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2,6-Di-tert-butyl-p-benzochinon

2,6-Di-t-butyl-p-benzoquinone

HCID 12867
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Grundinformationen

CAS
719-22-2
Standard-SMILES
CC(C)(C)C1=CC(=O)C=C(C(C)(C)C)C1=O
InChIKey
RDQSIADLBQFVMY-UHFFFAOYSA-N
Summenformel
C14H20O2
Durchschnittliche Molmasse
220,31 g/mol
Monoisotopische Masse
220,14632988

Überblick

2,6-Di-tert-butylbenzoquinone is a member of 1,4-benzoquinones.

Namen und Bezeichner

Bevorzugter Name
2,6-Di-t-butyl-p-benzoquinone
IUPAC
2,6-ditert-butylcyclohexa-2,5-diene-1,4-dione
Lokaler Name
2,6-Di-tert-butyl-p-benzochinon
Englischer Name
2,6-Di-tert-butyl-p-benzoquinone
Summenformel
C14H20O2
Molmasse
220.31

Namen und Synonyme

719-22-22,6-Di-tert-butyl-P-benzoquinone2,6-Di-tert-butylcyclohexa-2,5-diene-1,4-dione2,6-Di-tert-butyl-1,4-benzoquinone2,6-Di-tert-butylbenzoquinone2,6-DI-T-BUTYL-P-BENZOQUINONE2,5-Cyclohexadiene-1,4-dione, 2,6-bis(1,1-dimethylethyl)-2,6-Bis(1,1-dimethylethyl)-2,5-cyclohexadiene-1,4-dionep-Benzoquinone, 2,6-di-tert-butyl-2,6-Di-t-butyl-1,4-benzoquinoneNSC 14448CCRIS 7070
Weitere Namen anzeigen
DBQBHT-QBHT-quinone2,6-Di-tert-butylquinoneDibutylpbenzoquinone
HSDB 27753,5-di-tert-butylquinoneEINECS 211-946-0NSC-144484C9D8L0Y0TAI3-610492,6-di-tert-butylbenzo-1,4-quinone3,5-DI-TERT-BUTYL-P-BENZOQUINONE

Datenbank-Bezeichner

CAS
719-22-2
PubChem CID
12867

Eigenschaften

Berechnete StruktureigenschaftenWird ergänzt

XLogP
3,4
Polarare Oberfläche (TPSA)
34,1 Ų
H-Brücken-Donoren
0
H-Brücken-Akzeptoren
2
Frei drehbare Bindungen
2
Schwere Atome
16
Formalladung
0
Komplexität
359

Experimentelle und physikochemische Eigenschaften

Chemical Classes · 2 Einträge

Other Classes -> Aromatic Ketones

Antioxidant

SpringerMaterials PropertiesChemical shift
LogP · 2 Einträge

log Kow = 4.42

4.42

Color/FormYellow crystals
Melting Point · 2 Einträge

65-67 °C

65-67 °C

Vapor Pressure0.000411 [mmHg]
Physical Description · 2 Einträge

Yellow solid; [HSDB] Orange crystalline powder; [MSDSonline]

Solid

Physikochemische Eigenschaften

Schmelzpunkt
65 · 65-67 °C(lit.)

Sicherheit und Regulatorisches

Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.

GHS-Klassifizierung

GHS Classification · 4 Einträge

Warning

H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]

P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 47 reports by companies from 5 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Gefahrenhinweise

Hazards SummaryAn irritant; Effects in high-dose animal studies include ulceration of the nasal septum and hemorrhage; [MSDSonline] See Quinone.
Hazard Classes and CategoriesSkin Irrit. 2 (100%)

Sicherheit und Schutzausrüstung

Disposal Methods · 1 Eintrag

SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.

