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Anthrone

Anthrone structure

Anthrone 

structure
  • CAS No:

    90-44-8

  • Formula:

    C14H10O

  • Chemical Name:

    Anthrone

  • Synonyms:

    9(10H)-Anthracenone;Anthrone;Anthracene,9,10-dihydro-9-oxo-;Carbothrone;9-Oxoanthracene;NSC 1965;Quino Power ATR

  • Categories:

    Chemical Reagents  >  Organic Reagents

Description

off-white to light yellow crystals


Anthrone is a member of the class of anthracenes that is 9,10-dihydroanthracene carrying an oxo group at C-9. It has a role as a radical scavenger. It is a tautomer of a 9-anthrol.

Anthrone Basic Attributes

194.23

194.23

1910173

201-994-0

FP0FJ7K744

1965

DTXSID1049431

ORTHORHOMBIC NEEDLES FROM BENZENE AND PETROLEUM ETHER|COLORLESS NEEDLES

29143990

Characteristics

17.1

3.66

Yellow Powder

1.2±0.1 g/cm3

155 °C

375.2 °C

150.3±17.3 °C

1.640

INSOLUBLE

2-8°C

mmo-sat 60 mg/plate MUREAV 157,149,85

Flammable; burning produces irritating fumes

ANY FLUORESCENCE PRESENT IS DUE TO ANTHRANOL|ADDITION CMPD WITH 4 MOLECULES DESOXYCHOLIC ACID, C110-H170-O17, MP 179 °C|EQUIL IN ABSOLUTE ALCOHOL: 89% ANTHRONE; 11% ANTHRANOL; TENDENCY TO CHANGE TO ANTHRAQUINONE

Safety Information

NONH for all modes of transport

3

36/37/38-20/21/22

26-36

CB8925500

Xi,Xn

Warehouse ventilated, low temperature and dry

Stable. Incompatible with strong oxidizing agents. Combustible.

P261-P305 + P351 + P338

H315-H319-H335

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.

|Warning|H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]|P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, and P501|Aggregated GHS information provided by 48 companies from 5 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Several unspecified isomers of anthrone were detected in chlorinated coal-tar leachate at unreported concentrations(1). A heavy-duty diesel exhaust particulate sample, NBS SRM 1650, contained anthrone at unreported concentrations(2). Diesel emission particulates, collected from a Volkswagen Rabbit contained anthrone(3). Fine particle emissions from the combined exhaust of a vented natural gas-fired residential space heater plus a water heater contained 21.4 pg/kJ anthrone(4).

Superficial marine sediments of Cortiou Creek, in the sewage area of Marseilles, France, are contaminated with anthrone at concentrations ranging from non-detectable to 300 ng/g (9 of 10 sites had measurable quantities of anthrone; detection limit not given)(1).

REMOTE: Anthrone was found on aerosols from the southern North Atlantic Ocean, at a mean concentration of 0.47 ng/cu m(1).

Anthrone was identified in the black weathering crusts of limestone building stones used in the major cathedrals of Sevilla, Spain, and Mechelen, Belgium at unreported concentrations(1).

Toxicity

Anthrone's production and use in organic synthesis and as a general reagent for carbohydrates(1) may result in its release to the environment through various waste streams(SRC).

TERRESTRIAL FATE: Based on a recommended classification scheme(1), an estimated Koc value of 2300(SRC), determined from a measured log Kow(2) and a recommended regression-derived equation(3), indicates that anthrone will have only slight mobility in soil(SRC). Biodegradation of anthrone is expected based on limited data and may be a major fate process for this compound in soil(SRC). A mixed bacterial population, isolated from a hydrocarbon-polluted creek, degraded 40% of anthrone to traces of anthrone and to anthraquinone in 30% yield(4). Anthrone's estimated values for vapor pressure(5) and Henry's Law constant(6,SRC) indicate that volatilization from dry and moist soil surfaces is not likely to be a major fate process for this compound(SRC).|AQUATIC FATE: Based on a recommended classification scheme(1), an estimated Koc value of 2300(SRC), determined from a measured log Kow(2) and a recommended regression-derived equation(3), indicates that anthrone should adsorb to sediment and suspended solids(SRC). Anthrone may volatilize slowly from water surfaces based on an estimated Henry's Law constant of 7.9X10-7 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). Estimated half-lives for a model river and model lake are 65 and 480 days, respectively(3,SRC). An estimated BCF value of 360(3,SRC), from a measured log Kow(2), suggests that anthrone will bioconcentrate in aquatic organisms(SRC), according to a recommended classification scheme(5).|ATMOSPHERIC FATE: According to a suggested classification scheme(1), an estimated vapor pressure of 1.8X10-5 mm Hg at 25 °C(2,SRC) indicates that anthrone will exist in both the vapor and particulate phases in the ambient atmosphere. Vapor-phase anthrone 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 40 hours(3,SRC). Particulate-phase anthrone may be physically removed from the air by dry deposition(SRC).

