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]

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-'''Trimethylsilyl chloride''', also known by its systematic name '''chlorotrimethylsilane''' (CTMS), is a chemical compound with the formula (CH₃)₃SiCl. This organosilicon compound is a colorless, volatile liquid that is used in various chemical synthesis and industrial applications, primarily as a silylating agent to introduce trimethylsilyl ([[TMS]]) protective groups.
+{{DISPLAYTITLE:Trimethylsilyl chloride}}
-== Properties ==
+== Trimethylsilyl Chloride ==
-Trimethylsilyl chloride is characterized by its ability to react with a wide range of nucleophiles, including alcohols, amines, and carboxylic acids, to form trimethylsilyl ethers, amines, and esters, respectively. These reactions typically require the presence of a base, such as triethylamine, to neutralize the hydrochloric acid by-product.
-=== Physical Properties ===
+[[File:tmscl_stick2.png|thumb|right|200px|Stick model of trimethylsilyl chloride]]
-* '''Molecular Weight''': 108.64 g/mol
-* '''Boiling Point''': 57-58°C at 760 mmHg
-* '''Density''': 0.856 g/mL at 25°C
-=== Chemical Properties ===
+'''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 highly reactive towards nucleophiles due to the presence of the silicon-chlorine bond, which is polarized, making the silicon atom electrophilic. This reactivity is exploited in organic synthesis, particularly in the protection of hydroxyl groups.
+== Structure and Properties ==
+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]].
+== Synthesis ==
+TMSCl is typically produced by the reaction of [[silicon tetrachloride]] with [[methyl lithium]] or [[methyl magnesium chloride]]:
+<math>\text{SiCl}_4 + 3 \text{CH}_3\text{MgCl} \rightarrow \text{(CH}_3\text{)}_3\text{SiCl} + 3 \text{MgCl}_2</math>
+This reaction involves the substitution of three chlorine atoms in silicon tetrachloride with methyl groups.
 == Applications ==
-The primary use of trimethylsilyl chloride is in the field of organic synthesis, where it serves as a silylating agent to protect hydroxyl groups in alcohols and phenols, as well as carboxylic acids and amines. This protection strategy is crucial in multi-step synthetic routes where selective reactions are required.
-=== In Organic Synthesis ===
+=== Protection of Functional Groups ===
-* '''Protection of Alcohols and Phenols''': Alcohols and phenols can be converted to their trimethylsilyl ethers, which are resistant to a variety of reaction conditions. Upon completion of the synthetic sequence, the protecting group can be removed to regenerate the alcohol or phenol.
-* '''Protection of Carboxylic Acids and Amines''': Similar to alcohols, carboxylic acids and amines can be protected as trimethylsilyl esters and amines, respectively.
+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:
-=== Industrial Applications ===
+<math>\text{ROH} + \text{(CH}_3\text{)}_3\text{SiCl} \rightarrow \text{ROSi(CH}_3\text{)}_3 + \text{HCl}</math>
-Beyond organic synthesis, trimethylsilyl chloride finds applications in the production of silicone polymers and as an intermediate in the manufacture of other organosilicon compounds.
+=== 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 corrosive and should be handled with care. It reacts violently with water, releasing hydrochloric acid, and requires storage in a cool, dry place, away from moisture. Appropriate personal protective equipment (PPE) should be worn when handling this chemical.
-== See Also ==
+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 ==
 * [[Organosilicon chemistry]]
-* [[Protecting group]]
+* [[Silicon tetrachloride]]
-* [[Silylation]]
+* [[Silyl ether]]
-* [[Silicone polymers]]
+* [[Silicone]]
-== References ==
-<references/>
 [[Category:Organosilicon compounds]]
-[[Category:Chlorides]]
 [[Category:Reagents for organic chemistry]]
-[[Category:Protecting groups]]
-{{Chem-stub}}