Trimethylsilyl chloride: Difference between revisions

Latest revision as of 11:26, 15 February 2025

Trimethylsilyl Chloride[edit]

Trimethylsilyl chloride (TMSCl) is an organosilicon compound with the formula (CH_)_SiCl. It is a colorless liquid that is widely used in organic synthesis and as a reagent in the protection of functional groups.

Structure and Properties[edit]

Trimethylsilyl chloride is a silicon compound where the silicon atom is bonded to three methyl groups and one chlorine atom. The compound is volatile and has a boiling point of approximately 57 °C. It is soluble in organic solvents such as benzene, toluene, and diethyl ether.

Synthesis[edit]

TMSCl is typically produced by the reaction of silicon tetrachloride with methyl lithium or methyl magnesium chloride:

${SiCl}_{4} + 3 {CH}_{3} MgCl \to {(CH}_{3})_{3} SiCl + 3 {MgCl}_{2}$

This reaction involves the substitution of three chlorine atoms in silicon tetrachloride with methyl groups.

Applications[edit]

Protection of Functional Groups[edit]

One of the primary uses of trimethylsilyl chloride is in the protection of hydroxyl groups in organic synthesis. It reacts with alcohols to form trimethylsilyl ethers, which are stable and can be deprotected under mild conditions:

$ROH + {(CH}_{3})_{3} SiCl \to {ROSi(CH}_{3})_{3} + HCl$

Silylation Reagent[edit]

TMSCl is also used as a silylation reagent in the preparation of silyl enol ethers and other silylated compounds. These derivatives are useful intermediates in various chemical transformations.

Other Uses[edit]

In addition to its role in organic synthesis, trimethylsilyl chloride is used in the production of silicones and as a precursor to other organosilicon compounds.

Safety and Handling[edit]

Trimethylsilyl chloride is a corrosive substance and should be handled with care. It reacts with water to produce hydrochloric acid, which is corrosive to skin and eyes. Proper personal protective equipment (PPE) such as gloves and goggles should be used when handling this chemical.

Related Pages[edit]

@@ Line 1: / Line 1: @@
-{{Short description|Chemical compound}}
+{{DISPLAYTITLE:Trimethylsilyl chloride}}
-{{Chembox
-| ImageFile = tmscl_stick2.png
-| ImageSize = 250px
-| ImageAlt = Stick model of trimethylsilyl chloride
-}}
-'''Trimethylsilyl chloride''' (abbreviated '''TMSCl''') is an organosilicon compound with the formula (CH<sub>3</sub>)<sub>3</sub>SiCl. It is a colorless liquid that is widely used in organic synthesis.
+== Trimethylsilyl Chloride ==
-==Structure and properties==
+[[File:tmscl_stick2.png|thumb|right|200px|Stick model of trimethylsilyl chloride]]
-Trimethylsilyl chloride is a volatile, colorless liquid with a pungent odor. It is soluble in organic solvents such as benzene, toluene, and diethyl ether. The compound is sensitive to moisture, reacting with water to produce hydrochloric acid and hexamethyldisiloxane.
-==Synthesis==
+'''Trimethylsilyl chloride''' (TMSCl) is an organosilicon compound with the formula (CH_)_SiCl. It is a colorless liquid that is widely used in organic synthesis and as a reagent in the protection of functional groups.
-Trimethylsilyl chloride is typically produced by the reaction of silicon tetrachloride with methylmagnesium chloride or methyl lithium:
-: SiCl<sub>4</sub> + 3 CH<sub>3</sub>MgCl _ (CH<sub>3</sub>)<sub>3</sub>SiCl + 3 MgCl<sub>2</sub>
+== Structure and Properties ==
-This reaction is carried out in an inert atmosphere to prevent the hydrolysis of the product.
+Trimethylsilyl chloride is a [[silicon]] compound where the silicon atom is bonded to three [[methyl group|methyl groups]] and one [[chlorine]] atom. The compound is volatile and has a boiling point of approximately 57 °C. It is soluble in organic solvents such as [[benzene]], [[toluene]], and [[diethyl ether]].
-==Applications==
+== Synthesis ==
-Trimethylsilyl chloride is primarily used as a silylating agent in organic synthesis. It is used to protect hydroxyl groups by converting them into trimethylsilyl ethers, which are more stable under certain conditions. This protection is particularly useful in multi-step synthesis processes where the hydroxyl group needs to be preserved.
-TMSCl is also used in the preparation of other organosilicon compounds, such as trimethylsilyl azide and trimethylsilyl cyanide, which are useful intermediates in organic synthesis.
+TMSCl is typically produced by the reaction of [[silicon tetrachloride]] with [[methyl lithium]] or [[methyl magnesium chloride]]:
-==Safety==
+<math>\text{SiCl}_4 + 3 \text{CH}_3\text{MgCl} \rightarrow \text{(CH}_3\text{)}_3\text{SiCl} + 3 \text{MgCl}_2</math>
-Trimethylsilyl chloride is corrosive and can cause burns upon contact with skin or eyes. It should be handled in a well-ventilated area, and appropriate personal protective equipment should be worn. Due to its reactivity with water, it should be stored in a dry environment.
+This reaction involves the substitution of three chlorine atoms in silicon tetrachloride with methyl groups.
+== Applications ==
+=== Protection of Functional Groups ===
+One of the primary uses of trimethylsilyl chloride is in the protection of [[hydroxyl group|hydroxyl groups]] in organic synthesis. It reacts with alcohols to form trimethylsilyl ethers, which are stable and can be deprotected under mild conditions:
+<math>\text{ROH} + \text{(CH}_3\text{)}_3\text{SiCl} \rightarrow \text{ROSi(CH}_3\text{)}_3 + \text{HCl}</math>
+=== Silylation Reagent ===
+TMSCl is also used as a silylation reagent in the preparation of [[silyl enol ether|silyl enol ethers]] and other silylated compounds. These derivatives are useful intermediates in various chemical transformations.
+=== Other Uses ===
+In addition to its role in organic synthesis, trimethylsilyl chloride is used in the production of [[silicone]]s and as a precursor to other organosilicon compounds.
+== Safety and Handling ==
+Trimethylsilyl chloride is a corrosive substance and should be handled with care. It reacts with water to produce [[hydrochloric acid]], which is corrosive to skin and eyes. Proper [[personal protective equipment]] (PPE) such as gloves and goggles should be used when handling this chemical.
+== Related Pages ==
-==Related pages==
 * [[Organosilicon chemistry]]
+* [[Silicon tetrachloride]]
 * [[Silyl ether]]
-* [[Silicon tetrachloride]]
+* [[Silicone]]
-==References==
-{{Reflist}}
 [[Category:Organosilicon compounds]]
 [[Category:Reagents for organic chemistry]]