Trimethylsilyl chloride: Difference between revisions

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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.
{{Short description|Chemical compound}}
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| ImageFile = tmscl_stick2.png
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| ImageAlt = Stick model of trimethylsilyl chloride
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== Properties ==
'''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 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 ===
==Structure and properties==
* '''Molecular Weight''': 108.64 g/mol
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.
* '''Boiling Point''': 57-58°C at 760 mmHg
* '''Density''': 0.856 g/mL at 25°C


=== Chemical Properties ===
==Synthesis==
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.
Trimethylsilyl chloride is typically produced by the reaction of silicon tetrachloride with methylmagnesium chloride or methyl lithium:


== Applications ==
: SiCl<sub>4</sub> + 3 CH<sub>3</sub>MgCl _ (CH<sub>3</sub>)<sub>3</sub>SiCl + 3 MgCl<sub>2</sub>
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 ===
This reaction is carried out in an inert atmosphere to prevent the hydrolysis of the product.
* '''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.


=== Industrial Applications ===
==Applications==
Beyond organic synthesis, trimethylsilyl chloride finds applications in the production of silicone polymers and as an intermediate in the manufacture of other organosilicon compounds.
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.


== Safety and Handling ==
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.
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 ==
==Safety==
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.
 
==Related pages==
* [[Organosilicon chemistry]]
* [[Organosilicon chemistry]]
* [[Protecting group]]
* [[Silyl ether]]
* [[Silylation]]
* [[Silicon tetrachloride]]
* [[Silicone polymers]]


== References ==
==References==
<references/>
{{Reflist}}


[[Category:Organosilicon compounds]]
[[Category:Organosilicon compounds]]
[[Category:Chlorides]]
[[Category:Reagents for organic chemistry]]
[[Category:Reagents for organic chemistry]]
[[Category:Protecting groups]]
{{Chem-stub}}

Revision as of 15:46, 9 February 2025

Chemical compound


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Trimethylsilyl chloride (abbreviated TMSCl) is an organosilicon compound with the formula (CH3)3SiCl. It is a colorless liquid that is widely used in organic synthesis.

Structure and properties

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

SiCl4 + 3 CH3MgCl _ (CH3)3SiCl + 3 MgCl2

This reaction is carried out in an inert atmosphere to prevent the hydrolysis of the product.

Applications

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.

Safety

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.

Related pages

References

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