4-METHYLSTYRENE

4-Methylstyrene is used as a monomer for polyesters and in plastics production.
4-Methylstyrene is also used as an intermediate in paint and coating additives.
4-Methylstyrene is used with other vinyltoluene isomers (3-vinyltoluene) as monomers for the preparation of poly(vinyltoluene).

CAS Number: 622-97-9
EC Number: 210-762-8
Molecular formula: C₉H₁₀
Molecular weight: 118.18 g/mol

SYNONYMS:
4-Vinyltoluene, 1-Ethenyl-4-methylbenzene, 1-Methyl-4-vinylbenzene, 4-Methylstyrene, Styrene, p-methyl- (8CI), 1-Ethenyl-4-methylbenzene, (4-Methylphenyl)ethene, (4-Tolyl)ethene, 1-(4-Methylphenyl)-1-ethene, 1-Methyl-4-vinylbenzene, 1-Vinyl-4-methylbenzene, 1-p-Tolylethene, 4-Ethenylmethylbenzene, 4-Methylstyrene, 4-Methylvinylbenzene, 4-Vinyltoluene, PMS, p-Methylstyrene, p-Tolylethylene, p-Vinyltoluene, 4-Methylstyrene, 4-Vinyltoluene, 4-Vinyl toluene, p-Vinyltoluene, p-Vinyl toluene, p-Methylstyrene, Para-Methylstyrene, p-Methyl-styrene, 1-Methyl-4-vinylbenzene, 1-Ethenyl-4-methylbenzene, 1-(4-Methylphenyl)ethene, 1-(4-Methylphenyl)-1-ethene, 4-Ethenyltoluene, 4-Vinyltoluol, 4-Methylstyrol, p-Methylstyrol, p-Vinyltoluol, Benzene, 1-ethenyl-4-methyl-, Benzene, 1-methyl-4-vinyl-, Benzene, 1-ethenyl-4-methyl-, (4-Tolyl)ethene, 1-p-Tolylethene, p-Tolyl ethene, Para-methyl styrene, Methylstyrene, P-Methylstyrene, Methylstyrene-P, 4-VT, p-MS, (4-Methylphenyl)ethene, 1-Methyl-4-vinylbenzene, 1-Vinyl-4-methylbenzene, 4-Vinyltoluene, 4-Methylvinylbenzene, 4-Vinyltoluene, p-Vinyltoluene

4-Methylstyrene is a low-molecular-weight aromatic vinyl monomer with the formula C₉H₁₀ and molecular weight 118.18 g/mol.
4-Methylstyrene is a clear, colorless to light-yellow liquid with a boiling point around 170–175 °C and a melting point around −34 to −38 °C.
Its most important chemical characteristic is the presence of a polymerizable vinyl group, which allows 4-Methylstyrene to participate in polymerization and copolymerization reactions.

4-Methylstyrene's primary industrial importance comes from its use in plastics, specialty polymers, polyester-related materials, poly(vinyltoluene), paint and coating additives and chemical synthesis.
4-Methylstyrene can also be used in specialized organometallic and coupling chemistry.

From a safety perspective, 4-Methylstyrene should not be treated as an ordinary hydrocarbon.
4-Methylstyrene is a polymerizable liquid, and commercial material is commonly stabilized with an inhibitor to suppress unwanted polymerization.
4-Methylstyrene is miscible with benzene.

4-Methylstyrene is slightly miscible with water.
4-Methylstyrene is an organic compound with the formula CH3C6H4CH=CH2.
4-Methylstyrene is a derivative of styrene and is used as a comonomer in the production of specialized polystyrenes.

4-Methylstyrene is produced by the dehydrogenation of 4-ethyltoluene.
4-Methylstyrene is an aromatic vinyl compound and a positional isomer of methylstyrene.
4-Methylstyrene consists of a benzene ring bearing a methyl group and a vinyl group in the para (4-) position.

4-Methylstyrene is therefore also called 4-vinyltoluene or p-vinyltoluene.
4-Methylstyrene contains a polymerizable carbon–carbon double bond, which makes it useful as a monomer and chemical intermediate, particularly in polymer and plastics chemistry.

ECHA identifies the substance as 4-methylstyrene, CAS 622-97-9, EC 210-762-8, with molecular formula C₉H₁₀ and IUPAC name 1-ethenyl-4-methylbenzene.
4-Methylstyrene is a para-substituted styrene derivative.
Its structure consists of a benzene ring substituted by a methyl group and a vinyl group at opposite positions.

4-Methylstyrene's simplified structural representation is: CH₃–C₆H₄–CH=CH₂
The vinyl group (–CH=CH₂) is the chemically reactive part of the molecule.
It can undergo addition polymerization, allowing 4-methylstyrene to act as a monomer for the production of polymeric materials.

