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77-83-8

Basic Information
CAS No.: 77-83-8
Name: Ethyl 3-methyl-3-phenylglycidate
Article Data: 25
Molecular Structure:
Molecular Structure of 77-83-8 (Ethyl 3-methyl-3-phenylglycidate)
Formula: C12H14O3
Molecular Weight: 206.241
Synonyms: Hydrocinnamicacid, a,b-epoxy-b-methyl-, ethyl ester (7CI,8CI);Oxiranecarboxylic acid, 3-methyl-3-phenyl-,ethyl ester (9CI);3-Methyl-3-phenylglycidic acid ethyl ester;Ethyl methylphenylglycidate;Ethyl a,b-epoxy-b-methylhydrocinnamate;Strawberry aldehyde;
EINECS: 201-061-8
Density: 1.139 g/cm3
Boiling Point: 273.5 °C at 760 mmHg
Flash Point: 109.371 °C
Appearance: clear yellow liquid
Hazard Symbols: IrritantXi
Risk Codes: 10-36/37/38
Safety: 16-26-36/37/39
Transport Information: UN 1993 3/PG 3
PSA: 38.83000
LogP: 1.86370
Synthetic route
617-33-4

ethyl dibromoacetate

98-86-2

acetophenone

77-83-8

fraeseol

Conditions
ConditionsYield
Stage #1: ethyl dibromoacetate; acetophenone With samarium diiodide In tetrahydrofuran at 20℃; for 2h;
Stage #2: With potassium hexamethyldisilazane In tetrahydrofuran; toluene
90%
105-39-5

chloroacetic acid ethyl ester

98-86-2

acetophenone

77-83-8

fraeseol

Conditions
ConditionsYield
With potassium n-butoxide88%
With sodium hydride In acetonitrile; mineral oil at 50 - 80℃; optical yield given as %de;64%
With sodium ethanolate Erhitzen auf 100grad;

2-Bromo-3-hydroxy-3-phenyl-butyric acid ethyl ester

77-83-8

fraeseol

Conditions
ConditionsYield
With potassium carbonate80%
91767-65-6

2-chloro-3-hydroxy-3-phenyl-butyric acid ethyl ester

77-83-8

fraeseol

Conditions
ConditionsYield
With potassium carbonate78%
623-73-4

diazoacetic acid ethyl ester

98-86-2

acetophenone

77-83-8

fraeseol

Conditions
ConditionsYield
methyltrioxorhenium(VII) at 50 - 60℃; for 72h;57%
98-86-2

acetophenone

sulfur

sulfur

77-83-8

fraeseol

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 86 percent / zinc chloride/silver acetate/bronze-coloured C8K / tetrahydrofuran / 0.33 h / -78 °C
2: 80 percent / K2CO3
View Scheme
Multi-step reaction with 2 steps
1: 90 percent / zinc chloride/silver acetate/bronze-coloured C8K / tetrahydrofuran / 0.67 h / -20 °C
2: 78 percent / K2CO3
View Scheme
945-93-7, 13979-22-1, 1504-72-9

ethyl (E)-3-phenylbut-2-enoate

77-83-8

fraeseol

Conditions
ConditionsYield
With 2-Ethylhexanoic acid; C36H40F6MnN6O6S2; dihydrogen peroxide In acetonitrile at 0℃; for 1h; Reagent/catalyst; enantioselective reaction;55 %Spectr.
98-86-2

acetophenone

77-83-8

fraeseol

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: sodium hydride / tetrahydrofuran; mineral oil / 0.5 h / 20 °C / Inert atmosphere
1.2: 0 - 20 °C / Inert atmosphere
2.1: C36H40F6MnN6O6S2; 2-Ethylhexanoic acid; dihydrogen peroxide / acetonitrile / 1 h / 0 °C
View Scheme
77-83-8

fraeseol

2-hydroxy-3-phenylbutyric acid ethyl ester

Conditions
ConditionsYield
With formic acid; triethylamine; Pd0-EnCatTM In ethyl acetate at 23℃; for 24h;94%
77-83-8

fraeseol

72655-88-0, 30913-58-7

2-Hydroxy-3-phenyl-3-butensaeureaethylester

Conditions
ConditionsYield
With perchloric acid In benzene at 80℃; for 0.5h; Inert atmosphere;93%
With Nafion-H In dichloromethane Heating;70%
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Consensus Reports

Reported in EPA TSCA Inventory.

