2,2,2-Trichloroethoxycarbonyl chloride[1]
Skeletal formula of 2,2,2-Trichlorethoxycarbonyl chloride
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
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.037.587
EC Number
  • 241-363-7
UNII
  • InChI=1S/C3H2Cl4O2/c4-2(8)9-1-3(5,6)7/h1H2 checkY
    Key: LJCZNYWLQZZIOS-UHFFFAOYSA-N checkY
  • InChI=1/C3H2Cl4O2/c4-2(8)9-1-3(5,6)7/h1H2
    Key: LJCZNYWLQZZIOS-UHFFFAOYAA
  • O=C(OCC(Cl)(Cl)Cl)Cl
  • ClC(Cl)(Cl)COC(Cl)=O
Properties
C3H2Cl4O2
Molar mass 211.85 g·mol−1
Density 1.539 g/cm3
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:
GHS05: CorrosiveGHS06: ToxicGHS07: Exclamation mark
Danger
H302, H314, H330, H331
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 [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)
Infobox references

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

  • Deprotection using zinc metal


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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