Conditions | Yield |
---|---|
With N,N-bis[2-oxo-3-oxazolidinyl]phosphorodiamidic chloride; triethylamine In dichloromethane at 20℃; for 0.5h; | 99% |
With magnesium dimethacrylate; di-tert-butyl dicarbonate at 25℃; for 4h; Reagent/catalyst; | 99% |
With 10H-phenothiazine; trifluorormethanesulfonic acid; acetic anhydride at 95℃; Reagent/catalyst; Temperature; | 95% |
Conditions | Yield |
---|---|
With pyridine; 1,1,1-trichloro-3,3,3-trifluoro-propan-2-one; water In toluene for 0.5h; Ambient temperature; | 93% |
With sodium hydroxide; tetrabutylammomium bromide In dichloromethane at -10℃; for 3h; | 80% |
With sodium hydroxide; tetrabutyl-ammonium chloride In toluene at -10℃; for 3h; | 7% |
Conditions | Yield |
---|---|
With triethylamine In benzene at 70℃; | 92% |
Stage #1: Methacryloyl chloride With pyridine; hydroquinone In toluene Stage #2: poly(methacrylic acid) In toluene at 50 - 65℃; | 83% |
With triethylamine In benzene | |
With sodium hydroxide In water | |
With sodium hydroxide In water |
sodium methacrylate
chloroformic acid ethyl ester
A
methacryloyl anhydride
B
carboethoxymethacrylic anhydride
Conditions | Yield |
---|---|
With 4-methoxy-phenol; tetrabutylammomium bromide In H2O (water) < 309.3g; toluene 192g at 15℃; for 4h; | A n/a B 87.5% |
With 4-methoxy-phenol In water at 5 - 35℃; for 7 - 30h; | |
tributylphenylphosphonium chloride at 10℃; for 3h; |
sodium methacrylate
chloroformic acid ethyl ester
A
methacryloyl anhydride
B
carboethoxymethacrylic anhydride
C
Diethyl carbonate
Conditions | Yield |
---|---|
With 4-methoxy-phenol; tetrabutylammomium bromide In water at 20℃; for 3h; | A n/a B 80% C n/a |
tetrabutyl phosphonium bromide at 10℃; for 4.5h; | |
methyl(tri-n-octyl)ammonium bromide at 10℃; for 1.5h; |
2-methyladamantan-2-ol
A
2-methyl-2-adamantyl methacrylate
B
methacryloyl anhydride
Conditions | Yield |
---|---|
A 40% B n/a |
Conditions | Yield |
---|---|
With oxygen; silica gel; Te/Pd-containing-silica-supported catalyst In water; tert-butyl alcohol at 75℃; under 18001.8 - 36003.6 Torr; for 0.75h; Product distribution / selectivity; Autoclave; | A 34.2% B 17.5% |
Conditions | Yield |
---|---|
With copper (I) acetate |
poly(methacrylic acid)
benzoyl chloride
A
methacryloyl anhydride
B
benzoyl (meth)acrylate
C
benzoic acid anhydride
Conditions | Yield |
---|---|
With P4-VP In dichloromethane at 0℃; for 1h; Yield given. Yields of byproduct given; |
methacryloyl anhydride
Conditions | Yield |
---|---|
With thionyl chloride; Petroleum ether |
chloroformic acid ethyl ester
potassium methacrylate
A
methacryloyl anhydride
B
carboethoxymethacrylic anhydride
C
Diethyl carbonate
Conditions | Yield |
---|---|
at 10℃; |
sodium methacrylate
chloroformic acid ethyl ester
A
methacryloyl anhydride
B
diethyl dicarbonate
C
carboethoxymethacrylic anhydride
D
Diethyl carbonate
Conditions | Yield |
---|---|
With phosphoric acid; acetic anhydride; sodium hydrogencarbonate In hexane; water |
Conditions | Yield |
---|---|
With sodium hydroxide; phosphoric acid; acetic anhydride In hexane; water | |
With sodium hydroxide; phosphoric acid; acetic anhydride In hexane; water |
isobutene
A
2-methylpropenal
B
poly(methacrylic acid)
C
methacryloyl anhydride
Conditions | Yield |
---|---|
With oxygen; 4-methoxy-phenol; palladium matal-containing silica-supported catalyst In water; tert-butyl alcohol at 90℃; for 6h; Product distribution / selectivity; | |
