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;
	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
Main hazards	toxicity
GHS pictograms
GHS Signal word	Danger
GHS hazard statements	H300, H310, H330, H373, H400, H410
GHS precautionary statements	P260, P262, P264, P270, P271, P273, P280, P284, P301+310, P302+350, P304+340, P310, P314, P320, P321, P322, P330, P361, P363, P391, P403+233, 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 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 0471936235.CS1 maint: uses authors parameter (link)
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.CS1 maint: uses authors parameter (link)
Shipman, Michael (2001). "Phenyl(tribromomethyl)mercury". Encyclopedia of Reagents for Organic Synthesis. Encyclopedia of Reagents for Organic Synthesis. doi:10.1002/047084289X.rp140. ISBN 0471936235.
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.CS1 maint: uses authors parameter (link)

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[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 0471936235.CS1 maint: uses authors parameter (link)

[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.CS1 maint: uses authors parameter (link)

[4] Shipman, Michael (2001). "Phenyl(tribromomethyl)mercury". Encyclopedia of Reagents for Organic Synthesis. Encyclopedia of Reagents for Organic Synthesis. doi:10.1002/047084289X.rp140. ISBN 0471936235.

[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.CS1 maint: uses authors parameter (link)