ethyl 2-((tert-butyl(1-(diethoxyphosphoryl)-2,2-dimethylpropyl)amino)oxy)-2-methylpropanoate
A
Diethyl phosphonate
B
diethyl (1-(tert-butyl((ethoxycarbonyl)oxy)amino)-2,2-dimethylpropyl)phosphonate
C
methyl methacrylate
Conditions | Yield |
---|---|
With thiophenol at 70℃; under 7.50075E-06 Torr; | A 85% B 15% C n/a |
Conditions | Yield |
---|---|
With pyridine In dichloromethane; water | A n/a B 84% |
Conditions | Yield |
---|---|
dodecacarbonyl-triangulo-triruthenium at 100℃; under 11400 Torr; for 3h; | 71% |
β-acetoxy-isobutyric acid ethyl ester
methyl methacrylate
Conditions | Yield |
---|---|
With 1,8-diazabicyclo[5.4.0]undec-7-ene In benzene at 80℃; for 5h; | 60% |
Conditions | Yield |
---|---|
phosphorus-molybdenum catalyst at 310℃; | 50% |
With oxygen at 80℃; under 22502.3 Torr; for 1h; Catalytic behavior; |
ethanol
chloroform
acetone
A
ethyl 2-chloro-2-methylpropanoate
B
methyl methacrylate
Conditions | Yield |
---|---|
With 1,8-diazabicyclo[5.4.0]undec-7-ene In benzonitrile; acetonitrile at 50℃; for 42h; | A 25% B 46% |
ethyl 2-bromoisobutyrate
dimanganese decacarbonyl
A
diethyl 2,2,3,3-tetramethylsuccinate
C
diethyl 2,2-dimethyl-4-methylenepenta-1,5-dioate
D
methyl methacrylate
E
Ethyl isobutyrate
Conditions | Yield |
---|---|
In tetrahydrofuran Irradiation (UV/VIS); (N2 or Ar); 250-W sun lamp, 3 h; colorless solution is filtered, (1)H-NMR; | A 45% B 13% C 5% D 12% E 17% |
In chloroform-d1 Irradiation (UV/VIS); (N2 or Ar); 250-W sun lamp, 3 h; colorless solution is filtered, (1)H-NMR; | A 36% B 9% C 4% D 5% E 13% |
ethyl 2-bromoisobutyrate
A
diethyl 2,2,3,3-tetramethylsuccinate
B
diethyl 2,2-dimethyl-4-methylenepenta-1,5-dioate
C
methyl methacrylate
D
Ethyl isobutyrate
Conditions | Yield |
---|---|
With {bis(triphenylphosphine)nitrogen}{manganese(carbonyl)5} In tetrahydrofuran for 5h; | A 36% B 3% C 6% D 35% |
ethyl 2-bromoisobutyrate
bis(triphenylphosphineiminium) pentacarbonylmanganate(1-)
A
diethyl 2,2,3,3-tetramethylsuccinate
B
diethyl 2,2-dimethyl-4-methylenepenta-1,5-dioate
C
methyl methacrylate
D
Ethyl isobutyrate
Conditions | Yield |
---|---|
In tetrahydrofuran (N2 or Ar); solution is allowed to stand for 5 h; determination by NMR and MS fragmentation; | A 36% B 3% C 6% D 35% |
ethyl 2-bromoisobutyrate
sodium pentacarbonyl manganate
A
diethyl 2,2,3,3-tetramethylsuccinate
B
diethyl 2,2-dimethyl-4-methylenepenta-1,5-dioate
C
methyl methacrylate
D
Ethyl isobutyrate
Conditions | Yield |
---|---|
In tetrahydrofuran (N2 or Ar); solution is allowed to stand for 5 h; determination by NMR and MS fragmentation; | A 14% B 1% C 16% D 36% |
Conditions | Yield |
---|---|
With quinoline | |
With N,N-diethylaniline |
Conditions | Yield |
---|---|
With water; diethylamine |
ethyl 2-ethoxy-2-methylpropanoate
methyl methacrylate
Conditions | Yield |
---|---|
With sulfuric acid; benzene | |
With acidic cation exchange resin Amberlyst 70 at 50 - 145℃; Flow reactor; Green chemistry; |
ethanol
2-ethoxy-2-methyl-propanoic acid
A
ethyl 2-ethoxy-2-methylpropanoate
B
methyl methacrylate
Conditions | Yield |
---|---|
With sulfuric acid; tannic acid |
ethyl 2-chloro-2-methylpropanoate
methyl methacrylate
Conditions | Yield |
---|---|
With quinoline; hydroquinone | |
With iron(III) chloride | |
With zinc |
Conditions | Yield |
---|---|
at 475℃; |
