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2-Methylpropyl methacrylate is a valuable intermediate in the field of polymer chemistry, offering a balance of performance characteristics such as flexibility, clarity, and weatherability, which are essential in many high-performance materials used in modern manufacturing and construction industries.
2-Methylpropyl methacrylate, also known by its more common name isobutyl methacrylate, is a synthetic organic compound that belongs to the family of methacrylate esters, which are widely used in the production of polymers and resins.
2-Methylpropyl methacrylate is an ester formed from methacrylic acid (a type of unsaturated carboxylic acid) and 2-methylpropanol, also known as isobutanol, a branched-chain alcohol.
CAS Number: 97-86-9
Molecular Formula: C8H14O2
Molecular Weight: 142.2
EINECS Number: 202-613-0
Synonyms: Isobutyl methacrylate, 97-86-9, 2-methylpropyl 2-methylprop-2-enoate, 2-Propenoic acid, 2-methyl-, 2-methylpropyl ester, Methacrylic acid, isobutyl ester, Isobutyl 2-methyl-2-propenoate, 2-METHYLPROPYL METHACRYLATE, Methacrylic Acid Isobutyl Ester, NSC 18607, Isobutylester kyseliny methakrylove, Isobutyl .alpha.-methacrylate, Isobutyl .alpha.-methylacrylate, DTXSID3025461, V11534UYZ0, NSC-18607, Isobutyl Methacrylate (stabilized with HQ), Isobutyl 2-methylacrylate, DTXCID505461, MFCD00008931, Isobutyl alpha-methacrylate, CAS-97-86-9, Isobutyl alpha-methylacrylate, CCRIS 4829, HSDB 5312, EINECS 202-613-0, UN2283, 2-Methylpropyl 2-methyl-2-propenoate, BRN 1747595, Propenoic acid, 2-methyl, isobutyl ester, UNII-V11534UYZ0, Isobutylester kyseliny methakrylove [Czech], Blemmer IBMA, Isobutylmethacrylate, i-butyl methacrylate, iso-butyl methacrylate, EC 202-613-0, Isobutyl 2-methylacrylate #, Isobutyl methacrylate, 97%, SCHEMBL24562, MLS002152907, Isobutyl methacrylate, inhibited, CHEMBL1453087, HMS3039B08, NSC18607, ISOBUTYL METHACRYLATE [HSDB], Tox21_201568, Tox21_303327, BBL010919, MFCD00084435, STK801852, AKOS005622614, UN 2283, NCGC00091087-01, NCGC00091087-02, NCGC00256982-01, NCGC00259117-01, WLN: 1Y1 & 1OVY1 & U1, SMR001224512, VS-02749, Isobutyl Methacrylate, (stabilized with HQ), M0132, NS00001412, Q27291392, Isobutyl methacrylate, inhibited [UN2283] [Flammable liquid], InChI=1/C8H14O2/c1-6(2)5-10-8(9)7(3)4/h6H,3,5H2,1-2,4H, 2-METHYL-ACRYLIC ACID ISOBUTYL ESTER;ISO-BUTYL NETHACRYLATE;ISOBUTYL METHACRYLATE;METHACRYLIC ACID ISOBUTYL ESTER;2-methyl-2-propenoicaci2-methylpropylester;2-methyl-2-propenoicacid,2-methylpropylester;2-Methylpropyl methacrylate;2-methylpropylmethacrylate
2-Methylpropyl methacrylate describes its molecular structure, indicating that the alcohol part is a 2-methylpropyl (isobutyl) group attached to the methacrylate molecule.
2-Methylpropyl methacrylate is a clear, colorless to slightly yellow liquid with a characteristic fruity odor, and is known for being highly flammable and volatile.
It has a double bond in its structure, making it capable of undergoing free-radical polymerization, a chemical process in which molecules link together to form long chains, resulting in solid materials known as polymers.
2-Methylpropyl methacrylate is primarily used as a monomer in the production of acrylic resins and copolymers, often in combination with other acrylates or methacrylates such as methyl methacrylate, butyl acrylate, or ethyl acrylate.
These polymers are then used in a wide variety of applications, including automotive and industrial coatings, adhesives, sealants, inks, and plastic modifiers, because of their excellent durability, flexibility, UV resistance, and adhesion properties.
The isobutyl side group on this molecule adds a degree of steric hindrance, which helps reduce the rigidity of the resulting polymer and gives it improved impact resistance and flexibility, making it suitable for surfaces that need to endure bending, vibration, or minor deformation without cracking.
This property makes it especially useful in protective coatings for vehicles, appliances, and outdoor structures.
Due to its chemical reactivity and tendency to polymerize spontaneously under heat, light, or contamination by peroxides, it is commonly stabilized with small amounts of polymerization inhibitors, such as hydroquinone (HQ), during storage and transport.
