2-Methylstyrene

HCID 11904

Basic information

CAS
25013-15-4
Standard SMILES
C=Cc1ccccc1C
InChIKey
NVZWEEGUWXZOKI-UHFFFAOYSA-N
Molecular formula
C9H10
Average molar mass
118.18 g/mol
Monoisotopic mass
118.07825032

Overview

2-vinyltoluene has been reported in Solanum lycopersicum with data available.

Names & identifiers

Preferred name
2-Methylstyrene
IUPAC
1-ethenyl-2-methylbenzene
English name
POLY(VINYLTOLUENE)
Molecular formula
C9H10
Molecular weight
118.1757

Names & synonyms

2-Methylstyrene611-15-42-Vinyltoluene1-Methyl-2-vinylbenzene1-Ethenyl-2-methylbenzeneStyrene, o-methyl-Benzene, 1-ethenyl-2-methyl-2-Ethenylmethylbenzene556UO5CL44RefChem:432175210-256-7o-Vinyltoluene
Show more names
VINYL TOLUENE RESINvinyltoluene homopolymerpoly(vinyltoluene),mixedisomersethenylmethyl-benzenhomopolymerBenzene,ethenylmethyl-,homopolymerPOLY(VINYLTOLUENE) ISO 9001:2015 REACHPOLYVINYLTOLUENE MIXED ISOMERS AVERAG&POLYVINYLTOLUENE, MIXED ISOMERS, UNIFORMpoly(vinyltoluene)mixedisomersaveragemwca.80,000(gpc)
O-METHYLSTYRENEVinyl tolueneMFCD00014936POLY(VINYLTOLUENE)2-Methyl-1-vinylbenzene2-METHYLSTYRENE (STABILIZED WITH TBC)1-methyl-2-vinyl-benzene1-ethenyl-2-methyl-benzene

Database identifiers

CAS
25013-15-4、611-15-4、9017-21-4
PubChem CID
11904
DTXSID
DTXSID2060599
ChEMBL
CHEMBL3427716
UNII
556UO5CL44
EC Number
210-256-7
Nikkaji
J43.392F

Properties

Computed structural properties

XLogP
3.2
Topological polar surface area
0 Ų
Hydrogen bond donors
0
Hydrogen bond acceptors
0
Rotatable bonds
1
Heavy atoms
9

Experimental & physicochemical properties

Chemical ClassesFlammable agents - 2nd degree
PolymersPlastics & Rubber -> Styrenes
SpringerMaterials PropertiesBoiling point
LogP3.580
Density · 5 items

0.9077 g/cu cm at 25 °C

0.91 g/cm³

Relative density of the vapour/air-mixture at 20 °C (air = 1): 1.00

0.89

0.89

Color/FormLiquid

Physicochemical properties

Melting point
206 · 206-210 °C
Boiling point
100 °C · 100 °C(lit.)
Density
1.05 g/mL · 1.05 g/mL at 25 °C(lit.)
refractive index
20 · n20/D 1.59
form
granular
Surface tension
39 mN/m · 39mN/m at 20°C

Safety & regulation

GHS classification

GHS Classification · 6 items

Warning

H332: Harmful if inhaled [Warning Acute toxicity, inhalation]

P261, P271, P273, P304+P340, P317, P391, and P501 (click each P-code to see the statement)

Danger

H226 (65%): Flammable liquid and vapor [Warning Flammable liquids]

P210, P233, P240, P241, P242, P243, P261, P264, P264+P265, P271, P273, P280, P301+P316, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P317, P321, P331, P332+P317, P337+P317, P362+P364, P370+P378, P391, P403+P235, P405, and P501 (click each P-code to see the statement)

Hazard information

Regulatory Information · 4 items

Chemical: Benzene, ethenylmethyl-

Benzene, ethenylmethyl- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Benzene, ethenylmethyl- are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)

Benzene, ethenylmethyl-: HSNO Approval: HSR001427 Approved with controls

The New Jersey Worker and Community Right to Know Act requires public and private employers to provide information about hazardous substances at their workplaces. (N.J.S.A. 34:5A-1 et. seq.)