ethyl 2-aminoisobutyrate hydrochloride
methyl methacrylate
Conditions | Yield |
---|---|
With hydrogenchloride; sodium nitrite at 20℃; |
poly(methacrylic acid)
propyl bromide
triethyl phosphite
A
β-diethoxyphosphoryl-isobutyric acid propyl ester
B
methyl methacrylate
C
phosphonic acid diethyl ester
Conditions | Yield |
---|---|
und Erwaermen des Reaktionsgemisches; |
sodium acetate
hydroquinone
3-hydroxy-2-methyl-propionic acid ethyl ester
methyl methacrylate
Conditions | Yield |
---|---|
Einw. von NaNO2-Loesung auf das Reaktionsprodukt; |
Conditions | Yield |
---|---|
With sulfuric acid |
Conditions | Yield |
---|---|
With phosphorus trichloride |
ethyl 2-hydroxy-2,2-dimethylethanoate
A
ethyl 2-chloro-2-methylpropanoate
B
methyl methacrylate
Conditions | Yield |
---|---|
With thionyl chloride anschliessenden Erwaermen mit wenig Pyridin; | |
With 1-chloro-1-(dimethylamino)-2-methyl-1-propene In dichloromethane at 20℃; for 2h; Inert atmosphere; | A 75 %Spectr. B 25 %Spectr. |
Brommethyl-methylmalonsaeure-ethyl-thioethylester
B
methyl methacrylate
Conditions | Yield |
---|---|
With ethyl [2]alcohol; vitamin B12s for 14h; Mechanism; Ambient temperature; other reactant; |
1-ethoxycarbonyl-1-methylethyl phenyl sulfoxide
methyl methacrylate
Conditions | Yield |
---|---|
In 1,4-dioxane at 90℃; Kinetics; Thermodynamic data; Ea, ΔS(excit.); |
methyl methacrylate
Conditions | Yield |
---|---|
In 1,4-dioxane at 70℃; Rate constant; |
methyl methacrylate
Conditions | Yield |
---|---|
In 1,4-dioxane at 70℃; Rate constant; |
methyl methacrylate
Conditions | Yield |
---|---|
In 1,4-dioxane at 70℃; Rate constant; |
methyl methacrylate
Conditions | Yield |
---|---|
In 1,4-dioxane at 70℃; Rate constant; |
methyl methacrylate
8-fluoro-5,11-dihydro-11-(4-piperidyldene)<1>benzoxepino<4,3-b>pyridine
Conditions | Yield |
---|---|
In ethanol Heating; | 100% |
Conditions | Yield |
---|---|
In tetrahydrofuran | 100% |
methyl methacrylate
ethyl 2-chloro-2-(hydroxyimino)acetate
5-Methyl-4,5-dihydro-isoxazole-3,5-dicarboxylic acid diethyl ester
Conditions | Yield |
---|---|
With triethylamine In diethyl ether Ambient temperature; | 99% |
α,α-dichloromethyl p-tolyl sulfoxide
methyl methacrylate
Conditions | Yield |
---|---|
With sodium hexamethyldisilazane In tetrahydrofuran at -78 - 0℃; for 2h; | 99% |
Conditions | Yield |
---|---|
With sodium hexamethyldisilazane In tetrahydrofuran at -78 - 20℃; | 99% |
With sodium hexamethyldisilazane In tetrahydrofuran at -78 - 20℃; for 3h; Inert atmosphere; | 90% |
With lithium diisopropyl amide In tetrahydrofuran diastereoselective reaction; | |
With sodium hexamethyldisilazane In tetrahydrofuran Inert atmosphere; |
(-)-(R)-dichloromethyl p-tolyl sulfoxide
methyl methacrylate
(1R,2S)-ethyl 2-chloro-1-methyl-2-((R)-p-tolylsulfinyl)cyclopropanecarboxylate
Conditions | Yield |
---|---|
With lithium diisopropyl amide In tetrahydrofuran at -85 - 20℃; Inert atmosphere; optical yield given as %ee; | 99% |
With lithium diisopropyl amide In tetrahydrofuran at -85 - 0℃; diastereoselective reaction; | 99% |
With (2R,5S)-menthone; sodium hexamethyldisilazane In tetrahydrofuran Inert atmosphere; |
n-perfluorohexyl iodide
methyl methacrylate
Ethyl 2-methyl-4,4,5,5,6,6,7,7,8,8,9,9,9-tridecafluorononanoate
Conditions | Yield |
---|---|
