2-Methylpropyl 2-methyl-2-propenoate is an organic compound that belongs to the ester family, specifically a type of methacrylate ester.
2-Methylpropyl 2-methyl-2-propenoates chemical structure is made by the reaction of methacrylic acid (2-methyl-2-propenoic acid) with isobutanol (2-methylpropanol), resulting in an ester linkage between them.
2-Methylpropyl 2-methyl-2-propenoate is subjected to heat for prolonged periods or becomes contaminated, Isobutyl methacrylate is subject to polymerization.
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 2-methyl-2-propenoate is produced by the esterification or transesterification of isobutyl alcohol with either methacrylic acid or methyl methacrylate .
2-Methylpropyl 2-methyl-2-propenoate is a colorless liquid with a flash point of 120°F.
When heated to high temperatures 2-Methylpropyl 2-methyl-2-propenoate may release acrid smoke and fumes.
If the polymerization takes place inside a container, the container may violently rupture.
The vapors are heavier than air. Isobutyl methacrylate may be irritating to skin and eyes and produce a narcotic effect. Isobutyl methacrylate is used in making acrylic resins.
This means it is a molecular combination of an acid and an alcohol, where the hydrogen of the acid is replaced by an alkyl group from the alcohol.
The name “2-Methylpropyl 2-methyl-2-propenoate” is the systematic IUPAC name for Isobutyl methacrylate, a colorless, flammable liquid with a fruity odor that is used as a monomer in the production of polymers and resins.
These polymers are often used in paints, coatings, adhesives, and plastics due to their excellent clarity, flexibility, and weather resistance.
2-Methylpropyl 2-methyl-2-propenoate is the IUPAC name for a compound more commonly known as isobutyl methacrylate.
2-Methylpropyl 2-methyl-2-propenoate is an organic ester formed through the esterification of methacrylic acid (2-methyl-2-propenoic acid) with isobutanol (2-methylpropan-1-ol).
The molecule consists of a methacrylate backbone, which contributes reactivity, and an isobutyl group, which imparts steric bulk and hydrophobic character.
In industry, 2-Methylpropyl 2-methyl-2-propenoate is valued for its ability to copolymerize with other acrylic or methacrylic compounds, creating materials with tailored physical and chemical properties.
Its structure provides both rigidity (from the methacrylate group) and flexibility (from the branched isobutyl group), which is useful for balancing durability and softness in finished products.
Because of its volatile and flammable nature, it must be handled with care, especially during storage and processing, typically under inhibited conditions (such as with hydroquinone, HQ) to prevent unwanted polymerization.
2-Methylpropyl 2-methyl-2-propenoate is a versatile and reactive ester compound, widely used in modern industrial chemistry for the production of flexible, durable, and weather-resistant polymeric materials.
2-Methylpropyl 2-methyl-2-propenoate is a branched-chain ester that results from the condensation of methacrylic acid, a carboxylic acid with a double bond (2-methyl-2-propenoic acid), and isobutanol (2-methylpropan-1-ol), a branched-chain primary alcohol.
The name reflects its molecular structure: the “2-methylpropyl” part represents the isobutyl group derived from the alcohol, while the “2-methyl-2-propenoate” portion denotes the methacrylate group derived from the acid.
2-Methylpropyl 2-methyl-2-propenoate belongs to the broader family of methacrylate esters, which are known for their ability to undergo free-radical polymerization, forming tough, glassy, transparent, and weather-resistant polymers.
Among the methacrylates, the isobutyl derivative is notable for its balance between flexibility and rigidity, due to the steric hindrance provided by the branched isobutyl side chain.
This feature makes the resulting polymers less brittle and more impact-resistant than those made from simpler methacrylates like methyl methacrylate.
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
In terms of appearance, 2-Methylpropyl 2-methyl-2-propenoate is typically a colorless, mobile liquid with a fruity, ester-like odor, and it is highly flammable and volatile.
Due to its chemical structure, 2-Methylpropyl 2-methyl-2-propenoate participates readily in free-radical polymerization, which makes it highly suitable as a monomer in the production of plastics, resins, and copolymers.
Industrially, 2-Methylpropyl 2-methyl-2-propenoate is used in the manufacture of acrylic resins and coatings, particularly in applications requiring clarity, weather resistance, UV stability, and flexibility.
These applications include surface coatings for automobiles and appliances, pressure-sensitive adhesives, sealants, and impact-modified plastics.
2-Methylpropyl 2-methyl-2-propenoate is also found in textile finishes, inks, and nail polish formulations, where its balance of hardness and elasticity is useful.
2-Methylpropyl 2-methyl-2-propenoate is particularly valued in copolymer formulations with other acrylates or methacrylates, where it improves flow characteristics, surface hardness, and flexibility.
Because the isobutyl group is branched, it reduces the polymer's tendency to crystallize, resulting in more amorphous and flexible materials.
From a safety perspective, 2-Methylpropyl 2-methyl-2-propenoate must be stabilized with inhibitors such as hydroquinone (HQ) during transport and storage, to prevent uncontrolled polymerization, which can be hazardous.
2-Methylpropyl 2-methyl-2-propenoate should be stored in tightly sealed containers away from heat, light, and sources of ignition.
Inhalation of its vapors or prolonged skin contact can cause irritation, and adequate ventilation and protective equipment are required during handling.
2-Methylpropyl 2-methyl-2-propenoate 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 2-methyl-2-propenoate polymerizes readily.
2-Methylpropyl 2-methyl-2-propenoate is a clear, colorless to pale yellow liquid, with a characteristic pleasant fruity or floral odor, and has a relatively low viscosity, which makes it easy to handle and mix into resin formulations.
