13159-52-9

Basic information

• Product Name: 3-CHLORO-2-HYDROXYPROPYL METHACRYLATE
• Synonyms: 2-methyl-2-propenoicaci3-chloro-2-hydroxypropylester;2-Propenoicacid,2-methyl-,3-chloro-2-hydroxypropylester;2-HYDROXY-3-CHLOROPROPYL METHACRYLATE;3-CHLORO-2-HYDROXYPROPYL METHACRYLATE;METHACRYLIC ACID 3-CHLORO-2-HYDROXYPROPYL ESTER;2-Propenoic acid, 2-methyl-, 3-chloro-2-hydroxypropyl ester 2-methyl-2-propenoic aci 3-chloro-2-hydroxypropyl ester 3-chloro-2-hydroxypropyl methacrylate 2-Propenoic acid,2-methyl-,3-chloro-2-hydroxypropyl ester;3-Chloro-2-hydroxypropyl Methacrylate (stabilized with HQ);2-Methylpropenoic acid 2-hydroxy-3-chloro-propyl ester
• CAS NO: 13159-52-9
• Molecular Formula: C₇H₁₁ClO₃
• Molecular Weight: 178.61
• EINECS: 236-097-3
• Product Categories: Acrylic Monomers;C6 to C7Monomers;Carbonyl Compounds;Esters;Methacrylate
• Mol File: 13159-52-9.mol

Chemical Properties

• Boiling Point: 95 °C2 mm Hg(lit.)
• Flash Point: >230 °F
• Appearance: /
• Density: 1.19 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.00028mmHg at 25°C
• Refractive Index: n20/D 1.475(lit.)
• Storage Temp.: 0-10°C
• PKA: 12.68±0.20(Predicted)
• CAS DataBase Reference: 3-CHLORO-2-HYDROXYPROPYL METHACRYLATE(CAS DataBase Reference)
• NIST Chemistry Reference: 3-CHLORO-2-HYDROXYPROPYL METHACRYLATE(13159-52-9)
• EPA Substance Registry System: 3-CHLORO-2-HYDROXYPROPYL METHACRYLATE(13159-52-9)

Safety Data

• Hazard Codes: Xn
• Statements: 22-38-41-43
• Safety Statements: 26-36
• WGK Germany: 3
• Hazardous Substances Data: 13159-52-9(Hazardous Substances Data)

Usage

Uses

Used in Polymer and Resin Production:
3-Chloro-2-hydroxypropyl methacrylate is used as a reactive monomer for the production of polymers and resins. Its ability to introduce hydroxyl and chlorine functional groups into polymers improves their adhesion and reactivity, making it a valuable component in this industry.
Used in Hydrogel Synthesis:
In the field of material science, 3-chloro-2-hydroxypropyl methacrylate is used as a crosslinking agent in the synthesis of hydrogels. Its reactive nature allows for the formation of stable hydrogel structures, which have applications in various fields, including drug delivery and tissue engineering.
Used in Adhesives and Coatings Production:
3-Chloro-2-hydroxypropyl methacrylate is utilized in the production of adhesives and coatings due to its ability to enhance the adhesion and reactivity of these materials. Its incorporation into adhesives and coatings improves their performance and durability, making it a preferred choice in the industry.
Used in Industrial Applications:
Beyond its specific uses in polymer, resin, hydrogel, adhesive, and coating production, 3-chloro-2-hydroxypropyl methacrylate is also employed in various other industrial applications. Its versatility and ability to improve the properties of materials make it a valuable component in a wide range of products.

