122-60-1 Usage
Description
This monoglycidyl derivative is a reactive diluent in
epoxy resins of the bisphenol A type. It is a component
of epoxy paints, epoxy glues, and epoxy resins.
Sensitization was observed in many professions, such
as in construction workers, marble workers, ceramic
workers, and in a shoemaker.
Chemical Properties
Different sources of media describe the Chemical Properties of 122-60-1 differently. You can refer to the following data:
1. colourless liquid
2. Phenyl glycidyl ether is a colorless liquid with an unpleasant sweet odor
Uses
Different sources of media describe the Uses of 122-60-1 differently. You can refer to the following data:
1. Chemical intermediate with high solvency
for halogenated materials
2. Phenyl glycidyl ether (PGE) is used as anintermediate in organic syntheses.
3. 2-Phenylglycidyl ether is an organic synthesis; chemical intermediate with high solvency for halogenated materials; reactive diluent of epoxy-resin systems; forms chemical bonds with the resin during cure and accelerates the curing process.
Production Methods
PGE is synthesized by condensation of phenol with epichlorohydrin,
with subsequent dehydrochlorination with caustic
to form the epoxy ring.
Synthesis Reference(s)
The Journal of Organic Chemistry, 50, p. 1784, 1985 DOI: 10.1021/jo00210a053
General Description
Colorless liquid.
Air & Water Reactions
Ethers tend to form unstable peroxides when exposed to oxygen. Ethyl, isobutyl, ethyl tert-butyl, and ethyl tert-pentyl ether are particularly hazardous in this respect. Ether peroxides can sometimes be observed as clear crystals deposited on containers or along the surface of the liquid. Slightly soluble in water.
Reactivity Profile
Glycidyl phenyl ether, an ether, can act as a base. They form salts with strong acids and addition complexes with Lewis acids. The complex between diethyl ether and boron trifluoride is an example. Ethers may react violently with strong oxidizing agents. In other reactions, which typically involve the breaking of the carbon-oxygen bond, ethers are relatively inert.
Health Hazard
PGE is a toxic compound exhibiting moderate irritant action and carcinogenicity inanimals. Application of 0.25 mg resulted insevere eye irritation in rabbits, while 500 mgcaused moderate skin irritation over a periodof 24 hours. Prolonged or repeated contactcan cause moderate irritation and skin sensitization in humans.The symptoms of its toxicity in animalswere depression of the central nervous system and paralysis of the respiratory tract.Prolonged exposure caused changes in thekidney, liver, thymus, and testes, and lossof hair in rats. The toxicity of this compound in humans is low and the health hazardcan arise primarily from its skin-sensitizationaction.LD50 value, oral (mice): 1400 mg/kgDGE showed carcinogenicity in rats, causingnasal cancer.
Fire Hazard
Glycidyl phenyl ether is probably combustible.
Contact allergens
This monoglycidyl derivative is a reactive diluent in
epoxy resins Bisphenol A type. It is a component of
epoxy paints, epoxy glues, and epoxy resins.
Sensitization has been observed in many professions,
such as in construction workers, marble workers,
ceramic workers, and shoemakers.
Safety Profile
Confirmed carcinogen with experimental carcinogenic data. Moderately toxic by ingestion, skin contact, and subcutaneous routes. A severe eye and skin irritant. Experimental reproductive effects. Mutation data reported. When heated to decomposition it emits acrid smoke and irritating fumes. Used as a chemical intermediate. See also ETHERS
Potential Exposure
PGE is used to increase storage time and stability of halogenated compounds; as a reactive diluent in uncured epoxy resins to reduce the viscosity of the uncured system for ease in casting; adhesive, and laminating applications. NIOSH once estimated that 8000 workers are potentially exposed to PGE.
Carcinogenicity
Chronic exposure of rats to 1 or 12ppm
6 hours/day, 5 days/week for 2 years caused an
increased incidence of rhinitis, squamous metaplasia,
and epidermal carcinomas of the nasal
cavity.4 The IARC has determined that there is
sufficient evidence for the carcinogenicity of
PGE in animals and that it is possibly carcinogenic
to humans.
Shipping
UN2810 Toxic liquids, organic, n.o.s., Hazard Class: 6.1; Labels: 6.1-Poisonous materials, Technical Name Required.
Incompatibilities
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, amines, and curing agents. PGE can presumably form explosive peroxides
Waste Disposal
Concentrated waste containing no peroxides-discharge liquid at a controlled rate near a pilot flame. Concentrated waste containing peroxidesperforation of a container of the waste from a safe distance followed by open burning.
Check Digit Verification of cas no
The CAS Registry Mumber 122-60-1 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 1,2 and 2 respectively; the second part has 2 digits, 6 and 0 respectively.
Calculate Digit Verification of CAS Registry Number 122-60:
(5*1)+(4*2)+(3*2)+(2*6)+(1*0)=31
31 % 10 = 1
So 122-60-1 is a valid CAS Registry Number.
