ETHYL CROTONATE

ETHYL CROTONATE Basic information
Product Name:ETHYL CROTONATE
Synonyms:ETHYL TRANS-CROTONATE;ETHYL TRANS-2-BUTENOATE;ETHYL T2 BUTENOATE;FEMA 3486;CROTONIC ACID ETHYL ESTER;2-Butenoicacid,ethylester;but-2-enoicacidethylester;Ethyl (2E)-2-butenoate
CAS:10544-63-5
MF:C6H10O2
MW:114.14
EINECS:210-808-7
Product Categories:Pharmaceutical Intermediates
Mol File:10544-63-5.mol
ETHYL CROTONATE Structure
ETHYL CROTONATE Chemical Properties
Melting point 37.22°C (estimate)
Boiling point 142-143 °C(lit.)
density 0.918 g/mL at 25 °C(lit.)
vapor density 3.9 (vs air)
refractive index n20/D 1.424(lit.)
FEMA 3486 | ETHYL TRANS-2-BUTENOATE
Fp 36 °F
storage temp. Flammables area
form Liquid
color Clear colorless
Odorat 10.00 % in dipropylene glycol. pungent fruity acrid ester
Odor Typefermented
JECFA Number1806
LogP1.806 (est)
EPA Substance Registry System2-Butenoic acid, ethyl ester (10544-63-5)
Safety Information
Hazard Codes F,C
Risk Statements 11-34
Safety Statements 16-26-36/37/39-45
RIDADR UN 1862 3/PG 2
WGK Germany 2
RTECS GQ3500000
HS Code 29161900
MSDS Information
ProviderLanguage
ACROS English
SigmaAldrich English
ALFA English
ETHYL CROTONATE Usage And Synthesis
Chemical Propertiesclear colorless liquid
Chemical PropertiesEthyl crotonate has a powerful, sour, caramellic-fruity odor.
OccurrenceReported found in Fragaria vesca. Also reported found in guava fruit, guava peel, pineapple, white wine, yellow passion fruit, fresh mango, naranjilla fruit, mussel, loganberry, apple, papaya, concord grape, strawberry, rum, cocoa, plum, kiwifruit and other natural sources.
UsesCrotonic Acid Ethyl Ester, is an intermediate for the preparation of various pharmaceutical compounds. It can be used for the synthesis of (+)-trans-Trikentrin A.
DefinitionChEBI: Ethyl crotonate is a fatty acid ester.
PreparationBy esterification of crotonic acid with ethyl alcohol in the presence of concentrated H2SO4.
Taste threshold valuesTaste characteristics at 10 ppm: rum, cognac and pungent with caramellic and fruity nuances.
Synthesis Reference(s)Journal of the American Chemical Society, 112, p. 2716, 1990 DOI: 10.1021/ja00163a038
Synthetic Communications, 14, p. 701, 1984 DOI: 10.1080/00397918408059583
General DescriptionA clear colorless liquid with a pungent odor. Flash point 36°F. Less dense than water and insoluble in water. Vapors heavier than air.
Air & Water ReactionsHighly flammable. Insoluble in water.
Reactivity ProfileETHYL CROTONATE is an ester. Esters react with acids to liberate heat along with alcohols and acids. Strong oxidizing acids may cause a vigorous reaction that is sufficiently exothermic to ignite the reaction products. Heat is also generated by the interaction of esters with caustic solutions. Flammable hydrogen is generated by mixing esters with alkali metals and hydrides.
Health HazardMay cause toxic effects if inhaled or absorbed through skin. Inhalation or contact with material may irritate or burn skin and eyes. Fire will produce irritating, corrosive and/or toxic gases. Vapors may cause dizziness or suffocation. Runoff from fire control or dilution water may cause pollution.
Fire HazardHIGHLY FLAMMABLE: Will be easily ignited by heat, sparks or flames. Vapors may form explosive mixtures with air. Vapors may travel to source of ignition and flash back. Most vapors are heavier than air. They will spread along ground and collect in low or confined areas (sewers, basements, tanks). Vapor explosion hazard indoors, outdoors or in sewers. Runoff to sewer may create fire or explosion hazard. Containers may explode when heated. Many liquids are lighter than water.
Safety ProfileSlightly toxic by ingestion. Corrosive. An eye irritant and lachrymator. A flammable liquid. When heated to decomposition it emits acrid smoke and irritating fumes.
ETHYL CROTONATE Preparation Products And Raw materials
Preparation ProductsEthyl 4-bromocrotonate-->Oxiracetam-->Ethyl 4-Methylpyrazole-3-carboxylate-->2-HYDROXY-4-METHYLQUINOLINE-->2-METHOXY-6-METHYLBENZOIC ACID ETHYL ESTER-->ETHYL 3-(METHYLTHIO)BUTYRATE-->3-(dimethylamino)butan-1-ol
2-CARBETHOXY-5,7-DIHYDROXY-4'-METHOXYISOFLAVONE DIETHYL DICYANOFUMARATE, 97 Ethyl 3,3-dimethylacrylate BUTOPYRONOXYL RESCINNAMINE Chlorogenic acid Ethyl 4-bromocrotonate ALPHA-CYANOCINNAMIC ACID ETHYL ESTER AFLATOXIN G1 Diethyl isopropylidenemalonate 5-Carbethoxy-4,6-dimethyl-2-pyrone DIETHYL ETHYLIDENEMALONATE CYTOCHALASIN A Monoethyl fumarate Benzyl cinnamate Ethyl 4-nitrocinnamate Ethyl cinnamate ETHYL 2-CYANO-3-METHYLCROTONATE

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