With tris-(trimethylsilyl)silane; sodium thiosulfate In dichloromethane; water at 20℃; for 4h; UV-irradiation; Sealed tube; | 99% |
Conditions | Yield |
---|---|
Stage #1: (S)-methyl p-tolyl sulfoxide With lithium diisopropyl amide In tetrahydrofuran at -70℃; for 0.916667h; Inert atmosphere; Stage #2: methyl methacrylate In tetrahydrofuran at -70 - -25℃; for 1.5h; Inert atmosphere; | 99% |
2-(propan-2-yl)adamantan-2-ol
methyl methacrylate
2-isopropyl-2-adamantyl methacrylate
Conditions | Yield |
---|---|
With sodium methylate In tetrahydrofuran at 77℃; for 24h; | 98% |
C-(p-nitrophenyl)-N-phenylnitrone
methyl methacrylate
Conditions | Yield |
---|---|
for 3h; | 97% |
methyl methacrylate
4-(2-perfluorodecyl)ethylbenzylalcohol
4-(2-perfluorodecyl)ethylbenzyl methacrylate
Conditions | Yield |
---|---|
With sodium hydride In benzene for 1h; Heating; | 97% |
methyl methacrylate
Conditions | Yield |
---|---|
With ethyl 2-methyl-2-methyl tellurium propionate; dimethyl ditelluride at 105℃; for 2h; | 97% |
methyl methacrylate
2-[4-(Benzyloxycarbonyl-methyl-amino)-benzoylamino]-malonic acid diethyl ester
2-[4-(Benzyloxycarbonyl-methyl-amino)-benzoylamino]-2-ethoxycarbonyl-4-methyl-pentanedioic acid diethyl ester
Conditions | Yield |
---|---|
With sodium ethanolate In ethanol Ambient temperature; | 96.4% |
2-aminopyridine
methyl methacrylate
N-(2-pyridyl)methylacrylamid, sodium salt
Conditions | Yield |
---|---|
With sodium In diethyl ether 1) 3h, 2) 12h, 20 deg C; | 96% |
Conditions | Yield |
---|---|
Stage #1: 3-(trifluoromethyl)pyridine With potassium phosphate; chloro(1,5-cyclooctadiene)rhodium(I) dimer; P,P'-(1,2-ethanediyl)bis{bis[3,5-di(trifluoromethyl)phenyl]phosphane} In toluene for 0.0833333h; Inert atmosphere; Microwave irradiation; Stage #2: methyl methacrylate In toluene at 120℃; for 24h; Inert atmosphere; Microwave irradiation; Sealed tube; regioselective reaction; | 96% |
Conditions | Yield |
---|---|
With potassium dihydrogenphosphate; chloro(1,5-cyclooctadiene)rhodium(I) dimer; P,P'-(1,2-ethanediyl)bis{bis[3,5-di(trifluoromethyl)phenyl]phosphane} In toluene at 120℃; for 24h; Inert atmosphere; Glovebox; Microwave irradiation; Sealed tube; | 96% |
methyl methacrylate
Conditions | Yield |
---|---|
With disodium hydrogenphosphate; (S)-STRIP; palladium diacetate; silver sulfate In toluene at 60℃; for 48h; Schlenk technique; stereoselective reaction; | 96% |
Conditions | Yield |
---|---|
With tetraethoxy orthosilicate; cesium fluoride In neat (no solvent) at 25℃; for 0.333333h; | 95% |
trimethyl(4-mercaptomethylphenyl)silane
methyl methacrylate
2-methyl-3-(4-trimethylsilanyl-benzylsulfanyl)-propionic acid ethyl ester
Conditions | Yield |
---|---|
With tetrabutyl ammonium fluoride In tetrahydrofuran at 20℃; for 0.5h; Michael addition; | 95% |
With tetrabutyl ammonium fluoride In tetrahydrofuran at 20℃; for 0.5h; Michael addition; | 95% |
(S)-2-benzyloxycarbonylamino-4-hydroxyphosphinoyl-butyric acid methyl ester
methyl methacrylate
Conditions | Yield |
---|---|
With N,O-bis-(trimethylsilyl)-acetamide In dichloromethane at 0 - 20℃; Inert atmosphere; | 95% |
methyl methacrylate
N,N-bis(2-butynyl)-(4-methylphenyl)sulfonamide
C21H27NO4S
Conditions | Yield |
---|---|
With bis(1,5-cyclooctadiene)rhodium(I) tetrafluoroborate; (R)-segphos In dichloromethane at 20℃; for 1h; Inert atmosphere; | 94% |
