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96-05-9

Basic Information
CAS No.: 96-05-9
Name: Allyl methacrylate
Article Data: 25
Molecular Structure:
Molecular Structure of 96-05-9 (Allyl methacrylate)
Formula: C7H10O2
Molecular Weight: 126.155
Synonyms: 2-Propenoicacid, 2-methyl-, 2-propenyl ester (9CI);Methacrylic acid, allyl ester(6CI,8CI);Allyl alcohol, methacrylate (6CI);2-Methyl-2-propenoic acid 2-propenyl ester;Acryester A;NSC 18597;2-Propenoic acid,2-methyl-, 2-propen-1-yl ester;
EINECS: 202-473-0
Density: 0.917 g/cm3
Melting Point: -65 °C
Boiling Point: 138.588 °C at 760 mmHg
Flash Point: 33.889 °C
Solubility: Soluble in most organic solvents, hardly soluble in water
Appearance: clear liquid
Hazard Symbols: ToxicT,DangerousN
Risk Codes: 10-21/22-23-50
Safety: 36/37-45-61
Transport Information: UN 2929 6.1/PG 2
PSA: 26.30000
LogP: 1.29170
Synthetic route
79-41-4

poly(methacrylic acid)

591-87-7

Allyl acetate

96-05-9

allyl methacrylate

Conditions
ConditionsYield
With [Ir(1,5-cyclooctadiene)2]PF6 In toluene at 100℃; for 5h;92%
106-91-2

2,3-Epoxypropyl methacrylate

96-05-9

allyl methacrylate

Conditions
ConditionsYield
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%
1393670-68-2

allyl 2-((tert-butyl(1-(diethoxyphosphoryl)-2,2-dimethylpropyl)amino)oxy)-2-methylpropanoate

A

96-05-9

allyl methacrylate

B

1393670-72-8

diethyl (1-(tert-butyl((4,4-dimethyl-5-oxotetrahydrofuran-3-yl)methoxy)amino)-2,2-dimethylpropyl)phosphonate

Conditions
ConditionsYield
In tert-butyl alcohol at 120℃; for 2h; Sealed tube;A n/a
B 50%
106-91-2

2,3-Epoxypropyl methacrylate

A

2-methyl-acrylic acid 3-chloro-2-iodo-propyl ester

B

96-05-9

allyl methacrylate

Conditions
ConditionsYield
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
874487-06-6

α-allyloxy-isobutyric acid allyl ester

96-05-9

allyl methacrylate

Conditions
ConditionsYield
at 60℃; mit Oxalsaeure, ZnCl2 oder besser P2O5;
408318-09-2

α-acetoxy-isobutyric acid allyl ester

96-05-9

allyl methacrylate

Conditions
ConditionsYield
at 475℃; Pyrolysis;
408318-09-2

α-acetoxy-isobutyric acid allyl ester

A

96-05-9

allyl methacrylate

B

64-19-7

acetic acid

Conditions
ConditionsYield
at 475℃; Kontaktzeit ca.4.7 sec.Pyrolysis;
79-41-4

poly(methacrylic acid)

107-18-6

allyl alcohol

96-05-9

allyl methacrylate

Conditions
ConditionsYield
With sulfuric acid
With toluene-4-sulfonic acid In toluene Heating;
With dmap; dicyclohexyl-carbodiimide In dichloromethane Inert atmosphere;
17859-93-7

2-allyloxy-2-methylpropanoic acid

107-18-6

allyl alcohol

A

96-05-9

allyl methacrylate

B

874487-06-6

α-allyloxy-isobutyric acid allyl ester

Conditions
ConditionsYield
With sulfuric acid; tannic acid
107-18-6

allyl alcohol

80-62-6

methacrylic acid methyl ester

96-05-9

allyl methacrylate

Conditions
ConditionsYield
With sodium methylate; 2-hydroxyresorcinol
With oxygen; 4-methoxy-phenol; hydroquinone; zirconium(IV) acetylacetonate at 70 - 117℃; Product distribution / selectivity; Reflux;
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    Name Allyl methacrylate CAS NO. 96-05-9 Molecular Formula C7H10O2 Molecular Weight 126.15 EINECS 202-473-0

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Consensus Reports

EPA Genetic Toxicology Program. Reported in EPA TSCA Inventory.

Specification

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%.

Allyl methacrylate can be prepared by 2-methyl-acrylic acid oxiranylmethyl ester at the ambient temperature

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%.

Allyl methacrylate can be used to produce 3-(chlorodimethylsilyl)propyl methacrylate at the temperature of 80 °C

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,