditions it is a colourless liquid, which is stable in the absence of water...
with anhydrous
Anhydrous
As a general term, a substance is said to be anhydrous if it contains no water. The way of achieving the anhydrous form differs from one substance to another...
sodium sulfide
Sodium sulfide
Sodium sulfide is the name used to refer to the chemical compound Na2S, but more commonly it refers to the hydrate Na2S·9H2O. Both are colorless water-soluble salts that give strongly alkaline solutions...
:
- 2 (CH3)3SiCl + Na2S → ((CH3)3Si)2S + 2 NaCl
((CH3)3Si)2S must be protected from air because it hydrolyzes
Hydrolysis
Hydrolysis is a chemical reaction during which molecules of water are split into hydrogen cations and hydroxide anions in the process of a chemical mechanism. It is the type of reaction that is used to break down certain polymers, especially those made by condensation polymerization...
readily:3Si)2S + H2O → ((CH3)3Si)2O
Hexamethyldisiloxane
Hexamethyldisiloxane is a organosilicon compound with the formula O[Si3]2. This volatile liquid is used as a solvent and as a reagent in organic synthesis. It is prepared by the hydrolysis of trimethylsilyl chloride...
+ H2S
Applications
(tms)2S is primarily used to convert oxides and chlorides into the corresponding sulfides. This transformation exploits the affinity of siliconSilicon
Silicon is a chemical element with the symbol Si and atomic number 14. A tetravalent metalloid, it is less reactive than its chemical analog carbon, the nonmetal directly above it in the periodic table, but more reactive than germanium, the metalloid directly below it in the table...
(IV) for oxygen and halides. An idealized reaction is:3Si)2S + MO → ((CH3)3Si)2O + MS
In a similar way, it has been used in the conversion of aldehyde
Aldehyde
An aldehyde is an organic compound containing a formyl group. This functional group, with the structure R-CHO, consists of a carbonyl center bonded to hydrogen and an R group....
s and ketone
Ketone
In organic chemistry, a ketone is an organic compound with the structure RCR', where R and R' can be a variety of atoms and groups of atoms. It features a carbonyl group bonded to two other carbon atoms. Many ketones are known and many are of great importance in industry and in biology...
s to the corresponding thiones.