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760-93-0

Basic Information
CAS No.: 760-93-0
Name: Methacrylic anhydride
Molecular Structure:
Molecular Structure of 760-93-0 (Methacrylic anhydride)
Formula: C8H10O3
Molecular Weight: 154.18
Synonyms: 2-Propenoicacid, 2-methyl-, anhydride (9CI);Methacrylic anhydride (6CI,8CI);Methacrylicacid anhydride;Methacryloyl anhydride;NSC 24159;
EINECS: 212-084-8
Density: 1.021 g/cm3
Melting Point: -20 °C
Boiling Point: 202.3 °C at 760 mmHg
Flash Point: 84.4 °C
Solubility:
Appearance: liquid
Hazard Symbols: HarmfulXn
Risk Codes: 20-37/38-41
Safety: 26-39
Transport Information: UN 3265 8/PG 2
PSA: 43.37000
LogP: 1.20840
Synthetic route
79-41-4

poly(methacrylic acid)

760-93-0

methacryloyl anhydride

Conditions
ConditionsYield
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%
920-46-7

Methacryloyl chloride

760-93-0

methacryloyl anhydride

Conditions
ConditionsYield
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%
79-41-4

poly(methacrylic acid)

920-46-7

Methacryloyl chloride

760-93-0

methacryloyl anhydride

Conditions
ConditionsYield
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
5536-61-8

sodium methacrylate

541-41-3

chloroformic acid ethyl ester

A

760-93-0

methacryloyl anhydride

B

21982-91-2

carboethoxymethacrylic anhydride

Conditions
ConditionsYield
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;
5536-61-8

sodium methacrylate

541-41-3

chloroformic acid ethyl ester

A

760-93-0

methacryloyl anhydride

B

21982-91-2

carboethoxymethacrylic anhydride

C

105-58-8

Diethyl carbonate

Conditions
ConditionsYield
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;
702-98-7

2-methyladamantan-2-ol

A

177080-67-0

2-methyl-2-adamantyl methacrylate

B

760-93-0

methacryloyl anhydride

Conditions
ConditionsYield
A 40%
B n/a
115-11-7

isobutene

A

79-41-4

poly(methacrylic acid)

B

760-93-0

methacryloyl anhydride

Conditions
ConditionsYield
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%
674-82-8

4-methyleneoxetan-2-one

79-41-4

poly(methacrylic acid)

760-93-0

methacryloyl anhydride

Conditions
ConditionsYield
With copper (I) acetate
79-41-4

poly(methacrylic acid)

98-88-4

benzoyl chloride

A

760-93-0

methacryloyl anhydride

B

46318-87-0

benzoyl (meth)acrylate

C

93-97-0

benzoic acid anhydride

Conditions
ConditionsYield
With P4-VP In dichloromethane at 0℃; for 1h; Yield given. Yields of byproduct given;
potassium methacrylate

potassium methacrylate

760-93-0

methacryloyl anhydride

Conditions
ConditionsYield
With thionyl chloride; Petroleum ether
920-46-7

Methacryloyl chloride

sodium methacrylate

sodium methacrylate

760-93-0

methacryloyl anhydride

541-41-3

chloroformic acid ethyl ester

6900-35-2

potassium methacrylate

A

760-93-0

methacryloyl anhydride

B

21982-91-2

carboethoxymethacrylic anhydride

C

105-58-8

Diethyl carbonate

Conditions
ConditionsYield
at 10℃;
5536-61-8

sodium methacrylate

541-41-3

chloroformic acid ethyl ester

A

760-93-0

methacryloyl anhydride

B

1609-47-8

diethyl dicarbonate

C

21982-91-2

carboethoxymethacrylic anhydride

D

105-58-8

Diethyl carbonate

2226-96-2

tempol

79-41-4

poly(methacrylic acid)

760-93-0

methacryloyl anhydride

Conditions
ConditionsYield
With phosphoric acid; acetic anhydride; sodium hydrogencarbonate In hexane; water
HO-TEMPO

HO-TEMPO

79-41-4

poly(methacrylic acid)

760-93-0

methacryloyl anhydride

Conditions
ConditionsYield
With sodium hydroxide; phosphoric acid; acetic anhydride In hexane; water
With sodium hydroxide; phosphoric acid; acetic anhydride In hexane; water
115-11-7

isobutene

A

78-85-3

2-methylpropenal

B

79-41-4

poly(methacrylic acid)

C

760-93-0

methacryloyl anhydride

Conditions
ConditionsYield
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.
79-41-4

poly(methacrylic acid)

108-24-7

acetic anhydride

760-93-0

methacryloyl anhydride

Conditions
ConditionsYield
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
79-41-4

poly(methacrylic acid)