Conditions | Yield |
---|---|
With palladium diacetate; acetic anhydride; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene In toluene at 70℃; for 24h; Inert atmosphere; Sealed tube; regioselective reaction; | 94% |
Conditions | Yield |
---|---|
Stage #1: 3-pyridinecarboxylic acid ethyl ester With potassium phosphate; chloro(1,5-cyclooctadiene)rhodium(I) dimer; P,P'-(1,2-ethanediyl)bis{bis[3,5-di(trifluoromethyl)phenyl]phosphane} In toluene for 0.0833333h; Inert atmosphere; Microwave irradiation; Stage #2: methyl methacrylate In toluene at 120℃; for 24h; Inert atmosphere; Microwave irradiation; Sealed tube; regioselective reaction; | 94% |
Conditions | Yield |
---|---|
With N-iodo-succinimide In tetrahydrofuran at 40℃; for 6h; Inert atmosphere; regioselective reaction; | 94% |
methyl phosphite
methyl methacrylate
3-(Dimethoxy-phosphoryl)-2-methyl-propionic acid ethyl ester
Conditions | Yield |
---|---|
With trimethylaluminum In dichloromethane; toluene Ambient temperature; | 93% |
tert-butylmercury chloride
methyl methacrylate
ethyl 2,4,4-trimethylpentanoate
Conditions | Yield |
---|---|
With triethylsilane In dimethyl sulfoxide at 35℃; for 11h; Irradiation; add of (E)-PhCH=CHI: competitive reaction; | 93% |
With triethylsilane; sodium thiosulfate 1.) DMSO, 11 h, 2.) DMSO; Yield given. Multistep reaction; |
methyl methacrylate
Conditions | Yield |
---|---|
With ethyl 2-bromoisobutyrate; [(1,3,5-iPr3C6H3)Ru(μ-Cl)3RuCl(C2H4)(PCy3)] In toluene at 35℃; | 93% |
4-methyl-benzaldehyde
methyl methacrylate
3-hydroxy-2,2-dimethyl-3-p-tolyl-propionic acid ethyl ester
Conditions | Yield |
---|---|
With C38H31F3O3P2PdSSn; triethylaluminum In tetrahydrofuran; toluene at 20 - 60℃; for 3h; | 93% |
Conditions | Yield |
---|---|
Stage #1: 3-(methylsulfonyl)pyridine With potassium phosphate; chloro(1,5-cyclooctadiene)rhodium(I) dimer; P,P'-(1,2-ethanediyl)bis{bis[3,5-di(trifluoromethyl)phenyl]phosphane} In toluene for 0.0833333h; Inert atmosphere; Microwave irradiation; Stage #2: methyl methacrylate In toluene at 120℃; for 24h; Inert atmosphere; Microwave irradiation; Sealed tube; regioselective reaction; | 93% |
Conditions | Yield |
---|---|
With cyclopentadienyl titanium(IV) trichloride; triethylsilyl chloride; zinc In tetrahydrofuran at 60℃; for 12h; Molecular sieve; Sealed tube; Inert atmosphere; | 93% |
The IUPAC name of Ethyl methacrylate is ethyl 2-methylprop-2-enoate. With the CAS registry number 97-63-2, it is also named as Methacrylic acid, ethyl ester. The product's categories are EQ - EZ; EQ - EZ Analytical Standards; Esters Gasoline, Diesel & Petroleum; Alpha Sort; Chemical Class; E-LAlphabetic; Olefins; Substance Classes; Volatiles / Semivolatiles; Acrylic Monomers; C6 to C7 Monomers; Carbonyl Compounds; Esters; Methacrylate. It is colourless liquid with an unpleasant odour which is incompatible with peroxides, oxidizing agents, bases, acids, reducing agents, halogens and amines. It can polymerize in the presence of light or heat. If polymerization takes place inside a container, the container may violently rupture. When heated to decomposition Ethyl methacrylate emits acrid smoke and irritating fumes. Additioanlly, this chemical should be sealed in the container and stored in the cool and dry place.
