p-トルキノン

Methyl-1,4-benzoquinone

HCID 11122CAS 553-97-9

基本情報

標準SMILES
CC1=CC(=O)C=CC1=O
InChIKey
VTWDKFNVVLAELH-UHFFFAOYSA-N
分子式
C7H6O2
平均分子量
122.12 g/mol
単同位体質量
122.03677943

概要

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

名称と識別子

優先名称
Methyl-1,4-benzoquinone
IUPAC
2-methylcyclohexa-2,5-diene-1,4-dione
現地名
p-トルキノン
英語名
p-Toluquinone
分子式
C7H6O2
分子量
122.12

名称と別名

p-Toluquinone553-97-9Methyl-p-benzoquinone2-METHYL-1,4-BENZOQUINONE2-methylcyclohexa-2,5-diene-1,4-dioneToluquinoneMethyl-1,4-benzoquinone2-MethylquinoneMethylbenzoquinoneTolylquinone1,4-Toluquinone2-Methylbenzoquinone
名称をさらに表示
p-トルキノンメチル-P-ベンゾキノンメチル-p-キノン2-メチル-1,4-ベンゾキノン2-メチル-2,5-シクロヘキサジエン-1,4-ジオン2-メチル-p-ベンゾキノントルキノンo-メチル-p-ベンゾキノンメチル-1,4-ベンゾキノン2-メチルシクロヘキサ-2,5-ジエン-1,4-ジオン5-メチル-p-ベンゾキノン3-メチル-2,5-シクロヘキサジエン-1,4-ジオン3-メチル-1,4-ベンゾキノン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

データベース識別子

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

物性

構造計算による物性

XLogP
0.7
極性表面積
34.1 Ų
水素結合供与体数
0
水素結合受容体数
2
回転可能結合数
0
重原子数
9

実験および物理化学的性質

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

log Kow = 0.72

0.67

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

YELLOW PLATES OR NEEDLES

YELLOW LEAFLETS OR NEEDLES

Solubility · 2 件

Slightly soluble in water; soluble in ethanol and ether

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

物理化学的性質

融点
66 · 66-67 °C(lit.)
沸点
187.52 °C · 187.52°C (rough estimate)
比重(密度)
1.08 · 1.0800
屈折率
1.5286 · 1.5286 (estimate)
貯蔵温度
Keep in dark place,Inert atmosphere,Room temperature
外見
結晶性

化学的性質

化学的特性yellow to brownish crystalline powder

安全と法規制

GHS分類

GHS Classification · 4 件

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.

危険有害性情報

Regulatory Information · 2 件

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%)

安全と保護具

Disposal Methods · 1 件

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.

毒性情報

Interactions · 1 件

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 件

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 件

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 件

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 件

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).

安全データ

F
8
wgk
3
tsca
TSCA listed
rtecs
DK6300000
hs_code
29146990
risk_code
22-36/37/38-25

化学と産業

薬理情報

Metabolism/Metabolites · 2 件

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/

用途と製造

General Manufacturing Information2,5-Cyclohexadiene-1,4-dione, 2-methyl-: ACTIVE
応用分野 · 1 件

使用Methyl-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.

調製方法

純化方法Crystallise p-toluoquinone from heptane or EtOH, dry rapidly (vacuum/P2O5) and stored in a vacuum. [Beilstein 7 IV 2088.]

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関連反応

12 件

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