2-Aminoanthraquinone
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117-79-3Nc1ccc2c(c1)C(=O)c1ccccc1C2=OXOGPDSATLSAZEK-UHFFFAOYSA-N2-Aminoanthraquinone can cause cancer according to California Labor Code.
117-79-3DTXSID6020068CHEMBL84685CHEBI:34258Dyes -> Anthraquinone Dyes
Carcinogens
log Kow = 3.31
3.3
Red needles from alcohol, acetic acid
Red or orange-brown needles
less than 1 mg/mL at 63 °F (NTP, 1992)
Insoluble in water, ethyl ether; slightly soluble in ethanol; soluble in acetone, benzene, chloroform
In water, 0.16 mg/L at 25 °C
Solubility in water: very poor
283 °C
283 °C closed cup
283 °C c.c.
Sublimes (NTP, 1992)
Sublimes
577 to 583 °F (NTP, 1992)
安全情報は参考情報です。供給元の安全データシート(SDS)、適用法令、専門家による評価に代わるものではありません。
This chemical does not meet GHS hazard criteria for 6% (3 of 50) of reports.
Warning
H351 (92%): Suspected of causing cancer [Warning Carcinogenicity]
P203, P280, P318, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 50 reports by companies from 7 notifications to the ECHA C&L Inventory.
Not Classified
Hazard Traits - Carcinogenicity
9,10-Anthracenedione, 2-amino-: Does not have an individual approval but may be used under an appropriate group standard
The New Jersey Worker and Community Right to Know Act requires public and private employers to provide information about hazardous substances at their workplaces. (N.J.S.A. 34:5A-1 et. seq.)
Flash point data for this compound are not available; however, it is probably combustible. (NTP, 1992)
Combustible. Gives off irritating or toxic fumes (or gases) in a fire.
ACUTE/CHRONIC HAZARDS: This compound may be absorbed through the skin and may cause irritation. It is a positive animal carcinogen. When heated to decomposition this material emits toxic fumes of carbon monoxide, carbon dioxide and nitrogen oxides. (NTP, 1992)
No listed effects of short-term or long-term exposure; [ICSC] Evidence for carcinogenicity (hepatocellular neoplasms and carcinomas) in rats and mice; Effects to female rats in sub-chronic and chronic feeding studies include nephrotoxicity and decreased hemoglobin; Emergency treatment: Anthraquinones; Anthraquinones have cathartic action after ingestion, and in severe cases, may cause kidney damage, liver enzyme elevation, GI hemorrhage, seizures, and coma; [HSDB] May cause irritation and be absorbed through skin; Carcinogenic to animals; [CAMEO] Not irritating to skin or eyes of rabbits; Evidence for mutagenicity includes positive results in six of seven Ames Tests using various strains of Salmonella typhimurium, two cytogenic assays, four mouse lymphoma assays, and three in-vitro micronucleus assays; [IUCLID]
In studies on Fischer rats at a dosage of 2% in the feed, besides the unchanged substance, the metabolites N-formyl-2-aminoanthracite, N-acetyl-2-aminoanthracite, and the hydroxy-derivatives of 2-aminoanthraquinone and N-acetyl-2-aminoanthraquinone were found in the urine. It was noted that in male rats, metabolic catabolism dominated, while in females, soluble metabolites prevailed. These metabolites are then rapidly precipitated in the kidneys. Nephrotoxicity of 2-aminoanthraquinone exhibits a distinct gender differentiation with rapid onset of nephritis and crystalline deposits in the kidney tubules of female animals. /Translated from German/
Deposition of 2-aminoanthraquinone & less soluble 2-acetylamino-anthraquinone in kidney tubules after dietary administration of 2-aminoanthraquinone to female Fischer rats. Hydroxy metabolite of 2-aminoanthraquinone was excreted in conjugated form in urine.
Feeding 2-aminoanthraquinone in diet to Fischer rats caused deposits of crystaline material in kidney tubules, material consisted of 2-aminoanthraquinone, N-formyl-2-aminoanthraquinone & N-acetyl-2-aminoanthraquinone.
