Phenylmercury acetate

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Phenylmercury acetate
Skeletal formula of phenylmercury acetate Phenylmercuric acetate.svg
Skeletal formula of phenylmercury acetate
Ball and stick model of the phenylmercury acetate molecule Phenylmercury(II)-acetate-from-xtal-3D-balls.png
Ball and stick model of the phenylmercury acetate molecule
Names
Systematic IUPAC name
acetyloxy(phenyl)mercury
Identifiers
3D model (JSmol)
3662930
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.000.484 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 200-532-5
83357
KEGG
MeSH Phenylmercuric+acetate
PubChem CID
RTECS number
  • OV6475000
UNII
UN number 1674
  • 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 Yes check.svgY
    Key: XEBWQGVWTUSTLN-UHFFFAOYSA-M Yes check.svgY
  • 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
  • CC(=O)O[Hg]C1=CC=CC=C1
  • CC(=O)O[Hg]c1ccccc1
Properties
CH3CO2HgC6H5
Molar mass 336.742 g·mol−1
Appearancecolorless, lustrous crystals
Melting point 148 to 151 °C (298 to 304 °F; 421 to 424 K)
Hazards
GHS labelling:
GHS-pictogram-acid.svg GHS-pictogram-skull.svg GHS-pictogram-silhouette.svg GHS-pictogram-pollu.svg
Danger
H301, H314, H372, H410
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).
X mark.svgN  verify  (what is  Yes check.svgYX mark.svgN ?)

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

Contents

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

References

  1. 1 2 Simon, Matthias; Jönk, Peter; Wühl-Couturier, Gabriele; Halbach, Stefan (2006). "Mercury, Mercury Alloys, and Mercury Compounds". Ullmann's Encyclopedia of Industrial Chemistry. doi:10.1002/14356007.a16_269.pub2. ISBN   978-3-527-30673-2.
  2. 1 2 Geier, J.; Lessmann, H.; Uter, W.; Schnuch, A. (2005). "Patch testing with phenylmercuric acetate". Contact Dermatitis. 53 (2): 117–8. doi:10.1111/j.0105-1873.2005.0650d.x. PMID   16033409. S2CID   42906373.
  3. 1 2 3 Xu, Y.; Zhao, D.; Gao, C.; Zhou, L.; Pang, G.; Sun, S. (2012). "In vitro activity of phenylmercuric acetate against ocular pathogenic fungi". Journal of Antimicrobial Chemotherapy . 67 (8): 1941–4. doi: 10.1093/jac/dks133 . PMID   22514262.
  4. ↑ Sunset Western Garden Book (1954), p.69
  5. ↑ Siebert, Jörg; Harke, Hans-Peter (2009). "Disinfectants". Ullmann's Encyclopedia of Industrial Chemistry. doi:10.1002/14356007.a08_551.pub2. ISBN   978-3-527-30673-2.
  6. ↑ Beaulieu, Harry J.; Beaulieu, Serrita; Brown, Chris (2008). "Phenyl Mercuric Acetate (PMA): Mercury-Bearing Flexible Gymnasium Floors in Schools — Evaluation of Hazards and Controlled Abatement". Journal of Occupational and Environmental Hygiene. 5 (6): 360–6. doi:10.1080/15459620802017425. PMID   18365889. S2CID   43701302.
  7. ↑ Maibach, H. I.; Johnson, H. L. (1975). "Contact Urticaria Syndrome: Contact Urticaria to Diethyltoluamide (Immediate-Type Hypersensitivity)". Archives of Dermatology. 111 (6): 726–30. doi:10.1001/archderm.1975.01630180054004. PMID   1137416.
  8. 1 2 Torresani, Claudio; Caprari, Elisabetta; Manara, Gian Carlo (1993). "Contact urticaria syndrome due to phyenylmercuric acetate". Contact Dermatitis. 29 (5): 282–3. doi:10.1111/j.1600-0536.1993.tb03574.x. PMID   8112079. S2CID   46255307.
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