2-Methylpropyl 2-methyl-2-propenoate has a boiling point around 155–160°C, and a flash point typically between 49°C and 52°C, which classifies it as flammable and necessitates strict controls during industrial storage and handling.
Chemically, the presence of the double bond adjacent to the ester group (a vinyl group) makes this molecule highly reactive in radical-initiated polymerization reactions.
2-Methylpropyl 2-methyl-2-propenoate can homopolymerize or copolymerize with other monomers such as methyl methacrylate, butyl acrylate, styrene, and acrylonitrile, allowing for the creation of customized copolymers with precisely tuned mechanical, optical, or adhesive properties.
In industrial applications, this monomer is used in the formulation of coatings (especially automotive and industrial paints), adhesives, sealants, elastomers, plastic additives, and specialty acrylics.
In surface coatings, it provides good gloss, UV stability, water resistance, and substrate adhesion, while in adhesives and sealants, it contributes to flexibility, tackiness, and elongation.
2-Methylpropyl 2-methyl-2-propenoate is also found in photopolymer resins used in printing, 3D printing, and UV-cured materials, where fast curing and durable finishes are required.
Uses:
2-Methylpropyl 2-methyl-2-propenoate 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 used as electron microscope to take off the water.
2-Methylpropyl 2-methyl-2-propenoate is used in the manufacture of adhesive fabric.
2-Methylpropyl 2-methyl-2-propenoate is 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 2-methyl-2-propenoate is primarily used as a monomer for acrylic resins .
One of the most significant uses of 2-Methylpropyl 2-methyl-2-propenoate is in the production of acrylic and methacrylic polymers, where it serves as a comonomer in the synthesis of specialized plastics and resins.
2-Methylpropyl 2-methyl-2-propenoate is particularly favored in formulations that require a balance between hardness and flexibility, making it ideal for impact-resistant coatings, adhesives, and sealants.
Its branched isobutyl group helps reduce brittleness in the final polymer, which is especially important in applications where materials are exposed to mechanical stress or vibration.
In the paints and coatings industry, 2-Methylpropyl 2-methyl-2-propenoate is widely used in automotive, marine, and industrial finishes, where it contributes to UV resistance, weather durability, and high gloss.
When incorporated into coating resins, it helps improve film-forming properties, resulting in smooth, long-lasting finishes that resist cracking, fading, and yellowing even under harsh outdoor conditions.
2-Methylpropyl 2-methyl-2-propenoate is also used in architectural coatings, where environmental exposure demands strong adhesion, chemical resistance, and thermal stability.
2-Methylpropyl 2-methyl-2-propenoate is also used in the production of pressure-sensitive adhesives (PSAs), where its flexibility and tack-enhancing properties allow for strong bonding to a wide variety of surfaces, including metal, glass, plastic, and fabric.
These adhesives are used in labels, tapes, medical bandages, and automotive parts, where consistent performance under both low and high temperatures is required.
In the cosmetic and personal care industry, 2-Methylpropyl 2-methyl-2-propenoate may be used as a monomer in the manufacture of nail care products, especially in UV-curable nail coatings and gels.
In this context, 2-Methylpropyl 2-methyl-2-propenoate helps create hard yet flexible films that are resistant to chipping and peeling, while maintaining a glossy, attractive appearance.
2-Methylpropyl 2-methyl-2-propenoate is also involved in the production of textile finishing agents and fabrics with special performance characteristics, such as water repellency, flexibility, and durability.
When used in fabric coatings or treatments, it enhances the fabric's resistance to dirt, moisture, and physical wear.
In electronics and optical applications, polymers made from this compound may be used in protective coatings, optical resins, and dielectric layers, where transparency, stability, and electrical insulation properties are critical.
2-Methylpropyl 2-methyl-2-propenoate is sometimes used in 3D printing resins and photopolymer formulations, particularly in UV-cured systems where rapid polymerization and fine detail resolution are needed.
Its inclusion in these resins allows for the creation of durable, flexible, and high-precision printed parts, often used in prototyping, dentistry, and jewelry.
Safety Profile:
2-Methylpropyl 2-methyl-2-propenoate may act as a sensitizer, meaning that repeated or prolonged skin contact can lead to allergic skin reactions, such as dermatitis, in some individuals.
For this reason, it is important that workers handling this material use appropriate personal protective equipment (PPE), including chemical-resistant gloves, safety goggles, and protective clothing.
One of the primary hazards associated with 2-Methylpropyl 2-methyl-2-propenoate is its flammability.
2-Methylpropyl 2-methyl-2-propenoate is classified as a flammable liquid with a relatively low flash point, typically around 49–52 °C, which means it can easily ignite if exposed to open flames, sparks, or hot surfaces.
In environments with poor ventilation or elevated temperatures, the accumulation of vapors can form explosive mixtures with air, posing a serious fire and explosion risk, especially in enclosed areas.
Therefore, it must always be handled in well-ventilated spaces, away from ignition sources.
From a health and toxicological perspective, this substance can be irritating to the skin, eyes, and respiratory tract.
Upon inhalation of its vapors, individuals may experience symptoms such as headache, dizziness, nausea, coughing, and throat irritation, particularly at higher concentrations or after prolonged exposure.
If it comes into direct contact with the skin, it may cause redness, dryness, or a burning sensation, especially in people with sensitive skin or in cases of repeated exposure.
Eye contact with the liquid or concentrated vapors can result in significant irritation, redness, and watering, and should be avoided at all times.