62-38-4 Usage
Chemical Properties
Different sources of media describe the Chemical Properties of 62-38-4 differently. You can refer to the following data:
1. white crystalline powder
2. Phenylmercury acetate is a white or yellow crystalline solid.
3. Phenylmercuric acetate occurs as a white to creamy white, odorless
or almost odorless, crystalline powder or as small white prisms or
leaflets.
Uses
Different sources of media describe the Uses of 62-38-4 differently. You can refer to the following data:
1. antiulcer
2. Herbicide; fungicide.
3. Phenylmercuric acetate is used as catalyst; fungicide; herbicide; algicide; preservative in antibiotic eye drops, eye cosmetics, shampoos, etc.
Production Methods
Phenylmercuric acetate is readily formed by heating benzene with
mercuric acetate.
General Description
Small lustrous prisms. Toxic by ingestion, inhalation and skin absorption. May severely irritate skin and eyes. Used as an herbicide and fungicide. as such, is mixed with organic solvent for the purpose of application.
Reactivity Profile
PHENYLMERCURIC ACETATE may react with strong oxidizing agents .
Health Hazard
Extremely toxic. The probable oral lethal dose for humans is 5-50 mg/kg, between 7 drops and 1 teaspoonful for a 70 kg (150 lb.) person.
Fire Hazard
Fire may produce irritating or poisonous gases. When heated to decomposition, very toxic mercuric fumes may be given off. Phenylmercuric ion is incompatible with halides, with which precipitates are formed.
Pharmaceutical Applications
Phenylmercuric acetate is used as an alternative antimicrobial
preservative to phenylmercuric borate or phenylmercuric nitrate in
a limited range of cosmetics (in concentrations not exceeding
0.007% of mercury calculated as the metal) and pharmaceuticals. It
may be used in preference to phenylmercuric nitrate owing to its
greater solubility.
Phenylmercuric acetate is also used as a spermicide;
Safety Profile
Poison by ingestion, intravenous, intraperitoneal, subcutaneous, and possibly other routes. An experimental teratogen. Other experimental reproductive effects. Mutation data reported. See also MERCURY COMPOUNDS. When heated to decomposition it emits toxic fumes of Hg.
Safety
Phenylmercuric acetate is mainly used as an antimicrobial
preservative in topical pharmaceutical formulations. A number of
adverse reactions to mercury-containing preservatives have been
reported; see Phenylmercuric Nitrate.
LD50 (chicken, oral): 60 mg/kg
LD50 (mouse, IP): 13 mg/kg
LD50 (mouse, IV): 18 mg/kg
LD50 (mouse, oral): 13 mg/kg
LD50 (mouse, SC): 12 mg/kg
LD50 (rat, oral): 41 mg/kg
Potential Exposure
Phenylmercury acetate is used as an antiseptic, fungicide; for fungal and bacterial control; herbicide and control of crabgrass; mildewcide for paints; slimicide in paper mills. It was also used in contraceptive gels and foams.
Environmental Fate
If released into air, soil, or water, phenylmercuric acetate is
unlikely to volatilize and is instead expected to be bound to
particulates based on a low vapor pressure (6 × 10-6 mm Hg)
and low Henry’s constant (5.66 × 10-10 atmm3 mol -1).
Photolysis has the potential to degrade phenylmercuric acetate,
releasing inorganic mercury which can volatilize and enter the
atmosphere from superficial soils or water. If released into soil,
the mobility of parent phenylmercuric acetic acid is expected to
be high based on a Koc of 60. Water releases would result in
quick dispersion since water solubility is high (4370 mg l-1).
Once in solution, especially with harder water, it will dissociate
into a salt. The cation will adsorb to particulates or humics suspended in the water column or in sediment, with little bioconcentration
in aquatic species.
storage
As for other phenylmercuric salts; see Phenylmercuric Nitrate.
Phenylmercuric acetate should be stored in a well-closed
container, protected from light, in a cool, dry place.
Shipping
UN1674 Phenylmercuric acetate, Hazard Class: 6.1; Labels: 6.1-Poisonous materials.
Purification Methods
It forms small colourless lustrous prisms from EtOH. Its solubility in H2O is 0.17%, but it is more soluble in EtOH, Me2CO and *C6H6. [Maynard J Am Chem Soc 46 1510 1925, Coleman et al. J Am Chem Soc 59 2703 1937, J Am Pharm Assoc 25 752 1936, Beilstein 16 IV 1720.] See PhHgOH below.
Toxicity evaluation
Toxic effects of phenylmercuric acetate are correlated with its
rapid metabolic breakdown into the mercuric ion. Generally,
mercury interferes with cellular enzymatic mechanisms by
combining with sulfhydryl (–SH) groups of different enzymes
and thereby produces nonspecific cell injury or death.
Incompatibilities
Different sources of media describe the Incompatibilities of 62-38-4 differently. You can refer to the following data:
1. A strong reducing agent. Incompatible with oxidizers (chlorates, nitrates, peroxides, permanganates, perchlorates, chlorine, bromine, fluorine, etc.); contact may cause fires or explosions. Keep away from alkaline materials, strong bases, strong acids, oxoacids, epoxides, halogens.