Used as an intermediate for dyes and pharmaceuticals; [HSDB]
CHEM INT FOR DYES (EG, C.I. VAT BLUE 6, 8.33%), (EG, C.I. PIGMENT BLUES 22 & 60)
It is the precursor of five dyes and one pigment, including Color Index Vat Blues 4, 6, 12, and 24, Vat Yellow 1, and Pigment Blue 22.
REACTION OF HEATED AQUEOUS AMMONIA AND NITROBENZENE WITH SODIUM ANTHRAQUINONE-2-SULFONATE; AMMONOLYSIS OF 2-CHLOROANTHRAQUINONE
読み込み中…
304.5 °C
302 °C
303 °C
5.0X10-11 mm Hg at 25 °C
Vapor pressure, Pa at 180 °C: 1.3
2-aminoanthraquinone appears as red needle-like crystals or dark brown granular solid. (NTP, 1992)
Red or orange-brown solid; [HSDB] Orange-brown powder; [MSDSonline]
RED OR ORANGE-BROWN SOLID IN VARIOUS FORMS.
化学的特性2-Aminoanthraquinone forms red or orangebrown needle-shaped crystalline solid. It is used as an intermediate for dyes and pharmaceuticals.
National Toxicology Program. Eleventh Report on Carcinogens (2005). The Report on Carcinogens is an informational scientific and public health document that identifies and discusses substances (including agents, mixtures, or exposure circumstances) that may pose a carcinogenic hazard to human health. 2-Aminoanthraquinone (117-79-3) is listed as reasonably anticipated to be a human carcinogen.[Available from, as of July 31, 2009: http://ntp.niehs.nih.gov/ntp/roc/eleventh/profiles/s012iq.pdf]
IARC. Monographs on the Evaluation of the Carcinogenic Risk of Chemicals to Man. Geneva: World Health Organization, International Agency for Research on Cancer, vol. 7, p. 194 (1982). IARC Monographs provide critical reviews of data on carcinogenicity for agents to which humans are known to be exposed and on specific exposure situations.[Available at: http://monographs.iarc.fr/index.php]
European Commission, ESIS; IUCLID Dataset, 2-Aminoanthraquinone (117-79-3) (2000 CD-ROM edition) contains information on use, toxicology, and environmental effects of this chemical as supplied to the European Union by industry.[Available from, as of September 29, 2010: http://esis.jrc.ec.europa.eu/]
Sendelbach LE; A Review of the Toxicity and Carcinogenicity of Anthraquinone Derivatives; Toxicology 57 (3): 227-40 (1989)
DHEW/NCI; Bioassay of 2-Aminoanthraquinone for Possible Carcinogenicity (1978) Technical Rpt Series No. 144 DHEW Pub No. (NIH) 78-1399
Carc. 2 (92%)
Carcinogens, Mutagens
Fires involving this compound can be controlled with a dry chemical, carbon dioxide or Halon extinguisher. (NTP, 1992)
Use water spray, powder, foam, carbon dioxide.
Fresh air, rest.
Rinse and then wash skin with water and soap.
First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention.
Rinse mouth.
EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop.
Suitable extinguishing media: Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide. Special protective equipment for fire-fighters: Wear self contained breathing apparatus for fire fighting if necessary.
Use dry chemical, carbon dioxide, water spray, or alcohol foam extinguishers ... If material or contaminated runoff enters waterways, notify downstream users of potentially contaminated waters. Notify local health and fire officials and pollution control agencies. From a secure, explosion-proof location, use water spray to cool exposed containers. If cooling streams are ineffective (venting sound increases in volume and pitch, tank discolors or shows any signs of deforming), withdraw immediately to a secure position ... The only respirators approved for fire fighting are self-contained breathing apparatuses that have full facepieces and are operated in a pressure-demand or other positive-pressure mode.
