Trichloroacetonitrile: Difference between revisions

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'''Trichloroacetonitrile''' is a [[chemical compound]] with the formula CCl3CN. It is a colorless liquid that is used as a [[reagent]] in [[organic chemistry]].  
{{Short description|Chemical compound}}
{{Chembox
| verifiedfields = changed
| verifiedrevid = 477239123
| Name = Trichloroacetonitrile
| ImageFile = Trichloroacetonitrile_Structure_V.1.svg
| ImageSize = 150px
| IUPACName = Trichloroacetonitrile
| OtherNames = Trichloroacetonitrile
}}


==Chemical Properties==
'''Trichloroacetonitrile''' is a [[nitrile]] with the chemical formula CCl_CN. It is a colorless liquid that is used as an intermediate in the synthesis of various chemical compounds.
Trichloroacetonitrile is a [[nitrile]] compound. Nitriles are organic compounds that contain a -C≡N functional group. They are often used as solvents or as starting materials for the synthesis of other compounds. Trichloroacetonitrile, specifically, is a trichloro compound, meaning it contains three chlorine atoms.  


==Synthesis==
==Synthesis==
Trichloroacetonitrile can be synthesized from [[trichloroacetic acid]] and [[ammonium chloride]]. The reaction is typically carried out in a [[solvent]] such as [[acetonitrile]].
Trichloroacetonitrile can be synthesized through several methods. One common method involves the reaction of [[trichloroacetamide]] with [[phosphorus pentoxide]]:


==Uses==
[[File:TCAN_via_Trichloracetamid.svg|thumb|center|500px|Synthesis of trichloroacetonitrile from trichloroacetamide]]
In organic chemistry, trichloroacetonitrile is used as a reagent for the [[conversion]] of carboxylic acids to acid chlorides. It is also used in the synthesis of [[peptides]] and other organic compounds.
 
Another method involves the chlorination of [[acetonitrile]]:
 
[[File:TCAN_via_Acetonitril.svg|thumb|center|500px|Synthesis of trichloroacetonitrile from acetonitrile]]
 
==Applications==
Trichloroacetonitrile is used as a reagent in organic synthesis. It is particularly useful in the preparation of [[imidates]] and [[glycosyl donors]].
 
===Imidate Formation===
Trichloroacetonitrile reacts with alcohols to form trichloroacetimidates, which are useful intermediates in organic synthesis:
 
[[File:Trichloracetimidat-Bildung.svg|thumb|center|500px|Formation of trichloroacetimidate]]
 
===Glycosylation Reactions===
Trichloroacetonitrile is used in the synthesis of glycosyl trichloroacetimidates, which are important in the formation of glycosidic bonds:
 
[[File:Alpha-Glycosyltrichloracetimidat.svg|thumb|center|500px|Synthesis of glycosyl trichloroacetimidate]]


==Safety==
==Safety==
Trichloroacetonitrile is a hazardous substance. It is harmful if swallowed, inhaled, or comes into contact with the skin. It can cause burns and eye damage. Proper [[safety measures]] should be taken when handling this compound.
Trichloroacetonitrile is a hazardous chemical and should be handled with care. It is toxic if inhaled or ingested and can cause skin and eye irritation.


==See Also==
==Related pages==
* [[Trichloroacetic acid]]
* [[Ammonium chloride]]
* [[Organic chemistry]]
* [[Nitrile]]
* [[Nitrile]]
* [[Chlorination]]
* [[Organic synthesis]]
==References==
{{Reflist}}
==Gallery==
<gallery>
File:Trichloroacetonitrile_Structure_V.1.svg|Structure of trichloroacetonitrile
File:TCAN_via_Trichloracetamid.svg|Synthesis from trichloroacetamide
File:TCAN_via_Acetonitril.svg|Synthesis from acetonitrile
File:Trichloroacetonitrile_dimensions.svg|Molecular dimensions
File:Allylchloride_via_Allylalkohole.svg|Related synthesis
File:2-Chlorpyridin_via_TCAN.svg|Synthesis of 2-chloropyridine
File:Hydroxyketone_via_TCAN.svg|Synthesis of hydroxyketone
File:Trichloracetimidat-Bildung.svg|Formation of trichloroacetimidate
File:Alpha-Glycosyltrichloracetimidat.svg|Glycosyl trichloroacetimidate
File:Octaacetyl-Trehalose.svg|Octaacetyl trehalose
File:Thiogalactose-Synthese.svg|Thiogalactose synthesis
</gallery>


[[Category:Chemical compounds]]
[[Category:Organic chemistry]]
[[Category:Nitriles]]
[[Category:Nitriles]]
[[Category:Reagents for organic chemistry]]
[[Category:Organochlorides]]
 
{{Chem-stub}}
{{medicine-stub}}

Revision as of 00:37, 10 February 2025

Chemical compound


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References

Trichloroacetonitrile is a nitrile with the chemical formula CCl_CN. It is a colorless liquid that is used as an intermediate in the synthesis of various chemical compounds.

Synthesis

Trichloroacetonitrile can be synthesized through several methods. One common method involves the reaction of trichloroacetamide with phosphorus pentoxide:

Synthesis of trichloroacetonitrile from trichloroacetamide

Another method involves the chlorination of acetonitrile:

Synthesis of trichloroacetonitrile from acetonitrile

Applications

Trichloroacetonitrile is used as a reagent in organic synthesis. It is particularly useful in the preparation of imidates and glycosyl donors.

Imidate Formation

Trichloroacetonitrile reacts with alcohols to form trichloroacetimidates, which are useful intermediates in organic synthesis:

Formation of trichloroacetimidate

Glycosylation Reactions

Trichloroacetonitrile is used in the synthesis of glycosyl trichloroacetimidates, which are important in the formation of glycosidic bonds:

Synthesis of glycosyl trichloroacetimidate

Safety

Trichloroacetonitrile is a hazardous chemical and should be handled with care. It is toxic if inhaled or ingested and can cause skin and eye irritation.

Related pages

References

<references group="" responsive="1"></references>


Gallery

  • Structure of trichloroacetonitrile
    Structure of trichloroacetonitrile
  • Synthesis from trichloroacetamide
    Synthesis from trichloroacetamide
  • Synthesis from acetonitrile
    Synthesis from acetonitrile
  • Molecular dimensions
    Molecular dimensions
  • Related synthesis
    Related synthesis
  • Synthesis of 2-chloropyridine
    Synthesis of 2-chloropyridine
  • Synthesis of hydroxyketone
    Synthesis of hydroxyketone
  • Formation of trichloroacetimidate
    Formation of trichloroacetimidate
  • Glycosyl trichloroacetimidate
    Glycosyl trichloroacetimidate
  • Octaacetyl trehalose
    Octaacetyl trehalose
  • Thiogalactose synthesis
    Thiogalactose synthesis
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