108-24-7

acetic anhydride

A

760-93-0

methacryloyl anhydride

B

76392-13-7

methacrylic acid acetate

C

64-19-7

acetic acid

Conditions
ConditionsYield
acidic ion exchanger Lewatit K2431 at 76℃; Polymerization inhibitior;
79-41-4

poly(methacrylic acid)

76392-13-7

methacrylic acid acetate

108-24-7

acetic anhydride

A

760-93-0

methacryloyl anhydride

B

64-19-7

acetic acid

Conditions
ConditionsYield
acidic ion exchanger Lewatit K2431 at 76℃; Polymerization inhibitior;
67-56-1

methanol

78-85-3

2-methylpropenal

A

5634-54-8

1,1-dimethoxy-2-methylprop-1-ene

B

187737-37-7

propene

C

79-41-4

poly(methacrylic acid)

D

547-63-7

Methyl isobutyrate

E

97-86-9

Isobutyl methacrylate

F

760-93-0

methacryloyl anhydride

G

78-84-2

isobutyraldehyde

H

80-62-6

methacrylic acid methyl ester

I

513-42-8

3-hydroxy-2-methyl-1-propene

Conditions
ConditionsYield
With magnesium hydroxide; oxygen at 80℃; under 2250.23 Torr; for 2h; Reagent/catalyst;
760-93-0

methacryloyl anhydride

7417-28-9

5-hydroxy-6-methyluracil

6-methyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-5-yl methacrylate

Conditions
ConditionsYield
With pyridine; hydroquinone at 20℃;100%
760-93-0

methacryloyl anhydride

17728-11-9

1-amino-4-hydroxy-2-[2'-[4'-(2'-hydroxyethoxy)phenoxy]ethoxy]anthraquinone

C28H25NO8

Conditions
ConditionsYield
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%
760-93-0

methacryloyl anhydride

THPE PO MA

Conditions
ConditionsYield
With pyridine at 80℃; for 6.5h;100%
760-93-0

methacryloyl anhydride

92-69-3

4-Phenylphenol

46904-74-9

[1,1'-biphenyl]-4-ylmethacrylate

Conditions
ConditionsYield
With dmap; 2,6-di-tert-butyl-4-methyl-phenol In toluene at 80℃; for 40h;100%
54731-72-5

dimethyl 2-hydroxyethylphosphonate

760-93-0

methacryloyl anhydride

22432-83-3

dimethyl (2-methacryloyloxyethyl)phosphonate

Conditions
ConditionsYield
With 1-methyl-1H-imidazole In butanone at 60℃; for 6h; Inert atmosphere;100%
760-93-0

methacryloyl anhydride

54731-74-7

dimethyl (γ-hydroxypropyl)phosphonate

252210-28-9

dimethyl (3-methacryloyloxypropyl)phosphonate

Conditions
ConditionsYield
With 1-methyl-1H-imidazole In butanone at 60℃; for 6h; Inert atmosphere;100%
760-93-0

methacryloyl anhydride

131991-61-2

6A-(6-aminohexylamino)-6A-deoxy-β-cyclodextrin

1080030-24-5

(1-methacrylamidohexyl)amino-6-deoxy-β-cyclodextrin

Conditions
ConditionsYield
In N,N-dimethyl-formamide at 20℃; Inert atmosphere;100%
760-93-0

methacryloyl anhydride

1361054-19-4

4-[(2-methylprop-2-enoyl)oxy]hexa-1,5-dien-3-yl 2-methylprop-2-enoate

Conditions
ConditionsYield
With dmap; triethylamine In dichloromethane at 20℃; for 1.5h;100%
760-93-0

methacryloyl anhydride

135-19-3

β-naphthol

10475-46-4

β-naphthyl methacrylic ester

Conditions
ConditionsYield
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%
760-93-0

methacryloyl anhydride

1137-42-4

4-Hydroxybenzophenone

56467-43-7

4-hydroxybenzophenone ester of metacrylic acid

Conditions
ConditionsYield
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;
760-93-0

methacryloyl anhydride

108-95-2

phenol

2177-70-0

phenyl methacrylate

Conditions
ConditionsYield
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;
108-30-5

succinic acid anhydride

inulin, MW: ca. 5000 Da, isolated from Dahlia Tubers

inulin, MW: ca. 5000 Da, isolated from Dahlia Tubers

760-93-0

methacryloyl anhydride

methacrylated/succinilated inulin, MW: 9000 Da

methacrylated/succinilated inulin, MW: 9000 Da

Conditions
ConditionsYield
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%
760-93-0

