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Basic Information
CAS No.: 122-60-1
Name: Glycidyl phenyl ether
Article Data: 127
Molecular Structure:
Molecular Structure of 122-60-1 (Glycidyl phenyl ether)
Formula: C9H10O2
Molecular Weight: 150.177
Synonyms: Propane, 1,2-epoxy-3-phenoxy- (8CI);(Phenyloxymethyl)oxirane;1,2-Epoxy-3-phenoxypropane;1-Phenoxy-2,3-epoxypropane;2,3-Epoxypropyl phenylether;2-(Phenoxymethyl)oxirane;3-(Phenyloxy)-1,2-epoxypropane;3-Phenoxy-1,2-epoxypropane;3-Phenoxypropylene oxide;Oxiranylmethyl phenyl ether;
EINECS: 204-557-2
Density: 1.123 g/cm3
Melting Point: 3.5 °C(lit.)
Boiling Point: 244.999 °C at 760 mmHg
Flash Point: 94.757 °C
Solubility: 2.4 g/L (20 ºC)
Appearance: Light yellow liquid
Hazard Symbols: ToxicT
Risk Codes: 45-20-37/38-43-52/53-68
Safety: 53-45-61
PSA: 21.76000
LogP: 1.46420
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    Molecular Formula:C9H10O2 Molecular Weight:150.19 Density:1.108 Melting Point:3.5 oC Boiling Point:245 oC Flash Point:115 oC Solubility:2.4 g/L …Appearance:colourless liquid

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Consensus Reports

IARC Cancer Review: Group 2B IMEMDT    IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man . 47 ,1989,p. 237.(World Health Organization, Internation Agency for Research on Cancer,Lyon, France.: ) (Single copies can be ordered from WHO Publications Centre U.S.A., 49 Sheridan Avenue, Albany, NY 12210) ; Animal Sufficient Evidence IMEMDT    IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man . 47 ,1989,p. 237.(World Health Organization, Internation Agency for Research on Cancer,Lyon, France.: ) (Single copies can be ordered from WHO Publications Centre U.S.A., 49 Sheridan Avenue, Albany, NY 12210) . Reported in EPA TSCA Inventory. EPA Genetic Toxicology Program.

Standards and Recommendations

OSHA PEL: TWA 1 ppm
ACGIH TLV: TWA 0.1 ppm (skin, sensitizer) Confirmed Animal Carcinogen with Unknown Relevance to Humans
DFG MAK: Confirmed Animal Carcinogen, Suspected Human Carcinogen
NIOSH REL: (Phenyl Glycidyl Ether) CL 1 ppm/15M

Analytical Methods

For occupational chemical analysis use NIOSH: Phenyl Glycidyl Ether S74.

Specification

The CAS registry number of Phenyl glycidyl ether is 122-60-1. The IUPAC name is 2-(phenoxymethyl)oxirane. Its EINECS registry number is 204-557-2. In addition, the molecular formula is C9H10O2 and the molecular weight is 150.17. It is a kind of colourless liquid and belongs to the classes of Oxiranes and Simple 3-Membered Ring Compounds.

Physical properties about this chemical are: (1)ACD/LogP: 1.47; (2)ACD/LogD (pH 5.5): 1.47; (3)ACD/LogD (pH 7.4): 1.47; (4)ACD/BCF (pH 5.5): 7.715; (5)ACD/BCF (pH 7.4): 7.715; (6)ACD/KOC (pH 5.5): 150.242; (7)ACD/KOC (pH 7.4): 150.242; (8)#H bond acceptors: 2; (9)#Freely Rotating Bonds: 3; (10)Polar Surface Area: 21.76 Å2; (11)Index of Refraction: 1.537; (12)Molar Refractivity: 41.772 cm3; (13)Molar Volume: 133.742 cm3; (14)Polarizability: 16.56 ×10-24cm3; (15)Surface Tension: 42.282 dyne/cm; (16)Density: 1.123 g/cm3; (17)Flash Point: 94.757 °C; (18)Enthalpy of Vaporization: 46.255 kJ/mol; (19)Boiling Point: 244.999 °C at 760 mmHg; (20)Vapour Pressure: 0.046 mmHg at 25°C.

Preparation of Phenyl glycidyl ether: it can be prepared by phenol and epoxychloropropane via condensation in the presence of sodium hydroxide. Mix phenol with sodium hydroxide by stirring, then cool the mixture to 5-6 °C. And add epoxychloropropane slowly. The reaction time is 45 hours by stirring at reaction temperature of 25 °C. Then you can get the product via a series of extraction by ether, drying by anhydrous potassium carbonate, filtering and vacuum distillation. The equation as follows:

Phenyl glycidyl ether can be prepared by phenol and epoxychloropropane in the presence of sodium hydroxide by condensation

Uses of Phenyl glycidyl ether: it can be used as reactive diluent for epoxy resin and intermediates for organic synthesis. And it can be used to get 3-phenoxy-propane-1,2-diol and 1-chloro-3-phenoxy-propan-2-ol. This reaction will need reagents LiCl and silica gel. The reaction time is 22 days with ambient temperature. The yield is about 33%.

Phenyl glycidyl ether can be used to get 3-phenoxy-propane-1,2-diol and 1-chloro-3-phenoxy-propan-2-ol.

When you are using this chemical, please be cautious about it as the following:
This chemical is harmful by inhalation, irritating to respiratory system and skin and may cause sensitization by skin contact. And it may cause cancer. It has risk of irreversible effects possibly. In addition, it is harmful to aquatic organisms, may cause long-term adverse effects in the aquatic environment. You should avoid exposure-obtain special instruction before use. In case of accident or if you feel unwell, seek medical advice immediately (show label where possible). And you should avoid release to the environment. What's more, you can refer to special instructions safety data sheet.

You can still convert the following datas into molecular structure:
(1)SMILES: c1ccc(cc1)OCC2CO2
(2)InChI: InChI=1/C9H10O2/c1-2-4-8(5-3-1)10-6-9-7-11-9/h1-5,9H,6-7H2
(3)InChIKey: FQYUMYWMJTYZTK-UHFFFAOYAO

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LC50 inhalation > 100ppm/4H (100ppm) LUNGS, THORAX, OR RESPIRATION: ACUTE PULMONARY EDEMA AMA Archives of Industrial Health. Vol. 14, Pg. 250, 1956.
mouse LD50 oral 1400mg/kg (1400mg/kg) BRAIN AND COVERINGS: RECORDINGS FROM SPECIFIC AREAS OF CNS

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

BEHAVIORAL: ATAXIA
AMA Archives of Industrial Health. Vol. 14, Pg. 250, 1956.
mouse LD50 subcutaneous 760mg/kg (760mg/kg) AUTONOMIC NERVOUS SYSTEM: "SMOOTH MUSCLE RELAXANT (MECHANISM UNDEFINED, SPASMOLYTIC)" Arzneimittel-Forschung. Drug Research. Vol. 15, Pg. 1355, 1965.
rabbit LD50 skin 1500uL/kg (1.5mL/kg)   AMA Archives of Industrial Hygiene and Occupational Medicine. Vol. 10, Pg. 61, 1954.
rat LC50 inhalation > 100ppm/8H (100ppm) LUNGS, THORAX, OR RESPIRATION: ACUTE PULMONARY EDEMA AMA Archives of Industrial Health. Vol. 14, Pg. 250, 1956.
rat LD50 oral 3850mg/kg (3850mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY)

BEHAVIORAL: ATAXIA
AMA Archives of Industrial Health. Vol. 14, Pg. 250, 1956.