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Methyl-p-benzochinon

Methyl-1,4-benzoquinone

HCID 11122
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Grundinformationen

CAS
553-97-9
Standard-SMILES
CC1=CC(=O)C=CC1=O
InChIKey
VTWDKFNVVLAELH-UHFFFAOYSA-N
Summenformel
C7H6O2
Durchschnittliche Molmasse
122,12 g/mol
Monoisotopische Masse
122,03677943

Überblick

2-methyl-1,4-benzoquinone has been reported in Hydropisphaera erubescens, Penicillium solitum, and Uloma tenebrionoides with data available.

Namen und Bezeichner

Bevorzugter Name
Methyl-1,4-benzoquinone
IUPAC
2-methylcyclohexa-2,5-diene-1,4-dione
Lokaler Name
Methyl-p-benzochinon
Englischer Name
p-Toluquinone
Summenformel
C7H6O2
Molmasse
122.12

Namen und Synonyme

p-Toluquinone553-97-9Methyl-p-benzoquinone2-METHYL-1,4-BENZOQUINONE2-methylcyclohexa-2,5-diene-1,4-dioneToluquinoneMethyl-1,4-benzoquinone2-MethylquinoneMethylbenzoquinoneTolylquinone1,4-Toluquinone2-Methylbenzoquinone
Weitere Namen anzeigen
2-methylnaphthalene-1,4-dione1,4-Toluchinon
p-Benzoquinone, 2-methyl-2,5-Cyclohexadiene-1,4-dione, 2-methyl-Methylquinone2-Methylbenzoquinone-1,42-Methyl-1,4-quinonepara-Toluquinone1,4-Benzoquinone, 2-methyl-VF06HB6AZN

Datenbank-Bezeichner

CAS
553-97-9
PubChem CID
11122
DTXSID
DTXSID8060290
ChEMBL
CHEMBL358225
UNII
VF06HB6AZN
EC Number
209-056-2
Nikkaji
J6.458K

Eigenschaften

Berechnete StruktureigenschaftenWird ergänzt

XLogP
0,7
Polarare Oberfläche (TPSA)
34,1 Ų
H-Brücken-Donoren
0
H-Brücken-Akzeptoren
2
Frei drehbare Bindungen
0
Schwere Atome
9
Formalladung
0
Komplexität
221

Experimentelle und physikochemische Eigenschaften

Chemical ClassesOther Classes -> Aromatic Ketones
SpringerMaterials PropertiesChemical shift
LogP · 2 Einträge

log Kow = 0.72

0.67

Density1.08 @ 75.5 °C/4 °C
Color/Form · 2 Einträge

YELLOW PLATES OR NEEDLES

YELLOW LEAFLETS OR NEEDLES

Solubility · 2 Einträge

Slightly soluble in water; soluble in ethanol and ether

Very sol in acetone, ethyl acetate, alcohol, ether, and benzene; soluble in hot water

Melting Point69 °C
Vapor Pressure0.03 [mmHg]
Physical DescriptionYellow solid; [HSDB] Yellow, gold colored, or light green crystalline solid; [MSDSonline]

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

H302 (98.2%): Harmful if swallowed [Warning Acute toxicity, oral]

P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 55 reports by companies from 6 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Gefahrenhinweise

Regulatory Information · 2 Einträge

Chemical: 2,5-Cyclohexadiene-1,4-dione, 2-methyl-

Methyl-p-benzoquinone: Does not have an individual approval but may be used under an appropriate group standard

Hazards SummaryAn eye irritant; [HSDB] An irritant; [MSDSonline] See Quinone.
Hazard Classes and CategoriesAcute Tox. 4 (98.2%)

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

Interactions

Chemie und Industrie

Pharmakologische Informationen

Metabolism/Metabolites · 2 Einträge

YIELDS METHYLBENZOSEMIQUINONE IN ESCHERICHIA. YIELDS METHYLQUINOL IN PIG; IN PEA; AND IN DESULFOVIBRIO. /FROM TABLE/

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/

Absorption, Distribution and ExcretionQUINONE IS READILY ABSORBED FROM GASTROENTERIC TRACT & SC TISSUES. IT IS PARTIALLY EXCRETED UNCHANGED; BUT BULK IS ELIMINATED IN CONJUGATION WITH HEXURONIC, SULFURIC, & OTHER ACIDS. /1,4-BENZOQUINONE/

Verwendung und Herstellung

General Manufacturing Information2,5-Cyclohexadiene-1,4-dione, 2-methyl-: ACTIVE
Anwendungen · 1 Eintrag

VerwendenMethyl-p-benzoquinone imine is the products were the tetrahedral adducts. Synthesis of 2H-indazole-4,7-dione derivatives from3-phenylsydnone and p-toluquinone. A Michael addition of 2-methylcyclopentane-1,3-dione to various p-toluquinone imides exclusively afforded the sole products in a regiospecific manner.

