2,2,2-Trichlorethoxycarbonyl chloride

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2,2,2-Trichlorethoxycarbonyl chloride[1]
Skeletal formula of 2,2,2-Trichlorethoxycarbonyl chloride
Ball-and-stick model of the 2,2,2-Trichlorethoxycarbonyl chloride molecule
IUPAC name
2,2,2-Trichlorethoxycarbonyl chloride
Other names
Trichloroethyl chloroformate
3D model (JSmol)
ECHA InfoCard 100.037.587
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)
Toxic (T), Corrosive (C)
R-phrases (outdated) R23, R34
S-phrases (outdated) S26, S36/37/39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)[edit]

Troc protecting group.png

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

Most common amine protection methods[edit]

Most common amine deprotection method[edit]