Phenyl(trichloromethyl)mercury

Phenyl(trichloromethyl)mercury
Identifiers
CAS Number	3294-57-3 ;
3D model (JSmol)	Interactive image;
ChemSpider	69255;
EC Number	221-960-9;
PubChem CID	76799;
UNII	JH955G783H ;
	InChI InChI=1S/C6H5.CCl3.Hg/c1-2-4-6-5-3-1;2-1(3)4;/h1-5H;; Key: MVIAEGXPYBMVPT-UHFFFAOYSA-N;
	SMILES C1=CC=C(C=C1)[Hg]C(Cl)(Cl)Cl;
Properties
Chemical formula	C7H5Cl3Hg
Molar mass	396.06 g·mol−1
Appearance	white solid
Melting point	117–118 °C (243–244 °F; 390–391 K)
Hazards
	Occupational safety and health (OHS/OSH):
Main hazards	toxicity
	GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H300, H310, H330, H373, H410
Precautionary statements	P260, P262, P264, P270, P271, P273, P280, P284, P301 P310, P302 P350, P304 P340, P310, P314, P320, P321, P322, P330, P361, P363, P391, P403 P233, P405, P501
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Phenyl(trichloromethyl)mercury is an organomercury compound with the formula C₆H₅HgCCl₃. It is a white solid that is soluble in organic solvents. The compound is used as a source of dichlorocarbene, e.g. in cyclopropanation reactions, illustrated with tetrachloroethylene as a substrate, the product being hexachlorocyclopropane:^[1]

C₆H₅HgCCl₃ → C₆H₅HgCl CCl₂

CCl₂ Cl₂C=CCl₂ → C₃Cl₆

The compound is prepared by treating phenylmercuric chloride [fi] with sources of dichlorocarbene. These include the base/haloform reaction and thermolysis of sodium trichloroacetate:^[2]^[3]

NaO₂CCCl₃ C₆H₅HgCl → C₆H₅HgCCl₃ NaCl CO₂

Related compounds

Closely related compounds include phenyl(bromodichloromethyl)mercury (CAS registry number 3294-58-4) and phenyl(tribromomethyl)mercury (CAS registry number 3294-60-8).^[4] According to X-ray crystallography, the former has nearly linear coordination geometry at mercury, with a C-Hg-C angle of 179° and Hg-C distances of 2.047 Å.^[5]

Also known is bis(trichloromethyl)mercury, Hg(CCl₃)₂.

References

^ José Barluenga; Miguel Tomás; José M. González (2001). "Phenyl(trichloromethyl)mercury". Encyclopedia of Reagents for Organic Synthesis. e-EROS Encyclopedia of Reagents for Organic Synthesis. doi:10.1002/047084289X.rp141. ISBN 0-471-93623-5.
^ Ted J. Logan (1966). "Phenyl(trichloromethyl)mercury". Organic Syntheses. 46: 969. doi:10.15227/orgsyn.046.0098.
^ Seyferth, D.; Lambert, R. L. (1969). "Halomethyl-metal compounds XX. An improved synthesis of phenyl(trihalomethyl)mercury compounds". Journal of Organometallic Chemistry. 16: 21–26. doi:10.1016/S0022-328X(00)81631-9.
^ Shipman, Michael (2001). "Phenyl(tribromomethyl)mercury". Encyclopedia of Reagents for Organic Synthesis. doi:10.1002/047084289X.rp140. ISBN 0-471-93623-5.
^ R. E. Bachman; B. R. Maughon; D. J. McCord; K. H. Whitmire; W. E. Billups (1995). "Bromodichloromethyl)phenylmercury". Acta Crystallogr. C. 51 (10): 2033–2035. doi:10.1107/S0108270195004501.

[1] José Barluenga; Miguel Tomás; José M. González (2001). "Phenyl(trichloromethyl)mercury". Encyclopedia of Reagents for Organic Synthesis. e-EROS Encyclopedia of Reagents for Organic Synthesis. doi:10.1002/047084289X.rp141. ISBN 0-471-93623-5.

[2] Ted J. Logan (1966). "Phenyl(trichloromethyl)mercury". Organic Syntheses. 46: 969. doi:10.15227/orgsyn.046.0098.

[3] Seyferth, D.; Lambert, R. L. (1969). "Halomethyl-metal compounds XX. An improved synthesis of phenyl(trihalomethyl)mercury compounds". Journal of Organometallic Chemistry. 16: 21–26. doi:10.1016/S0022-328X(00)81631-9.

[4] Shipman, Michael (2001). "Phenyl(tribromomethyl)mercury". Encyclopedia of Reagents for Organic Synthesis. doi:10.1002/047084289X.rp140. ISBN 0-471-93623-5.

[5] R. E. Bachman; B. R. Maughon; D. J. McCord; K. H. Whitmire; W. E. Billups (1995). "Bromodichloromethyl)phenylmercury". Acta Crystallogr. C. 51 (10): 2033–2035. doi:10.1107/S0108270195004501.

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