Record Information
Version1.0
Creation Date2009-06-19 21:58:40 UTC
Update Date2016-11-09 01:08:28 UTC
Accession NumberCHEM001181
Identification
Common NamePhenylmercuric borate
ClassSmall Molecule
DescriptionPhenylmercuric borate is an organomercuric compound. It is used as a topical antiseptic and disinfectant. Mercury is a heavy, silvery d-block metal and one of six elements that are liquid at or near room temperature and pressure. It is a naturally occuring substance, and combines with other elements such as chlorine, sulfur, or oxygen to form inorganic mercury compounds (salts). Mercury also combines with carbon to make organic mercury compounds. (6, 12)
Contaminant Sources
  • T3DB toxins
  • ToxCast & Tox21 Chemicals
Contaminant Type
  • Aromatic Hydrocarbon
  • Drug
  • Household Toxin
  • Mercury Compound
  • Organic Compound
  • Organometallic
  • Pollutant
  • Synthetic Compound
Chemical Structure
Thumb
Synonyms
ValueSource
Phenylmercuric boric acidGenerator
(Dihydrogen borato)phenylmercuryMeSH
ExomycolMeSH
MerfenMeSH
SurgilubeMeSH
Phenyl mercuric borateMeSH
Phenylhydrargum borasMeSH
Phenylhydrargyri borasMeSH
Phenylmercury borateMeSH
Chemical FormulaC6H7BHgO3
Average Molecular Mass338.520 g/mol
Monoisotopic Mass340.019 g/mol
CAS Registry Number102-98-7
IUPAC Name[(phenylmercurio)oxy]boronic acid
Traditional Namephenylmercuric borate
SMILESOB(O)O[Hg]C1=CC=CC=C1
InChI IdentifierInChI=1S/C6H5.BH2O3.Hg/c1-2-4-6-5-3-1;2-1(3)4;/h1-5H;2-3H;/q;-1;+1
InChI KeyVUXSPDNLYQTOSY-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as benzene and substituted derivatives. These are aromatic compounds containing one monocyclic ring system consisting of benzene.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassNot Available
Direct ParentBenzene and substituted derivatives
Alternative Parents
Substituents
  • Metal aryl
  • Aryl mercury compound
  • Monocyclic benzene moiety
  • Organic borate
  • Organic metalloid salt
  • Organic transition metal salt
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organic salt
  • Organometallic compound
  • Organomercurial-compound
  • Organic transition metal moeity
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Cytoplasm
  • Extracellular
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting Point112.5°C
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility54.1 g/LALOGPS
logP0.28ALOGPS
logP1.2ChemAxon
logS-0.8ALOGPS
pKa (Strongest Acidic)9.12ChemAxon
pKa (Strongest Basic)-5.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area49.69 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity31.95 m³·mol⁻¹ChemAxon
Polarizability15.9 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-0069000000-07779231dd0b2d32003cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004m-2097000000-c65399d1560d1a5cfec2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01ta-3090000000-de90810e89e9d9ef422cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0009000000-43130b3982c9cf044024Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000j-4059000000-945d9dcaf803fd1d3722Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9001000000-f0a6403706ffbe6f8161Spectrum
Toxicity Profile
Route of ExposureOral (8) ; inhalation (8) ; dermal (8)
Mechanism of ToxicityHigh-affinity binding of the divalent mercuric ion to thiol or sulfhydryl groups of proteins is believed to be the major mechanism for the activity of mercury. Through alterations in intracellular thiol status, mercury can promote oxidative stress, lipid peroxidation, mitochondrial dysfunction, and changes in heme metabolism. Mercury is known to bind to microsomal and mitochondrial enzymes, resulting in cell injury and death. For example, mercury is known to inhibit aquaporins, halting water flow across the cell membrane. It also inhibits the protein LCK, which causes decreased T-cell signalling and immune system depression. Mercury is also believed to inhibit neuronal excitability by acting on the postsynaptic neuronal membrane. It also affects the nervous system by inhibiting protein kinase C and alkaline phosphatase, which impairs brain microvascular formation and function, as well as alters the blood-brain barrier. Organic mercury exerts developmental effects by binding to tubulin, preventing microtubule assembly and causing mitotic inhibition. Mercury also produces an autoimmune response, likely by modification of major histocompatibility complex (MHC) class II molecules, self peptides, T-cell receptors, or cell-surface adhesion molecules. (8, 3, 4, 5)
MetabolismOrganic mercury is absorbed mainly by the gastrointestinal tract, then distributed throughout the body via the bloodstream. Organic mercury complexes with free cysteine and the cysteine and sulfhydryl groups on proteins such as haemoglobin. These complexes are able to mimic methionine and thus be transported throughout the body, including through the blood-brain barrier and placenta. Organic mercury is metabolized into inorganic mercury, which is eventually excreted in the urine and faeces. (13)
Toxicity ValuesNot Available
Lethal Dose100 mg for an adult human (average for organic mercurials). (14)
Carcinogenicity (IARC Classification)No indication of carcinogenicity (not listed by IARC). (11)
Uses/SourcesPhenylmercuric borate is used as a topical antiseptic and disinfectant. (12)
Minimum Risk LevelChronic Inhalation: 0.0002 mg/m3 (10)
Health EffectsMercury mainly affects the nervous system. Exposure to high levels of metallic, inorganic, or organic mercury can permanently damage the brain, kidneys, and developing fetus. Effects on brain functioning may result in irritability, shyness, tremors, changes in vision or hearing, and memory problems. Acrodynia, a type of mercury poisoning in children, is characterized by pain and pink discoloration of the hands and feet. Mercury poisoning can also cause Hunter-Russell syndrome and Minamata disease. (8)
SymptomsCommon symptoms include peripheral neuropathy (presenting as paresthesia or itching, burning or pain), skin discoloration (pink cheeks, fingertips and toes), edema (swelling), and desquamation (dead skin peels off in layers). (1)
TreatmentMercury poisoning is treated by immediate decontamination and chelation therapy using DMSA, DMPS, DPCN, or dimercaprol. (2)
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDNot Available
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkPhenylmercuric borate
Chemspider IDNot Available
ChEBI IDNot Available
PubChem Compound ID7627
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General ReferencesNot Available