3-(ethylthio)-butanoic acid, ethyl ester
ethyl (E)-crotonate
Conditions | Yield |
---|---|
With tetrabutylammomium bromide In ethanol electrolysis; | 98% |
Conditions | Yield |
---|---|
di(rhodium)tetracarbonyl dichloride In benzene under 20685.9 Torr; for 18h; Ambient temperature; | 97% |
diethoxyphosphoryl-acetic acid ethyl ester
acetaldehyde
ethyl (E)-crotonate
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 |
---|---|
With CF3CO2H In benzene-d6 React. at 25°C, 10 h.; Monitored by (1)H-NMR.; | 95% |
Conditions | Yield |
---|---|
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% |
(E)-crotonaldehyde diethyl acetal
ethyl (E)-crotonate
Conditions | Yield |
---|---|
With tert.-butylhydroperoxide; dipyridinium dichromate In dichloromethane for 7h; Ambient temperature; | 67% |
diethoxyphosphoryl-acetic acid ethyl ester
4-methyl-benzaldehyde
ethyl (E)-crotonate
Conditions | Yield |
---|---|
C-200 (barium hydroxide) In tetrahydrofuran; water for 0.166667h; Ambient temperature; sonication; | 61% |
Conditions | Yield |
---|---|
With tetrakis(triphenylphosphine)nickel(0) In N,N,N,N,N,N-hexamethylphosphoric triamide for 3h; Heating; | 55% |
3-aminobutanoic acid ethyl ester
4-chloro-2,2-dimethyl-2H-benzo[e][1,3]oxazine
A
2,4-bis(2-hydroxyphenyl)-6-methylpyrimidine
C
ethyl (E)-crotonate
Conditions | Yield |
---|---|
at 150 - 160℃; for 4h; | A 38% B 10% C n/a |
at 150 - 160℃; for 4h; Product distribution; Mechanism; | A 38% B 10% C n/a |
(E)-but-2-enoic acid
(2,2-diethoxyvinylidene)triphenylphosphorane
A
ethyl (E)-crotonate
B
ethyl (triphenylphosphoranylidene)acetate
Conditions | Yield |
---|---|
In tetrahydrofuran for 3h; Ambient temperature; | A 33% B n/a |
ethanol
carbon monoxide
3-chloroprop-1-ene
A
ethyl 3-butenoate
B
ethyl (E)-crotonate
Conditions | Yield |
---|---|
carbonylchlorobis(triethylphosphine)rhodium(I) at 120℃; under 30002.4 Torr; for 4h; | A 28% B 12 % Turnov. |
3-aminobutanoic acid ethyl ester
4-chloro-2-methyl-2-methoxycarbonylmethyl-2H-1,3-benzoxazine
A
2-(2-hydroxyphenyl)-6-methyl-4(3H)-pyrimidinone
B
ethyl (E)-crotonate
Conditions | Yield |
---|---|
at 170 - 180℃; for 3h; | A 26% B n/a |
ethyl (E)-crotonate
Conditions | Yield |
---|---|
With aluminium amalgam In diethyl ether; ethanol Ambient temperature; | 18% |
Conditions | Yield |
---|---|
With sulfuric acid | |
With sulfuric acid |
Conditions | Yield |
---|---|
With aluminum oxide at 325 - 350℃; |
ethanol
trans-chrotonyl chloride
ethyl (E)-crotonate
Conditions | Yield |
---|---|
With sodium hydroxide at 0 - 5℃; |
Conditions | Yield |
---|---|
With ethanol; ammonia |
3-methyl-1,4-diphenyl-1,2,3,4-tetrahydro-1,4-epoxido-naphthalene-2-carboxylic acid ethyl ester
A
1,3-diphenylisobenzofuran
B
ethyl (E)-crotonate
Conditions | Yield |
---|---|
und Erhitzen des Reaktionsprodukts mit Kaliumacetat; |
Conditions | Yield |
---|---|
With piperidine; pyridine |
diethyl ether
2-methyl-butane-1,3,3-tricarboxylic acid triethyl ester
sodium ethanolate
methyl iodide
A
2,2-dimethylmalonic acid diethyl ester
B
ethyl (E)-crotonate
Conditions | Yield |
---|---|
unter Kuehlung; |
Conditions | Yield |
---|---|
With N,N-diethylaniline |
Conditions | Yield |
---|---|
With (isomerization); diethylamine In diethyl ether at 40℃; Kinetics; other catalysts; |
4-methyloxetan-2-one
