177080-67-0

Basic information

• Product Name: 2-Methyl-2-adamantylmethacrylate
• Synonyms: 2-methacryloyloxy-2-methyladamantane;2-Methyl-2-adamantyl methacrylate;2-Methacryloyloxy-2-MethyladaMantane (stabilized with MEHQ);2-Methyl-2-adamantyl Methacrylate Methacrylic Acid 2-Methyl-2-adamantyl Ester;2-Methyl-2-adaMantyl Methacrylte;2-MethyladaMantan-2-yl Methacrylate
• CAS NO: 177080-67-0
• Molecular Formula: C₁₅H₂₂O₂
• Molecular Weight: 234.33
• Product Categories: We have in stock now.
• Mol File: 177080-67-0.mol
• Article Data: 14

Chemical Properties

• Boiling Point: 301.311 °C at 760 mmHg
• Flash Point: 120°C(lit.)
• Appearance: /
• Density: 1.061 g/cm³
• Vapor Pressure: 0.001mmHg at 25°C
• Refractive Index: 1.5050 to 1.5090
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 2-Methyl-2-adamantylmethacrylate(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Methyl-2-adamantylmethacrylate(177080-67-0)
• EPA Substance Registry System: 2-Methyl-2-adamantylmethacrylate(177080-67-0)

Safety Data

• Hazardous Substances Data: 177080-67-0(Hazardous Substances Data)

Usage

Synthesis

The synthesis of?2-Methyl-2-adamantylmethacrylate is as follows:Add 3546ml of n-heptane in the 5L four-necked flask equipped with stirring paddle, condenser tube and thermometer, turn on stirring, add 126.3g of 2-methyladamantanol to the system, and slowly add 0.022g polymerization inhibitor tetrachlorobenzoquinone to the reaction, add 110.8g basic ion exchange resin, adjust pH=7-8, cool down to -13°C, slowly add 110.8g vinyl methacrylate dropwise to the reaction system, keep the reaction for 7h, monitor the reaction progress, and take samples for detection After the reaction was completed, 1000 ml of water was added to the reaction system, and the mixture was stirred and extracted for phase separation. The organic phase was dried, concentrated under reduced pressure and evaporated to dryness to obtain 167 g of 2-methyl-2-adamantyl methacrylate product with a yield of 93.78%.

InChI:InChI=1/C15H22O2/c1-9(2)14(16)17-15(3)12-5-10-4-11(7-12)8-13(15)6-10/h10-13H,1,4-8H2,2-3H3

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Relevant articles and documents

Method for synthesizing adamantyl (meth) acrylate

The invention discloses a method for synthesizing adamantyl (meth) acrylate, and relates to the field of organic synthesis. The method for synthesizing adamantyl (meth) acrylate comprises the steps: 1, reacting (methyl) acrylic acid with alkyl sulfonyl chloride to generate mixed anhydride S1; 2, reacting 2-adamantanone with halogenated alkane under the action of a lithium reagent or a Grignard reagent to generate an intermediate S2; and 3, reacting the mixed anhydride S1 with the intermediate S2 to generate the adamantyl (meth) acrylate. The invention provides a synthetic method of adamantyl (meth) acrylate, and provides more selectivity for synthesis of adamantyl (meth) acrylate. The synthesis method disclosed by the invention is high in yield, high in product purity and low in synthesis cost.

Adamantyl ester monomer composition

The present invention discloses an adamantyl ester monomer composition characterized by containing at least an adamantyl ester monomer having at least one polymerizable unsaturated bond in the molecule, and a compound represented by the following general formula (1): (in the formula, R1 is an alkyl group of 1 to 5 carbon atoms, R2 is an alkyl group of 1 to 5 carbon atoms, R3 is a hydrogen atom or an alkyl group of 1 to 5 carbon atoms, and R4 is a hydrogen atom or a methyl group). The composition has high storage stability and, by subjecting it to distillation, an adamantyl ester monomer of high purity can be obtained easily.

Processes for preparation of 2-alkyl-2adamantyl esters

A magnesium halide salt of a 2-alkyl-2-adamantanol is reacted with a carboxylic acid halide such as acrylic chloride or the like in the presence of a tertiary amine to produce a 2-alkyl-2-adamantyl ester (the first invention). A 2-alkyl-2-adamantanol is reacted with a carboxylic acid such as acrylic acid or the like in the presence of an acid catalyst such as concentrated sulfuric acid or the like and a drying agent composed of an acidic or neutral inorganic compound (e.g. magnesium sulfate) which is a solid at ordinary temperature in a dried state or of a water-absorbing high-molecular compound, to produce a 2-alkyl-2-admantyl ester (the second invention). The above ester is important as a raw material for a resist for semiconductor production.