InChI:InChI=1/C6H10O3.C6H6O/c1(5-3-8-5)7-2-6-4-9-6;7-6-4-2-1-3-5-6/h5-6H,1-4H2;1-5,7H
122-60-1Relevant articles and documents
Sustainable Synthesis of a Potent and Selective 5-HT7Receptor Antagonist Using a Mechanochemical Approach
Canale, Vittorio,Frisi, Valeria,Bantreil, Xavier,Lamaty, Frédéric,Zajdel, Pawe?
, p. 10958 - 10965 (2020)
A mechanochemical procedure was developed to obtain PZ-1361, a potent and selective 5-HT7 receptor antagonist, with antidepressant properties in rodents. The elaborated protocol offered several advantages over classical batch synthesis, including improvement of the overall yield (from 34% to 64%), reduction of reaction time (from 60 to 5.5 h), limitation of the use of toxic solvents, and the formation of byproducts. This approach represents a rare example of the synthesis of biologically active compounds exclusively performed using mechanochemical reactions.
A facile and efficient method for synthesis of β-iodocarboxylates from terminal epoxides
Zhu, Ye-Fu,Wei, Bo-Le,Wang, Wen-Qiong,Xuan, Li-Jiang
, (2019)
A facile and efficient method has been developed for synthesis of β-iodocarboxylates in the presences of Ph3P/I2. Starting from epoxides, a series of β-iodocarboxylate compounds can be directly obtained in toluene media with excellent yields. Moreover, the method was successfully applied for the late-stage modification of natural products, such as isosteviol and vincamine derivatives, achieving the corresponding β-iodocarboxylates in good yields.
A novel method for synthesis of aryl glycidyl ethers
Liu,Chen,Cao,Li
, p. 833 - 838 (1994)
A solid-liquid phase-transfer catalytic method for the synthesis of aryl glycidyl ethers has been described, and the factors affecting the reaction yield have been examined.
Selective epoxidation of olefins by hydrogen peroxide in water using a polyoxometalate catalyst supported on chemically modified hydrophobic mesoporous silica gel
Sakamoto,Pac
, p. 10009 - 10012 (2000)
A new heterogeneous catalyst prepared by immobilisation of polyoxometalates on chemically modified hydrophobic mesoporous silica gel has been successfully applied to the selective epoxidation of olefins with 15% aqueous H2O2 without the use of organic solvent. (C) 2000 Elsevier Science Ltd.
-
Markevich et al.
, (1979)
-
Discovery of a Potent and Selective Chikungunya Virus Envelope Protein Inhibitor through Computer-Aided Drug Design
álvarez, Diego E.,Battini, Leandro,Bollini, Mariela,Fidalgo, Daniela M.
, p. 1503 - 1518 (2021/06/28)
The worldwide expansion of chikungunya virus (CHIKV) into tropical and subtropical areas in the last 15 years has posed a currently unmet need for vaccines and therapeutics. The E2-E1 envelope glycoprotein complex binds receptors on the host cell and promotes membrane fusion during CHIKV entry, thus constituting an attractive target for the development of antiviral drugs. In order to identify CHIKV antivirals acting through inhibition of the envelope glycoprotein complex function, our first approach was to search for amenable druggable sites within the E2-E1 heterodimer. We identified a pocket located in the interface between E2 and E1 around the fusion loop. Then, via a structure-based virtual screening approach and in vitro assay of antiviral activity, we identified compound 7 as a specific inhibitor of CHIKV. Through a lead optimization process, we obtained compound 11 that demonstrated increased antiviral activity and low cytotoxicity (EC50 1.6 μM, CC50 56.0 μM). Molecular dynamics simulations were carried out and described a possible interaction pattern of compound 11 and the E1-E2 dimer that could be useful for further optimization. As expected from target site selection, compound 11 inhibited virus internalization during CHIKV entry. In addition, virus populations resistant to compound 11 included mutation E2-P173S, which mapped to the proposed binding pocket, and second site mutation E1-Y24H. Construction of recombinant viruses showed that these mutations conferred antiviral resistance in the parental background. Finally, compound 11 presents acceptable solubility values and is chemically and enzymatically stable in different media. Altogether, these findings uncover a suitable pocket for the design of CHIKV entry inhibitors with promising antiviral activity and pharmacological profiles.
Visible-light assisted of nano Ni/g-C3N4 with efficient photocatalytic activity and stability for selective aerobic C?H activation and epoxidation
Akrami, Zahra,Hosseini-Sarvari, Mona
supporting information, (2020/10/13)
A selective, economical, and ecological protocol has been described for the oxidation of methyl arenes and their analogs to the corresponding carbonyl compounds and epoxidation reactions of alkenes with molecular oxygen (O2) or air as a green oxygen source, under mild reaction conditions. The nano Ni/g-C3N4 exhibited high photocatalytic activity, stability, and selectivity in the C?H activation of methyl arenes, methylene arenes, and epoxidation of various alkenes under visible- light irradiation without the use of an oxidizing agent and under base free conditions.