If not properly stabilized, it may undergo hazardous runaway polymerization, releasing heat and potentially causing pressure build-up in sealed containers.
Moreover, this compound plays a role in the development of UV-curable systems, such as those used in 3D printing resins, dental materials, and high-speed printing inks, where rapid curing under ultraviolet light is essential.
Its ability to cure quickly while still offering mechanical resilience makes it highly valuable in precision applications.
Environmentally and biologically, 2-Methylpropyl methacrylate is considered moderately hazardous, particularly if inhaled or brought into prolonged contact with the skin.
2-Methylpropyl methacrylate can act as a sensitizer, meaning repeated exposure can lead to allergic reactions such as dermatitis.
Its vapors may also cause respiratory tract irritation, headaches, and dizziness, particularly in poorly ventilated areas.
Additionally, it contributes to volatile organic compound (VOC) emissions, which are strictly regulated in many countries due to their role in photochemical smog formation and overall air quality degradation.
Melting point: -37 °C
Boiling point: 155 °C (lit.)
Density: 0.886 g/mL at 25 °C (lit.)
vapor density: 3.82 (vs air)
vapor pressure: 3.5 mm Hg (20 °C)
refractive index: n₂₀/D 1.420 (lit.)
Flash point: 107 °F
storage temp.: 2–8 °C
form: Liquid
color: Clear colorless
Odor: ether-like odor
Viscosity: 1.01 mm²/s
Water Solubility: Soluble in water at 20 °C, 2 g/L
BRN: 1747595
Stability: Light, heat and air sensitive. Polymerizes readily. Combustible. Incompatible with strong oxidizing agents.
LogP: 2.95 at 20 °C
2-Methylpropyl methacrylate is a colorless liquid with a flash point of 120°F.
When heated to high temperatures
2-Methylpropyl methacrylate may release acrid smoke and fumes.
If 2-Methylpropyl methacrylate is subjected to heat for prolonged periods or becomes contaminated, Isobutyl methacrylate is subject to polymerization.
If the polymerization takes place inside a container, the container may violently rupture.
The vapors are heavier than air.
2-Methylpropyl methacrylate may be irritating to skin and eyes and produce a narcotic effect.
2-Methylpropyl methacrylate is used in making acrylic resins.
2-Methylpropyl methacrylate is an ester.
Esters react with acids to liberate heat along with alcohols and acids.
Strong oxidizing acids may cause a vigorous reaction that is sufficiently exothermic to ignite the reaction products.
Heat is also generated by the interaction of esters with caustic solutions.
Flammable hydrogen is generated by mixing esters with alkali metals and hydrides.
2-Methylpropyl methacrylate polymerizes readily.
2-Methylpropyl methacrylate, also commonly known as isobutyl methacrylate, is a synthetic monomer in the methacrylate ester family, characterized by the presence of both an ester functional group and a reactive carbon–carbon double bond, which gives the molecule its ability to undergo polymerization.
The structure consists of a methacrylic acid-derived backbone connected to a branched 2-methylpropyl (isobutyl) group, which not only influences its physical properties but also affects the characteristics of the polymers it helps form.
As a clear, flammable, and volatile liquid, it has a pleasant, ester-like odor and is typically found in technical-grade purity stabilized with inhibitors like hydroquinone (HQ) or methylhydroquinone (MEHQ).
These inhibitors are added to prevent uncontrolled polymerization, which could otherwise occur spontaneously when the compound is exposed to light, heat, free radicals, or even metal ions.
Due to its low flash point and high vapor pressure, it must be handled with care in well-ventilated, explosion-proof environments, especially during bulk storage or transport.
In polymer chemistry, 2-Methylpropyl methacrylate is valued for its copolymerization capabilities, meaning it readily forms copolymers when combined with other monomers such as methyl methacrylate (MMA), ethyl acrylate, butyl acrylate, or styrene.
The inclusion of the isobutyl side group imparts flexibility, impact resistance, and hydrophobicity to the final material, making it particularly suitable for applications where environmental resistance and mechanical strength are required together.
This distinguishes it from simpler methacrylate esters like MMA, which can yield more brittle or rigid materials.
Industrially, this compound is used to create high-performance acrylic polymers that are incorporated into protective coatings, especially in automotive topcoats, industrial maintenance paints, and marine finishes, where they provide weather resistance, UV protection, and excellent surface appearance.
These coatings can maintain gloss, clarity, and color stability over long periods, even in harsh outdoor environments.
Beyond coatings, 2-Methylpropyl methacrylate is also a core component in pressure-sensitive adhesives (PSAs), where its presence enhances the balance between cohesive strength and peelability, making it useful for products like labels, tapes, and medical adhesives that must adhere well yet remove cleanly.
2-Methylpropyl methacrylate is also found in the formulation of inks, textiles, plastics, and sealants, especially in cases where low-temperature flexibility, long-term durability, and resistance to yellowing are required.