Vor- und nachgelagerte Produkte

Nachgelagerte Produkte

2-Methylnaphthalin-1,4-diol4-Brom-m-kresol2-Methoxy-3-methylphenol2-Methyl-4-nitroanisol

Zugehörige Reaktionen

12
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Reaktionsgleichung von HRID 46695
HRID 46695als Eduktuspto-grants-1979_11
Reaktionsgleichung von HRID 344565
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Reaktionsgleichung von HRID 436594
HRID 436594als Eduktuspto-grants-1977_02
Reaktionsgleichung von HRID 727477
HRID 727477als Produktuspto-grants-1998_01
Reaktionsgleichung von HRID 727481
HRID 727481als Produktuspto-grants-1998_01
Reaktionsgleichung von HRID 985745
HRID 985745als Produktuspto-grants-2005_03
Reaktionsgleichung von HRID 985746
HRID 985746als Produktuspto-grants-2005_03
Reaktionsgleichung von HRID 1074900
HRID 1074900als Produktuspto-grants-1983_07
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Other Experimental Properties
SUBLIMES

Physikochemische Eigenschaften

Schmelzpunkt
66 · 66-67 °C(lit.)
Siedepunkt
187.52 °C · 187.52°C (rough estimate)
Dichte
1.08 · 1.0800
Brechungsindex
1.5286 · 1.5286 (estimate)
storage temp.
Keep in dark place,Inert atmosphere,Room temperature
Aggregatzustand
Crystalline
Farbe
Yellowish green
Wasserlöslichkeit
insoluble
BRN
471387 · 471387
Henry's Law Constant
3.1 · 3.1×100 mol/(m3Pa) at 25℃, Wang et al. (2017)
InChI
1S/C7H6O2/c1-5-4-6(8)2-3-7(5)9/h2-4H,1H3
InChIKey
VTWDKFNVVLAELH-UHFFFAOYSA-N
SMILES
CC1=CC(=O)C=CC1=O
CAS Datenbank
553 · 553-97-9(CAS DataBase Reference)
NIST chemische Informationen
2 · p-Benzoquinone, 2-methyl-(553-97-9)
EPA chemische Informationen
2 · 2-Methyl-p-benzoquinone (553-97-9)
· 1 Eintrag

WHEN 0.1% SOLN /IN BENZENE/ WAS.../PAINTED ON SKIN/, 41 MICE SURVIVED MORE THAN 200 DAYS, & 6 DEVELOPED SKIN PAPILLOMAS, 2 DEVELOPED SKIN CARCINOMAS & 10 DEVELOPED LUNG ADENOCARCINOMAS... OF 46 SURVIVING CONTROLS TREATED WITH BENZENE, 1 DEVELOPED SKIN PAPILLOMA, & 2 DEVELOPED LUNG ADENOCARCINOMAS... /1,4-BENZOQUINONE/

Environmental Fate · 3 Einträge

TERRESTRIAL FATE: Estimated Koc values of 2(1,SRC) and 60(2,SRC), determined from a structure estimation method(1) and an experimental log Kow(3), respectively, indicate that 2-methyl-1,4-benzoquinone may have high to very high mobility in soil(SRC), according to a recommended classification scheme(4). Incomplete information is available regarding 2-methyl-1,4-benzoquinone's potential for biodegradation. 2-Methyl-1,4-benzoquinone, present in wastewater from 1-4 ng/g, was not detected following activated sludge treatment(5,6) suggesting that this compound can be aerobically biodegraded(SRC). Slow volatilization of 2-methyl-1,4-benzoquinone may occur from dry soil surfaces(SRC) based on an estimated vapor pressure of 3.4X10-2 mm Hg(7,SRC); however, it is not expected to be a major fate process from moist soil surfaces(SRC) given a Henry's Law constant of 1.9X10-9 atm-cu m/mole(8,SRC).