The methyl group modifies the physical and electronic characteristics of the styrene molecule while retaining the highly useful polymerizable vinyl functionality.
Because it combines an aromatic ring with a reactive vinyl group, 4-methylstyrene is important in polymer chemistry, plastics production, polyester chemistry, coatings and specialty chemical synthesis.

USES and APPLICATIONS of 4-METHYLSTYRENE:
4-Methylstyrene is used as a monomer for polyesters and in plastics production.
4-Methylstyrene is also used as an intermediate in paint and coating additives.
Further, 4-Methylstyrene is used with other vinyltoluene isomers (3-vinyltoluene) as monomers for the preparation of poly(vinyltoluene).

In addition to this, 4-Methylstyrene is employed as a bi- ligand in the preparation of cationic, two-coordinate triphenylphosphine-gold(I)-pi complexes.
Further, 4-Methylstyrene is involved in Heck coupling reactions with chlorobenzene.
4-Methylstyrene is also sometimes used in the production of styrene-free polyester resin.

-Plastics production uses of 4-Methylstyrene:
4-Methylstyrene is used as a monomer in plastics production.
Its polymerizable vinyl group makes 4-Methylstyrene useful for producing specialty aromatic polymers.
Commercial chemical suppliers specifically identify plastics production as an application.

-Polyester uses of 4-Methylstyrene:
4-Methylstyrene is used as a monomer for polyester-related materials.
4-Methylstyrene can be incorporated into specialized polymer systems where an aromatic vinyl component is desirable.

-Poly(4-methylstyrene) uses of 4-Methylstyrene:
4-Methylstyrene can be polymerized to form poly(4-methylstyrene).
This polymer is also referred to as poly(p-methylstyrene).
Poly(p-methylstyrene) has been investigated for applications requiring properties different from conventional polystyrene.
Research has reported that replacement of styrene with 4-Methylstyrene in certain reinforced plastic composites can improve thermal stability.

-Poly(vinyltoluene) uses of 4-Methylstyrene:
4-Methylstyrene can be used together with other vinyltoluene isomers, particularly 3-vinyltoluene, as a monomer for producing poly(vinyltoluene) materials.
This is particularly relevant when commercial vinyltoluene mixtures are used rather than an isolated para isomer.

-Paint and coating additives uses of 4-Methylstyrene:
4-Methylstyrene is used as an intermediate in paint and coating additives.
Its aromatic and polymerizable character makes 4-Methylstyrene suitable as a building block for specialty coating chemistry.

-Specialty polymer synthesis uses of 4-Methylstyrene:
4-Methylstyrene is useful as a building block for specialty polymers where an aromatic ring and polymerizable vinyl functionality are required.
The para methyl group can modify polymer properties such as hydrophobicity, steric environment and thermal behavior.

-Chemical synthesis uses of 4-Methylstyrene:
4-Methylstyrene is also useful as an organic synthesis reagent because its alkene can participate in addition and coupling reactions.
Commercial sources specifically report 4-Methylstyrene's involvement in Heck coupling reactions with chlorobenzene.
Organometallic chemistry: 4-Methylstyrene has been employed as a π-ligand precursor/component in organometallic chemistry, including work involving cationic two-coordinate triphenylphosphine-gold(I)-π complexes.

BENEFITS AND INDUSTRIAL VALUE of 4-METHYLSTYRENE:
The main industrial advantage of 4-methylstyrene is its combination of aromatic rigidity and polymerizable vinyl functionality.
Its vinyl group allows 4-Methylstyrene to become chemically incorporated into polymer chains.
4-Methylstyrene's benzene ring provides aromatic rigidity.

4-Methylstyrene's methyl group modifies the electronic and steric properties of the monomer.
Its relatively low molecular weight allows 4-Methylstyrene to be handled as a conventional liquid monomer.
4-Methylstyrene's boiling point around 170–175 °C is sufficiently high for many industrial processing environments while remaining suitable for purification by distillation.
Its low water solubility also makes 4-Methylstyrene compatible with many organic-phase polymerization and formulation systems.

MOLECULAR CHARACTERISTICS of 4-METHYLSTYRENE:
4-Methylstyrene contains one benzene ring and one carbon–carbon double bond outside the aromatic ring.
4-Methylstyrene therefore contains two important structural components:
Aromatic component: the benzene ring.

Polymerizable component: the vinyl group, –CH=CH₂.
The methyl group is attached to the aromatic ring in the para position relative to the vinyl group.
The molecule contains no oxygen, nitrogen, sulfur or halogen atoms.
Consequently, 4-Methylstyrene is a relatively nonpolar hydrocarbon with a very low calculated polar surface area.