The other characteristics of this product can be summarized as: (1)ACD/LogP: 1.88; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 1.88; (4)ACD/LogD (pH 7.4): 1.88; (5)ACD/BCF (pH 5.5): 15.72; (6)ACD/BCF (pH 7.4): 15.72; (7)ACD/KOC (pH 5.5): 250.06; (8)ACD/KOC (pH 7.4): 250.06; (9)#H bond acceptors: 2; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 3; (12)Index of Refraction: 1.409; (13)Molar Refractivity: 31.18 cm3; (14)Molar Volume: 125.9 cm3; (15)Polarizability: 12.36×10-24 cm3; (16)Surface Tension: 24.6 dyne/cm; (17)Enthalpy of Vaporization: 35.86 kJ/mol; (18)Boiling Point: 120.5 °C at 760 mmHg; (19)Vapour Pressure: 15.2 mmHg at 25 °C; (20)Rotatable Bond Count: 3; (21)Exact Mass: 114.06808; (22)MonoIsotopic Mass: 114.06808; (23)Topological Polar Surface Area: 26.3; (24)Heavy Atom Count: 8; (25)Complexity: 105.
Preparation of Ethyl methacrylate: It can be obtained by esterification of methacrylic acid and ethanol. Putting methacrylic acid and ethanol to reactor and adding a small amount of concentrated sulfuric acid. Heating and refluxing to occur ester layer. Cooling and separating the ester layer. After caustic washing, water washing, drying and vacuum fractionation, we can get the product.
Uses of Ethyl methacrylate: It is used in the manufacture of acrylates copolymers, adhesives and coatings. It is also used in organic synthesis, in the preparation of plexiglass and as a solvent. In addition, it can react with piperidine to get b-piperidino-isobutyric acid ethyl ester. This reaction needs reagent acetic acid at temperature of 70 °C. The reaction time is 17 hours. The yield is 82%.
When you are using this chemical, please be cautious about it as the following:
It is highly flammable, so people should keep it away from sources of ignition and keep container in a well-ventilated place. It is also irritating to eyes, respiratory system and skin, so people should not empty into drains and must take precautionary measures against static discharges.
People can use the following data to convert to the molecule structure.
1. SMILES:O=C(OCC)\C(=C)C
2. InChI:InChI=1/C6H10O2/c1-4-8-6(7)5(2)3/h2,4H2,1,3H3
3. InChIKey:SUPCQIBBMFXVTL-UHFFFAOYAN
The following are the toxicity data which has been tested.
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
dog | LDLo | intravenous | 137uL/kg (0.137mL/kg) | Journal of Pharmaceutical Sciences. Vol. 63, Pg. 376, 1974. | |
mouse | LD50 | intraperitoneal | 1369mg/kg (1369mg/kg) | Journal of Pharmaceutical Sciences. Vol. 62, Pg. 778, 1973. | |
mouse | LD50 | oral | 7836mg/kg (7836mg/kg) | Toxicology Letters. Vol. 11, Pg. 125, 1982. | |
rabbit | LD | skin | > 10mL/kg (10mL/kg) | Journal of Industrial Hygiene and Toxicology. Vol. 23, Pg. 343, 1941. | |
rabbit | LDLo | oral | 3630mg/kg (3630mg/kg) | BEHAVIORAL: MUSCLE WEAKNESS LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION BEHAVIORAL: COMA | Journal of Industrial Hygiene and Toxicology. Vol. 23, Pg. 343, 1941. |
rat | LC50 | inhalation | 8300ppm/4H (8300ppm) | SENSE ORGANS AND SPECIAL SENSES: OTHER CHANGES: OLFACTION SENSE ORGANS AND SPECIAL SENSES: OTHER: EYE LUNGS, THORAX, OR RESPIRATION: DYSPNEA | Journal of Toxicology and Environmental Health. Vol. 16, Pg. 811, 1985. |
rat | LD50 | intraperitoneal | 1223mg/kg (1223mg/kg) | Journal of Dental Research. Vol. 51, Pg. 1632, 1972. | |
rat | LD50 | oral | 14800mg/kg (14800mg/kg) | BEHAVIORAL: MUSCLE WEAKNESS BEHAVIORAL: COMA LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION | Journal of Industrial Hygiene and Toxicology. Vol. 23, Pg. 343, 1941. |
rat | LDLo | subcutaneous | 25gm/kg (25000mg/kg) | BEHAVIORAL: MUSCLE WEAKNESS BEHAVIORAL: COMA LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION | Journal of Industrial Hygiene and Toxicology. Vol. 23, Pg. 343, 1941. |
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