AQUATIC FATE: Estimated Koc values of 2(1,SRC) and 60(2,SRC), determined from a structure estimation method(1) and an experimental log Kow(3), respectively, suggest that 2-methyl-1,4-benzoquinone will not adsorb to suspended solids and sediment(SRC) in the water column(2). 2-Methyl-1,4-benzoquinone is not expected to volatilize from water surfaces based on an estimated Henry's Law constant of 1.9X10-9 atm-cu m/mole(SRC), developed using a fragment constant estimation method(5). According to a recommended classification scheme(6), an estimated BCF value of 2(2,SRC), from an experimental log Kow(3), suggests that 2-methyl-1,4-benzoquinone will not bioconcentrate in aquatic organisms(SRC). 2-Methyl-1,4-benzoquinone may not be readily biodegraded as initial wastewater concentrations of 1-4 ng/g were unchanged in final effluents following activated sludge treatment(7).

ATMOSPHERIC FATE: According to a suggested classification scheme(1), an estimated vapor pressure of 3.4X10-2 mm Hg at 25 °C(2,SRC) indicates that 2-methyl-1,4-benzoquinone will exist mainly in the vapor phase in the ambient atmosphere. Vapor-phase 2-methyl-1,4-benzoquinone is degraded in the atmosphere by reaction with photochemically produced hydroxyl radicals(SRC); the half-life for this reaction in air is estimated to be about 29.5 hours(3,SRC).

Effluent ConcentrationsRaw wastewater samples from the petroleum refining industry, which had passed through dissolved air flotation treatment, contained 2-methyl-1,4-benzoquinone at concentrations of <1 to 4 ng/g (unreported detection limit)(1).
Soil Adsorption/Mobility · 1 Eintrag

Using a structure estimation method based on molecular connectivity indices(1), the Koc for 2-methyl-1,4-benzoquinone can be estimated to be about 2(SRC). The Koc of 2-methyl-1,4-benzoquinone is estimated as approximately 60(SRC), using an experimental log Kow of 0.72(2) and a recommended regression-derived equation(3,SRC). According to a suggested classification scheme(4), these estimated Koc values suggest that 2-methyl-1,4-benzoquinone has high to very high mobility in soil(SRC).

Human Toxicity Excerpts · 4 Einträge

ULCERATION OF CORNEA HAS RESULTED FROM ONE BRIEF EXPOSURE TO HIGH CONCN OF VAPOR OF QUINONE, AS WELL AS FROM REPEATED EXPOSURES TO MODERATELY HIGH CONCN. ...RECOVERY OCCURRED PROMPTLY & SPONTANEOUSLY... /1,4-BENZOQUINONE/

CAN CAUSE DERMATITIS WITH DISCOLORATION, ERYTHEMA, FORMATION OF PAPULES & VESICLES. IN SEVERE CASES THERE CAN BE NECROTIC CHANGES IN SKIN. VAPORS ACTING ON EYE CAN CAUSE SERIOUS DISTURBANCES, INCL CONJUNCTIVITIS & EVEN CORNEAL ULCERATION. DISCOLORATION OF CONJUNCTIVA & CORNEA HAVE BEEN REPORTED. /1,4-BENZOQUINONE/

...@ 0.5 PPM VAPORS ARE IRRITATING TO EYES, & @ 3.0 PPM THEY ARE VERY IRRITATING. /1,4-BENZOQUINONE/

Chronic neurotoxic effects include vision disturbances. /From table; Quinones/

Artificial Pollution Sources · 1 Eintrag

The presence of 2-methyl-1,4-benzoquinone in wastewater from a petroleum oil refinery(1) and in retort water from an oil-shale operation(2), suggests that this compound may be released in various waste streams during the extraction and refining of oil(SRC).

Environmental BiodegradationRaw wastewater samples from the petroleum refining industry (containing concentrations of <1 to 4 ng/g 2-methyl-1,4-benzoquinone), were not biodegraded following activated sludge treatment (unreported method detection limit)(1).
Environmental Bioconcentration · 1 Eintrag

An estimated BCF value of 2 was calculated for 2-methyl-1,4-benzoquinone(SRC) using an experimental log Kow of 0.72(1) and a recommended regression-derived equation(2,SRC). According to a suggested classification scheme(3), this BCF value suggests that bioconcentration of 2-methyl-1,4-benzoquinone in aquatic organisms will not be an important fate process(SRC).