methacryloyl anhydride

1664-40-0

N-(2-aminoethyl)benzeneamine

1149340-19-1

N-phenylethylenediamine methacrylamide

Conditions
ConditionsYield
In methanol at 0℃; for 3h;99%
760-93-0

methacryloyl anhydride

6284-40-8

1-deoxy-1-(methylamino)-D-glucitol

N-methacryloyl-N-methyl-1-amino-1-deoxy-D-glucitol

Conditions
ConditionsYield
In methanol at 15 - 25℃; for 2h; Solvent;99%
571-60-8

1,4-Dihydroxynaphthalene

760-93-0

methacryloyl anhydride

1,4-dimethacryloyloxynaphthalene

Conditions
ConditionsYield
With dmap In dichloromethane at 35℃; Flow reactor;99%
760-93-0

methacryloyl anhydride

652-67-5

Isosorbide

108646-62-4

isosorbide bis-methacrylate

Conditions
ConditionsYield
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%
α,β-poly(N-2-hydroxyethyl)-D,L-aspartamide

α,β-poly(N-2-hydroxyethyl)-D,L-aspartamide

760-93-0

methacryloyl anhydride

copolymer PHM containing vinyl groups

copolymer PHM containing vinyl groups

Conditions
ConditionsYield
With triethylamine In N,N-dimethyl acetamide at 40℃; for 48h;98%
760-93-0

methacryloyl anhydride

7321-13-3

1,4-bis-[(2-hydroxy-ethylsulfanyl)-methyl]-benzene

112503-98-7

1,4-bis(2-methacryloyloxyethylthio)xylylene

Conditions
ConditionsYield
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%
760-93-0

methacryloyl anhydride

117420-69-6

1,2-bis(hydroxyethylthiomethyl)benzene

154865-01-7

1,2-bis(methacryloyloxyethylthiomethyl)benzene

Conditions
ConditionsYield
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%
760-93-0

methacryloyl anhydride

C21H41NO2

C25H45NO3

Conditions
ConditionsYield
With dmap at 60℃;98%
760-93-0

methacryloyl anhydride

90-15-3

α-naphthol

19102-44-4

1-naphthyl methacrylate

Conditions
ConditionsYield
With lithium carbonate at 80℃; for 2h; Reagent/catalyst;98%
760-93-0

methacryloyl anhydride

135304-82-4

1,3,6-trimethyl-isobarbituric acid

1,3,6-trimethyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-5-yl methacrylate

Conditions
ConditionsYield
With pyridine; hydroquinone at 20℃; for 1h;97%
79-41-4

poly(methacrylic acid)

760-93-0

methacryloyl anhydride

123-31-9

hydroquinone

A

5363-70-2

hex-1-ene-2,5-dicarboxylic acid

B

31480-93-0

4-hydroxyphenyl methacrylate

Conditions
ConditionsYield
at 120℃; for 4h; Product distribution / selectivity;A 1%
B 97%
700-58-3

2-Adamantanone

760-93-0

methacryloyl anhydride

917-54-4

methyllithium

177080-67-0

2-methyl-2-adamantyl methacrylate

Conditions
ConditionsYield
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%
760-93-0

methacryloyl anhydride

491878-98-9

bis(O,S-triphenylsilyl)-2-mercaptoethanol

1113062-54-6

C24H24O2SSi

Conditions
ConditionsYield
In dichloromethane at 20℃; for 3h;97%
760-93-0

methacryloyl anhydride

94594-90-8

(2R)-bornane-10,2-sultam

116195-15-4

(3aS,6R,7aR)-1-[(2E)-but-2-enoyl]-8,8-dimethylhexahydro-3a,6-methano-2,1-benzisothiazole 2,2-dioxide

Conditions
ConditionsYield
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%
HO-[G3]-PGLSA-PEG-OMe

HO-[G3]-PGLSA-PEG-OMe

760-93-0

methacryloyl anhydride

MA-[G3]-PGLSA-PEG-OMe

MA-[G3]-PGLSA-PEG-OMe

Conditions
ConditionsYield
With dmap In dichloromethane at 20℃;96%
With dmap In dichloromethane at 20℃;96%
760-93-0

methacryloyl anhydride

C5H10O5S2

C9H14O6S2

Conditions
ConditionsYield
With dmap; triethylamine In dichloromethane at 20℃; for 12h;96%
760-93-0

methacryloyl anhydride

C21H41NO2

C26H47NO3

Conditions
ConditionsYield
With dmap at 60℃;96%
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Chemistry

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

Uses

 Methacrylic anhydride (CAS NO.760-93-0) is used as light-curing coatings, cross-linked materials such as synthetic resin.

Toxicity Data With Reference

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.

Consensus Reports

EPA Extremely Hazardous Substances List. Reported in EPA TSCA Inventory.

Safety Profile

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

Specification

 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.