Keep container tightly closed in a dry and well-ventilated place. Keep in a dry place.
Store in tightly closed containers in a refrigerator or cool, well ventilated area away from strong oxidizers.
ACCIDENTAL RELEASE MEASURES. Personal precautions: Use personal protective equipment. Avoid dust formation. Avoid breathing dust. Ensure adequate ventilation. Environmental precautions: Do not let product enter drains. Methods for cleaning up: Pick up and arrange disposal without creating dust. Keep in suitable, closed containers for disposal.
Evacuate persons not wearing protective equipment from area of spill or leak until clean-up is complete. Remove all ignition sources. Dampen spilled material with toluene to avoid airborne dust. Collect powdered material in the most convenient and safe manner and deposit in vapor-tight sealed containers. Ventilate area after clean-up is complete. It may be necessary to contain and dispose of this chemical as a hazardous waste. If material or contaminated runoff enters waterways, notify downstream users of potentially contaminated waters. Contact your Department of Environmental Protection or your regional office of the federal EPA for specific recommendations.
SMALL SPILLS AND LEAKAGE: If you spill this chemical, you should dampen the solid spill material with water, then transfer the dampened material to a suitable container. Use absorbent paper dampened with water to pick up any remaining material. Seal your contaminated clothing and the absorbent paper in a vapor-tight plastic bag for eventual disposal. Wash all contaminated surfaces with a soap and water solution. Do not reenter the contaminated area until the Safety Officer (or other responsible person) has verified that the area has been properly cleaned.
Observe all federal, state, and local environmental regulations. Contact a licensed professional waste disposal service to dispose of this material. Dissolve or mix the material with a combustible solvent and burn in a chemical incinerator equipped with an afterburner and scrubber.
SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational harm/injury/toxicity or environmental contamination. Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in soil or water; effects on animal and plant life; and conformance with environmental and public health regulations.
Handle in accordance with good industrial hygiene and safety practice. Wash hands before breaks and at the end of workday.
If inhaled ..., move person into fresh air. If not breathing give artificial respiration. Consult a physician. In case of skin contact, wash off with soap and plenty of water. Consult a physician. In case of eye contact, rinse thoroughly with plenty of water for at least 15 minutes and consult a physician. If swallowed, never give anything by mouth to an unconscious person. Rinse mouth with water. Consult a physician.
Avoid formation of dust and aerosols. Provide appropriate exhaust ventilation at places where dust is formed.
SRP: Local exhaust ventilation should be applied wherever there is an incidence of point source emissions or dispersion of regulated contaminants in the work area. Ventilation control of the contaminant as close to its point of generation is both the most economical and safest method to minimize personnel exposure to airborne contaminants. Ensure that the local ventilation moves the contaminant away from the worker.
For more Preventive Measures (Complete) data for 2-Aminoanthraquinone (7 total), please visit the HSDB record page.
The role of gonadal hormones in the nephrotoxicity of the hepatocarcinogen 2-aminoanthraquinone (2-AAQ) was investigated. Intact and castrated four week old Fischer rats of both sexes and castrated female rats with subcutaneous implants of testosterone propionate pellets were fed 2% 2-AAQ in a Wayne meal diet. After 12 weeks of ad libitum feeding the animals were then given control diet. Based on survival, body, liver,and kidney weights, and the histopathological evaluation of the kidneys, castrated female rats given testosterone propionate were afforded the greatest protective effect against the nephrotoxicity of 2-AAQ.