CHEMICAL CHARACTERISTICS of 4-METHYLSTYRENE:
The most chemically significant feature of 4-methylstyrene is its vinyl double bond.
The carbon–carbon double bond can participate in:

Addition polymerization,
Free-radical polymerization,
Cationic polymerization,
Copolymerization,
Cross-coupling-related chemistry,
and other alkene reactions.

The aromatic ring is comparatively stable but can participate in electrophilic aromatic substitution reactions.
The methyl substituent is electron donating and influences the electronic properties of the aromatic ring.
Because there are no heteroatoms, 4-Methylstyrene has essentially no conventional hydrogen-bonding capacity.

POLYMERIZATION CHARACTERISTICS of 4-METHYLSTYRENE:
4-Methylstyrene is a polymerizable vinyl aromatic monomer.
The vinyl group allows molecules to link together to form poly(4-methylstyrene), also called poly(p-methylstyrene).
The polymerization may be carried out by different mechanisms, including free-radical and cationic approaches.

Research has demonstrated photochemical and thermal cationic polymerization of p-methylstyrene, producing poly(p-methylstyrene) with potentially high molecular weight.
4-Methylstyrene formed from this monomer can possess different thermal and physical properties from conventional polystyrene because the para methyl substituent changes the polymer's structure.

VAPOR AND VOLATILITY CHARACTERISTICS of 4-METHYLSTYRENE:
4-Methylstyrene is a relatively volatile organic liquid compared with high-molecular-weight polymers, although its boiling point is considerably higher than that of many low-molecular-weight solvents.
4-Methylstyrene's vapor can accumulate in low-lying areas because the vapor is denser than air.
Vapor density of 4-Methylstyrene is approximately 4.1 relative to air.

NOTES of 4-METHYLSTYRENE:
Store 4-Methylstyrene in a cool place.
Keep 4-Methylstyrene the container tightly closed in a dry and well-ventilated place.
4-Methylstyrene is incompatible with strong oxidizing agents and strong acids.

CHEMICAL STABILITY of 4-METHYLSTYRENE:
Under recommended storage conditions, stabilized 4-methylstyrene can be stored as a liquid monomer.
However, 4-Methylstyrene's stability is strongly connected to temperature, inhibitor concentration, contamination and exposure to reactive chemicals.

CHARACTERISTICS of 4-METHYLSTYRENE:
4-Methylstyrene is:
An aromatic hydrocarbon
A styrene derivative
A vinyl monomer
A para-substituted compound
A liquid at room temperature
A colorless to light-yellow liquid
A relatively nonpolar molecule
A low-water-solubility compound
A combustible/flammable liquid
A polymerizable material
Normally supplied with a polymerization inhibitor
A useful monomer for specialty polymers
A chemical intermediate
A material used in plastics and polyester-related applications
A compound used in coating-additive chemistry
A compound relevant to organometallic and coupling chemistry

PHYSICAL and CHEMICAL PROPERTIES of 4-METHYLSTYRENE:
Chemical name: 4-Methylstyrene
IUPAC name: 1-Ethenyl-4-methylbenzene
Alternative systematic name: 1-Methyl-4-vinylbenzene
CAS Number: 622-97-9
EC Number: 210-762-8
EINECS Number: 210-762-8
PubChem CID: 12161
ChemSpider ID: 11661
Molecular Formula: C₉H₁₀
Molecular Weight: 118.18 g/mol
Exact Mass: 118.078250319 Da

Monoisotopic Mass: 118.078250319 Da
Chemical class: Aromatic hydrocarbon / alkyl-substituted styrene / vinyl aromatic monomer
Physical state: Liquid at room temperature
Appearance: Clear, colorless to almost colorless liquid
Odor: Aromatic odor
IUPAC structure: para-methyl-substituted styrene
SMILES: Cc1ccc(C=C)cc1
InChI: InChI=1S/C9H10/c1-3-9-6-4-8(2)5-7-9/h3-7H,1H2,2H3
InChIKey: JLBJTVDPSNHSKJ-UHFFFAOYSA-N
ECHA and PubChem agree on the principal identity information, while PubChem gives the molecular weight as 118.18 g/mol and the PubChem CID as 12161.
Molecular formula: C₉H₁₀

Molecular weight: 118.18 g/mol
Exact mass: 118.078250319 Da
Monoisotopic mass: 118.078250319 Da
Melting point: approximately −38 to −34 °C; PubChem reports −37.8 °C, while ChemicalBook reports −34 °C.
Boiling point: approximately 170–175 °C; PubChem reports 172 °C.
Density: approximately 0.896–0.897 g/mL at 25 °C.
Relative density: approximately 0.90 compared with water.
Refractive index: approximately 1.542–1.543 at 20 °C.
Flash point: approximately 45–53 °C, depending on test method; ChemicalBook reports 114 °F (~45.6 °C), while PubChem gives several reported values including 46 °C and 52.8 °C.
Autoignition temperature: approximately 515 °C.
Vapor pressure: less than approximately 1 mmHg at 20 °C according to ChemicalBook.

