Conditions | Yield |
---|---|
With [Ir(1,5-cyclooctadiene)2]PF6 In toluene at 100℃; for 5h; | 92% |
Conditions | Yield |
---|---|
With Silphos; iodine In N,N-dimethyl-formamide at 20℃; for 3h; | 90% |
With zirconium(IV) chloride; sodium iodide In acetonitrile for 0.0166667h; Heating; | 88% |
With bis(cyclopentadienyl)titanium dichloride; magnesium In tetrahydrofuran for 12h; Ambient temperature; | 87% |
allyl 2-((tert-butyl(1-(diethoxyphosphoryl)-2,2-dimethylpropyl)amino)oxy)-2-methylpropanoate
A
allyl methacrylate
B
diethyl (1-(tert-butyl((4,4-dimethyl-5-oxotetrahydrofuran-3-yl)methoxy)amino)-2,2-dimethylpropyl)phosphonate
Conditions | Yield |
---|---|
In tert-butyl alcohol at 120℃; for 2h; Sealed tube; | A n/a B 50% |
Conditions | Yield |
---|---|
Stage #1: 2,3-Epoxypropyl methacrylate With N-chloro-succinimide; triphenylphosphine In acetonitrile at 20℃; Stage #2: With N-iodo-succinimide; triphenylphosphine In acetonitrile for 10h; Heating; | A 44% B n/a |
α-allyloxy-isobutyric acid allyl ester
allyl methacrylate
Conditions | Yield |
---|---|
at 60℃; mit Oxalsaeure, ZnCl2 oder besser P2O5; |
α-acetoxy-isobutyric acid allyl ester
allyl methacrylate
Conditions | Yield |
---|---|
at 475℃; Pyrolysis; |
α-acetoxy-isobutyric acid allyl ester
A
allyl methacrylate
B
acetic acid
Conditions | Yield |
---|---|
at 475℃; Kontaktzeit ca.4.7 sec.Pyrolysis; |
Conditions | Yield |
---|---|
With sulfuric acid | |
With toluene-4-sulfonic acid In toluene Heating; | |
With dmap; dicyclohexyl-carbodiimide In dichloromethane Inert atmosphere; |
2-allyloxy-2-methylpropanoic acid
allyl alcohol
A
allyl methacrylate
B
α-allyloxy-isobutyric acid allyl ester
Conditions | Yield |
---|---|
With sulfuric acid; tannic acid |
Conditions | Yield |
---|---|
With sodium methylate; 2-hydroxyresorcinol | |
With oxygen; 4-methoxy-phenol; hydroquinone; zirconium(IV) acetylacetonate at 70 - 117℃; Product distribution / selectivity; Reflux; |
allyl 2-hydroxyisobutyrate
allyl methacrylate
Conditions | Yield |
---|---|
With phosphorus pentachloride In toluene at 80℃; | |
Multi-step reaction with 2 steps 1: H3PO4 / 80 - 110 °C 2: 475 °C / Pyrolysis View Scheme |
Conditions | Yield |
---|---|
at 60℃; |
2-allyloxy-2-methylpropanoic acid
allyl methacrylate
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: concentrated H2SO4; tannin 2: 60 °C / mit Oxalsaeure, ZnCl2 oder besser P2O5 View Scheme |
Conditions | Yield |
---|---|
Stage #1: 2-methylpropenal With tert-butylhypochlorite In tetrachloromethane at 20 - 50℃; for 5.5 - 6.5h; Stage #2: allyl alcohol In tetrachloromethane at 0 - 20℃; for 15.5h; |
allyl dodecanoate
methyl methacrylate
A
allyl methacrylate
B
ethyl laurate
Conditions | Yield |
---|---|
With 15percent (w/w) Candida antarctica lipase B immobilised onto macroporous acrylic resin at 50℃; for 1h; Enzymatic reaction; | A 34.2 %Chromat. B n/a |
2-bromo-2-methylpropionic acid
allyl methacrylate
methacrylic acid methyl ester
Conditions | Yield |
---|---|
Multistep reaction.; | 100% |
Triethoxysilane
allyl methacrylate
3-methacryloyloxypropyltriethoxysilane
Conditions | Yield |
---|---|
With platinum-containing olefin organic polymer catalyst at 25℃; for 24h; | 98% |
