7534-94-3

Basic information

• Product Name: Isobornyl methacrylate
• Synonyms: 2-methyl-,1,7,7-trimethylbicyclo(2.2.1)hept-2-ylester,exo-2-propenoicaci;2-methyl-,1,7,7-trimethylbicyclo[2.2.1]hept-2-ylester,exo-2-Propenoicacid;2-propenoicacid,2-methyl-,1,7,7,-trimethylbicyclo[9.2.1]hept-2-ylester,exo-;(1,7,7-TRIMETHYLTRICYCLO[2.2.1]HEPTEN-2-YL)-2-METHYL-2-PROPENOATE;METHACRYLIC ACID ISOBORNYL ESTER;ISOBORNYL METHACRYLATE;exo-1,7,7-trimethylbicyclo[2.2.1]hept-2-yl methacrylate;ISOBORNYL METHACRYLATE, TECH.
• CAS NO: 7534-94-3
• Molecular Formula: C₁₄H₂₂O₂
• Molecular Weight: 222.32
• EINECS: 231-403-1
• Product Categories: Bicyclic Monoterpenes;Biochemistry;Terpenes
• Mol File: 7534-94-3.mol
• Article Data: 0

Chemical Properties

• Melting Point: -60 °C
• Boiling Point: 127-129 °C15 mm Hg(lit.)
• Flash Point: 225 °F
• Appearance: Clear colorless to yellow/Liquid
• Density: 0.983 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.0105mmHg at 25°C
• Refractive Index: n20/D 1.477(lit.)
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• Water Solubility: negligible
• CAS DataBase Reference: Isobornyl methacrylate(CAS DataBase Reference)
• NIST Chemistry Reference: Isobornyl methacrylate(7534-94-3)
• EPA Substance Registry System: Isobornyl methacrylate(7534-94-3)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 2
• Hazardous Substances Data: 7534-94-3(Hazardous Substances Data)

Usage

Description

Isobornyl methacrylate is a reactive solvent that is clear and colorless to yellow in appearance. It has low vapor pressure and is a versatile hydrophobic monomer. This monomer is known for its good combination of hardness and flexibility, which can significantly improve the chemical and water resistance of polymer systems. Additionally, it facilitates free radical polymerization by forming a polymer with a high glass transition temperature (Tg).

Uses

Used in Polymer Industry:
Isobornyl methacrylate is used as a monomer for the production of polymers with enhanced chemical and water resistance. Its ability to improve the hardness and flexibility of polymer systems makes it a valuable component in the creation of durable and robust materials.
Isobornyl methacrylate is also used as a comonomer in the synthesis of copolymers, where it contributes to the overall performance and properties of the final product. This application takes advantage of its reactive nature and its capacity to form polymers with high glass transition temperatures (Tg), which can be beneficial for various industrial applications.
Used in Coatings Industry:
In the coatings industry, Isobornyl methacrylate is used as a component in the formulation of high-performance coatings. Its hydrophobic nature and ability to enhance the chemical and water resistance of polymer systems make it an ideal additive for creating coatings with improved durability and resistance to environmental factors.
Used in Adhesives Industry:
Isobornyl methacrylate is utilized as a key ingredient in the development of adhesives with superior bonding properties. Its combination of hardness and flexibility allows for the creation of adhesives that maintain their bond strength under various conditions, making them suitable for a wide range of applications.
Used in Dental Industry:
Isobornyl methacrylate is employed as a component in dental composites and restorative materials. Its contribution to the hardness and flexibility of these materials, along with its hydrophobic nature, results in dental restorations with increased durability and resistance to wear and tear.

Characteristics

Isobornyl methacrylate is a colorless transparent liquid. It is a monomer that unifies hardness and flexibility. Due to its molecular structure, its polymer has excellent high gloss, sharp image, scratch resistance, medium resistance and weather resistance, and Its hygroscopicity is significantly lower than that of MMA (methyl methacrylate). In addition, IBOMA-added acrylic resin has good compatibility with polyester, alkyd and many volatile paint film-forming substances.

Preparation

Isobornyl methacrylate was synthesized by direct esterification of camphene and methacrylic acid.

Flammability and Explosibility

Notclassified

Synthesis

Isobornyl methacrylate is obtained by reacting (1S,2S,4S)-(+)-isoborneol and 4-methoxyphenol.Dissolve5g (1S,2S,4S)-(+)-isoborneol in 15 mL toluene. Add 4 mg (0.032 mmol) 4-methoxyphenol to the solution. After the addition of 0.4 g (3.24 mmol)4-dimethylamino pyridine, add a solution of 10 g (64.8 mmol) methacrylic anhydride (MAA) in 10 mL toluene dropwise to the mixture. Heat the reaction mixture to 80 °C. Stir the reaction mixture for 16 hours. After cooling down to room temperature, wash the mixture with 50 mL 1M sodium bicarbonate solution four times. Wash the organic phase with 50 mL brine two times. Separate the organic phase. Remove the toluene by rotary evaporation followed by a fractional distillation under reduced pressure. 1H NMR (CDCl3, 300 MHz): δ(ppm) = 6.06 (dq, 1H, 1); 5.51 (dq, 1H, 2); 4.71 (m ,1H, 4); 1.93 (dd, 3H, 3); 1.87-1.5 (m, 5H, 6,7,8); 1.23-1.04 (m, 2H, 5); 1.012 (s, 3H, 9);0.86 (s, 3H, 10); 0.85 (s, 3H, 11). IR (film): ν(cm-1) = 2954 (CH2), 2879 (CH2), 1715 (C=O) 1454 (CH2), 1157 and 1053 (C=O). Fig The synthetic method of Isobornyl methacrylate

InChI:InChI=1/C14H22O2/c1-9(2)12(15)16-11-8-10-6-7-14(11,5)13(10,3)4/h10-11H,1,6-8H2,2-5H3/t10-,11+,14-/m0/s1