Toxikologische Informationen

Environmental Fate · 3 Einträge

TERRESTRIAL FATE: Based on a recommended classification scheme(3), an estimated Koc value of 6000(SRC), determined from a measured log Kow(2) and a recommended regression-derived equation(1), indicates that suggests that 2,6-di-t-butyl-p-benzoquinone will be essentially immobile in soil(3). In an unconfined aquifer, however, 2,6-di-t-butyl-p-benzoquinone was transported an estimated 2710 meters over a 43 year period(2,4). 2,6-Di-t-butyl-p-benzoquinone is not expected to volatilize from moist soil surfaces based on an estimated Henry's Law constant of 1.6X10-8 atm-cu m/mole(5,SRC). It may, however, volatilize from the surface of dry soils given an estimated vapor pressure of 4.1X10-4 mm Hg(6,SRC). Incomplete information is available regarding the biodegradation potential of 2,6-di-t-butyl-p-benzoquinone; Rhine River water which was subjected to bank filtration had lower concentrations of 2,6-di-t-butyl-p-benzoquinone than the original water(7). Adsorption to soil however, was not measured(7,SRC)).

Chemie und Industrie

Pharmakologische Informationen

Metabolism/Metabolites · 2 Einträge

THE URINARY & FECAL EXCRETION OF 3 NEW METABOLITES OF BUTYLATED HYDROXYTOLUENE (BHT, 3,5-DI-TERT-BUTYL-4-HYDROXYTOLUENE) WERE REVEALED BY GAS CHROMATOGRAPHY AFTER IP ADMIN TO MALE WISTAR RATS. THE STRUCTURES OF THESE METABOLITES, 2,6-DI-TERT-BUTYL-P-BENZOQUINONE, 2,6-DI-TERT-BUTYLHYDROQUINONE, & 2,6-DI-TERT-BUTYL-4-((METHYLTHIO)METHYL)PHENOL WERE IDENTIFIED BY COMPARISON OF GAS CHROMATOGRAPHIC & MASS SPECTRAL DATA WITH THOSE OF AUTHENTIC SAMPLES.

Quinones (ie, 6,12-dione) have been shown to undergo oxidation-reduction cycles involving quinone, hydroquinone, and molecular oxygen, resulting in the formation of oxygen radicals and semiquinone radicals. /Quinones/

Cellular LocationsMembrane

Verwendung und Herstellung

Uses · 2 Einträge

Used as an oxidant and polymerization catalyst; [HSDB]

Oxidant, polymerization catalyst

General Manufacturing Information2,5-Cyclohexadiene-1,4-dione, 2,6-bis(1,1-dimethylethyl)-: ACTIVE

Anwendungen

Verwenden2.6-Di-tert-butyl-p-benzoquinone was used as a treatment agent to improve germination, plant health and yield.

Vor- und nachgelagerte Produkte

Vorgelagerte Rohstoffe

2,6-Di-tert-butyl-4-methoxyphenol4,5-Dichlor-3,6-dioxocyclohexa-1,4-dien-1,2-dicarbonitril1,4-Benzenediol, 2,6-bis(1,1-dimethylethyl)-, 4-acetate

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Auf dieser SeiteGrundinformationenÜberblickNamen und BezeichnerEigenschaftenSicherheit und RegulatorischesChemie und IndustrieZugehörige ReaktionenNotizen zur Verbindung
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DTXSID
DTXSID7021493
ChEMBL
CHEMBL3185121
ChEBI
CHEBI:89187
UNII
4C9D8L0Y0T
EC Number
211-946-0
Nikkaji
J65.911H
Siedepunkt
75 · 75-80 °C (0.7 mmHg)
Dichte
1.0106 · 1.0106 (rough estimate)
Brechungsindex
1.497 · 1.4970 (estimate)
Flammpunkt
110 ° · >110°(230°F)
storage temp.
-20 °C · Amber Vial, -20°C Freezer, Under inert atmosphere
Löslichkeit
Chloroform (Slightly), Methanol (Slightly)
Aggregatzustand
Crystals or Crystalline Powder
Farbe
Orange to brown
Wasserlöslichkeit
Insoluble in water.
BRN
1911512 · 1911512
Henry's Law Constant
6.2 · 6.2×102 mol/(m3Pa) at 25℃, HSDB (2015)
Stabilität
Light sensitive
InChI
1S/C14H20O2/c1-13(2,3)10-7-9(15)8-11(12(10)16)14(4,5)6/h7-8H,1-6H3
InChIKey
RDQSIADLBQFVMY-UHFFFAOYSA-N
SMILES
CC(C)(C)C1=CC(=O)C=C(C1=O)C(C)(C)C
CAS Datenbank
719 · 719-22-2(CAS DataBase Reference)
NIST chemische Informationen
2 · 2,5-Cyclohexadiene-1,4-dione, 2,6-bis(1,1-dimethylethyl)-(719-22-2)
EPA chemische Informationen
2 · 2,6-Di-tert-butylbenzoquinone (719-22-2)

