157859-20-6

Basic information

• Product Name: TRIISOPROPYLSILYL ACRYLATE
• Synonyms: TRIS(ISOPROPYL)SILYL ACRYLATE;TRIISOPROPYLSILYL ACRYLATE;ACRYLOXYTRIISOPROPYLSILANE;Acrylic acid trisisopropylsilyl ester;TIPX(Triisopropyl silyl acrylate);TIPSA;Tri(propan-2-yl)silyl prop-2-enoate;Triisopropylsilyl Acrylate (stabilized with BHT)
• CAS NO: 157859-20-6
• Molecular Formula: C₁₂H₂₄O₂Si
• Molecular Weight: 228.4
• Product Categories: PAINT AND COATING
• Mol File: 157859-20-6.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 230.7 °C at 760 mmHg
• Flash Point: 77.6 °C
• Appearance: /
• Density: 0.871 g/cm³
• Vapor Pressure: 0.0649mmHg at 25°C
• Refractive Index: 1.43
• Storage Temp.: 2-8°C
• Water Solubility: 60-1000000mg/L at 20-25℃
• CAS DataBase Reference: TRIISOPROPYLSILYL ACRYLATE(CAS DataBase Reference)
• NIST Chemistry Reference: TRIISOPROPYLSILYL ACRYLATE(157859-20-6)
• EPA Substance Registry System: TRIISOPROPYLSILYL ACRYLATE(157859-20-6)

Safety Data

• Hazardous Substances Data: 157859-20-6(Hazardous Substances Data)

Usage

Chemical Properties

Colorless Transparent Liquid

Flammability and Explosibility

Notclassified

InChI:InChI=1/C12H24O2Si/c1-8-12(13)14-15(9(2)3,10(4)5)11(6)7/h8-11H,1H2,2-7H3

Synthetic route

triisopropylsilyl chloride (13154-24-0) + potassium acrylate (10192-85-5) → tri(isopropyl)silyl acrylate (157859-20-6)

Conditions	Yield
With 2,6-di-tert-butyl-4-methyl-phenol In toluene at 45 - 50℃; for 6h; Reagent/catalyst; Inert atmosphere;	86%

triisopropylsilyl chloride (13154-24-0) + acrylic acid (79-10-7) → tri(isopropyl)silyl acrylate (157859-20-6)

Conditions	Yield
With triethylamine In dichloromethane at 0 - 20℃;	54.6%
With triethylamine In toluene at 15 - 25℃; for 2.5h;	508.9 g

triisopropylsilanol (17877-23-5) + acrylic acid (79-10-7) → tri(isopropyl)silyl acrylate (157859-20-6)

Conditions	Yield
With 4-methoxy-phenol; tetrabutyl ammonium fluoride In n-heptane at 125 - 130℃; under 760.051 Torr; Azeotropic distillation;

tri(isopropyl)silyl acrylate (157859-20-6) + methacrylic acid methyl ester (80-62-6) + ethyl acrylate (140-88-5) → Reaxys ID: 11380046

Conditions	Yield
With 2,2'-azobis(isobutyronitrile) In xylene for 10h; Product distribution / selectivity;

tri(isopropyl)silyl acrylate (157859-20-6) + methacrylic acid methyl ester (80-62-6) → Reaxys ID: 11380091

Conditions	Yield
With 2,2'-azobis(isobutyronitrile) In xylene for 10h;

tri(isopropyl)silyl acrylate (157859-20-6) + gamma-aminopropylmethyldimethoxysilane (3663-44-3) → N-(2-triisopropylsiloxycarbonyl)ethyl-3-aminopropyl(methyl)dimethoxysilane (1393671-01-6)

Conditions	Yield
at 70℃; for 7h;

tri(isopropyl)silyl acrylate (157859-20-6) + 3-(trimethoxysilyl)propan-1-amine (13822-56-5) → N-(2-triisopropylsiloxycarbonylethyl)-3-aminopropyltrimethoxysilane (1393671-00-5)

Conditions	Yield
In acetonitrile at 70℃; for 5h;

tri(isopropyl)silyl acrylate (157859-20-6) + 3-aminopropyltriethoxysilane (919-30-2) → N-(2-triisopropylsiloxycarbonyl)ethyl-3-aminopropyltriethoxy-silane (1393671-03-8)

Conditions	Yield
at 70℃; for 7h;

tri(isopropyl)silyl acrylate (157859-20-6) + 3-(diethoxy-methyl-silanyl)-propylamine (3179-76-8) → N-(2-triisopropylsiloxycarbonyl)ethyl-3-aminopropylmethyl-diethoxysilane (1393671-10-7)

Conditions	Yield
at 70℃; for 7h;

Upstream product

• 13154-24-0 triisopropylsilyl chloride 
• 10192-85-5 potassium acrylate 
• 79-10-7 acrylic acid 
• 17877-23-5 triisopropylsilanol 

Relevant articles and documents

Synthesis of homopolymers, diblock copolymers, and multiblock polymers by organocatalyzed group transfer polymerization of various acrylate monomers

The group transfer polymerization (GTP) with N-(trimethylsilyl)bis(trifluoromethanesulfonyl)imide (Me3SiNTf2) and 1-methoxy-1-triisopropylsiloxy-2-methyl-1-propene (iPr-SKA) has been studied using methyl acrylate (MA), ethyl acrylate (EA), n-butyl acrylate (nBA), 2-ethylhexyl acrylate (EHA), cyclohexyl acrylate (cHA), dicyclopentanyl acrylate (dcPA), tert-butyl acrylate (tBA), 2-methoxyethyl acrylate (MEA), 2-(2-ethoxyethoxy)ethyl acrylate (EEA), 2-(dimethylamino)ethyl acrylate (DMAEA), allyl acrylate (AlA), propargyl acrylate (PgA), 2-(triisopropylsiloxy)ethyl acrylate (TIPS-HEA), and triisopropylsilyl acrylate (TIPSA). Except for tBA and DMAEA, the GTPs of all other monomers described above proceeded rapidly in a living manner and produced well-defined homo acrylate polymers. The living nature of the GTPs of such acrylate monomers was further applied to the postpolymerizations of MA, EA, nBA, and MEA and also to the sequential GTPs of diverse acrylate monomers for preparing di- and multiblock acrylate polymers. In greater detail, the AB and BA diblock copolymers, (ABC)4 dodecablock terpolymer, (ABCD)3 dodecablock quaterpolymer, and ABCDEF hexablock sestopolymer were synthesized by sequential GTP methods using various acrylate monomers.

DISTILLATION METHOD FOR UNSATURATED CARBOXYLIC ACID SILYL ESTER

PROBLEM TO BE SOLVED: To provide a distillation method where the formation of polymeric substance is hardly present, and further, unsaturated carboxylic acid silyl ester can be refined by distillation, even if the distillation operation takes a long time, with a high product recovery rate. SOLUTION: When unsaturated carboxylic acid, triorganomonochlorosilane and a base are reacted in a solvent to produce unsaturated carboxylic acid silyl ester so as to be distillated, after the completion of the reaction, the reaction liquid is added with an amine-based polymerization inhibitor, and distillation is performed: as the amine-based polymerization inhibitor, N-i-propyl-N'-phenyl-p-phenylene diamine, N-(1,3-dimethylbutyl)-N'-phenyl-p-phenylenediamine, N,N'-di-2-naphthyl-p-phenylenediamine is preferable. SELECTED DRAWING: None COPYRIGHT: (C)2017,JPO&INPIT