1-(1,1-Dimethylethyl)-4-methylbenzol

4-tert-Butyltoluene

HCID 7390CAS 98-51-1

Grundinformationen

Standard-SMILES
Cc1ccc(C(C)(C)C)cc1
InChIKey
QCWXDVFBZVHKLV-UHFFFAOYSA-N
Summenformel
C11H16
Durchschnittliche Molmasse
148,24 g/mol
Monoisotopische Masse
148,12520051

Überblick

P-tert-butyltoluene is a clear colorless liquid with an aromatic gasoline-like odor. (NTP, 1992)

Namen und Bezeichner

Bevorzugter Name
4-tert-Butyltoluene
IUPAC
1-tert-butyl-4-methylbenzene
Lokaler Name
1-(1,1-Dimethylethyl)-4-methylbenzol
Englischer Name
4-tert-Butyltoluene
Summenformel
C11H16
Molmasse
148.24

Namen und Synonyme

4-tert-Butyltoluene98-51-1p-tert-Butyltoluene1-tert-Butyl-4-methylbenzene4-T-BUTYLTOLUENE1-Methyl-4-tert-butylbenzenep-Methyl-tert-butylbenzeneToluene, p-tert-butyl-Benzene, 1-(1,1-dimethylethyl)-4-methyl-4-tert-Butyl-1-methylbenzenePTBT4-Methyl-tert-butylbenzene
Weitere Namen anzeigen
tbtPTBtbt[qr]ptbt[qr]p-tbt[qr]ai3-26435[qr]4-tert.-ButyltP-T-BUTYLTOLUENEtert-Butyltoluen
8-Methylparacymenep-TBTDTXSID1024704AI3-26435NSC-6589DTXCID404704589519D43LBenzene, 1-methyl-4-(1,1-dimethylethyl)-

Datenbank-Bezeichner

CAS
98-51-1
PubChem CID
7390
DTXSID
DTXSID1024704
ChEMBL
CHEMBL1489547
UNII
589519D43L
EC Number
202-675-9
Nikkaji
J54.420E

Eigenschaften

Berechnete Struktureigenschaften

XLogP
4,5
Polarare Oberfläche (TPSA)
0 Ų
H-Brücken-Donoren
0
H-Brücken-Akzeptoren
0
Frei drehbare Bindungen
1
Schwere Atome
11

Experimentelle und physikochemische Eigenschaften

Chemical ClassesFlammable agents - 2nd degree
SolventsSolvents -> Aromatic Solvents
SpringerMaterials Properties13C nuclear magnetic resonance spectrum
FragrancesFragrance Ingredient (4-tert-Butyltoluene) -> IFRA transparency List
LogP4.35
Odor · 3 Einträge

DISTINCT AROMATIC ODOR

Gasoline-like odor

Distinct aromatic odor, somewhat like gasoline.

Physikochemische Eigenschaften

Schmelzpunkt
-54 °C · -54 °C
Siedepunkt
191 °C · 191 °C (lit.)
Dichte
0.858 g/mL · 0.858 g/mL at 25 °C (lit.)
Dampfdruck
1.3 hPa · 1.3hPa at 30℃
Brechungsindex
20 · n20/D 1.492(lit.)
Flammpunkt
150 °F · 150 °F

Sicherheit und Regulatorisches

GHS-Klassifizierung

GHS Classification · 6 Einträge

Danger

H226 (93.3%): Flammable liquid and vapor [Warning Flammable liquids]

P203, P210, P233, P240, P241, P242, P243, P260, P261, P264, P264+P265, P270, P271, P273, P280, P284, P301+P317, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P308+P316, P316, P317, P318, P319, P320, P321, P330, P332+P317, P337+P317, P362+P364, P370+P378, P391, P403+P233, P403+P235, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 300 reports by companies from 15 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Warning

H227: Combustible liquid [Warning Flammable liquids]

Gefahrenhinweise

Regulatory Information · 4 Einträge

Chemical: Benzene, 1-(1,1-dimethylethyl)-4-methyl-

Status: Active Update: 15-10-2021 https://echa.europa.eu/registration-dossier/-/registered-dossier/22796

4-t-Butyltoluene: Does not have an individual approval but may be used under an appropriate group standard

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.)

DOT LabelPoison
Fire Hazards · 2 Einträge

This chemical is combustible. (NTP, 1992)

Combustible. Above 63 °C explosive vapour/air mixtures may be formed.

