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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 | Hazard Symbols | F,T+,Xi | |
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 |
Conditions | Yield |
---|---|
With oxalyl dichloride; N,N-dimethyl-formamide at 20 - 60℃; for 0.166667h; | 99% |
Conditions | Yield |
---|---|
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 chloride | 74% |
Conditions | Yield |
---|---|
With chlorine at 400 - 470℃; |
Conditions | Yield |
---|---|
With pyrographite |
Conditions | Yield |
---|---|
With pyridine |
Methacryloyl chloride
Conditions | Yield |
---|---|
With trichlorophosphate |
methacryloyl anhydride
dichloro(fluoro)(phenyl)silane
A
PhSiFClOC(O)C(CH3)=CH2
B
Methacryloyl chloride
Conditions | Yield |
---|---|
at 20℃; |
Methacryloyl chloride
Conditions | Yield |
---|---|
In (2)H8-toluene at 110℃; for 4h; Kinetics; Sealed tube; |
poly(methacrylic acid)
(trichloromethyl)mesitylene
A
mesitylene-2-carboxylic acid chloride
B
Methacryloyl chloride
Conditions | Yield |
---|---|
With iron(III) chloride In n-heptane at 100℃; for 4h; Inert atmosphere; | A 2.8 kg B 1.2 kg |
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%.
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%.
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. |