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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