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
• Article Data: 10

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

General Description

3-Chloro-2-hydroxypropyl methacrylate is a chemical compound with the formula C6H9ClO3. It is a reactive monomer that is commonly used in the production of polymers and resins. 3-CHLORO-2-HYDROXYPROPYL METHACRYLATE is used to introduce hydroxyl and chlorine functional groups into polymers, which increases their adhesion and reactivity. It is also used as a crosslinking agent in the synthesis of hydrogels and other materials. Additionally, 3-Chloro-2-hydroxypropyl methacrylate is used in the production of adhesives, coatings, and other industrial applications. It is important to handle this chemical with care as it is a skin and eye irritant and can cause respiratory issues if inhaled.

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 

Relevant articles and documents

Difluorocarbene induced of facile synthesis of chlorohydrins from glycidyl ethers

A novel and unusual approach based on a ClCF2COONa-DMF system has been developed for the synthesis of chlorohydrins via an unexpected mechanism. In a first ever report for the synthesis of chlorohydrins from glycidyl ethers, e.g., CH2=CH-CH2-O-Z, CH 3CH2-O-Z, C6H5-O-Z, C 6H4(o-CH3)-O-Z, CH2=C(CH 3)C(=O)-O-Z, etc., (where Z = glycidyl), difluorocarbene-induced facile regioselective ring opening of epoxides has generated the compound in high yield (70%-83%).

1,3,2,4-diazadiphosphetidine-based phosphazane oligomers as source of P(III) atom economy reagents: Conversion of epoxides to vic -haloalcohols, vic -dihalides, and alkenes in the presence of halogen sources

1,3,2,4-Diazadiphosphetidines (P1-P3), as easily prepared, stable, and heterogeneous P(III) compounds, were used for the efficient conversion of epoxides to vic-halohydrins, vic-dihalides, or alkenes in the presence of different halogen sources in CH3CN. Of these phosphazanes, P3 is most suitable and contains 4 phosphorous atoms with the advantage of having greater atom economy and its phosphorus oxide byproduct can be easily separated from the reaction mixture by simple filtration. The nitrogen atoms in this molecule can also act as acid scavengers in the reaction.

Regioselective synthesis of vic-halo alcohols and symmetrical or unsymmetrical vic-dihalides from epoxides using triphenylphosphine -N-halo imides

A simple, novel, and highly regioselective cleavage of epoxides into vicinal halo alcohols and symmetrical or unsymmetrical dihalides is described using different stoichiometries of triphenylphosphine (PPh3) and N-halo succinimide (NXS) or N-halo saccharine (NXSac).