1-Chloroanthraquinone
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1-Chloroanthraquinone
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CAS No:
82-44-0
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Formula:
C14H7ClO2
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Chemical Name:
1-Chloroanthraquinone
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Synonyms:
9,10-Anthracenedione,1-chloro-;Anthraquinone,1-chloro-;1-Chloro-9,10-anthracenedione;1-Chloroanthraquinone;1-Chloro-9,10-anthraquinone;α-Chloroanthraquinone;α-Monochloroanthraquinone;NSC 30428;NSC 5138;1-Chloro-9,10-dihydroanthracene-9,10-dione
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CAS No:
1-Chloroanthraquinone Basic Attributes
242.66
242.66
201-421-4
96S5SQV15V
30428|5138
DTXSID7052571
YELLOW NEEDLES FROM TOLUENE OR ALCOHOL
29147090
Characteristics
34.1
4
light yellow crystalline powder
1.4±0.1 g/cm3
162 °C
Sublimes
179.7±26.2 °C
1.666
Soluble in oxygenated solvents
Store in a tightly closed container. Store in a cool, dry, well-ventilated area away from incompatible substances.
LD50 orally in Rabbit: 15100 mg/kg
UV: 15813 (Sadtler Research Laboratories Spectral Collection) /2-Chloroanthraquinone/
Safety Information
NONH for all modes of transport
3
R36/37/38
S26-S37/39-S24/25
CB6150000
Xi
Stable at room temperature in closed containers under normal storage and handling conditions.
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 (97.67%): 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 47 companies from 4 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
SRP: The scientific literature for the use of contact lenses in industry is conflicting. The benefit or detrimental effects of wearing contact lenses depend not only upon the substance, but also on factors including the form of the substance, characteristics and duration of the exposure, the uses of other eye protection equipment, and the hygiene of the lenses. However, there may be individual substances whose irritating or corrosive properties are such that the wearing of contact lenses would be harmful to the eye. In those specific cases, contact lenses should not be worn. In any event, the usual eye protection equipment should be worn even when contact lenses are in place.
A skin, eye irritant.
1-Chloroanthraquinone was detected in an extract of flyash from a municipal incinerator in Ontario, Canada at unreported concentrations(1).
Toxicity
WASTE WATERS FROM ALPHA-DISULFATION OF ANTHRAQUINONE, WHICH CONTAIN ANTHRAQUINONESULFONIC ACIDS, ARE TREATED TO FORM HALOANTHRAQUINONES.|1-Chloroanthraquinone's production and subsequent use as an intermediate in the production of dyes, including Disperse Red 9, Disperse Red 22, Vat Brown 1, Vat Brown 44, Vat Yellow 28(1), may result in its release to the environment through various waste streams(SRC).
TERRESTRIAL FATE: An estimated Koc value of 3500(1,SRC), based on an estimated log Kow of 3.99(2,SRC) suggests that 1-chloroanthraquinone will have only slight mobility in soil(SRC), based upon a recommended classification scheme(3). Under reducing conditions, this compound has been shown to form the chloroanthrone with measured half-lives of <0.4 to 2.4 daysin sediments(4) and this may also occur in soils(SRC). Incomplete information is available regarding the biodegradation potential of 1-chloroanthraquinone; however, this compound was resistant to biodegradation under aerobic conditions using an activated sludge inoculum; only 2.8% of the theoretical BOD was reported following 2 weeks incubation(5). 1-Chloroanthraquinone is not expected to volatilize from moist soil surfaces based on an estimated Henry's Law constant of 2.4X10-9 atm-cu m/mole(6,SRC).|AQUATIC FATE: Based upon an estimated Koc value of 3500(SRC) from an estimated log Kow(2,SRC), 1-chloroanthraquinone may adsorb to suspended solids and sediments(SRC) based upon a recommended classification scheme(1). In anoxic sediments, 1-chloroanthraquinone has been shown to quickly reduce resulting in the formation of an unspecified chloroanthrone(4). Half-lives of <0.4 to 2.4 days are reported for this compound dependent on the source of the sediment(4). An estimated BCF value of 630(3,SRC), based on an estimated log Kow(2,SRC) and measured BCF values of 118-351 in carp(5) indicate that 1-chloroanthraquinone may bioconcentrate in aquatic organisms(SRC). Incomplete information is available regarding the biodegradation potential of 1-chloroanthraquinone; however, this compound was resistant to biodegradation under aerobic conditions using an activated sludge inoculum; only 2.8% of theoretical BOD was reported following 2 weeks incubation(5). 1-Chloroanthraquinone is not expected to volatilize from water surfaces based on an estimated Henry's Law constant of 2.2X10-12 atm-cu m/mole(SRC), developed using a fragment constant method(6).|ATMOSPHERIC FATE: Based on an estimated vapor pressure value of 8.74X10-7 mm Hg at 25 °C(1,SRC), 1-chloroanthraquinone will exist in both the vapor phase and the particulate phase in the ambient atmosphere(2,SRC). 1-Chloroanthraquinone will degrade fairly rapidly in the vapor phase by reaction with photochemically produced hydroxyl radicals with an estimated half-life of about 13 days(3,SRC). Particulate phase 1-chloroanthraquinone may be physically removed from the air by wet and dry deposition(SRC).