Fire HazardsFlammable. Above 58 °C explosive vapour/air mixtures may be formed.
Fire PotentialFlammable.
Hazards Summary · 1 item

Vinyl toluene is similar to styrene in its toxicological properties. Fatty degeneration of the liver occurs in acute animal studies. Human subjects found the odor detectable at 50 ppm and objectionable at 300 ppm. [ACGIH] Mainly an eye and respiratory tract irritant, it can cause central nervous system depression after absorption of high doses. [NIOSH Guidelines for Chemical Hazards] A skin, eye, and respiratory tract irritant; Inhalation of high concentrations may cause CNS effects; May cause liver injury; [ICSC] Vinyltoluenes, stabilized (UN2618) has warning of explosive polymerization; [ERG 2016]

DOT ID and Guide2618 130P(inhibited)
EC ClassificationSymbol: Xn, N; R: 20-51/53; S: (2)-24-61

Safety & protection

Fire FightingUse water spray, foam, powder, carbon dioxide. In case of fire: keep drums, etc., cool by spraying with water.
First Aid Measures · 4 items

Fresh air, rest. Refer for medical attention.

Remove contaminated clothes. Rinse and then wash skin with water and soap. Refer for medical attention .

First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention.

Rinse mouth. Do NOT induce vomiting. Refer for medical attention .

First Aid(General first aid procedures)
Safe StorageFireproof. Separated from strong oxidants and strong acids. Well closed. Store only if stabilized. Provision to contain effluent from fire extinguishing. Store in an area without drain or sewer access.
Exposure Control and Personal Protection20.0 [ppm]
Fire Fighting Procedures · 4 items

Suitable extinguishing media: Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide.

Advice for firefighters: Wear self contained breathing apparatus for fire fighting if necessary.

Further information: Use water spray to cool unopened containers.

Use water spray, foam, powder, carbon dioxide. In case of fire: keep drums, etc., cool by spraying with water.

Toxicology

Target OrgansEyes, skin, respiratory system, central nervous system
Environmental Fate · 3 items

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 730(SRC), determined from a structure estimation method(2), indicates that 2-vinyltoluene is expected to have low mobility in soil(SRC). Volatilization of 2-vinyltoluene from moist soil surfaces is expected(SRC) given an estimated Henry's Law constant of 3.0X10-3 atm-cu m/mole(SRC), developed using a fragment constant estimation method(2). 2-Vinyltoluene is expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 1.85 mm Hg at 25 °C(3). Biodegradation data in soil were not available(SRC, 2018).

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 730(SRC), determined from a structure estimation method(2), indicates that 2-vinyltoluene is expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is expected(3) based upon an estimated Henry's Law constant of 3.0X10-3 atm-cu m/mole(SRC), developed using a fragment constant estimation method(2). Using this Henry's Law constant and an estimation method(3), volatilization half-lives for a model river and model lake are 3.5 hours and 4.4 days, respectively(SRC). 2-Vinyltoluene is not expected to undergo hydrolysis in the environment due to the lack of functional groups that hydrolyze under environmental conditions(3). According to a classification scheme(4), an estimated BCF of 90(SRC), from an estimated log Kow of 3.44(2) and a regression-derived equation(2), suggests the potential for bioconcentration in aquatic organisms is moderate. Biodegradation data in water were not available(SRC, 2018).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), 2-vinyltoluene, which has a vapor pressure of 1.85 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase 2-vinyltoluene is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals and ozone(SRC); the half-lives for these reactions in air are estimated to be 12 and 13 hours(SRC), calculated from respective rate constants of 3.1X10-11 and 2.1X10-17 cu cm/molecule-sec at 25 °C(SRC) that were derived using a structure estimation method(3). Based on structural analogy with 3- and 4-vinyltoluene which absorb weakly at wavelengths >290 nm(4), 2-vinyltoluene may be susceptible to direct photolysis by sunlight(SRC).