AQUATIC FATE: 2,6-Di-t-butyl-p-benzoquinone should adsorb to suspended solids and organic matter in the water column based on an estimated Koc of 6100(1,SRC) from an experimental log Kow(2) and a suggested classification scheme(3). 2,6-Di-t-butyl-p-benzoquinone (at 0.3 ug/L) had a half-life in Rhine River water of 3.4 days; measurements were made at Lobith and 24.5 hours later at Gorinchem(4). Loss of this compound during this stretch of river may have been due to adsorption to particulates or to biodegradation(4,SRC). An estimated BCF value of 1400(1,SRC), from an experimental log Kow(2), suggests that 2,6-di-t-butyl-p-benzoquinone will bioconcentrate in aquatic organisms. This compound has been detected in fish from the Great Lakes(5). 2,6-Di-t-butyl-p-benzoquinone is not expected to volatilize from water surfaces based on an estimated Henry's Law constant of 1.6X10-8 atm-cu m/mole(SRC) using a fragment constant estimation method(6).

ATMOSPHERIC FATE: Based on an estimated vapor pressure of 4.1X10-4 mm Hg at 25 °C(1,SRC), 2,6-di-t-butyl-p-benzoquinone should exist in both the vapor phase and particulate phase in the ambient atmosphere(2,SRC). 2,6-Di-t-butyl-p-benzoquinone should degrade in the vapor phase by reaction with photochemically produced hydroxyl radicals with an estimated half-life of about 17 hours(3,SRC). Particulate-phase 2,6-di-t-butyl-p-benzoquinone may be physically removed from the air by wet and dry deposition(SRC).

Effluent Concentrations1 of 21 samples of wastewater from the photographic industry contained unreported concentrations of 2,6-di-t-butyl-p-benzoquinone(1). 1 of 10 POTW plants sampled contained 2,6-di-t-butyl-p-benzoquinone in the final effluent(2).
Soil Adsorption/Mobility · 1 Eintrag

Based on an experimental log Kow of 4.42(1), the Koc of 2,6-di-t-butyl-p-benzoquinone is estimated as approximately 6100 using a regression-derived equation(2,SRC). According to a suggested classification scheme(3), this estimated Koc value suggests that 2,6-di-t-butyl-p-benzoquinone will be immobile in soil(SRC). Sewage which had been through secondary treatment was subjected to rapid infiltration; the concentration of 2,6-di-t-butyl-p-benzoquinone in the initial sewage was from 0.022-0.037 ug/L and ranged from barely detected to 0.005 ug/L in the groundwater below the rapid infiltration beds(4). It was believed that the loss of this compound was due to adsorption as the sewage had already been through secondary treatment(4). In an unconfined aquifer, however, 2,6-di-t-butyl-p-benzoquinone was shown to have been transported for a considerable distance(between 1940-1983, estimated 2710 m)(1,5).

