2,2,2-Trichloroethoxycarbonyl chloride

2,2,2-Trichloroethoxycarbonyl chloride^[1]
Names
	Preferred IUPAC name 2,2,2-Trichloroethyl carbonochloridate
	Other names 2,2,2-Trichlorethoxycarbonyl chloride; Trichloroethyl chloroformate
Identifiers
CAS Number	17341-93-4 ;
3D model (JSmol)	Interactive image; Interactive image;
ChemSpider	78534 ;
ECHA InfoCard	100.037.587
EC Number	241-363-7;
PubChem CID	87063;
UNII	99UY6LZN4R;
CompTox Dashboard (EPA)	DTXSID3066188 ;
	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/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:
Pictograms
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 [77 °F], 100 kPa). verify (what is ?) 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)

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 temperature^[2]

Electrolysis

Deprotection using zinc metal

References

^ 2,2,2-Trichloroethyl chloroformate Archived 2012-09-09 at archive.today at Sigma-Aldrich
^ 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.

[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.

[1]

[2]

Names


Preferred IUPAC name 2,2,2-Trichloroethyl carbonochloridate
Other names 2,2,2-Trichlorethoxycarbonyl chloride Trichloroethyl chloroformate
Identifiers
CAS Number	17341-93-4^Y
3D model (JSmol)	Interactive image Interactive image
ChemSpider	78534^Y
ECHA InfoCard	100.037.587
EC Number	241-363-7
PubChem CID	87063
UNII	99UY6LZN4R
CompTox Dashboard (EPA)	DTXSID3066188
InChI InChI=1S/C3H2Cl4O2/c4-2(8)9-1-3(5,6)7/h1H2^Y Key: LJCZNYWLQZZIOS-UHFFFAOYSA-N^Y 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/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:
Pictograms
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 [77 °F], 100 kPa). N verify (what is ^YN ?) Infobox references