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623-70-1

Basic Information
CAS No.: 623-70-1
Name: Ethyl crotonate
Article Data: 76
Molecular Structure:
Molecular Structure of 623-70-1 (Ethyl crotonate)
Formula: C6H10O2
Molecular Weight: 114.144
Synonyms: 2-Butenoicacid, ethyl ester, (E)-;Crotonic acid, ethyl ester, (E)- (8CI);(E)-2-Butenoicacid ethyl ester;(E)-Ethyl but-2-enoate;Ethyl (E)-2-butenoate;Ethyl trans-2-butenoate;Ethyl trans-crotonate;trans-2-Butenoicacid ethyl ester;
EINECS: 210-808-7
Density: 0.915 g/cm3
Melting Point: -79oC
Boiling Point: 137.999 °C at 760 mmHg
Flash Point: 28.333 °C
Solubility: Soluble in ethanol, ethyl ether, insoluble in water
Appearance: Colorless oily liquid with piquancy taste
Hazard Symbols: FlammableF,CorrosiveC,IrritantXi
Risk Codes: 11-34-36
Safety: 16-26-36/37/39-45-9-33
Transport Information: UN 1862 3/PG 2
PSA: 26.30000
LogP: 1.12560
Synthetic route
90201-28-8

3-(ethylthio)-butanoic acid, ethyl ester

623-70-1

ethyl (E)-crotonate

Conditions
ConditionsYield
With tetrabutylammomium bromide In ethanol electrolysis;98%
107467-99-2

ethyl trans-2-methylthiirane carboxylate

CO

CO

623-70-1

ethyl (E)-crotonate

Conditions
ConditionsYield
di(rhodium)tetracarbonyl dichloride In benzene under 20685.9 Torr; for 18h; Ambient temperature;97%
867-13-0

diethoxyphosphoryl-acetic acid ethyl ester

75-07-0

acetaldehyde

623-70-1

ethyl (E)-crotonate

Conditions
ConditionsYield
With potassium carbonate In 1,4-dioxane at 25℃; for 2.2h;95%
With sodium hydride In tetrahydrofuran 1.) r.t., 1 h; 2.) -70 deg C then up to 0 deg C over 2 h;90%
Stage #1: diethoxyphosphoryl-acetic acid ethyl ester With sodium hydride In tetrahydrofuran; mineral oil at 20℃; for 0.5h;
Stage #2: acetaldehyde In tetrahydrofuran; mineral oil at 0 - 20℃;

fac-tricarbonyl{1-ethoxy-1-oxo-2-butenyl-C(3),O}(triphenylphosphine)rhenium

623-70-1

ethyl (E)-crotonate

Conditions
ConditionsYield
With CF3CO2H In benzene-d6 React. at 25°C, 10 h.; Monitored by (1)H-NMR.;95%
86294-63-5

ethyl α-bromo-α-trimethylsilylacetate

75-07-0

acetaldehyde

623-70-1

ethyl (E)-crotonate

Conditions
ConditionsYield
silver-graphite; zinc In tetrahydrofuran at -78℃; for 0.166667h;79%
64-17-5

ethanol

107-93-7

(E)-but-2-enoic acid

623-70-1

ethyl (E)-crotonate

Conditions
ConditionsYield
With sulfuric acid In benzene Heating;78.5%
With sulfuric acid; magnesium sulfate In benzene Heating; Yield given;
With phosphorus pentoxide 1.) 0-5 deg C, 2.) reflux, 3 h; Yield given. Multistep reaction;
With bis(2,2,2-trifluoroethoxy)diphenylsulfurane 1.) THF, -78 deg C, 2.) THF, -78 deg C; Yield given. Multistep reaction;
2969-81-5

4-bromoethylbutanoate

623-70-1

ethyl (E)-crotonate

Conditions
ConditionsYield
With bis(triphenylphosphine)nickel(II) chloride; n-butyllithium; 1,8-diazabicyclo[5.4.0]undec-7-ene; triphenylphosphine In tetrahydrofuran; hexane Ambient temperature;77%
623-81-4

diethyl sulphite

107-93-7

(E)-but-2-enoic acid

623-70-1

ethyl (E)-crotonate

Conditions
ConditionsYield
sulfuric acid In ethanol for 2h; Heating;73%
201230-82-2

carbon monoxide

141-52-6

sodium ethanolate

106-95-6

allyl bromide

A

1617-18-1

ethyl 3-butenoate

B

623-70-1

ethyl (E)-crotonate

Conditions
ConditionsYield
Na2PdCl4-dppe In ethanol at 50℃; for 2h;A 17%
B 72%
107-93-7