Fire PotentialFlammable. Moderately dangerous fire risk.
Health HazardsExcerpt from NIOSH Pocket Guide for p-tert-Butyltoluene:
Hazards Summary · 1 Eintrag

Liver injury occurs in chronic inhalation studies of experimental animals. Giddiness was observed in volunteers exposed at 160 ppm. [ACGIH] A skin, eye, and respiratory tract irritant; Inhalation of high concentrations can cause CNS depression; [ICSC]

Sicherheit und Schutzausrüstung

Fire Fighting · 2 Einträge

Fires involving this compound should be controlled with a dry chemical, carbon dioxide or halon extinguisher. (NTP, 1992)

Use water spray, alcohol-resistant foam, dry powder, carbon dioxide.

First Aid Measures · 4 Einträge

Fresh air, rest. Half-upright position. Refer immediately for medical attention.

Rinse and then wash skin with water and soap.

Rinse with plenty of water for several minutes (remove contact lenses if easily possible).

Rinse mouth. Give one or two glasses of water to drink. Refer for medical attention .

First Aid · 2 Einträge

EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop.

(General first aid procedures)

Safe StorageSeparated from food and feedstuffs and strong oxidants. Well closed. Keep in a well-ventilated room. Store in an area without drain or sewer access. Provision to contain effluent from fire extinguishing.
Exposure Control and Personal Protection360.0 [ppm]
Cleanup MethodsAbsorb on paper. Evaporate on a glass or an iron dish in hood. Burn the paper.

Toxikologische Informationen

Target OrgansEyes, skin, respiratory system, cardiovascular system, central nervous system, bone marrow, liver, kidneys
Ecotoxicity ValuesLD50 Goldfish 3 mg/l/24 hr (modified ASTM-D1345) /Conditions of bioassay not specified/
Environmental Fate · 3 Einträge

TERRESTRIAL FATE: Based upon estimated Koc values of 1700 and 1900, 4-t-butyltoluene will have low mobility in soil(1-2,SRC). A single biodegradation screening study suggests that 4-t-butyltoluene does not biodegrade easily(3). Evaporation from dry surfaces can be expected to occur(SRC).

AQUATIC FATE: Volatilization will be an important transport process for 4-t-butyltoluene in natural water. Volatilization half-lives (which exclude adsorption to sediment) of 3.6 and 43 hr can be estimated for a model river and model environmental pond, respectively(1-2,SRC); if adsorption is included in the pond simulation (Koc of 1900), the volatilization half-life increases to 13 days(2,SRC). A single biodegradation screening study suggests that 4-t-butyltoluene does not biodegrade easily(3). Aquatic hydrolysis is not an important fate process(SRC).

ATMOSPHERIC FATE: Based upon an extrapolated vapor pressure of 0.671 mm Hg at 25 °C(1), 4-t-butyltoluene is expected to exist almost entirely in the vapor-phase in the ambient atmosphere(2,SRC). The dominant degradation process in the atmosphere is the vapor-phase reaction with photochemically produced hydroxyl radicals which has an estimated half-life of 2.2 days(3,SRC).

Adverse Effects · 2 Einträge

Neurotoxin - Acute solvent syndrome

Compound with “poor evidence” of ototoxicity (it is a questionably ototoxic substance).

Exposure Routes · 2 Einträge

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

inhalation, ingestion, skin and/or eye contact

Signs and Symptoms · 5 Einträge

Cough. Sore throat. Metallic taste. Laboured breathing. Nausea. Dizziness. Headache. Tremor. Weakness.

Redness.

Redness. Pain.

Confusion. Convulsions. See Inhalation.

irritation eyes, skin; dry nose, throat; headache; low blood pressure, tachycardia, abnormal cardiovascular system stress; central nervous system, hematopoietic depression; metallic taste; liver, kidney injury

Regulatorische Informationen

TSCA Requirements · 1 Eintrag

Pursuant to section 8(d) of TSCA, EPA promulgated a model Health and Safety Data Reporting Rule. The section 8(d) model rule requires manufacturers, importers, and processors of listed chemical substances and mixtures to submit to EPA copies and lists of unpublished health and safety studies. p-tert-Butyltoluene is included on this list.

