HuagongsheHuagongshe Chemistry Print Report · For research reference only
1-Chloroanthraquinone
1-CHLOROANTHRACENE-9,10-DIONE · 1-CHLOROANTHRAQUINONE · 1-CHLORO AQ · TIMTEC-BB SBB000825 · 1-Chloranthrachinon · 1-Chloro anthraquino · -Chloroanthraquinone · 1-Chloroantraquinone
Identifiers & Physical Properties
| CAS No. | 26264-07-3 |
|---|---|
| Molecular formula | C14H7ClO2 |
| Average molar mass | 242.65 g/mol |
| Monoisotopic mass | 242.01345714 g/mol |
| SMILES | O=C1c2ccccc2C(=O)c2c(Cl)cccc21 |
| InChIKey | BOCJQSFSGAZAPQ-UHFFFAOYSA-N |
| PubChem CID | 6709 |
| ChEMBL | CHEMBL3560876 |
| EC No. | 201-421-4 |
| DTXSID | DTXSID7052571 |
Chemical & Physical Properties
| XLogP | 4 |
|---|---|
| Topological polar surface area | 34.1 |
| Hydrogen bond donors | 0 |
| Hydrogen bond acceptors | 2 |
| Rotatable bonds | 0 |
| Heavy atoms | 17 |
| Formal charge | 0 |
| Complexity | 352 |
| Chemical classes | Other Classes -> Aromatic Ketones |
| SpringerMaterials Properties | 13C nuclear magnetic resonance spectrum |
| Color/Form | YELLOW NEEDLES FROM TOLUENE OR ALCOHOL |
| Solubility | INSOL IN WATERSLIGHTLY SOL IN HOT ALCOHOLSOL IN NITROBENZENE & HOT AMYL ALCOHOLSol in ethanol, benzene, acetic acidSoluble in oxygenated solventsSoluble in hot toluene. (almost transparency) |
| Boiling point | Sublimes345.65°C (rough estimate) |
| Decomposition | When heated to decomp it emits very toxic fumes of /hydrogen chloride and nitrogen oxides/. |
| Melting point | 162 °C159-160 °C (lit.) |
| Vapor pressure | 0.00000087 [mmHg] |
| Physical Description | Yellow solid[HSDB] Yellow powder[MSDSonline] |
| Other Experimental Properties | UV: 15813 (Sadtler Research Laboratories Spectral Collection) /2-Chloroanthraquinone/ |
| Density | 1.2377 (rough estimate) |
| Refractive index | 1.5380 (estimate) |
| Storage conditions | Store below +30°C. |
| Physical state | Powder or Chunks |
| Color | Light yellow to yellow |
| BRN | 1912752 |
| Henry's law constant | 4.3×102 mol/(m3Pa) at 25℃, Abraham and Jr. (2019) |
| InChI | InChI=1S/C14H7ClO2/c15-11-7-3-6-10-12(11)14(17)9-5-2-1-4-8(9)13(10)16/h1-7H |
| InChIKey | BOCJQSFSGAZAPQ-UHFFFAOYSA-N |
| SMILES | C1(Cl)=C2C(C(=O)C3=C(C2=O)C=CC=C3)=CC=C1 |
| CAS DataBase Reference | 82-44-0(CAS DataBase Reference) |
| EWG's Food Scores | 1 |
| FDA UNII | 96S5SQV15V |
| NIST Chemistry Reference | 9,10-Anthracenedione, 1-chloro-(82-44-0) |
| EPA Substance Registry System | 1-Chloroanthraquinone (82-44-0) |
| UNSPSC Code | 12352115 |
| NACRES | NA.22 |
| GHS pictogram | GHS07 |
| Signal word | Warning |
| GHS hazard statements | H315-H319-H335-H320-H412 |
| GHS precautionary statements | P261-P280a-P304+P340-P305+P351+P338-P405-P501a-P264-P273-P305+P351+P338+P337+P313-P501 |
| Personal protective equipment (PPE) | dust mask type N95 (US), Eyeshields, Gloves |
| Hazard symbols | Xi |
| Risk statements (R) | 36/37/38 |
| Safety statements (S) | 26-37/39-24/25 |
| Water hazard class (WGK) | 3 |
| RTECS number | CB6150000 |
| TSCA inventory status | TSCA listed |
| Customs code | 29147090 |
| Storage class | 11 - Combustible Solids |
| Hazardous substances data | 82-44-0(Hazardous Substances Data) |
| Toxicity | LD50 orally in Rabbit: 15100 mg/kg |
Safety & Regulations
| GHS classification | This chemical does not meet GHS hazard criteria for 8.5% (4 of 47) of reports.WarningH315 (89.4%): 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 4 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies. |
|---|---|
| Regulatory information | Chemical: 9,10-Anthracenedione, 1-chloro-9,10-Anthracenedione, 1-chloro-: Does not have an individual approval but may be used as a component in a product covered by a group standard. It is not approved for use as a chemical in its own right. |
| Hazards summary | A skin and eye irritant[HSDB] Causes abnormal liver function test results after subcutaneous injection of experimental animals[RTECS] An irritantEffects in high-dose animal studies include impaired liver function tests[MSDSonline] See Anthraquinone. |
| Hazard Classes and Categories | Skin Irrit. 2 (89.4%) |
| Skin, Eye, and Respiratory Irritations | A skin, eye irritant. |
| Disposal methods | 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. |
| Preventive Measures | 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. |
| Environmental fate | 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-chloroanthraquinonehowever, this compound was resistant to biodegradation under aerobic conditions using an activated sludge inoculumonly 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-chloroanthraquinoneonly 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). |