(E)-but-2-enoic acid

Fe(ClO4)3(CH3CH2OH)6/SiO2

Fe(ClO4)3(CH3CH2OH)6/SiO2

623-70-1

ethyl (E)-crotonate

Conditions
ConditionsYield
for 2h; Solid phase reaction; esterification;69%
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    CAS 623-70-1 C6H10O2 Ethyl crotonate Physical State: Liquid Color: clear, colorless Odor: none reported pH: Not available. Vapor Pressure: Not available. Viscosity: Not available. Boiling Point: 142.0 -

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    CAS RN.: 623-70-1;10544-63-5 EINECS: 210-808-7;234-125-9 Molecular Weight:

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    Name :Ethyl crotonate Synonyms :Ethyl 2-butenoate; Ethyl (E)-2-butenoate Molecular Formula :C6H10O2 Molecular Weight :114.14 FEMA :3486 Dens…Appearance:colorless liquid Storage:stored in airtight containers in a cool, dry, ventilated place Packa

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Consensus Reports

Reported in EPA TSCA Inventory.

Standards and Recommendations

DOT Classification:  3; Label: Flammable Liquid

Specification

The Ethyl (E)-crotonate, with the CAS registry number 623-70-1, is also known as 2-Butenoic acid, ethylester, (2E)-. It belongs to the product categories of C6 to C7; Carbonyl Compounds; Esters. Its EINECS number is 210-808-7. This chemical's molecular formula is C6H10O2 and molecular weight is 114.14. What's more, its systematic name is Ethyl (2E)-2-butenoate. Its classification code is Skin / Eye Irritant. It should be sealed and stored in a cool and dry place. Moreover, it should be protected from oxides, heat, water and moisture. It is used as an organic synthesis intermediates, and it can be also used as paint and coating softener and solvent of cellulose ester.

Physical properties of Ethyl (E)-crotonate are: (1)ACD/LogP: 1.806; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 1.81; (4)ACD/LogD (pH 7.4): 1.81; (5)ACD/BCF (pH 5.5): 13.89; (6)ACD/BCF (pH 7.4): 13.89; (7)ACD/KOC (pH 5.5): 228.88; (8)ACD/KOC (pH 7.4): 228.88; (9)#H bond acceptors: 2; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 3; (12)Polar Surface Area: 26.3 Å2; (13)Index of Refraction: 1.422; (14)Molar Refractivity: 31.679 cm3; (15)Molar Volume: 124.673 cm3; (16)Polarizability: 12.558×10-24cm3; (17)Surface Tension: 26.48 dyne/cm; (18)Density: 0.916 g/cm3; (19)Flash Point: 28.333 °C; (20)Enthalpy of Vaporization: 37.532 kJ/mol; (21)Boiling Point: 137.999 °C at 760 mmHg; (22)Vapour Pressure: 6.87 mmHg at 25°C.

Preparation: this chemical can be prepared by acetic acid ethyl ester and but-2-enoic acid at the ambient temperature. This reaction will need reagent iron (III) perchlorate (ITP) with the reaction time of 2 hours. The yield is about 60%.

Ethyl (E)-crotonate can be prepared by acetic acid ethyl ester and but-2-enoic acid at the ambient temperature

Uses of Ethyl (E)-crotonate: it can be used to produce 5-butyl-3-methyl-dihydro-furan-2-one at the temperature of 0 °C. It will need reagents SmI2, t-BuOH and solvent tetrahydrofuran with the reaction time of 10 hours. The yield is about 70%.

Ethyl (E)-crotonate can be used to produce 5-butyl-3-methyl-dihydro-furan-2-one at the temperature of 0 °C

When you are using this chemical, please be cautious about it as the following:
It is highly flammable, so you should keep it away from sources of ignition - No smoking. It is irritating to eyes and can cause burns. You need to keep the container in a well-ventilated place and take precautionary measures against static discharges. In case of contact with eyes, you should rinse immediately with plenty of water and seek medical advice. When using it, you need to wear suitable protective clothing, gloves and eye/face protection. In case of accident or if you feel unwell, you must seek medical advice immediately (show the label where possible).

You can still convert the following datas into molecular structure:
(1)SMILES: O=C(OCC)/C=C/C
(2)Std. InChI: InChI=1S/C6H10O2/c1-3-5-6(7)8-4-2/h3,5H,4H2,1-2H3/b5-3+
(3)Std. InChIKey: ZFDIRQKJPRINOQ-HWKANZROSA-N

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
guinea pig LD50 skin > 5gm/kg (5000mg/kg)   Food and Cosmetics Toxicology. Vol. 19, Pg. 115, 1981.
rat LD50 oral 3gm/kg (3000mg/kg)   Journal of Industrial Hygiene and Toxicology. Vol. 26, Pg. 269, 1944.