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2,2,2-Trichloroethoxycarbonyl chloride

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2,2,2-Trichloroethoxycarbonyl chloride
Skeletal formula of 2,2,2-Trichlorethoxycarbonyl chloride
Skeletal formula of 2,2,2-Trichlorethoxycarbonyl chloride
Ball-and-stick model of the 2,2,2-Trichlorethoxycarbonyl chloride molecule
Ball-and-stick model of the 2,2,2-Trichlorethoxycarbonyl chloride molecule
Names
Preferred IUPAC name 2,2,2-Trichloroethyl carbonochloridate
Other names 2,2,2-Trichlorethoxycarbonyl chloride
Trichloroethyl chloroformate
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.037.587 Edit this at Wikidata
EC Number
  • 241-363-7
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C3H2Cl4O2/c4-2(8)9-1-3(5,6)7/h1H2Key: LJCZNYWLQZZIOS-UHFFFAOYSA-N
  • InChI=1/C3H2Cl4O2/c4-2(8)9-1-3(5,6)7/h1H2Key: LJCZNYWLQZZIOS-UHFFFAOYAA
SMILES
  • O=C(OCC(Cl)(Cl)Cl)Cl
  • ClC(Cl)(Cl)COC(Cl)=O
Properties
Chemical formula C3H2Cl4O2
Molar mass 211.85 g·mol
Density 1.539 g/cm
Melting point 0 °C (32 °F; 273 K)
Boiling point 171 to 172 °C (340 to 342 °F; 444 to 445 K)
Hazards
GHS labelling:
Pictograms GHS05: CorrosiveGHS06: ToxicGHS07: Exclamation mark
Signal word Danger
Hazard statements H302, H314, H330, H331
Precautionary statements P260, P261, P264, P270, P271, P280, P284, P301+P312, P301+P330+P331, P303+P361+P353, P304+P340, P305+P351+P338, P310, P311, P320, P321, P330, P363, P403+P233, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). ☒N verify (what is  ?) Infobox references
Chemical compound

Trichloroethyl chloroformate is used in organic synthesis for the introduction of the trichloroethyl chloroformate (Troc) protecting group for amines, thiols and alcohols. It readily cleaves vs other carbamates and can be used in an overall protecting group strategy.

The troc group is traditionally removed via Zn insertion in the presence of acetic acid, resulting in elimination and decarboxylation.

Amine protection – 2,2,2-Trichloroethoxycarbonyl (Troc)

Troc protecting group on an amine

2,2,2-Trichloroethoxycarbonyl (Troc) group is largely used as a protecting group for amines in organic synthesis.

Most common amine protection methods


References

  1. 2,2,2-Trichloroethyl chloroformate Archived 2012-09-09 at archive.today at Sigma-Aldrich
  2. Marullo, N. P.; Wagener, E. H. (1969-01-01). "Structural organic chemistry by nmr. III. Isomerization of compounds containing the carbon-nitrogen double bond". Tetrahedron Letters. 10 (30): 2555–2558. doi:10.1016/S0040-4039(01)88566-X.
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