The rate constant for the vapor-phase reaction of anthrone with photochemically produced hydroxyl radicals has been estimated as 9.8X10-12 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1,SRC). This corresponds to an atmospheric half-life of about 40 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1,SRC).

An estimated BCF value of 360 was calculated for anthrone(SRC), using a measured log Kow of 3.66(1) and a recommended regression-derived equation(2). According to a recommended classification scheme(3), this BCF value suggests that bioconcentration in aquatic organisms will be an important fate process(SRC).

The Koc of anthrone is estimated as approximately 2300(SRC), using a measured log Kow of 3.66(1) and a regression-derived equation(2,SRC). According to a recommended classification scheme(3), this estimated Koc value suggests that anthrone has only slight mobility in soil(SRC).

The Henry's Law constant for anthrone is estimated as 7.9X10-7 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This value indicates that anthrone will slowly volatilize from water surfaces(2,SRC). Based on this Henry's Law constant, the volatilization half-life from a model river (1 m deep, flowing 1 m/sec, wind velocity of 3 m/sec) is estimated as approximately 65 days(2,SRC). The volatilization half-life from a model lake (1 m deep, flowing 0.05 m/sec, wind velocity of 0.5 m/sec) is estimated as approximately 480 days(2,SRC). Anthrone's values for vapor pressure(3) and Henry's Law constant(1,SRC) indicate that volatilization from dry and moist soil surfaces is not likely to be a major fate process for this compound(SRC).

DRINKING WATER: Two samples of Ottawa drinking water, one collected in January and the other in February 1978, contained non-detectable (detection limit not reported) and 1.4 ng/L anthrone, respectively(1).

NIOSH (NOES Survey 1981-1983) has statistically estimated that 28 workers are potentially exposed to anthrone in the USA(1).

Drug Information

YIELDS ANTHRAQUINONE & 9-HYDROXYANTHRACENE IN RATS. /FROM TABLE/

anthrone

Anthrone Use and Manufacturing

Methods of Manufacturing

Obtained from anthraquinone through the following reaction. Mix 104g of anthraquinone, 100g of tin particles, and 750ml of glacial acetic acid to boiling, then add 250ml of concentrated hydrochloric acid (relative density is 1.19) one by one, after about 2h, the anthraquinone should be completely dissolved in the reaction solution, otherwise, need to Add tin particles and hydrochloric acid. Then reflux for 1.5h, decolorize and filter, the filtrate was diluted with 100ml of water, cooled to 10 ℃, precipitated anthrone crystals, filtered, washed with water to pH = 7 to obtain crude crystals, dry weight 80g. The crude product can be recrystallized from a mixture of acetone or benzene and petroleum ether (3:1) to obtain about 60 g of anthrone with a melting point of 154-155°C.

Uses

Anthrone is a tricyclic aromatic ketone and related compound of anthracene. Anthrone is used as a reagent in the colorometric determination of carbohydrates.

9(10H)-Anthracenone: ACTIVE

SAMPLES OF OTTAWA DRINKING WATER WERE ANALYZED BY GAS CHROMATOGRAPHY/MASS SPECTROMETRY FOR POLYCYCLIC AROMATIC HYDROCARBONS FOLLOWING EXTRACTION OF THE ORGANIC SPECIES USING AMBERLITE XAD-2 MACRORETICULAR RESIN.|Several isomers of anthrone were detected in coal-tar leachate using capillary GC/MS using electron-impact and chemical ionization.|Anthrone was detected in drinking water using XAD-2 resin cartridges, organic elution, followed by analysis with GC/MS.|Anthrone was detected in heavy-duty diesel exhaust particulate sample using capillary column GC coupled to both low- and high-resolution MS using electron impact and negative ion chemical ionization.

Computed Properties

Molecular Weight:194.23
XLogP3:3.7
Hydrogen Bond Acceptor Count:1
Exact Mass:194.073164938
Monoisotopic Mass:194.073164938
Topological Polar Surface Area:17.1
Heavy Atom Count:15
Complexity:234
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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