2. As for other phenylmercuric salts; see Phenylmercuric Nitrate.
Incompatible with: halides; anionic emulsifying agents and
suspending agents; tragacanth; starch; talc; sodium metabisulfite;
sodium thiosulfate; disodium edetate; silicates; aluminum and other
metals; amino acids; ammonia and ammonium salts; sulfur
compounds; rubber; and some plastics.
Phenylmercuric acetate is reported to be incompatible with
cefuroxime and ceftazidime.
Waste Disposal
Consult with environmental regulatory agencies for guidance on acceptable disposal practices. Generators of waste containing this contaminant (≥100 kg/mo) must conform with EPA regulations governing storage, transportation, treatment, and waste disposal. React to produce soluble nitrate form, precipitate as mercuric sulfide. Return to supplier.
Regulatory Status
Included in the FDA Inactive Ingredients Database (ophthalmic
ointments; topical emulsions/creams; vaginal emulsions/creams).
Included in the Canadian List of Acceptable Non-medicinal
Ingredients (ophthalmic, nasal and otic preparations up to
0.004%; there must be no other suitable alternative preservative
available).
Phenylmercuric acetate is no longer permitted to be used as a
pesticide in the USA. Its use in cosmetic products in the USA is
limited to eye area cosmetics at not more than 0.0065% provided
that there is no other suitable available preservative. It is specifically
prohibited in vaginal contraceptive drug products and antimicrobial
diaper rash drug products in the USA. Phenylmercuric
compounds are prohibited from use in cosmetic products in
Canada.
In Europe, use in cosmetic products is limited to eye makeup and
eye makeup remover at concentrations not exceeding 0.007%
mercury alone or in combination with other permitted mercurial
compounds.In France, a maximum concentration of 0.01% is
permitted for use in pharmaceuticals. The use of mercurial
compounds in cosmetics in Japan is limited to concentrated
shampoo or cream at not more than 0.003% Hg and eye makeup
at not more than 0.0065% Hg.
Check Digit Verification of cas no
The CAS Registry Mumber 62-38-4 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 6 and 2 respectively; the second part has 2 digits, 3 and 8 respectively.
Calculate Digit Verification of CAS Registry Number 62-38:
(4*6)+(3*2)+(2*3)+(1*8)=44
44 % 10 = 4
So 62-38-4 is a valid CAS Registry Number.
InChI:InChI=1/C6H5.C2H4O2.Hg/c1-2-4-6-5-3-1;1-2(3)4;/h1-5H;1H3,(H,3,4);/q;;+1/p-1/rC6H5Hg.C2H4O2/c7-6-4-2-1-3-5-6;1-2(3)4/h1-5H;1H3,(H,3,4)/q+1;/p-1
62-38-4Relevant articles and documents
Schramm et al.
, p. 843 (1951)
Process for preparing alkyl- and arylmalonic acids
-
, (2008/06/13)
Alkyl- and arylmalonic acids of the formula I STR1 where R1 =H, C1 -C12 -alkyl, phenyl, C1 -C4 -alkylphenyl, C2 -C4 -dialkylphenyl, R2 =C1 -C12 -alkyl, phenyl, C1 -C4 -alkylphenyl, C2 -C4 -dialkylphenyl or R1 +R2 =--CH2 --CH2 --, are prepared by alkaline saponification by hydrolyzing the corresponding C1 -C4 -alkyl esters of the malonic acid of formula I, with alkali metal hydroxide dissolved in an aqueous alkali metal salt solution containing salt at 90-100% of saturation, acidifying the hydrolysis product with a mineral acid, removing the precipitated alkali metal salt which forms upon acidification, and extracting the alkyl- and arylmalonic acid formed from the aqueous solution with the aid of an organic solvent.
Nucleophilic cleavage of the Si-C bond in organotrifluorosilanes and diorganodifluorosilanes
Voronkov, M. G.,Chermov, N. F.,Perlova, E. M.
, p. 225 - 230 (2007/10/02)
The Si-C bond in aryltrifluorosilanes, 4-XC6H4SiF3 (X = H, CH3, Cl, Br or NO2), is readily cleaved by mercury(II) salts HgY2 (Y = Cl, Br, I, CN or OCOCH3) or HgO to form organomercurials of the type 4-XC6H4HgY or (4-XC6H4)2Hg, respectively.Electron-donating substituent X facilitate the reaction, whereas electron-withdrawing substituents make it more difficult.Mercury(II) salts and mercury(II) oxide also cleave the Si-C bond in chloromethyltrifluorosilanes, F3Si(CH3-nCln) (n = 1-3) to produce the corresponding organic mercurials containing an Hg(CH3-nCln) group.The substitution of the fluorine atom in organotrifluorosilanes by an alkyl group hinders the bond cleavage between the silicon atom and the electronegative organic substituent.The reactions studied are believed to follow a nucleophilic mechanism involving asynchronous formation of a four-centered transition state with a pentacoordinate silicon atom.