Adverse EffectsNeurotoxin - Acute solvent syndrome
Exposure Routes · 2 items

The substance can be absorbed into the body by inhalation and by ingestion.

inhalation, ingestion, skin and/or eye contact

Toxicity Summary · 1 item

IDENTIFICATION AND USE: 2-Vinyltoluene (ortho-vinyltoluene) is a liquid. Commercial vinyl toluene is primarily a mixture of meta- and para-vinyl toluene, usually with 56-60% meta, 40-45% para and 1% ortho. HUMAN STUDIES: A patient known from previous studies to be sensitive to styrene was patch tested with styrene and 18 compounds structurally related to styrene. Positive results were obtained with 2-vinyltoluene, and other isomers. The substance is irritating to the eyes, skin and respiratory tract. Central nervous system effects, such as depression, poor memory, slow visuomotor performance and electrophysiological changes, have often been associated with heavy occupational exposures to vinyl toluenes. Significant increases in the frequencies of sister chromatid exchange were observed in human lymphocytes exposed in whole blood cultures to ortho, meta and para isomers. The strongest responses were seen with the meta and para isomers, which are the dominant species in vinyl toluene. ANIMAL STUDIES: There are no data available.

Plant Concentrations2-Vinyl toluene has been identified in the essential oil of Distichlis spicata, a marsh grass found in Mississippi salt marshes in the USA, possibly as a result of uptake and metabolism of polluted water(1).

Safety data

wgk
3
tsca
TSCA listed
Signal word
Warning
Symbol(GHS)
GHS07
safety_code
24/25
Hazard statements
H335-H315-H319

Chemistry & industry

Pharmacology

Metabolism/Metabolites · 1 item

o-Vinyltoluene, m-vinyltoluene and p-vinyltoluene were given i.p. to rats and urine was analyzed for acidic metabolites by gas chromatography mass spectrometry. Different derivatives were prepared and used to identify the structure of the metabolites. Different types (11) of metabolites were found, although all metabolites were not produced from each vinyltoluene isomer. The metabolites identified were: methylphenylethylene glycol, methylmandelic acid, methylphenylglyoxylic acid, hydroxymethylphenylethylene glycol, carboxyphenylethylene glycol, hydroxymethylphenylglyoxylic acid, methylbenzoylglycine, methylphenylacetylglycine, vinylbenzoylglycine, N-acetylcysteine conjugate of methylphenylethanol and glucuronide of methylphenylethylene glycol. Metabolites (> 90%) recovered were excreted during the 1st 24 hr. For the sum of all metabolites, there was an approximately linear relation between given dose and recovered amount of metabolites. Repeated daily administration was not followed by any appreciable increase in metabolite excretion and no enzyme induction phenomenon was apparent.

Uses & manufacturing

Uses · 2 items

Used as a monomer in the production of plastics and surface coatings and as an intermediate in the synthesis of certain insecticides; [ACGIH]

Plastic Composites Manufacturing [Category: Industry]

U.S. Production2023: 10,000,000 - <50,000,000 lb
Consumer UsesFuel agents
Industry UsesSurface modifier
Formulations/Preparations · 1 item

Commercial vinyl toluene is primarily a mixture of meta- and para-vinyl toluene, usually with 56-60% meta, 40-45% para and 1% ortho. It is available as a commercial product with the following characteristics: purity, 99.2 wt% minimum; polymer, 25 ppm maximum; and para-tert-butylcatechol (inhibitor), 10-15 ppm or 45-55 ppm.

General Manufacturing Information · 2 items

Wholesale and Retail Trade

Benzene, ethenylmethyl-: ACTIVE

Related reactions

20 records

Compound notes

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