Male and female Fischer 344 rats were fed 2-aminoanthraquinone in their diet for 12 weeks, dosage 2% in the feed (approx. 1670 mg/kg), and were observed for up to 80 weeks post-treatment. A control group received no treatment. The study examined the influence of testosterone on the known nephrotoxicity of the test substance. Therefore groups of castrated animals (male and female) and female animals treated with testosterone were included in the study. Female animals in the test group (normal and castrated) died within 30 weeks while male animals and testosterone treated females survived 80 weeks. Histopathology revealed crystallization in cortical kidney tubules in normal and castrated females which was not seen in male animals or those females treated with testosterone. It was concluded from these results that testosterone offers a protective effect from the toxicity of the test substance that gender alone cannot explain. /Translated from German/
TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 4,300(SRC), determined from a log Kow of 3.31(2) and a regression-derived equation(3), indicates that 2-aminoanthraquinone is expected to have slight mobility in soil(SRC). Volatilization of 2-aminoanthraquinone from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 9.2X10-11 atm-cu m/mole(SRC), derived from its vapor pressure, 5.0X10-11 mm Hg(4), and water solubility, 0.163 mg/L(6). 2-Aminoanthraquinone is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(4). Utilizing the Japanese MITI test, 1% of the Theoretical BOD was reached in 4 weeks(2) indicating that biodegradation is not an important environmental fate process in soil(SRC).
AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 4,300(SRC), determined from a log Kow of 3.31(2) and a regression-derived equation(3), indicates that 2-aminoanthraquinone is expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(4) based upon an estimated Henry's Law constant of 9.2X10-11 atm-cu m/mole(SRC), derived from its vapor pressure, 5.0X10-11 mm Hg(5), and water solubility, 0.163 mg/L(6). According to a classification scheme(7), a BCF range of 18-46(2), suggests the potential for bioconcentration in aquatic organisms is moderate(SRC). Utilizing the Japanese MITI test, 1% of the Theoretical BOD was reached in 4 weeks(2) indicating that biodegradation is not an important environmental fate process in water(SRC).
ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), 2-aminoanthraquinone, which has a vapor pressure of 5.0X10-11 mm Hg at 25 °C(2), is expected to exist solely in the particulate phase in the ambient atmosphere. Particulate-phase 2-aminoanthraquinone may be removed from the air by wet or dry deposition(SRC). 2-Aminoanthraquinone contains chromophores that absorb at wavelengths >290 nm(3), and therefore may be susceptible to direct photolysis by sunlight(SRC).
The following link will take the user to the National Toxicology Program (NTP) Test Agent Search Results page, which tabulates all of the "Standard Toxicology & Carcinogenesis Studies", "Developmental Studies", and "Genetic Toxicity Studies" performed with this chemical. Clicking on the "Testing Status" link will take the user to the status (i.e., in review, in progress, in preparation, on test, completed, etc.) and results of all the studies that the NTP has done on this chemical.[Available from: http://ntp-apps.niehs.nih.gov/ntp_tox/index.cfm?fuseaction=ntpsearch.searchresults&searchterm=117-79-3]
The Koc of 2-aminoanthraquinone is estimated as 4,300(SRC), using a log Kow of 3.31(1) and a regression-derived equation(2). According to a classification scheme(3), this estimated Koc value suggests that 2-aminoanthraquinone is expected to have slight mobility in soil.
/SIGNS AND SYMPTOMS/ May be harmful if inhaled. May cause respiratory tract irritation. May be harmful if absorbed through skin. May cause skin irritation. May cause eye irritation. May be harmful if swallowed.
/SIGNS AND SYMPTOMS/ Short Term Exposure: Irritates eyes and skin.
2-Aminoanthraquinone
Group 3: Not classifiable as to its carcinogenicity to humans
Volume 27: (1982) Some Aromatic Amines, Anthraquinones and Nitroso Compounds, and Inorganic Fluorides Used in Drinking-water and Dental Preparations
1987
1987
2-Amino-anthraquinone
BCF values of 18-46 and 27-43 were measured in fish for 2-aminoanthraquinone using carp (Cyprinus carpio) which were exposed over a 6-week period to test chemical concentrations of 5 and 50 mg/L, respectively(1). According to a classification scheme(3), these BCF ranges suggest the potential for bioconcentration in aquatic organisms is moderate(SRC).