| Adverse effects | Occupational hepatotoxin - Secondary hepatotoxins: the potential for toxic effect in the occupational setting is based on cases of poisoning by human ingestion or animal experimentation. |
| Effluent Concentrations | 1-Chloroanthraquinone was detected in an extract of flyash from a municipal incinerator in Ontario, Canada at unreported concentrations(1). |
| Soil Adsorption/Mobility | 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). |
| Human Toxicity Excerpts | CAUTION: LOW SYSTEMIC TOXICITY, BUT MAY CAUSE SKIN IRRITATION, SENSITIZATION. /ANTHRAQUINONE/Chronic neurotoxic effects include vision disturbances. /From tableQuinones/ |
| Artificial Pollution Sources | 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). |
| Environmental Biodegradation | 1-Chloroanthraquinone (100 mg/l), inoculated with activated sludge, had a theoretical BOD of 2.8% after a two week period(1). This suggests that 1-chloroanthraquinone may be resistant to biodegradation(1). |
| Environmental Bioconcentration | 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). |
| Volatilization from Water/Soil | 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). |
| Non-Human Toxicity Excerpts | ...MICE...UNHARMED BY SINGLE ORAL DOSES OF 5,000 MG/KG. /ANTHRAQUINONE/ANTHRAQUINONE...HAS BEEN NOTED ONLY IN EXPTL ANIMAL EYES TO CAUSE IRRITATION & INFLAMMATION WHEN APPLIED TO THE EYE. ...IT IS POSSIBLE THAT IRRITATION IS DUE TO MECH ACTION OF POWDER RATHER THAN TO TOXIC EFFECT... /ANTHRAQUINONE/Anthraquinones (incl 1-chloroanthraquinone) admin orally at 100-200 mg/kg to mice and at 200-400 mg/kg to rats were effective laxatives. Anthraquinones were weak laxatives in mice. In the range tested (100-400 mg/kg), the cmpd were not toxic in rats and mice.Acute neurotoxic effects reported in animals include convulsionsmedullary paralysis. /From tableQuinones/ |
| Environmental Abiotic Degradation | 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). |
| Environmental Fate/Exposure Summary | 1-Chloroanthraquinone's production and subsequent use as an intermediate in the production of dyes may result in its release to the environment through various waste streams. 1-Chloroanthraquinone may also be introduced directly to the environment as a product of the treatment of waste waters from the alpha-disulfation of anthraquinone. If released to the atmosphere, 1-chloroanthraquinone should exist in both the vapor phase and the particulate phase based on an estimated vapor pressure of 8.7X10-7 mm Hg. In the vapor phase, 1-chloroanthraquinone will react with hydroxyl radicals with an estimated half-life of about 13 days. Particulate phase 1-chloroanthraquinone may be physically removed from the atmosphere by wet and dry deposition. An estimated Koc of 3500 suggests that 1-chloroanthraquinone will have only slight mobility in soil. It is not expected to volatilize from moist soil surfaces given an estimated Henry's Law constant of 2.4X10-9 atm-cu m/mol. Incomplete information is available regarding the biodegradation potential of 1-chloroanthraquinonehowever, this compound was resistant to biodegradation under aerobic conditions using an activated sludge inoculumonly 2.8% BOD was reported following 2 weeks incubation. In water, 1-chloroanthraquinone is expected to adsorb to organic matter and suspended solids in the water column based on its Koc value. In reducing sediments, this compound will rapidly form the chloroanthrone with measured half-lives for the parent compound of <0.4 to 2.4 days. 1-Chloroanthraquinone may bioconcentrate in aquatic organismsBCF values of 118-351 were measured in carp, an estimated BCF value of 630 was calculated using an estimated log Kow. (SRC) |
| Personal protective equipment (PPE) | dust mask type N95 (US), Eyeshields, Gloves |
| Water hazard class (WGK) | 3 |
| TSCA inventory status | TSCA listed |
| RTECS number | CB6150000 |
| Customs code | 29147090 |
| Toxicity | LD50 orally in Rabbit: 15100 mg/kg |
| Risk statements (R) | 36/37/38 |
| Signal word | Warning |
| GHS pictogram | GHS07 |
| Hazard symbols | Xi |
| Safety statements (S) | 26-37/39-24/25 |
| Storage class | 11 - Combustible Solids |
| GHS hazard statements | H315-H319-H335-H320-H412 |
| GHS precautionary statements | P261-P280a-P304+P340-P305+P351+P338-P405-P501a-P264-P273-P305+P351+P338+P337+P313-P501 |
| Hazardous substances data | 82-44-0(Hazardous Substances Data) |
Applications & Uses
Uses
1-Chloroanthraquinone is an intermediate for manufacturing vat dyes such as CI Vat Brown 1.
Uses
1-Chloroanthraquinone is used to characterize anthraquinone intercalators as carrier molecules for second-generation platinum anticancer drugs.