93-59-4 Usage
Chemical Properties
Volatile solid with a pungent odor; sublimes;mp 41–43°C (105.8–109°F); bp 100–105°C(212–221°F) at 15 torr (partially decomposes); slightly soluble in water but mixesreadily with most organic solvents.
Uses
Different sources of media describe the Uses of 93-59-4 differently. You can refer to the following data:
1. Perbenzoic acid is used to convert ethylenic compounds into oxides; in analysis of unsatd compounds, to determine the number of double bonds.
2. Peroxybenzoic acid is used in organic analyses to measure the degree of unsaturation,and in making epoxides.
Synthesis Reference(s)
Tetrahedron, 23, p. 3327, 1967 DOI: 10.1016/S0040-4020(01)92300-2
Health Hazard
The toxicity of peroxybenzoic acid is verylow on animals. In humans it is almostnontoxic. Peroxybenzoic acid caused skintumor in mice on prolonged contact (NIOSH1986). Its tumorigenic action was lower thanthat of peroxyacetic acid. Its carcinogenicityin humans is unknown.
Fire Hazard
The presence of the peroxide functional
group renders its strong oxidizing properties similar to those of other peroxy compounds. However, this compound is not
hazardous like peroxyacetic or peroxyformic
acids. It is not shock sensitive. Violent
decomposition may occur only at high temperatures and/or in conjunction with certain organic contaminants that are easily
oxidizable. Although there is no report
of its explosion, general safety measures
for handling peroxy compounds should be
followed.
Safety Profile
Moderately irritating to skin, eyes, and mucous membranes by ingestion and inhalation. Questionable carcinogen with experimental tumorigenic data by skin contact. A dangerous fire hazard when exposed to heat, flame, or reducing materials. A powerful oxid
Purification Methods
Crystallise the peracid from *benzene or pet ether. It sublimes readily and is steam volatile. It is soluble in CHCl3, CCl4 and Et2O. [Braun Org Synth Coll Vol I 431 1941.] EXPLOSIVE.
Check Digit Verification of cas no
The CAS Registry Mumber 93-59-4 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 9 and 3 respectively; the second part has 2 digits, 5 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 93-59:
(4*9)+(3*3)+(2*5)+(1*9)=64
64 % 10 = 4
So 93-59-4 is a valid CAS Registry Number.
InChI:InChI=1/C7H6O3/c8-7(10-9)6-4-2-1-3-5-6/h1-5,9H
93-59-4Relevant articles and documents
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Kolthoff,Lee,Mairs
, p. 199,200 (1947)
-
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Moyer,Manley
, p. 2099 (1964)
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Solvation Accounts for the Counterintuitive Nucleophilicity Ordering of Peroxide Anions
Mayer, Robert J.,Tokuyasu, Takahiro,Mayer, Peter,Gomar, Jér?me,Sabelle, Stéphane,Mennucci, Benedetta,Mayr, Herbert,Ofial, Armin R.
supporting information, p. 13279 - 13282 (2017/10/17)
The nucleophilic reactivities (N, sN) of peroxide anions (generated from aromatic and aliphatic peroxy acids or alkyl hydroperoxides) were investigated by following the kinetics of their reactions with a series of benzhydrylium ions (Ar2CH+) in alkaline aqueous solutions at 20 °C. The second-order rate constants revealed that deprotonated peroxy acids (RCO3?), although they are the considerably weaker Br?nsted bases, react much faster than anions of aliphatic hydroperoxides (ROO?). Substitution of the rate constants of their reactions with benzhydrylium ions into the linear free energy relationship lg k=sN(N+E) furnished nucleophilicity parameters (N, sN) of peroxide anions, which were successfully applied to predict the rates of Weitz–Scheffer epoxidations. DFT calculations with inclusion of solvent effects by means of the Integral Equation Formalism version of the Polarizable Continuum Model were performed to rationalize the observed reactivities.
One-pot epoxidation of alkenes using aerobic photoperoxidation of toluenes
Taguchi, Miyabi,Nagasawa, Yoshitomo,Yamaguchi, Eiji,Tada, Norihiro,Miura, Tsuyoshi,Itoh, Akichika
supporting information, p. 230 - 232 (2015/12/31)
We developed an aerobic photooxidative synthesis of peroxybenzoic acids from toluenes using anthraquinone-2-carboxylic acid (AQN-2-CO2H) as a photocatalyst. We also found a one-pot epoxidation reaction of alkenes using 4-tert-butylperoxybenzoic acid produced in situ by aerobic photooxidative synthesis.