Phenylmercury acetate

Phenylmercuric acetate is an organomercury compound with the chemical formula CH₃CO₂HgC₆H₅. It was used as a preservative, disinfectant, and antitranspirant.

Phenylmercury acetate

Skeletal formula of phenylmercury acetate
Ball and stick model of the phenylmercury acetate molecule
Names
Systematic IUPAC name acetyloxy(phenyl)mercury
Identifiers
CAS Number	62-38-4 Y
3D model (JSmol)	Interactive image Interactive image
Beilstein Reference	3662930
ChEBI	CHEBI:27684 Y
ChEMBL	ChEMBL1333953 Y
ChemSpider	10294750 Y
ECHA InfoCard	100.000.484
EC Number	200-532-5
Gmelin Reference	83357
KEGG	D05464 Y
MeSH	Phenylmercuric+acetate
PubChem CID	16682730
RTECS number	OV6475000
UNII	OSX88361UX Y
UN number	1674
CompTox Dashboard (EPA)	DTXSID7021150
InChI InChI=1S/C6H5.C2H4O2.Hg/c1-2-4-6-5-3-1;1-2(3)4;/h1-5H;1H3,(H,3,4);/q;;+1/p-1 Y Key: XEBWQGVWTUSTLN-UHFFFAOYSA-M Y InChI=1S/C6H5.C2H4O2.Hg/c1-2-4-6-5-3-1;1-2(3)4;/h1-5H;1H3,(H,3,4);/q;;+1/p-1 Key: XEBWQGVWTUSTLN-UHFFFAOYSA-M
SMILES CC(=O)O[Hg]C1=CC=CC=C1 CC(=O)O[Hg]c1ccccc1
Properties
Chemical formula	CH3CO2HgC6H5
Molar mass	336.742 g·mol−1
Appearance	colorless, lustrous crystals
Melting point	148 to 151 °C (298 to 304 °F; 421 to 424 K)
Hazards
GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H301, H314, H372, H410
Precautionary statements	P260, P264, P270, P273, P280, P301+P310, P301+P330+P331, P303+P361+P353, P304+P340, P305+P351+P338, P310, P314, P321, P330, P363, P391, P405, P501
Safety data sheet (SDS)	Oxford MSDS
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

Properties

Phenylmercuric acetate forms colorless, lustrous crystals, and is soluble in ethanol, benzene, acetic acid, and sparingly in water.^[1]

Applications

Phenylmercuric acetate has been used as a preservative in eyedrops and paint, disinfectant, former fungicide in agriculture, and a potential fungicide in leather processing.^[1][2][3] It kills crabgrass, the seedlings of which are especially vulnerable, but leaves most lawn grasses intact.^[4] It exhibits anti-fungal activity against a broad range of ocular pathogenic fungi, with the greatest activity against Fusarium sporotrichioides, and has been investigated as a potential treatment for keratomycosis.^[3]

Phenylmercuric acetate was used for disinfecting mucous membranes, but due to toxicological and ecotoxicological reasons, is no longer used.^[5] Phenylmercuric acetate was used as a catalyst during commercial 3M Tartan brand polyurethane flexible floor manufacture. That flooring became popular for public buildings, especially school gymnasia, in the 1950s through the 1970s; and traces of the catalyst remained detectable in Idaho public schools as late as 2006.^[6]

Hazards

Contact with phenylmercuric acetate can cause allergic reactions.,^[2] such as erythema and contact urticaria syndrome.^[7][8] IgE plays a crucial role in contact urticaria syndrome pathogenesis.^[8]

A rare side effect of phenylmercuric acetate in eye drops is mercurialentis, the buildup of pigment on the anterior capsule of the lens. This has been estimated to affect 18 of 500 patients who have used eye drops containing phenylmercuric acetate two to four times a day for more than six years. The pigmentation is not associated with visual impairment nor any ocular abnormalities.^[3]

See also

• Phenylmercuric borate
• Phenylmercuric nitrate