The Henry's Law constant for 2-aminoanthraquinone is estimated as 9.2X10-11 atm-cu m/mole(SRC) derived from its vapor pressure, 5.0X10-11 mm Hg(1), and water solubility, 0.163 mg/L(2). This Henry's Law constant indicates that 2-aminoanthraquinone is expected to be essentially nonvolatile from water surfaces(3). 2-Aminoanthraquinone's estimated Henry's Law constant indicates that volatilization from moist soil surfaces may not occur(SRC). 2-Aminoanthraquinone is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(1).
/LABORATORY ANIMALS: Acute Exposure/ Skin irritation test in rabbit, result: not irritating.
/LABORATORY ANIMALS: Acute Exposure/ Eye irritation test in rabbit, result: not irritating.
/LABORATORY ANIMALS: Subchronic or Prechronic Exposure/ After 12-14 wk of admin of 2-aminoanthraquinone at level of 2% in diet to Fischer F344 rats, females showed weight loss, alopecia, emaciation, ataxia, and convulsions prior to death or sacrifice. Cumulative nephrotoxicity in females treated with 2-aminoanthraquinone was unexpected. Hematological studies in females showed depression of hematocrit values and decline in hemoglobin and erythrocyte count, while both sexes showed elevation of total leukocytes.
/LABORATORY ANIMALS: Subchronic or Prechronic Exposure/ Male and female Fischer 344 rats were fed 2-aminoanthraquinone continuously in their feed for 12-14 weeks, dosage 1% or 2% (approx. 830 or 1670 mg/kg). A control group received no treatment. Equivalent dosage /over duration of the study/ at 1%: 22 g for males and 11.6 g for females, at 2%: 47 g for males and 18 g for females. After 10 weeks the dosage was reduced 0.25-0.5%. The 2% dose was determined in a preliminary experiment. Female animals in both groups experienced weight loss, alopecia, emaciation, ataxia, and preagonal convulsions. All female animals in both test groups died within 18 (2% group) and 21 (2% group) weeks. Hematological symptoms seen in female animals included a reduction in hematocrit, hemoglobin, and RBC. In both sexes there was an increase in blood glucose levels and serum calcium concentration as well as a large increase in serum urea concentration in female animals. Histopathological findings seen in female animals were primarily kidney damage as interstitial fibrosis and multitudinous tubular metaplasia as well as bone marrow hyperplasia. What was most striking was the minimal toxic effect found in male animals. /Translated from German/
For more Non-Human Toxicity Excerpts (Complete) data for 2-Aminoanthraquinone (23 total), please visit the HSDB record page.
By reduction of nitroanthraquinones, or by substitution of amino radical direct for sulfonic acid.
解説【Ⅰ】1-aminoおよび2-aminoanthraquinone.C14H9NO2(223.23).モノアミノアントラキノンには1-および2-アミノアントラキノンの二つの異性体がある.1-アミノアントラキノンはアントラキノン-1-スルホン酸のアンモノリシス,あるいは1-クロロアントラキノンとp-トルエンスルホンアミドを加熱して生成した1-トシルアミノアントラキノンの加水分解によって得られる."赤色の結晶.融点253 ℃.硫酸呈色は淡黄色で,エタノール,ベンゼン,酢酸,クロロホルムなどに熱時溶ける.建染め染料,酸性染料,分散染料などの中間体として重要である.2-アミノアントラキノンは,アントラキノン-2-スルホン酸または2-クロロアントラキノンから1-アミノアントラキノンと同様にして合成できる.橙色の結晶.融点302 ℃.濃硫酸呈色は淡黄色.建染め染料,とくにインダスレンブルーRSの原料として重要である.森北出版「化学辞典(第2版)
用途建染め染料の原料
用途染料中間体
使用2-Aminoanthraquinone was used in fabrication of high performance electrode of supercapacitor based on chemically modified graphene hydrogel. It was used in preparation of ordered assemblies of organic and biological molecules on gold(111) surfaces.
一般的な説明2-aminoanthraquinone appears as red needle-like crystals or dark brown granular solid. (NTP, 1992)