Phenyl(trichloromethyl)mercury is an

organomercury compound Organomercury refers to the group of organometallic compounds that contain mercury. Typically the Hg–C bond is stable toward air and moisture but sensitive to light. Important organomercury compounds are the methylmercury(II) cation, CH3Hg+; et ...

with the formula C₆H₅HgCCl₃. It is a white solid that is soluble in

organic solvent A solvent (s) (from the Latin '' solvō'', "loosen, untie, solve") is a substance that dissolves a solute, resulting in a solution. A solvent is usually a liquid but can also be a solid, a gas, or a supercritical fluid. Water is a solvent for p ...

s. The compound is used as a source of

dichlorocarbene Dichlorocarbene is the reactive intermediate with chemical formula CCl2. Although this chemical species has not been isolated, it is a common intermediate in organic chemistry, being generated from chloroform. This bent diamagnetic molecule rapidly ...

, e.g. in

cyclopropanation In organic chemistry, cyclopropanation refers to any chemical process which generates cyclopropane () rings. It is an important process in modern chemistry as many useful compounds bear this motif; for example pyrethroids and a number of quinolon ...

reactions, illustrated with tetrachloroethylene as a substrate, the product being hexachlorocyclopropane: :C₆H₅HgCCl₃ → C₆H₅HgCl + CCl₂ :CCl₂ + Cl₂C=CCl₂ → C₃Cl₆ The compound is prepared by treating phenylmercuric chloride with sources of dichlorocarbene. These include the base/

haloform In chemistry, trihalomethanes (THMs) are chemical compounds in which three of the four hydrogen atoms of methane () are replaced by halogen atoms. Many trihalomethanes find uses in industry as solvents or refrigerants. THMs are also environmenta ...

reaction and thermolysis of

sodium trichloroacetate Sodium trichloroacetate is a chemical compound with a formula of CCl3CO2Na. It is used to increase sensitivity and precision during transcript mapping. It was previously used as an herbicide starting in the 1950s but regulators removed it from t ...

: :NaO₂CCCl₃ + C₆H₅HgCl → C₆H₅HgCCl₃ + NaCl + CO₂

Related compounds

Closely related compounds include phenyl(bromodichloromethyl)mercury (CAS

registry number A CAS Registry Number (also referred to as CAS RN or informally CAS Number) is a unique identification number assigned by the Chemical Abstracts Service (CAS), US to every chemical substance described in the open scientific literature. It inclu ...

3294-58-4) and phenyl(tribromomethyl)mercury (CAS registry number 3294-60-8). According to

X-ray crystallography X-ray crystallography is the experimental science determining the atomic and molecular structure of a crystal, in which the crystalline structure causes a beam of incident X-rays to diffract into many specific directions. By measuring the angles ...

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

References

{{Mercury compounds Organomercury compounds Phenyl compounds Trichloromethyl compounds