ethyl iodide
ethyl (E)-crotonate
Conditions | Yield |
---|---|
With 18-crown-6 ether; potassium naphthalenide 1) THF, 20 deg C, 10 min; Yield given. Multistep reaction; |
Conditions | Yield |
---|---|
With 2,5,8,9-tetraaza-1-phosphabicyclo[3.3.3]undecane 2,8,9-tris(1-methylethyl) In various solvent(s) at 20℃; for 4h; Michael addition; | 100% |
Conditions | Yield |
---|---|
Stage #1: C26H38N2O4 With lithium hexamethyldisilazane In tetrahydrofuran at -78℃; for 1h; Stage #2: ethyl (E)-crotonate In tetrahydrofuran at -78 - -20℃; for 2h; Michael addition; | 100% |
Conditions | Yield |
---|---|
With lithium perchlorate; triethylamine In diethyl ether for 16h; Michael addition; | 100% |
Methyl thioglycolate
ethyl (E)-crotonate
4-ethoxycarbonyl-2-methylthiolan-3-one
Conditions | Yield |
---|---|
In ethyl acetate; N,N-dimethyl-formamide | 100% |
Conditions | Yield |
---|---|
In tetrahydrofuran | 100% |
nitromethane
ethyl (E)-crotonate
3-methyl-4-nitrobutyric acid ethyl ester
Conditions | Yield |
---|---|
With 2,5,8,9-tetraaza-1-phosphabicyclo[3.3.3]undecane 2,8,9-tris(1-methylethyl) In various solvent(s) at -63℃; for 0.15h; Michael addition; | 99% |
With N,N,N',N'-tetramethylguanidine for 18h; | 99.2% |
With N,N,N',N'-tetramethylguanidine at 20℃; for 24h; Michael addition; | 91% |
With N,N,N',N'-tetramethylguanidine at 20℃; for 24h; Inert atmosphere; | 82% |
dimethyl amine
ethyl (E)-crotonate
3-Dimethylamino-buttersaeureethylester
Conditions | Yield |
---|---|
With carbon dioxide for 1h; Ambient temperature; | 99% |
p-methoxybenzyl chloride
ethyl (E)-crotonate
ethyl 4-(4-methoxyphenyl)-3-methylbutanoate
Conditions | Yield |
---|---|
Stage #1: p-methoxybenzyl chloride With iodine; magnesium In tetrahydrofuran for 2h; Stage #2: With copper(l) iodide; N,N,N,N,-tetramethylethylenediamine In tetrahydrofuran at -78℃; for 0.833333h; Stage #3: ethyl (E)-crotonate With chloro-trimethyl-silane In tetrahydrofuran at -30℃; for 18h; | 99% |
With copper(l) iodide; chloro-trimethyl-silane; N,N,N,N,-tetramethylethylenediamine; iodine; magnesium Yield given. Multistep reaction; |
Conditions | Yield |
---|---|
With indium(III) chloride In 1,2-dichloro-ethane at 60℃; for 18h; Inert atmosphere; | 99% |
2-aminophenylboronic acid
ethyl (E)-crotonate
4-methyl-3,4-dihydroquinolin-2(1H)-one
Conditions | Yield |
---|---|
With [Rh(OH)(cod)]2; potassium carbonate In water at 50℃; for 5h; Inert atmosphere; | 99% |
Conditions | Yield |
---|---|
With bromine In tetrachloromethane for 2h; Heating; | 98% |
With bromine In tetrachloromethane for 24h; Heating; | 78% |
With N-Bromosuccinimide In 1,4-dioxane; water |
butyraldehyde
ethyl (E)-crotonate
3-methyl-4-oxo-heptanoic acid ethyl ester
Conditions | Yield |
---|---|
With triisopropylsilanethiol; trans-di-O-tert-butyl hyponitrite In 1,4-dioxane at 60℃; for 3.5h; | 98% |
trimethyl(4-mercaptomethylphenyl)silane
ethyl (E)-crotonate
3-(4-trimethylsilanyl-benzylsulfanyl)-butyric acid ethyl ester
Conditions | Yield |
---|---|
With tetrabutyl ammonium fluoride In tetrahydrofuran at 20℃; for 0.5h; Michael addition; | 98% |
With tetrabutyl ammonium fluoride In tetrahydrofuran at 20℃; for 0.5h; Michael addition; | 98% |
N-(diphenylmethylene)glycine tert-butyl ester
ethyl (E)-crotonate
Conditions | Yield |
---|---|
