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Methacryloyl chloride

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Name

Methacryloyl chloride

EINECS 213-058-9
CAS No. 920-46-7 Density 1.076 g/cm3
PSA 17.07000 LogP 1.32790
Solubility Miscible with alcohols, ethers and organic solvents. Slightly miscible with water. Melting Point -60 °C
Formula C4H5ClO Boiling Point 96 °C at 760 mmHg
Molecular Weight 104.536 Flash Point 27.7 °C
Transport Information UN 3383 6.1/PG 1 Appearance Colorless clear liquid
Safety 26-28-36/37/39-45-27-16-33-29 Risk Codes 11-26/27/28-34-26-22-43
Molecular Structure Molecular Structure of 920-46-7 (Methacryloyl chloride) Hazard Symbols FlammableF,VeryT+,IrritantXi
Synonyms

Methacryloylchloride (6CI,7CI,8CI);2-Methyl-2-propenoyl chloride;2-Methylacryloylchloride;2-Methylpropenoic acid chloride;Methacrylic acid chloride;Methacrylic chloride;a-Methylacryloylchloride;Methacryloyl chloride;

Article Data 117

Methacryloyl chloride Synthetic route

79-10-7

acrylic acid

920-46-7

Methacryloyl chloride

Conditions
ConditionsYield
With oxalyl dichloride; N,N-dimethyl-formamide at 20 - 60℃; for 0.166667h;99%
79-41-4

poly(methacrylic acid)

920-46-7

Methacryloyl chloride

Conditions
ConditionsYield
With thionyl chloride; N,N-dimethyl-formamide at 60℃; for 4h;80%
With thionyl chloride In N,N-dimethyl-formamide for 2h; Inert atmosphere; Reflux;75%
With thionyl chloride74%
78-85-3

2-methylpropenal

920-46-7

Methacryloyl chloride

Conditions
ConditionsYield
With chlorine at 400 - 470℃;
7623-10-1

2-methyl-3-chloropropionyl chloride

920-46-7

Methacryloyl chloride

Conditions
ConditionsYield
With pyrographite
79-41-4

poly(methacrylic acid)

98-88-4

benzoyl chloride

920-46-7

Methacryloyl chloride

79-41-4

poly(methacrylic acid)

98-09-9

benzenesulfonyl chloride

920-46-7

Methacryloyl chloride

Conditions
ConditionsYield
With pyridine
potassium methacrylate

potassium methacrylate

920-46-7

Methacryloyl chloride

Conditions
ConditionsYield
With trichlorophosphate
760-93-0

methacryloyl anhydride

368-44-5

dichloro(fluoro)(phenyl)silane

A

1344680-46-1

PhSiFClOC(O)C(CH3)=CH2

B

920-46-7

Methacryloyl chloride

Conditions
ConditionsYield
at 20℃;

6-chloro-3,4-dihydro-2,5-dimethyl-2H-pyran-2-carbonyl chloride

920-46-7

Methacryloyl chloride

Conditions
ConditionsYield
In (2)H8-toluene at 110℃; for 4h; Kinetics; Sealed tube;
79-41-4

poly(methacrylic acid)

707-74-4

(trichloromethyl)mesitylene

A

938-18-1

mesitylene-2-carboxylic acid chloride

B

920-46-7

Methacryloyl chloride

Conditions
ConditionsYield
With iron(III) chloride In n-heptane at 100℃; for 4h; Inert atmosphere;A 2.8 kg
B 1.2 kg

Methacryloyl chloride Consensus Reports

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

Methacryloyl chloride Specification

The Methacryloyl chloride with CAS registry number of 920-46-7 is also known as Methacrylic acid chloride. The IUPAC name is 2-Methylprop-2-enoyl chloride. It belongs to product categories of Acid chlorideS; Acid Halides; Carbonyl Compounds; Organic Building Blocks; Acrylic Monomers; Methacrylate; Monomers. Its EINECS registry number is 213-058-9. In addition, the formula is C4H5ClO and the molecular weight is 104.53. This chemical is a colorless clear liquid and should be stored in sealed containers in cool, dry place with protection of inert gas away from oxidizing agents, alkali, alcohol, radiation and so on.

Physical properties about Methacryloyl chloride are:
 (1)ACD/LogP: 1.61; (2)ACD/LogD (pH 5.5): 1.61; (3)ACD/LogD (pH 7.4): 1.61; (4)ACD/BCF (pH 5.5): 9.83; (5)ACD/BCF (pH 7.4): 9.83; (6)ACD/KOC (pH 5.5): 178.65; (7)ACD/KOC (pH 7.4): 178.65; (8)#H bond acceptors: 1; (9)#Freely Rotating Bonds: 1; (10)Index of Refraction: 1.424; (11)Molar Refractivity: 25.02 cm3; (12)Molar Volume: 97.9 cm3; (13)Surface Tension: 25.4 dyne/cm; (14)Density: 1.067 g/cm3; (15)Flash Point: 27.7 °C; (16)Enthalpy of Vaporization: 33.56 kJ/mol; (17)Boiling Point: 96 °C at 760 mmHg; (18)Vapour Pressure: 44.4 mmHg at 25 °C.

Preparation of Methacryloyl chloride:
it is prepared by reaction of 2-methyl-acrylic acid. The reaction needs reagent SOCl2 at 80 °C. The yield is about 55%.Methacryloyl chloride is prepared by reaction of 2-methyl-acrylic acid.

Uses of Methacryloyl chloride:
 it is used in organic synthesis as intermediate and rubber antioxidant. It is used to produce methacrylic acid-(4-chloro-anilide) by reaction with 4-chloro-aniline. The reaction occurs with reagent Et3N  and solvent CH2Cl2 at the temperature of 0-20 °C. The yield is about 69%.
This chemical is used to produce methacrylic acid-(4-chloro-anilide) by reaction with 4-chloro-aniline.

Safety Information of Methacryloyl chloride:
When you are using this chemical, please be cautious about it. As a chemical, it is very toxic by inhalation, in contact with skin and if swallowed. It is highly flammable that may cause burns. During using it, wear suitable protective clothing, gloves and eye/face protection. Keep away from sources of ignition and take precautionary measures against static discharges. After using it, take off immediately all contaminated clothing. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. If accident happens or you feel unwell seek medical advice immediately.

You can still convert the following datas into molecular structure:
1. Canonical SMILES: CC(=C)C(=O)Cl
2. InChI: InChI=1S/C4H5ClO/c1-3(2)4(5)6/h1H2,2H3
3. InChIKey: VHRYZQNGTZXDNX-UHFFFAOYSA-N

The toxicity data Methacryloyl chloride is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LC50 inhalation 115mg/m3/2H (115mg/m3)   "Toxicometric Parameters of Industrial Toxic Chemicals Under Single Exposure," Izmerov, N.F., et al., Moscow, Centre of International Projects, GKNT, 1982Vol. -, Pg. 80, 1982.
rat LC50 inhalation 60mg/m3/4H (60mg/m3)   "Toxicometric Parameters of Industrial Toxic Chemicals Under Single Exposure," Izmerov, N.F., et al., Moscow, Centre of International Projects, GKNT, 1982Vol. -, Pg. 80, 1982.

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