Water solubility: low; approximately 0.089 g/L is reported by ChemicalBook.
Solubility: slightly soluble in water and miscible with several organic solvents including benzene; TCI lists miscibility with methanol, benzene, ethanol and ether.
Log Kow / Log P: approximately 3.35–3.6, depending on source and calculation method.
Viscosity: approximately 0.79 cP at 25 °C in ChemicalBook data.
Explosive limits: approximately 1.1–5.2% by volume in air according to ChemicalBook.
Vapor density: approximately 4.1 relative to air in PubChem/HSDB-derived information.
Physical form: Liquid.
Color: Clear/colorless to light yellow.
Odor: Aromatic.
Polar surface area: 0 Ų.
Hydrogen-bond donor count: 0.

Hydrogen-bond acceptor count: 0.
Rotatable bond count: 1.
Formal charge: 0.
Heavy atom count: 9.
Aromatic rings: 1
Carbon atoms: 9.
Hydrogen atoms: 10.
Heteroatoms: 0.
Topological polar surface area: 0 Ų.

Linear Formula: CH3C6H4CH=CH2
CAS Number: 622-97-9
Molecular Weight: 118.18
UNSPSC Code: 12162002
NACRES: NA.23
PubChem Substance ID: 24897220
EC Number: 210-762-8
Beilstein/REAXYS Number: 1209317
MDL Number: MFCD00008621
Physical State: liquid

Color: No data available
Odor: No data available
Melting Point/Freezing Point: No data available
Initial Boiling Point and Boiling Range: 170 - 175 °C - lit.
Flammability (Solid, Gas): No data available
Upper/Lower Flammability or Explosive Limits: Upper explosion limit: 5,2 %(V)
Lower explosion limit: 1,1 %(V)
Flash Point: 45 °C

Autoignition Temperature: No data available
Decomposition Temperature: No data available
pH: No data available
Viscosity: Viscosity, kinematic: No data available
Viscosity, dynamic: No data available
Water Solubility: No data available
Partition Coefficient: n-octanol/water: No data available
Vapor Pressure: No data available

Density: 0,897 g/cm3 at 25 °C - lit.
Relative Density: No data available
Relative Vapor Density: No data available
Particle Characteristics: No data available
Explosive Properties: No data available
Oxidizing Properties: none
Other Safety Information: No data available
Chemical Formula: C9H10
Molar Mass: 118.179 g·mol−1
Appearance: colorless liquid
Boiling Point: 170–175 °C (338–347 °F; 443–448 K)

FIRST AID MEASURES of 4-METHYLSTYRENE:
-Description of first-aid measures
*General advice:
Show this material safety data sheet to the doctor in attendance.
*If inhaled:
After inhalation: 
Fresh air.
*In case of skin contact: 
Take off immediately all contaminated clothing. 
Rinse skin with
water/ shower.
*In case of eye contact:
After eye contact: 
Rinse out with plenty of water. 
Call in ophthalmologist. 
Remove contact lenses.
*If swallowed:
After swallowing: 
Immediately make victim drink water (two glasses at most). 
Consult a physician.
-Indication of any immediate medical attention and special treatment needed.
No data available

ACCIDENTAL RELEASE MEASURES of 4-METHYLSTYRENE:
-Environmental precautions:
Do not let product enter drains.
-Methods and materials for containment and cleaning up:
Cover drains. 
Collect, bind, and pump off spills. 
Observe possible material restrictions. 
Take up dry. 
Dispose of properly. 
Clean up affected area.

FIRE FIGHTING MEASURES of 4-METHYLSTYRENE:
-Extinguishing media:
*Suitable extinguishing media:
Carbon dioxide (CO2) 
Foam 
Dry powder
*Unsuitable extinguishing media:
For this substance/mixture no limitations of extinguishing agents are given.
-Further information:
Prevent fire extinguishing water from contaminating surface water or the ground water system.

EXPOSURE CONTROLS/PERSONAL PROTECTION of 4-METHYLSTYRENE:
-Control parameters:
--Ingredients with workplace control parameters:
-Exposure controls:
--Personal protective equipment:
*Eye/face protection:
Use equipment for eye protection. 
Safety glasses
*Body Protection:
protective clothing
*Respiratory protection:
Recommended Filter type: Filter A 
-Control of environmental exposure:
Do not let product enter drains.

HANDLING and STORAGE of 4-METHYLSTYRENE:
-Conditions for safe storage, including any incompatibilities:
*Storage conditions:
Tightly closed. 
Dry.

STABILITY and REACTIVITY of 4-METHYLSTYRENE:
-Chemical stability:
The product is chemically stable under standard ambient conditions (room temperature).
-Possibility of hazardous reactions:
No data available

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