The rate constant for the vapor phase reaction of 1-chloroanthraquinone with photochemically produced hydroxyl radicals has been estimated as 1.3X10-12 cu cm/molecule-sec at 25 °C(1). The half-life of 1-chloroanthraquinone is approximately 13 days based on a concentration of 5X10+5 hydroxyl radicals per cu cm(1,SRC). 1-Chloroanthraquinone, added to lake bottom sediments, resulted in the formation of a chlorine containing anthrone(2). 1-Chloroanthraquinone had measured first-order rate constants of 1.2X10-2 to 6.5X10-2/hr giving half-lives from <0.4 to 2.4 days for this anoxic sediment-water system(2).
199.53|Experimental BCF values of 118-351 were measured using carp(1). An estimated BCF value of 630 was calculated for 1-chloroanthraquinone(SRC), using an estimated log Kow of 3.99(2,SRC) and a recommended regression-derived equation(3). These BCF values suggest that 1-chloroanthraquinone may bioconcentrate in aquatic organisms(SRC).
Based on an estimated log Kow of 3.99(1,SRC), the Koc of 1-chloroanthraquinone is estimated as approximately 3500(SRC) using a regression-derived equation(2). According to a suggested classification scheme(3), this estimated Koc value suggests that 1-chloroanthraquinone will have only slight mobility in soil(SRC).
The Henry's Law constant for 1-chloroanthraquinone is estimated as 2.36X10-9 atm-cu m/mole(1,SRC). This indicates that 1-chloroanthraquinone will essentially not volatilize from water surfaces(2,SRC).
Drug Information
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/
0.59 Days
CAUTION: LOW SYSTEMIC TOXICITY, BUT MAY CAUSE SKIN IRRITATION, SENSITIZATION. /ANTHRAQUINONE/|Chronic neurotoxic effects include vision disturbances. /From table; Quinones/
1-Chloroanthraquinone Use and Manufacturing
REACTION OF 1-HYDROXYANTHRAQUINONE WITH PHOSPHORUS PENTACHLORIDE IN NITROBENZENE|1-Chloroanthraquinone is prepared from anthraquinone-1-sulfonic acid or from 1-nitro-anthraquinone. Purification by high temperature distillation.|1-Chloroanthraquinone is prepared from anthraquinone-1-sulfonic acid, sodium salt and sodium chlorate (sulfonate displacement).
1-Chloroanthraquinone is an intermediate for manufacturing vat dyes such as CI Vat Brown 1.
(1972) 5.17X10+7 G|(1975) GREATER THAN 4.54X10+5 G (EST)
9,10-Anthracenedione, 1-chloro-: ACTIVE
1-Chloroanthraquinone was detected in municipal incinerator flyash following Soxhlet extraction, normal-phase HPLC, and capillary GC/MS.
Computed Properties
Molecular Weight:242.65
XLogP3:4
Hydrogen Bond Acceptor Count:2
Exact Mass:242.0134572
Monoisotopic Mass:242.0134572
Topological Polar Surface Area:34.1
Heavy Atom Count:17
Complexity:352
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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