With dihydrogen hexachloroplatinate; Triethoxyvinylsilane; isopropyl alcohol In pentane at 50℃; for 1.5h; Product distribution; Mechanism; influence unsaturated Si-comp. on rate of hydrosilylation; effect of different solvents; further functionalized alkenes; | 66 % Chromat. |
Stage #1: Triethoxysilane; allyl methacrylate With dihydrogen hexachloroplatinate; tetramethyldivinyldisiloxane; N,N'-diphenyl-1,4-phenylenediamine; triphenylphosphine In isopropyl alcohol at 95 - 135℃; for 2.25h; Stage #2: With dmap In isopropyl alcohol |
Conditions | Yield |
---|---|
With trichlorosilane; [SG]-S-Pt In hexane | 98% |
dimethylmonochlorosilane
allyl methacrylate
3-Methacryloxypropyldimethylchlorosilane
Conditions | Yield |
---|---|
Stage #1: dimethylmonochlorosilane; allyl methacrylate With 10H-phenothiazine; platinum(0)-1,3-divinyl-1,1,3,3-tetramethyldisiloxane complex In 5,5-dimethyl-1,3-cyclohexadiene at 80℃; under 5171.62 Torr; for 0.666667h; Flow reactor; Sealed tube; Inert atmosphere; Stage #2: With 2,6-di-tert-butyl-4-methyl-phenol In 5,5-dimethyl-1,3-cyclohexadiene at 80℃; for 1h; Temperature; Inert atmosphere; | 97.9% |
With platinum(0)-1,3-divinyl-1,1,3,3-tetramethyldisiloxane complex In toluene at 70℃; for 3h; | 96% |
With dihydrogen hexachloroplatinate; 10H-phenothiazine In tetrahydrofuran at 80℃; for 0.5h; | 72% |
With N,N-dimethyl-(3,5-di-tert-butyl-4-hydroxybenzyl)ammonium chloride; Platinum(0)-1,3-divinyl-1,1,3,3-tetramethyldisiloxane complex at 65 - 80℃; for 1h; |
Dichloromethylsilane
allyl methacrylate
3-(dichloromethylsilyl)propyl methacrylate
Conditions | Yield |
---|---|
With platinum(0)-1,3-divinyl-1,1,3,3-tetramethyldisiloxane complex In toluene at 70℃; for 3h; | 97% |
With dihydrogen hexachloroplatinate; 10H-phenothiazine In tetrahydrofuran at 80℃; for 0.5h; | 83% |
With dihydrogen hexachloroplatinate; 2-Ethylhexyl alcohol; 2,6-di-tert-butyl-4-methyl-phenol; platinum In toluene at 70 - 80℃; for 4h; |
Conditions | Yield |
---|---|
With complex of alkali-neutralized chloroplatinic acid with vinyl siloxane, containing 0.5percent of platinum In methyl cyclohexane; toluene at 70 - 100℃; for 2h; | 97% |
allyl methacrylate
trichlorosilane
3-(trichlorosilyl)propyl 2-methylprop-2-enoate
Conditions | Yield |
---|---|
With platinum(0)-1,3-divinyl-1,1,3,3-tetramethyldisiloxane complex In toluene at 70℃; for 3h; | 96% |
Conditions | Yield |
---|---|
platinum 1,3-divinyl-1,1,3,3-tetramethyldisiloxane In toluene; xylene at 20℃; Inert atmosphere; | 95.8% |
Conditions | Yield |
---|---|
With 2,2'-azobis(isobutyronitrile) In toluene at 80℃; for 8h; radical copolymerization; | 95.6% |
Conditions | Yield |
---|---|
With 1,3,5-trimethyl-2,4,6-tris-(3,5-di-tert-butyl-4-hydroxybenzyl)benzene; tris(pentafluorophenyl)borate In toluene at 40 - 50℃; for 3.3h; | 95.6% |
Conditions | Yield |
---|---|
With 1,3,5-trimethyl-2,4,6-tris-(3,5-di-tert-butyl-4-hydroxybenzyl)benzene; tris(pentafluorophenyl)borate In toluene at 1.5 - 12℃; for 12h; | 94.8% |
trimethoxysilane
allyl methacrylate
[3-(methacryloyloxy)propyl]trimethoxysilane
Conditions | Yield |
---|---|
With dihydrogen hexachloroplatinate; 10H-phenothiazine at 85℃; under 1125.11 - 3000.3 Torr; for 4h; Catalytic behavior; Pressure; Autoclave; Inert atmosphere; | 94.3% |