Volatilization from Water/Soil · 1 Eintrag

The Henry's Law constant for 2-methyl-1,4-benzoquinone is estimated as 1.9X10-9 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This value indicates that 2-methyl-1,4-benzoquinone essentially will not volatilize from water surfaces(2,SRC). 2-Methyl-1,4-benzoquinone's low Henry's Law constant(1,SRC) suggests that volatilization from moist soil surfaces will not occur(SRC). However, this compound's estimated vapor pressure, 3.4X10-2 mm Hg(3,SRC), indicates that volatilization from dry soil surfaces may occur slowly(SRC).

Non-Human Toxicity Excerpts · 5 Einträge

...25 MICE...EXPOSED /BY INHALATION/ TO 5 MG PARA-QUINONE IN 130-L CHAMBER FOR 1 HR, 6 TIMES/WK; 25 MICE WERE UNTREATED... IN 11 TREATED MICE THAT SURVIVED... 100 DAYS, 2 LUNG ADENOCARCINOMAS WERE OBSERVED. AMONG 12 CONTROLS THAT DIED AFTER MORE THAN 100 DAYS, 2 LUNG ADENOMAS WERE OBSERVED. /1,4-BENZOQUINONE/

...24 RATS (15 WISTAR...& 9 HYBRIDS), WEIGHING ABOUT 200 G EACH, WERE INJECTED SC WITH 0.5 ML SOLN OF P-QUINONE IN PROPYLENE GLYCOL @ WEEKLY INTERVALS. CONCN...1ST 53 DAYS WAS 1%...0.2% FROM DAYS 54-173...0.4% AFTER 173 DAYS. 17 RATS SURVIVED...394 DAYS...TOTAL OF 32 INJECTIONS... INJECTION-SITE FIBROSARCOMAS...IN 2 RATS. /1,4-BENZOQUINONE/

ASPHYXIA APPEARS TO PLAY IMPORTANT ROLE IN TERMINAL PICTURE...BECAUSE OF PULMONARY DAMAGE RESULTING FROM EXCRETION OF QUINONE INTO ALVEOLI & BECAUSE OF CERTAIN NOT TOO WELL-DEFINED EFFECTS OF QUINONE UPON HEMOGLOBIN. URINE OF SEVERELY POISONED ANIMALS MAY CONTAIN PROTEIN, BLOOD, CASTS... /1,4-BENZOQUINONE/

ABSORPTION OF LARGE DOSES OF QUINONE FROM GASTROENTERIC TRACT OR FROM SC TISSUES OF ANIMALS INDUCED LOCAL CHANGES, CRYING, CLONIC CONVULSIONS, RESPIRATORY DIFFICULTIES, DROP OF BLOOD PRESSURE, & DEATH BY PARALYSIS OF MEDULLARY CENTERS. /1,4-BENZOQUINONE/

For more Non-Human Toxicity Excerpts (Complete) data for 2-METHYL-1,4-BENZOQUINONE (9 total), please visit the HSDB record page.

Environmental Abiotic Degradation · 1 Eintrag

The rate constant for the vapor-phase reaction of 2-methyl-1,4-benzoquinone with photochemically produced hydroxyl radicals has been estimated as 1.3X10-11 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of approximately 29.5 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1,SRC).

Probable Routes of Human ExposureNIOSH has statistically estimated that 1821 workers (273 of total are female) are potentially exposed to 2-methyl-1,4-benzoquinone in the USA(1).

Sicherheitsdaten

F
8
wgk
3
tsca
TSCA listed
hs_code
29146990
RTECS-Nr.
DK6300000
risk_code
22-36/37/38-25
hazard_code
Xn,T
safety_code
26-45-37/39-28A
Speicherklasse
11 - Combustible Solids
Giftige Stoffe Daten
553-97-9(Hazardous Substances Data)
Hazard Classifications
Acute Tox. 4 OralEye Irrit. 2Skin Irrit. 2STOT SE 3
Ethylethoxyacetat
p-Kresol
Dinatrium-2,2'-[(2-methyl-3,6-dioxo-1,4-cyclohexadien-1,4-diyl)bis[imino(2-methyl-4,1-phenylen)imino]]bis(5-nitrobenzolsulfonat)