With 4 A molecular sieve; calcium bis-iso-propoxide; 2,2'-methylene bis((4S)-4-phenyl-2-oxazoline) In tetrahydrofuran at -30℃; for 12h; Michael addition; | 98% |
ethyl (E)-crotonate
Conditions | Yield |
---|---|
With dichlorobis(tri-O-tolylphosphine)palladium; tetrabutylammomium bromide; triethylamine In N,N-dimethyl-formamide at 110℃; Inert atmosphere; | 98% |
With tetrakis(tris(2-methyl)phenyl)phosphinepalladium; tetrabutylammomium bromide; triethylamine In N,N-dimethyl-formamide at 110℃; Inert atmosphere; | 81% |
Conditions | Yield |
---|---|
With ytterbium(III) triflate In tetrahydrofuran for 6h; Ambient temperature; | 97% |
With 1,8-diazabicyclo[5.4.0]undec-7-ene In acetonitrile for 20h; Kinetics; Solvent; Temperature; Time; Michael Addition; Reflux; | 86% |
In ethanol at 20℃; for 38h; | 84.3% |
Conditions | Yield |
---|---|
With chloro-trimethyl-silane; copper(l) chloride In tetrahydrofuran for 1h; 0 to 20 deg C; | 97% |
ethyl (E)-crotonate
((R)-1-Phenyl-ethyl)-(3-trimethylsilanyl-prop-2-ynyl)-amine
(R)-3-[((R)-1-Phenyl-ethyl)-(3-trimethylsilanyl-prop-2-ynyl)-amino]-butyric acid ethyl ester
Conditions | Yield |
---|---|
97% |
ethyl (E)-crotonate
Conditions | Yield |
---|---|
With 1,8-diazabicyclo[5.4.0]undec-7-ene In 1-methyl-pyrrolidin-2-one at 140℃; for 1h; Michael Addition; | 97% |
Conditions | Yield |
---|---|
With tetraethoxy orthosilicate; cesium fluoride In neat (no solvent) at 25℃; for 0.166667h; | 96% |
Ethyl propionate
ethyl (E)-crotonate
Diethyl 2,3-dimethylpentanedioate
Conditions | Yield |
---|---|
With lithium diisopropyl amide In tetrahydrofuran; hexane at -78℃; for 1h; | 96% |
Conditions | Yield |
---|---|
With chloro-trimethyl-silane; copper(l) chloride In tetrahydrofuran 0 to 20 deg C, 0.5-1.5 h; other α,β-ethylenic ester, other organomanganese chlorides; | 96% |
With chloro-trimethyl-silane; copper(l) chloride In tetrahydrofuran 0 to 20 deg C, 0.5-1.5 h; | 96% |
ethyl (E)-crotonate
3-azidobutyric acid ethyl ester
Conditions | Yield |
---|---|
With tris-(2-chloro-ethyl)-amine; triethylamine In benzene at 80℃; for 24h; | 96% |
para-iodoanisole
ethyl (E)-crotonate
(E)-ethyl 3-(4-methoxyphenyl)but-2-enoate
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide at 110℃; for 6h; Heck Reaction; Inert atmosphere; | 96% |
With potassium carbonate; triphenylphosphine; palladium diacetate In N,N-dimethyl-formamide for 0.15h; Heck reaction; microwave irradiation; | 87% |
ethyl (E)-crotonate
(2S,3R)-ethyl 2,3-dihydroxybutanoate
Conditions | Yield |
---|---|
With methanesulfonamide In water; tert-butyl alcohol at 0 - 24℃; Sharpless dihydroxylation; | 96% |
N-methoxylamine hydrochloride
ethyl (E)-crotonate
(2E)-N-methoxybut-2-enamide
Conditions | Yield |
---|---|
Stage #1: N-methoxylamine hydrochloride With lithium hexamethyldisilazane In tetrahydrofuran at -78℃; for 1h; Stage #2: ethyl (E)-crotonate In tetrahydrofuran | 96% |
ethyl (E)-crotonate
Conditions | Yield |
---|---|
In toluene at 40℃; for 24h; Inert atmosphere; | 96% |
ethyl (E)-crotonate
Conditions | Yield |
---|---|
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium carbonate In N,N-dimethyl-formamide at 110℃; for 4h; Inert atmosphere; | 96% |
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. |
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