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2,2,2-Trichloroethoxycarbonyl chloride
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Troc the car Volkswagen T-Roc
changed changed 477198803 2,2,2-Trichloroethyl chloroformate https://archive.today/20120909093657/http://www.sigmaaldrich.com/catalog/search/ProductDetail/FLUKA/23258 2012-09-09 at Sigma-Aldrich 2,2,2-Trichlorethoxycarbonyl chloride.svg Skeletal formula of 2,2,2-Trichlorethoxycarbonyl chloride 2,2,2-Trichlorethoxycarbonyl chloride-3D.png Ball-and-stick model of the 2,2,2-Trichlorethoxycarbonyl chloride molecule 2,2,2-Trichloroethyl carbonochloridate 2,2,2-Trichlorethoxycarbonyl chlorideTrichloroethyl chloroformate correct CAS 17341-93-4 correct chemspider 78534 241-363-7 87063 99UY6LZN4R 1/C3H2Cl4O2/c4-2(8)9-1-3(5,6)7/h1H2 LJCZNYWLQZZIOS-UHFFFAOYAA ClC(Cl)(Cl)COC(Cl)=O correct chemspider 1S/C3H2Cl4O2/c4-2(8)9-1-3(5,6)7/h1H2 correct chemspider LJCZNYWLQZZIOS-UHFFFAOYSA-N O=C(OCC(Cl)(Cl)Cl)Cl
3 2 4 2 1.539 g/cm3 0 171 to 172 05 06 07 Danger 302 314 330 331 260 261 264 270 271 280 284 301+312 301+330+331 303+361+353 304+340 305+351+338 310 311 320 321 330 363 403+233 405 501
Trichloroethyl chloroformate is used in organic synthesis for the introduction of the trichloroethoxycarbonyl (Troc) protecting group for amines, thiols and alcohols. It readily cleaves in the presence of other carbamates.
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)
thumb|left|Troc protecting group on an amine
The 2,2,2-Trichloroethoxycarbonyl (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 temperatureMarullo 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 10.1016/S0040-4039(01)88566-X
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Electrolysis
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Deprotection using zinc metal
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References
Category:Chloroformates
Category:Protecting groups
Category:Reagents for organic chemistry