Specification

The Ethyl 3-methyl-3-phenylglycidate, with the CAS registry number 77-83-8, is also known as 3-Methyl-3-phenyl glycidic acid ethyl ester. It belongs to the classification code of Mutation Data . Its EINECS registry number is 201-061-8. This chemical's molecular formula is C12H14O3 and molecular weight is 206.24. What's more, both its IUPAC name and systematic name are the same which is called Ethyl 3-methyl-3-phenyloxirane-2-carboxylate. It should be stored in a cool, dry and well-ventilated place. Because of its pleasant taste and aroma, it finds use in the fragrance industry, in artificial flavors, and in cosmetics. Its end applications include perfumes, soaps, beauty care products, detergents, pharmaceuticals, baked goods, candies, ice cream, and others.

Physical properties about Ethyl 3-methyl-3-phenylglycidate are: (1)ACD/LogP: 1.655; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 1.66; (4)ACD/LogD (pH 7.4): 1.66; (5)ACD/BCF (pH 5.5): 10.66; (6)ACD/BCF (pH 7.4): 10.66; (7)ACD/KOC (pH 5.5): 189.29; (8)ACD/KOC (pH 7.4): 189.29; (9)#H bond acceptors: 3; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 4; (12)Polar Surface Area: 38.83 Å2; (13)Index of Refraction: 1.525; (14)Molar Refractivity: 55.47 cm3; (15)Molar Volume: 181.009 cm3; (16)Polarizability: 21.99×10-24cm3; (17)Surface Tension: 39.792 dyne/cm; (18)Density: 1.139 g/cm3; (19)Flash Point: 109.371 °C; (20)Enthalpy of Vaporization: 51.185 kJ/mol; (21)Boiling Point: 273.5 °C at 760 mmHg; (22)Vapour Pressure: 0.006 mmHg at 25 °C.

Preparation of Ethyl 3-methyl-3-phenylglycidate: this chemical can be prepared by chloroacetic acid ethyl ester with 1-phenyl-ethanone. This reaction needs reagent sodium ethoxide and solvent diethyl ether at ambient temperature. The reaction time is 1 hour.

Ethyl 3-methyl-3-phenylglycidate  can be prepared by chloroacetic acid ethyl ester with 1-phenyl-ethanone.

Uses of Ethyl 3-methyl-3-phenylglycidate: it is used to produce other chemicals. For example, it can react with guanidine; nitrate to get 2-guanidino-3-phenylbutanoic acid. The reaction occurs with reagent sodium ethoxide and solvent ethanol at temperature of 25 °C. The reaction time is 14 hours. The yield is 65 %.

Ethyl 3-methyl-3-phenylglycidate can react with guanidine; nitrate to get 2-guanidino-3-phenylbutanoic acid.

When you are dealing with this chemical, you should be very careful. This chemical may cause inflammation to the skin or other mucous membranes and it is flammable. It is irritating to eyes, respiratory system and skin. Therefore, you should wear suitable protective clothing, gloves and eye/face protection. In addition, you should keep away from sources of ignition. In case of contacting with eyes, you should rinse immediately with plenty of water and seek medical advice.

You can still convert the following datas into molecular structure:
(1) SMILES: O=C(OCC)C2OC2(c1ccccc1)C
(2) InChI: InChI=1S/C12H14O3/c1-3-14-11(13)10-12(2,15-10)9-7-5-4-6-8-9/h4-8,10H,3H2,1-2H3
(3) InChIKey: LQKRYVGRPXFFAV-UHFFFAOYSA-N

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
guinea pig LD50 oral 4050mg/kg (4050mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

GASTROINTESTINAL: OTHER CHANGES
Food and Cosmetics Toxicology. Vol. 2, Pg. 327, 1964.
rat LD50 oral 5470mg/kg (5470mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

SENSE ORGANS AND SPECIAL SENSES: OTHER: EYE

SKIN AND APPENDAGES (SKIN): HAIR: OTHER
Food and Cosmetics Toxicology. Vol. 2, Pg. 327, 1964.