2,2,2-Trichlorethoxycarbonyl chloride

2,2,2-Trichlorethoxycarbonyl chloride^[1]

Names
IUPAC name 2,2,2-Trichlorethoxycarbonyl chloride
Other names Trichloroethyl chloroformate
Identifiers
CAS Number	17341-93-4
3D model (Jmol)	Interactive image Interactive image
ChemSpider	78534
ECHA InfoCard	100.037.587
PubChem	10387
InChI InChI=1S/C3H2Cl4O2/c4-2(8)9-1-3(5,6)7/h1H2 Key: LJCZNYWLQZZIOS-UHFFFAOYSA-N InChI=1/C3H2Cl4O2/c4-2(8)9-1-3(5,6)7/h1H2 Key: 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^−1
Density	1.539 g/cm^3
Melting point	0 °C (32 °F; 273 K)
Boiling point	171 to 172 °C (340 to 342 °F; 444 to 445 K)
Hazards
EU classification (DSD)	Toxic (T), Corrosive (C)
R-phrases	R23, R34
S-phrases	S26, S36/37/39
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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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-Trichloroethyl (Troc)

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

Most common amine protection methods

• 2,2,2-Trichloroethyl chloroformate, pyridine or aqueous sodium hydroxide at ambient temperature^[2]
  

Most common amine deprotection method

• Electrolysis
  

References

1. 2,2,2-Trichloroethyl chloroformate 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.