With 4-aminotriphenylamine; 2,6-di-tert-butyl-4-methyl-phenol; acetone; dihydrogen hexachloroplatinate(IV) hexahydrate at 75℃; under 18751.9 Torr; Inert atmosphere; | |
With dihydrogen hexachloroplatinate(IV) hexahydrate In acetylacetone at 105℃; |
Conditions | Yield |
---|---|
Stage #1: oct-1-ene; octakis(dimethylsiloxy)octasilsesquioxane With bis(1,5-cyclooctadiene)diiridium(I) dichloride; Karstedt's catalyst In toluene at 90℃; Stage #2: allyl methacrylate In toluene at 60℃; | 94% |
Conditions | Yield |
---|---|
Stage #1: allyl methacrylate; para-thiocresol In 1,2-dichloro-ethane; acetonitrile at 20℃; for 2.3h; Stage #2: With triphenylphosphine In 1,2-dichloro-ethane; acetonitrile for 2h; | 93% |
With oxygen; copper diacetate; 4-methoxybenzoic acid In 1,2-dichloro-ethane at 50℃; for 3h; | 88% |
styrene
allyl methacrylate
Conditions | Yield |
---|---|
With 2,2'-azobis(isobutyronitrile) In toluene at 80℃; for 8h; radical copolymerization; | 92.3% |
Conditions | Yield |
---|---|
With 2,2'-azobis(isobutyronitrile) In toluene at 80℃; for 8h; radical copolymerization; | 92.3% |
Conditions | Yield |
---|---|
With 2,2'-azobis(isobutyronitrile) In toluene at 80℃; for 8h; radical copolymerization; | 91.8% |
allyl methacrylate
diethyl 8-oxo-8H-cyclopenta-(a)-acenaphthylene-7,9-dicarboxylate
Conditions | Yield |
---|---|
In chloroform for 4h; Heating; | 91% |
allyl methacrylate
3-methyl-5H-furan-2-one
Conditions | Yield |
---|---|
With C28H32Cl2N2ORu In toluene at 70℃; for 18h; Inert atmosphere; | 91% |
styrene
allyl methacrylate
Conditions | Yield |
---|---|
With 2,2'-azobis(isobutyronitrile) In toluene at 80℃; for 8h; radical copolymerization; | 90.7% |
allyl methacrylate
Conditions | Yield |
---|---|
Grubbs catalyst first generation In dichloromethane at 20℃; for 2h; | 90% |
Conditions | Yield |
---|---|
Stage #1: Triethoxyvinylsilane; octakis(dimethylsiloxy)octasilsesquioxane With bis(1,5-cyclooctadiene)diiridium(I) dichloride; Karstedt's catalyst In toluene at 90℃; Stage #2: allyl methacrylate In toluene at 60℃; | 90% |
styrene
allyl methacrylate
Conditions | Yield |
---|---|
With 2,2'-azobis(isobutyronitrile) In toluene at 80℃; for 8h; radical copolymerization; | 89.1% |
styrene
allyl methacrylate
Conditions | Yield |
---|---|
With 2,2'-azobis(isobutyronitrile) In toluene at 80℃; for 8h; radical copolymerization; | 88.4% |
Conditions | Yield |
---|---|
With dihydrogen hexachloroplatinate; 10H-phenothiazine; trichlorosilane In tetrahydrofuran at 80℃; for 0.5h; | 88% |
With dihydrogen hexachloroplatinate; Triethoxyvinylsilane; trichlorosilane at 50 - 80℃; for 2.5h; |
Conditions | Yield |
---|---|
With (4s,6s)-2,4,5,6-tetra(9H-carbazol-9-yl)isophthalonitrile; potassium tert-butylate In acetonitrile at 20℃; Inert atmosphere; Sealed tube; Irradiation; | 88% |
allyl methacrylate
diethyltin dihydride
Diethyl-bis-<2-allyloxycarbonyl-propyl>-stannan
Conditions | Yield |
---|---|
In neat (no solvent) closed tube, 90-100°C, 1h, N2;; | 86.8% |
In not given reaction in a bomb tube at 90-100°C for 1 h;; |
Conditions | Yield |
---|---|
With 2,2'-azobis(isobutyronitrile) In toluene at 80℃; for 8h; radical copolymerization; | 86% |
EPA Genetic Toxicology Program. Reported in EPA TSCA Inventory.