Atmospheric ConcentrationsURBAN/SUBURBAN: 2,6-Di-t-butyl-p-benzoquinone was detected in the personal air (1 of 8 samples total) of 12 people located either in New Jersey or North Carolina(1).
Human Toxicity ExcerptsChronic neurotoxic effects include vision disturbances. /From table/ /Quinones/
Fish/Seafood ConcentrationsComposite fish samples (lake trout, walleye) were found to contain 2,6-di-t-butyl-p-benzoquinone in 3 of 8 locations in the Great Lakes (two sites in Lake Erie, one site in Lake Michigan)(1).
Artificial Pollution Sources · 2 Einträge

VOLATILE POLLUTANTS, INCLUDING 2,6-DI-T-BUTYL-P-BENZOQUINONE, WERE PRODUCED FROM SEVERAL RUBBER GOODS MANUFACTURING PROCESSES & ANALYZED BY GAS CHROMATOGRAPHY/MASS SPECTROMETRY. THEIR CUMULATIVE CONCN RANGED FROM 25-27,000 UG/CU M.

2,6-Di-t-butyl-p-benzoquinone's production and subsequent use as an oxidant and polymerization catalyst(1), may result in its release to the environment through various waste streams(SRC). 2,6-Di-t-butyl-p-benzoquinone is also an environmental product of the oxidation of 2,6-di-t-butyl phenol, a common antioxidant additive(2,3).

Environmental Biodegradation · 1 Eintrag

2,6-Di-t-butyl-p-benzoquinone (at 0.3 ug/l) had a half-life in Rhine River water of 3.4 days; measurements were made at Lobith and 24.5 hours later at Gorinchem(1). Degradation of this compound was believed due to aerobic and anaerobic biodegradation(1); however, adsorption to suspended solids and organic matter in the water column was not measured(1,SRC). 2,6-di-t-butyl-p-benzoquinone (at 2 ug/L) initially present in Rhine River water was not detected once the water was passed through a bank filtration process(2). It was not specified whether the loss of this compound was due to biodegradation or adsorption(2,SRC).

Sediment/Soil Concentrations · 1 Eintrag

2,6-Di-t-butyl-p-benzoquinone was present in Pawtuxet River sediment located downstream of a plant which produced antioxidants (at concentrations of 1 ppm to 80 ppm(1). 2,6-Di-t-butyl-p-benzoquinone was present in sediment (0.1-40 ppm) located downstream from a specialty chemicals manufacturing plant(2).

Environmental Bioconcentration · 1 Eintrag

An estimated BCF value of 1400 was calculated for 2,6-di-t-butyl-p-benzoquinone, using a measured log Kow of 4.42(1) and a recommended regression-derived equation(2,SRC). This BCF value suggests that 2,6-di-t-butyl-p-benzoquinone will bioconcentrate in aquatic organisms(2,SRC).This compound was detected in fish in the Great Lakes(3) suggesting that bioconcentration may occur(SRC).

Volatilization from Water/Soil · 1 Eintrag

The Henry's Law constant for 2,6-di-t-butyl-p-benzoquinone is estimated as 1.6X10-8 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This indicates that 2,6-di-t-butyl-p-benzoquinone will essentially not volatilize from water surfaces(2,SRC).

Non-Human Toxicity ExcerptsAcute neurotoxic effects reported in animals include convulsions; medullary paralysis. /From table/ /Quinones/

Sicherheitsdaten

wgk
3
tsca
TSCA listed
hs_code
29146990
RTECS-Nr.
DK3970000
risk_code
36/37/38
hazard_code
Xi
safety_code
26-36-36/37/39-22
Speicherklasse
11 - Combustible Solids
Giftige Stoffe Daten
719-22-2(Hazardous Substances Data)
Hazard Classifications
Eye Irrit. 2Skin Irrit. 2STOT SE 3
2,4,6-Tri-tert-butylphenol
3,3',5,5'-Tetra-tert-butyl-4,4'-dibenzochinon
2,6-Di-tert-butylphenol

Nachgelagerte Produkte

3,3',5,5'-Tetra-tert-butylbiphenyl-4,4'-diol2,6-Di-tert-butylhydrochinon