Uses:
2-Methylpropyl methacrylate is used in the manufacture of containing active hydroxyl acrylic resin.
Coatings with epoxy resin, diisocyanate and melamine formaldehyde resin configuration used for preparing a two-component coating.
In oil industry as additives for lubricating oil washing.
In electronics industry 2-Methylpropyl methacrylate used as electron microscope to take off the water.
Textile industry used in the manufacture of adhesive fabric. Used as chemical reagents in analytical chemistry.
In addition, also used for water immiscible embedding agent, used in the synthesis of medical polymer materials, thermosetting coatings and adhesives.
2-Methylpropyl methacrylate is predominantly used as a monomer in the manufacture of various acrylic and methacrylic polymers and copolymers, which find extensive applications across many industries due to their outstanding physical and chemical properties.
One of its most important roles is in the formulation of high-performance coatings, where it is incorporated into paints and varnishes designed for automotive finishes, industrial equipment, and architectural surfaces.
The polymers derived from this monomer contribute to coatings that exhibit exceptional gloss retention, weather resistance, UV stability, and mechanical durability, allowing vehicles and structures to maintain their aesthetic and protective qualities for extended periods even under harsh environmental exposure.
In addition to coatings, 2-Methylpropyl methacrylate is widely employed in the production of pressure-sensitive adhesives (PSAs), where its unique combination of rigidity and flexibility enhances the adhesive’s ability to bond firmly to substrates such as plastics, metals, and glass, while still allowing for easy removal when necessary.
These adhesives are critical components in products like labeling tapes, medical dressings, and mounting films, where performance under varying temperature and humidity conditions is essential for user safety and product reliability.
2-Methylpropyl methacrylate is also utilized in the manufacture of sealants and elastomers, particularly those used in construction and automotive industries, where flexibility and resistance to weathering, chemicals, and mechanical stress are required.
These sealants often protect joints, seams, and surfaces from water ingress and mechanical damage, extending the life of buildings, vehicles, and machinery.
In the field of plastics and molded materials, 2-Methylpropyl methacrylate serves as a comonomer that modifies the physical properties of polymers such as polymethyl methacrylate (PMMA), imparting improved impact resistance and flexibility without compromising transparency.
This makes it valuable in the production of clear plastic components, lenses, lighting fixtures, and display panels where clarity and toughness are both essential.
Additionally, it finds application in the formulation of UV-curable resins used in advanced manufacturing technologies like 3D printing, coatings for electronics, and dental materials, where fast curing times coupled with high mechanical strength and chemical resistance are critical.
The monomer’s ability to polymerize rapidly under ultraviolet light enables the production of detailed, durable parts and coatings with precise dimensional control.
Moreover, due to its ester functionality and branched structure, this monomer can influence the hydrophobicity and flexibility of copolymers, making it suitable for use in textile finishes, inks, and specialty coatings that require water repellency and enhanced wear resistance.
In the printing industry, polymers containing 2-Methylpropyl methacrylate improve ink adhesion and durability on various substrates, leading to longer-lasting printed materials.
2-Methylpropyl methacrylate is primarily used as a monomer for acrylic resins .
Safety Profile:
2-Methylpropyl methacrylate poses several significant hazards related to its flammability, chemical reactivity, and potential health effects, all of which require careful management to ensure safe handling and use.
Primarily, it is classified as a flammable liquid due to its low flash point, which means that it can readily ignite if exposed to open flames, sparks, or even static electricity.
In industrial environments where large quantities may be stored or processed, vapors can accumulate and form explosive mixtures with air, especially in poorly ventilated or confined spaces, increasing the risk of fires or explosions if appropriate precautions are not followed.
From a chemical stability standpoint, 2-Methylpropyl methacrylate is prone to spontaneous polymerization, a highly exothermic reaction that can be triggered by exposure to heat, light, or contaminants such as peroxides or metal ions.
If inhibitors such as hydroquinone (HQ) are absent or depleted, this runaway polymerization may occur violently, releasing substantial heat and pressure, potentially causing containers to rupture or explode.
Therefore, it is crucial to store 2-Methylpropyl methacrylate under controlled conditions with proper stabilizers and away from sources of ignition and contamination.
Regarding human health, exposure to this substance can lead to irritation of the skin, eyes, and respiratory tract.
Inhalation of its vapors may cause symptoms like headaches, dizziness, nausea, and coughing, especially when exposure levels are high or prolonged.
Direct skin contact can result in redness, dryness, and in some cases allergic sensitization, leading to dermatitis upon repeated exposure.
Eye contact with the liquid or concentrated vapors may cause significant irritation, redness, and watering.
Because it can act as a skin sensitizer, workers handling 2-Methylpropyl methacrylate should use appropriate personal protective equipment, including gloves, goggles, and protective clothing, and ensure good ventilation in the working area.