Allyl methacrylate is an organic compound with the formula C7H10O2, and its systematic name is the same with the product name. With the CAS registry number 96-05-9, it is also named as 2-Propenoic acid,2-methyl-, 2-propen-1-yl ester. It belongs to the product categories of Acrylic Monomers; C6 to C7 Monomers; Carbonyl Compounds; Esters; Methacrylate; Ester series. Its EINECS number is 202-473-0. In addition, the molecular weight is 126.15. Its classification code is Skin / Eye Irritant. This chemical should be sealed and stored in a cool and ventilated place. Moreover, it should be protected from oxides, heat and fire. This chemical is widely used as comonomer and grafting monomer in producing organic glass, and it is also used as cross-linking agent in tooth repairing.
Physical properties of Allyl methacrylate are: (1)ACD/LogP: 1.567; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 1.57; (4)ACD/LogD (pH 7.4): 1.57; (5)ACD/BCF (pH 5.5): 9.14; (6)ACD/BCF (pH 7.4): 9.14; (7)ACD/KOC (pH 5.5): 169.59; (8)ACD/KOC (pH 7.4): 169.59; (9)#H bond acceptors: 2; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 4; (12)Polar Surface Area: 26.3 Å2; (13)Index of Refraction: 1.43; (14)Molar Refractivity: 35.547 cm3; (15)Molar Volume: 137.553 cm3; (16)Polarizability: 14.092×10-24cm3; (17)Surface Tension: 25.65 dyne/cm; (18)Density: 0.917 g/cm3; (19)Flash Point: 33.889 °C; (20)Enthalpy of Vaporization: 37.588 kJ/mol; (21)Boiling Point: 138.588 °C at 760 mmHg; (22)Vapour Pressure: 6.68 mmHg at 25°C.
Preparation of Allyl methacrylate: this chemical can be prepared by 2-methyl-acrylic acid oxiranylmethyl ester at the ambient temperature. This reaction will need reagents Mg, Cp2TiCl2 and solvent tetrahydrofuran with the reaction time of 12 hours. The yield is about 87%.
Uses of Allyl methacrylate: it can be used to produce 3-(chlorodimethylsilyl)propyl methacrylate at the temperature of 80 °C. It will need reagents 0.05 N H2PtCl6, phenothiazine and solvent tetrahydrofuran with the reaction time of 30 min. The yield is about 72%.
When you are using this chemical, please be cautious about it as the following:
It is flammable and harmful in contact with skin and if swallowed. It is toxic by inhalation and very toxic to aquatic organisms. When using it, you need to wear suitable protective clothing and gloves. In case of accident or if you feel unwell, you must seek medical advice immediately (show the label where possible). You should avoid releasing it to the environment, and you need to refer to special instructions/safety data sheet.
You can still convert the following datas into molecular structure:
(1)SMILES: O=C(OC\C=C)\C(=C)C
(2)Std. InChI: InChI=1S/C7H10O2/c1-4-5-9-7(8)6(2)3/h4H,1-2,5H2,3H3
(3)Std. InChIKey: FBCQUCJYYPMKRO-UHFFFAOYSA-N
The toxicity data is as follows:
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
mouse | LC50 | inhalation | 5500mg/m3 (5500mg/m3) | Gigiena Truda i Professional'nye Zabolevaniya. Labor Hygiene and Occupational Diseases. Vol. 34(8), Pg. 59, 1990. | |
mouse | LD50 | oral | 57mg/kg (57mg/kg) | Gigiena Truda i Professional'nye Zabolevaniya. Labor Hygiene and Occupational Diseases. Vol. 34(8), Pg. 59, 1990. | |
mouse | LD50 | parenteral | 57mg/kg (57mg/kg) | National Technical Information Service. Vol. OTS0559078, | |
rabbit | LD50 | skin | 500uL/kg (.5mL/kg) | American Industrial Hygiene Association Journal. Vol. 30, Pg. 470, 1969. | |
rat | LC50 | inhalation | 1800mg/m3 (1800mg/m3) | Gigiena Truda i Professional'nye Zabolevaniya. Labor Hygiene and Occupational Diseases. Vol. 34(8), Pg. 59, 1990. | |
rat | LD50 | oral | 70mg/kg (70mg/kg) | Gigiena Truda i Professional'nye Zabolevaniya. Labor Hygiene and Occupational Diseases. Vol. 34(8), Pg. 59, 1990. | |
rat | LD50 | parenteral | 70mg/kg (70mg/kg) | National Technical Information Service. Vol. OTS0559078, |
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