With oxygen at 110℃; under 36003.6 Torr; Gas phase; | A 27.8 %Chromat. B 53 %Chromat. C 7.4 %Chromat. |
Conditions | Yield |
---|---|
With TEMPOL; 2,6-di-tert-butyl-4-methyl-phenol; 2,4-dimethyl-6-tert-butylphenol at 93℃; under 18 - 140 Torr; Product distribution / selectivity; Air atmosphere; | |
With 10H-phenothiazine at 80 - 90℃; under 760.051 Torr; | |
With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; 10H-phenothiazine at 100 - 105℃; for 2h; | 135.5 g |
poly(methacrylic acid)
acetic anhydride
A
methacryloyl anhydride
B
methacrylic acid acetate
C
acetic acid
Conditions | Yield |
---|---|
acidic ion exchanger Lewatit K2431 at 76℃; Polymerization inhibitior; |
poly(methacrylic acid)
methacrylic acid acetate
acetic anhydride
A
methacryloyl anhydride
B
acetic acid
Conditions | Yield |
---|---|
acidic ion exchanger Lewatit K2431 at 76℃; Polymerization inhibitior; |
methanol
2-methylpropenal
A
1,1-dimethoxy-2-methylprop-1-ene
B
propene
C
poly(methacrylic acid)
D
Methyl isobutyrate
E
Isobutyl methacrylate
F
methacryloyl anhydride
G
isobutyraldehyde
H
methacrylic acid methyl ester
I
3-hydroxy-2-methyl-1-propene
Conditions | Yield |
---|---|
With magnesium hydroxide; oxygen at 80℃; under 2250.23 Torr; for 2h; Reagent/catalyst; |
Conditions | Yield |
---|---|
With pyridine; hydroquinone at 20℃; | 100% |
methacryloyl anhydride
1-amino-4-hydroxy-2-[2'-[4'-(2'-hydroxyethoxy)phenoxy]ethoxy]anthraquinone
Conditions | Yield |
---|---|
Stage #1: methacryloyl anhydride; 1-amino-4-hydroxy-2-[2'-[4'-(2'-hydroxyethoxy)phenoxy]ethoxy]anthraquinone With triethylamine; dmap; hydroquinone In DMF (N,N-dimethyl-formamide) at 20℃; for 24h; Stage #2: Heating / reflux; | 100% |
Conditions | Yield |
---|---|
With pyridine at 80℃; for 6.5h; | 100% |
Conditions | Yield |
---|---|
With dmap; 2,6-di-tert-butyl-4-methyl-phenol In toluene at 80℃; for 40h; | 100% |
dimethyl 2-hydroxyethylphosphonate
methacryloyl anhydride
dimethyl (2-methacryloyloxyethyl)phosphonate
Conditions | Yield |
---|---|
With 1-methyl-1H-imidazole In butanone at 60℃; for 6h; Inert atmosphere; | 100% |
methacryloyl anhydride
dimethyl (γ-hydroxypropyl)phosphonate
dimethyl (3-methacryloyloxypropyl)phosphonate
Conditions | Yield |
---|---|
With 1-methyl-1H-imidazole In butanone at 60℃; for 6h; Inert atmosphere; | 100% |
methacryloyl anhydride
6A-(6-aminohexylamino)-6A-deoxy-β-cyclodextrin
(1-methacrylamidohexyl)amino-6-deoxy-β-cyclodextrin
Conditions | Yield |
---|---|
In N,N-dimethyl-formamide at 20℃; Inert atmosphere; | 100% |
hexa-1,5-diene-3,4-diol
methacryloyl anhydride
4-[(2-methylprop-2-enoyl)oxy]hexa-1,5-dien-3-yl 2-methylprop-2-enoate
Conditions | Yield |
---|---|
With dmap; triethylamine In dichloromethane at 20℃; for 1.5h; | 100% |
Conditions | Yield |
---|---|
With triphenyl phosphite; 2,6-di-tert-butyl-4-methyl-phenol; magnesium oxide In toluene at 80℃; for 3h; Reagent/catalyst; | 100% |
With magnesium oxide In toluene at 80℃; for 3h; Catalytic behavior; Concentration; Reagent/catalyst; Temperature; | 100% |
methacryloyl anhydride
4-Hydroxybenzophenone
4-hydroxybenzophenone ester of metacrylic acid
Conditions | Yield |
---|---|
With 2,4-dimethyl-6-tert-butylphenol; sulfuric acid; 4-methoxy-phenol at 90℃; for 6h; Air introduction; | 99.4% |
