Trichloroacetonitrile: Difference between revisions

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{{Short description|Chemical compound}}
{{Short description|Chemical compound}}
{{Chembox
{{Chembox
| verifiedfields = changed
| ImageFile = Trichloroacetonitrile.png
| verifiedrevid = 477239123
| ImageSize = 200px
| Name = Trichloroacetonitrile
| ImageAlt = Structural formula of trichloroacetonitrile
| ImageFile = Trichloroacetonitrile_Structure_V.1.svg
| ImageSize = 150px
| IUPACName = Trichloroacetonitrile
| IUPACName = Trichloroacetonitrile
| OtherNames = Trichloroacetonitrile
| OtherNames = Trichloroacetonitrile
| Section1 = {{Chembox Identifiers
  | CASNo = 545-06-2
  | PubChem = 11230
  | ChemSpiderID = 10757
  | UNII = 3X1W1O0V7A
  | SMILES = C(#N)C(Cl)(Cl)Cl
  | InChI = 1S/C2Cl3N/c3-2(4,5)1-6
  | InChIKey = ZFQYQXKZKJXQNO-UHFFFAOYSA-N
}}
}}
| Section2 = {{Chembox Properties
  | C = 2
  | Cl = 3
  | N = 1
  | Appearance = Colorless liquid
  | Density = 1.44 g/cm_
  | MeltingPt = -45 °C
  | BoilingPt = 82 °C
}}
}}
'''Trichloroacetonitrile''' is a [[chemical compound]] with the formula CCl_CN. It is a colorless liquid that is used as an intermediate in the synthesis of various organic compounds.


'''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.
==Structure and Properties==
Trichloroacetonitrile consists of a nitrile group (_C_N) attached to a trichloromethyl group (_CCl_). The presence of the three chlorine atoms makes the compound highly electronegative and reactive. The compound is a volatile liquid with a relatively low boiling point of 82 °C and a melting point of -45 °C. It has a density of 1.44 g/cm_, making it denser than water.


==Synthesis==
==Synthesis==
Trichloroacetonitrile can be synthesized through several methods. One common method involves the reaction of [[trichloroacetamide]] with [[phosphorus pentoxide]]:
Trichloroacetonitrile can be synthesized through the chlorination of [[acetonitrile]] in the presence of a suitable catalyst. The reaction involves the substitution of hydrogen atoms in acetonitrile with chlorine atoms, resulting in the formation of trichloroacetonitrile.
 
[[File:TCAN_via_Trichloracetamid.svg|thumb|center|500px|Synthesis of trichloroacetonitrile from trichloroacetamide]]
 
Another method involves the chlorination of [[acetonitrile]]:
 
[[File:TCAN_via_Acetonitril.svg|thumb|center|500px|Synthesis of trichloroacetonitrile from acetonitrile]]


==Applications==
==Applications==
Trichloroacetonitrile is used as a reagent in organic synthesis. It is particularly useful in the preparation of [[imidates]] and [[glycosyl donors]].
Trichloroacetonitrile is primarily used as an intermediate in the production of [[pharmaceuticals]], [[agrochemicals]], and other organic compounds. Its reactivity makes it a valuable building block in organic synthesis, particularly in the formation of more complex molecules.


===Imidate Formation===
==Safety and Handling==
Trichloroacetonitrile reacts with alcohols to form trichloroacetimidates, which are useful intermediates in organic synthesis:
Trichloroacetonitrile is a hazardous chemical and should be handled with care. It is toxic if inhaled or ingested and can cause irritation to the skin and eyes. Proper [[personal protective equipment]] (PPE) such as gloves and goggles should be worn when handling this compound. It should be stored in a cool, well-ventilated area away from sources of ignition.


[[File:Trichloracetimidat-Bildung.svg|thumb|center|500px|Formation of trichloroacetimidate]]
==Environmental Impact==
 
Due to its volatility and reactivity, trichloroacetonitrile can pose environmental risks if not managed properly. It should be disposed of in accordance with local regulations to prevent contamination of water sources and soil.
===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==
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==
==Related pages==
* [[Acetonitrile]]
* [[Chlorination]]
* [[Nitrile]]
* [[Nitrile]]
* [[Chlorination]]
* [[Organic synthesis]]
* [[Organic synthesis]]


==References==
[[Category:Chemical compounds]]
{{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:Nitriles]]
[[Category:Nitriles]]
[[Category:Organochlorides]]
[[Category:Organochlorides]]

Latest revision as of 17:43, 18 February 2025

Chemical compound


Chemical Compound
Identifiers
CAS Number
PubChem CID
ChemSpider ID
UNII
ChEBI
ChEMBL
Properties
Chemical Formula
Molar Mass
Appearance
Density
Melting Point
Boiling Point
Hazards
GHS Pictograms [[File:|50px]]
GHS Signal Word
GHS Hazard Statements
NFPA 704 [[File:|50px]]
References

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

Structure and Properties[edit]

Trichloroacetonitrile consists of a nitrile group (_C_N) attached to a trichloromethyl group (_CCl_). The presence of the three chlorine atoms makes the compound highly electronegative and reactive. The compound is a volatile liquid with a relatively low boiling point of 82 °C and a melting point of -45 °C. It has a density of 1.44 g/cm_, making it denser than water.

Synthesis[edit]

Trichloroacetonitrile can be synthesized through the chlorination of acetonitrile in the presence of a suitable catalyst. The reaction involves the substitution of hydrogen atoms in acetonitrile with chlorine atoms, resulting in the formation of trichloroacetonitrile.

Applications[edit]

Trichloroacetonitrile is primarily used as an intermediate in the production of pharmaceuticals, agrochemicals, and other organic compounds. Its reactivity makes it a valuable building block in organic synthesis, particularly in the formation of more complex molecules.

Safety and Handling[edit]

Trichloroacetonitrile is a hazardous chemical and should be handled with care. It is toxic if inhaled or ingested and can cause irritation to the skin and eyes. Proper personal protective equipment (PPE) such as gloves and goggles should be worn when handling this compound. It should be stored in a cool, well-ventilated area away from sources of ignition.

Environmental Impact[edit]

Due to its volatility and reactivity, trichloroacetonitrile can pose environmental risks if not managed properly. It should be disposed of in accordance with local regulations to prevent contamination of water sources and soil.

Related pages[edit]