InChI:InChI=1/C7H11ClO3/c1-5(2)7(10)11-4-6(9)3-8/h6,9H,1,3-4H2,2H3

Synthetic route

2,3-Epoxypropyl methacrylate (106-91-2) → 3-chloro-2-hydroxypropyl methacrylate (13159-52-9)

Conditions	Yield
With quaternary ammonium chloride; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; water In acetonitrile for 0.5h; Heating;	96%
With N-chloro-succinimide; triphenylphosphine In water; acetonitrile at 20℃; for 0.05h;	95%
With N-chloro-succinimide; Silphos at 20℃; for 0.0833333h;	94%

poly(methacrylic acid) (79-41-4) + 3-monochloro-1,2-propanediol (96-24-2) → 3-chloro-2-hydroxypropyl methacrylate (13159-52-9)

Conditions	Yield
With toluene-4-sulfonic acid; hydroquinone

3-monochloro-1,2-propanediol (96-24-2) + Methacryloyl chloride (920-46-7) → 3-chloro-2-hydroxypropyl methacrylate (13159-52-9)

Conditions	Yield
With triethylamine; acetonitrile

poly(methacrylic acid) (79-41-4) + epichlorohydrin (106-89-8) → 2-Methyl-acrylic acid 2-chloro-1-hydroxymethyl-ethyl ester (109573-57-1) + 3-chloro-2-hydroxypropyl methacrylate (13159-52-9)

Conditions	Yield
Sn-P In benzene for 20h; Heating; Yield given. Yields of byproduct given. Title compound not separated from byproducts;
With chromium(lll) acetate for 80h; Kinetics; Solvent;
With diethylene glycol dimethyl ether; chromium(lll) acetate at 10℃; Kinetics; Temperature; Solvent; regioselective reaction;

poly(methacrylic acid) (79-41-4) + epichlorohydrin (106-89-8) → 3-chloro-2-hydroxypropyl methacrylate (13159-52-9)

Conditions	Yield
With diethylene glycol dimethyl ether; chromium(lll) acetate at 80℃; Kinetics; Temperature; Solvent; regioselective reaction;

N-(2,2,6,6-tetramethyl-4-piperidyl)-n-dodecylamine (66545-45-7) + 3-chloro-2-hydroxypropyl methacrylate (13159-52-9) → C28H54N2O3

Conditions	Yield
With potassium carbonate In acetonitrile for 24h; Reflux;	98%
With potassium carbonate In acetonitrile for 24h; Reflux;

sodium methylate (124-41-4) + 3-chloro-2-hydroxypropyl methacrylate (13159-52-9) → 3-methoxy-2-hydroxypropyl methacrylate (23056-15-7)

Conditions	Yield
With 10H-phenothiazine for 6h; Temperature; Reflux;	79%

3-chloro-2-hydroxypropyl methacrylate (13159-52-9) → 2-bromo-3-chloropropyl methacrylate

Conditions	Yield
With tetraalkylammonium bromide; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone In acetonitrile for 0.5h; Heating;

sodium diselenide + 3-chloro-2-hydroxypropyl methacrylate (13159-52-9) → C14H22O6Se2 (1352427-00-9)

Conditions	Yield
In ethanol; water at 20℃; for 3h;

C35H52N3P(2+)*2Br(1-) + 3-chloro-2-hydroxypropyl methacrylate (13159-52-9) → C42H62N3O3P(2+)*2Br(1-)

Conditions	Yield
With potassium carbonate In acetonitrile for 24h; Reflux;

C53H64N2P2(2+)*2Br(1-) + 3-chloro-2-hydroxypropyl methacrylate (13159-52-9) → C60H75N2O3P2(3+)*2Br(1-)*Cl(1-)

Conditions	Yield
In methanol for 24h; Reflux;

C31H42N2P(1+)*Br(1-) + 3-chloro-2-hydroxypropyl methacrylate (13159-52-9) → C38H52N2O3P(1+)*Br(1-)

Conditions	Yield
In methanol for 24h; Reflux;

Upstream product

• 79-41-4 poly(methacrylic acid) 
• 96-24-2 3-monochloro-1,2-propanediol 
• 920-46-7 Methacryloyl chloride 
• 106-89-8 epichlorohydrin 
• 106-91-2 2,3-Epoxypropyl methacrylate 

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