With sulfuric acid In methanol at 90℃; for 2h; Temperature; Large scale; | 99.7% |
With tempol; 2,4-dimethyl-6-tert-butylphenol; 4-methoxy-phenol; magnesium bromide at 90℃; for 6h; Reagent/catalyst; |
Conditions | Yield |
---|---|
With sulfuric acid at 80℃; for 8h; Product distribution / selectivity; | 99.1% |
at 25℃; for 24h; | 90% |
With sulfuric acid at 80℃; for 8h; Product distribution / selectivity; Industry scale; | |
at 120℃; for 5h; Product distribution / selectivity; | |
With magnesium monohydroxide; di-tert-butyl dicarbonate; lithium chloride at 25℃; under 760.051 Torr; for 24h; Time; |
Conditions | Yield |
---|---|
Stage #1: inulin, MW: ca. 5000 Da, isolated from Dahlia Tubers; methacryloyl anhydride; triethylamine In N,N-dimethyl-formamide at 25℃; for 24h; Stage #2: succinic acid anhydride; triethylamine In N,N-dimethyl-formamide at 25℃; for 24h; Further stages.; | 99% |
methacryloyl anhydride
N-(2-aminoethyl)benzeneamine
N-phenylethylenediamine methacrylamide
Conditions | Yield |
---|---|
In methanol at 0℃; for 3h; | 99% |
Conditions | Yield |
---|---|
In methanol at 15 - 25℃; for 2h; Solvent; | 99% |
Conditions | Yield |
---|---|
With dmap In dichloromethane at 35℃; Flow reactor; | 99% |
Conditions | Yield |
---|---|
With dmap In dichloromethane at 0 - 20℃; for 18h; | 98.2% |
With dmap; triethylamine In dichloromethane at 0℃; Inert atmosphere; Cooling with ice; | 90.8% |
methacryloyl anhydride
Conditions | Yield |
---|---|
With triethylamine In N,N-dimethyl acetamide at 40℃; for 48h; | 98% |
methacryloyl anhydride
1,4-bis-[(2-hydroxy-ethylsulfanyl)-methyl]-benzene
1,4-bis(2-methacryloyloxyethylthio)xylylene
Conditions | Yield |
---|---|
Stage #1: methacryloyl anhydride; 1,4-bis-[(2-hydroxy-ethylsulfanyl)-methyl]-benzene With triethylamine In dichloromethane at 20℃; for 48h; Stage #2: With sodium hydrogencarbonate In dichloromethane; water for 0.5h; | 98% |
methacryloyl anhydride
1,2-bis(hydroxyethylthiomethyl)benzene
1,2-bis(methacryloyloxyethylthiomethyl)benzene
Conditions | Yield |
---|---|
Stage #1: methacryloyl anhydride; 1,2-bis(hydroxyethylthiomethyl)benzene With triethylamine In dichloromethane at 20℃; for 48h; Stage #2: With sodium hydrogencarbonate In dichloromethane; water for 0.5h; | 98% |
Conditions | Yield |
---|---|
With dmap at 60℃; | 98% |
Conditions | Yield |
---|---|
With lithium carbonate at 80℃; for 2h; Reagent/catalyst; | 98% |
methacryloyl anhydride
1,3,6-trimethyl-isobarbituric acid
Conditions | Yield |
---|---|
With pyridine; hydroquinone at 20℃; for 1h; | 97% |
poly(methacrylic acid)
methacryloyl anhydride
hydroquinone
A
hex-1-ene-2,5-dicarboxylic acid
B
4-hydroxyphenyl methacrylate
Conditions | Yield |
---|---|
at 120℃; for 4h; Product distribution / selectivity; | A 1% B 97% |
2-Adamantanone
methacryloyl anhydride
methyllithium
2-methyl-2-adamantyl methacrylate
Conditions | Yield |
---|---|
Stage #1: 2-Adamantanone; methyllithium In tetrahydrofuran; diethyl ether at -25 - -20℃; for 1h; Stage #2: methacryloyl anhydride With triethylamine In tetrahydrofuran; diethyl ether at 25℃; for 1.5h; | 97% |
Stage #1: 2-Adamantanone; methyllithium In tetrahydrofuran; diethyl ether at -25 - -20℃; for 1h; Stage #2: methacryloyl anhydride In tetrahydrofuran; diethyl ether at 55℃; for 3h; | 90% |
methacryloyl anhydride
bis(O,S-triphenylsilyl)-2-mercaptoethanol
C24H24O2SSi
