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Phenylmercury acetate

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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
3D model (JSmol)
Beilstein Reference 3662930
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.000.484 Edit this at Wikidata
EC Number
  • 200-532-5
Gmelin Reference 83357
KEGG
MeSH Phenylmercuric+acetate
PubChem CID
RTECS number
  • OV6475000
UNII
UN number 1674
CompTox Dashboard (EPA)
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-1Key: XEBWQGVWTUSTLN-UHFFFAOYSA-M
  • 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)OC1=CC=CC=C1
  • CC(=O)Oc1ccccc1
Properties
Chemical formula C8H8HgO2
Molar mass 336.742 g·mol
Melting point 148 to 151 °C (298 to 304 °F; 421 to 424 K)
Hazards
GHS labelling:
Pictograms GHS05: CorrosiveGHS06: ToxicGHS08: Health hazardGHS09: Environmental hazard
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 , 100 kPa). ☒N verify (what is  ?) Infobox references
Chemical compound

Phenylmercuric acetate is an organomercury compound used as a preservative, disinfectant, and antitranspirant.

Properties

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

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. It kills crabgrass, the seedlings of which are especially vulnerable, but leaves most lawn grasses intact. It exhibits anti-fungal activity against a broad range of ocular pathogenic fungi, with the greatest activity against Fusarium spp, and has been investigated as a potential treatment for keratomycosis.

Phenylmercuric acetate was used for disinfecting mucous membranes, but due to toxicological and ecotoxicological reasons, is no longer used. 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.

Hazards

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

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.

See also

References

  1. ^ 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. ^ 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. ^ 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. ^ 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.
Mercury compounds
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Organomercury
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