Sicherheitsdaten

OEB
A
OEL
TWA: 10 ppm (60 mg/m3), STEL: 20 ppm (120 mg/m3)
wgk
2
IDLA
100 ppm
tsca
TSCA listed
ridadr
UN 1993 3/PG 3

Chemie und Industrie

Pharmakologische Informationen

Metabolism/Metabolites · 1 Eintrag

Little information had been available on the metabolism of TBT until 1983, when an extensive study was conducted ... TBT /was administered/ to rats and guinea pigs intragastrically at a dose of 100 mg/kg and analyzed metabolites of TBT in glucuronidase-sulfatase-treated urine using gas chromatographic and mass spectrometric methods. In this study, p-tert-butylbenzoic acid and its alcohol derivative, 2-(p-carboxyphenyl)-2-methylpropan-1-ol, were identified as the major (17-22% of dose) urinary metabolites in rats, whereas p-tert-butylbenzoylglycine was found to be the most prominent metabolite (34% of dose) in guinea pigs. Minor metabolites (2-4% of dose) found in rat urine were 2-methyl-2-p-tolyl-propan-1-ol and p-tert-butylbenzoylglycine , while those in the guinea pig were p-tert-butylbenzoic acid, 2-methyl-2-p-tolylpropan-1-ol, and 2-methyl-2-p-tolylpropionic acid which was not detected at all in rats. Trace amounts (<0.5% of dose) of p-tert-butylbenzyl alcohol were found both in rat and guinea pig urine. 2-(p-Carboxyphenyl)-2-methylpropionic acid, a trace amount, was detected only in rat urine. Similar metabolism of TBT was also found when the chemical was given by inhalation. In this case, trace amounts of 2-(p-carboxyphenyl)-2- methylpropan-1-ol, which was not identified after intragastric administration, was detected in the urine of guinea pigs.

Absorption, Distribution and Excretion · 3 Einträge

TBT IS ABSORBED INTO BLOOD BY INHALATION OF VAPOR & BY ORAL ADMIN OF LIQ. ... PROBABLE THAT OWING TO ITS LOW VAPOR PRESSURE ONLY SMALL AMT IS EXHALED UNCHANGED, MAJOR PART BEING METABOLIZED IN LIVER & EXCRETED AS WATER SOL METABOLITES IN URINE, AS CONJUGATES OF ALCOHOLS OR CARBOXYLIC ACIDS WITH GLUCURONIC ACIDS OR GLYCINE.

In mice exposed to 1000 ppm TBT, a substantial amount of the chemical was detected in the blood (2.1 ug/ml) 15 min after the start of inhalation and reached a plateau level (4.8-5.3 ug/ml) 4 hr after continous exposure. It can also be absorbed into blood following oral administration and skin application.

The excretion rate of radioactivity in the urine of rats given an intragastric dose (100 mg/kg) of (methyl-(14)C) TBT followed a biphasic curve; the half-life of the first phase was about 19 hr and that of the second phase was about 82 hr. This suggests that accumulation of TBT within the animal body could be expected following repeated exposures to the chemical.

Verwendung und Herstellung

Uses · 4 Einträge

Used as solvent for resins and as a chemical intermediate for the chemical and pharmaceutical industries; [HSDB]

Plastic Composites Manufacturing [Category: Industry]

AS A SOLVENT FOR RESINS; AS A PRIMARY INTERMEDIATE IN CHEM INDUSTRY

CHEM INT FOR P-TERT-BUTYLBENZOIC ACID-RESIN RAW MATERIAL, PHARMACEUTICALS; SOLVENT FOR RESIN PREPN

U.S. Production · 2 Einträge

(1977) PROBABLY GREATER THAN 2.04X10+7 GRAMS

(1978) 3.18X10+9 GRAMS (CONSUMPTION)

Consumption PatternsCHEM INT FOR P-TERT-BUTYL BENZOIC ACID, 90%; OTHER USES, 10% (1978)
Methods of ManufacturingALKYLATION OF TOLUENE WITH ISO-BUTYLENE
Formulations/PreparationsGrade: Technical
Use ClassificationFragrance Ingredients

Anwendungen

Verwenden4-tert-Butyltoluene is used as pharmaceutical intermediate, Solvent for resins, intermediate in organic synthesis. It is an intermediate for the production of the acaricide pyridaben.

Darstellung · 1 Eintrag

synthetischeSynthesis of 4-tert-butyltoluene: Put toluene in the reaction kettle, add catalyst, then add tert-butane chloride, after the reaction, wash with water and layer, and the organic layer is distilled to obtain the product. Alkylation of isobutylene and toluene in the presence of sulfuric acid can also be used to produce 4-tert-butyltoluene.

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