Conditions | Yield |
---|---|
In dichloromethane at 20℃; for 3h; | 97% |
methacryloyl anhydride
(2R)-bornane-10,2-sultam
(3aS,6R,7aR)-1-[(2E)-but-2-enoyl]-8,8-dimethylhexahydro-3a,6-methano-2,1-benzisothiazole 2,2-dioxide
Conditions | Yield |
---|---|
Stage #1: (2R)-bornane-10,2-sultam With triethylamine; lithium chloride In tetrahydrofuran at -20℃; for 0.166667h; Stage #2: methacryloyl anhydride In tetrahydrofuran at -20 - -10℃; for 0.0833333h; Product distribution / selectivity; | 96% |
With triethylamine; lithium chloride In tetrahydrofuran for 4h; Ambient temperature; | 95% |
methacryloyl anhydride
Conditions | Yield |
---|---|
With dmap In dichloromethane at 20℃; | 96% |
With dmap In dichloromethane at 20℃; | 96% |
Conditions | Yield |
---|---|
With dmap; triethylamine In dichloromethane at 20℃; for 12h; | 96% |
Conditions | Yield |
---|---|
With dmap at 60℃; | 96% |
Product Name: Methacrylic anhydride (CAS NO.760-93-0)
MF: C8H10O3
MW: 154.16
Mol File: 760-93-0.mol
EINECS: 212-084-8
Surface Tension: 29 dyne/cm
Density: 1.021 g/ml
Flash Point: 84.4 °C
MP: -20°C
Enthalpy of Vaporization: 43.85 kJ/mol
Boiling Point: 202.3 °C at 760 mmHg
Vapour Pressure: 0.294 mmHg at 25°C
BRN: 1761982
Index of Refraction: 1.443
Molar Refractivity: 40.05 cm3
Molar Volume: 150.9 cm3
XLogP3-AA: 1.8
H-Bond Donor: 0
H-Bond Acceptor: 3
Structure Descriptors of Methacrylic anhydride (CAS NO.760-93-0):
IUPAC Name: 2-methylprop-2-enoyl 2-methylprop-2-enoate
Canonical SMILES: CC(=C)C(=O)OC(=O)C(=C)C
InChI: InChI=1S/C8H10O3/c1-5(2)7(9)11-8(10)6(3)4/h1,3H2,2,4H3
InChIKey: DCUFMVPCXCSVNP-UHFFFAOYSA-N
Product Categories: Organic acids; Carbonyl Compounds; Carboxylic Acid Anhydrides; Organic Building Blocks; Anhydride Monomers; Monomers; Polymer Science
Methacrylic anhydride (CAS NO.760-93-0) is used as light-curing coatings, cross-linked materials such as synthetic resin.
1. | ihl-mus LC50:450 mg/m3/2H | 85GMAT Toxicometric Parameters of Industrial Toxic Chemicals Under Single Exposure Izmerov, N.F., et al.,Moscow, USSR.: Centre of International Projects, GKNT,1982,80. |
EPA Extremely Hazardous Substances List. Reported in EPA TSCA Inventory.
Poison by inhalation. A combustible liquid. When heated to decomposition it emits acrid smoke and irritating fumes. See also ANHYDRIDES.
Safety information of Methacrylic anhydride (CAS NO.760-93-0):
Hazard Codes: Xn
Risk Statements: 20-37/38-41
R20:Harmful by inhalation ;
R37/38:Irritating to respiratory system and skin ;
R41:Risk of serious damage to eyes ;
Safety Statements: 26-39
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice ;
S39:Wear eye/face protection ;
RIDADR: UN 3265 8/PG 2
WGK Germany: 1
RTECS: OZ5700000
F: 10-21
HazardClass: 8
PackingGroup: II
Methacrylic anhydride , its CAS NO. is 760-93-0, the synonyms are 1-Methylacrylic anhydride ; 2-Propenoicacid,2-methyl-,anhydride ; 2-Methyl-2-propenoicacianhydride ; Methacrylic acid anhydride ; Methacryloyl anhydride ; Methacrylicacidanhydride ; Methacryloylanhydride . Methacrylic anhydride (CAS NO.760-93-0) reacts exothermically with water. The reactions are sometimes slow, but can become violent when local heating accelerates their rate. Acids accelerate the reaction with water. Incompatible with acids, strong oxidizing agents, alcohols, amines, and bases.
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