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CAS No.: | 623-70-1 |
---|---|
Name: | Ethyl crotonate |
Article Data: | 76 |
Molecular Structure: | |
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: | F,C,Xi |
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 |
3-(ethylthio)-butanoic acid, ethyl ester
ethyl (E)-crotonate
Conditions | Yield |
---|---|
With tetrabutylammomium bromide In ethanol electrolysis; | 98% |
Conditions | Yield |
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di(rhodium)tetracarbonyl dichloride In benzene under 20685.9 Torr; for 18h; Ambient temperature; | 97% |
Conditions | Yield |
---|---|
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℃; |
ethyl (E)-crotonate
Conditions | Yield |
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With CF3CO2H In benzene-d6 React. at 25°C, 10 h.; Monitored by (1)H-NMR.; | 95% |
Conditions | Yield |
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silver-graphite; zinc In tetrahydrofuran at -78℃; for 0.166667h; | 79% |
Conditions | Yield |
---|---|
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; |
Conditions | Yield |
---|---|
With bis(triphenylphosphine)nickel(II) chloride; n-butyllithium; 1,8-diazabicyclo[5.4.0]undec-7-ene; triphenylphosphine In tetrahydrofuran; hexane Ambient temperature; | 77% |
Conditions | Yield |
---|---|
sulfuric acid In ethanol for 2h; Heating; | 73% |
carbon monoxide
sodium ethanolate
allyl bromide
A
ethyl 3-butenoate
B
ethyl (E)-crotonate
Conditions | Yield |
---|---|
Na2PdCl4-dppe In ethanol at 50℃; for 2h; | A 17% B 72% |
Conditions | Yield |
---|---|
for 2h; Solid phase reaction; esterification; | 69% |
Reported in EPA TSCA Inventory.
DOT Classification: 3; Label: Flammable Liquid
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%.
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%.
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. |