1-Amino-2,4-dibromanthrachinon

1-Amino-2,4-dibromoanthraquinone

HCID 6681CAS 81-49-2

Grundinformationen

Standard-SMILES
Nc1c(Br)cc(Br)c2c1C(=O)c1ccccc1C2=O
InChIKey
ZINRVIQBCHAZMM-UHFFFAOYSA-N
Summenformel
C14H7Br2NO2
Durchschnittliche Molmasse
381,02 g/mol
Monoisotopische Masse
378,88435

Namen und Bezeichner

Bevorzugter Name
1-Amino-2,4-dibromoanthraquinone
IUPAC
1-amino-2,4-dibromoanthracene-9,10-dione
Lokaler Name
1-Amino-2,4-dibromanthrachinon
Englischer Name
1-Amino-2,4-dibromoanthraquinone
Summenformel
C14H7Br2NO2
Molmasse
381.02

Namen und Synonyme

1-AMINO-2,4-DIBROMOANTHRAQUINONE81-49-2Dibromoaminoanthraquinone1-Amino-2,4-dibromanthrachinon9,10-Anthracenedione, 1-amino-2,4-dibromo-Anthraquinone, 1-amino-2,4-dibromo-NCI-C554582,4-Dibromo-1-anthraquinonylamineDTXSID4039235RF75O3IKOZNSC3529NSC-3529
Weitere Namen anzeigen
AKOS NCG-00671-AMINO-2,4-DIBROMOANTHRAQUI1-amino-2,4-dibromo-anthraquinon2-Amino-2,4-dibromoanthraquinone
DTXCID9052ADBAQ1-amino-2,4-dibromo-9,10-AnthracenedioneRefChem:429163CI-55458201-354-01-amino-2,4-dibromoanthracene-9,10-dione1-Amino-2,4-dibromo-anthraquinone

Datenbank-Bezeichner

CAS
81-49-2
PubChem CID
6681
DTXSID
DTXSID4039235
ChEMBL
CHEMBL559749
ChEBI
CHEBI:82304
UNII
RF75O3IKOZ
EC Number
201-354-0
Nikkaji
J53.419F

Eigenschaften

Berechnete Struktureigenschaften

XLogP
4,1
Polarare Oberfläche (TPSA)
60,2 Ų
H-Brücken-Donoren
1
H-Brücken-Akzeptoren
3
Frei drehbare Bindungen
0
Schwere Atome
19

Experimentelle und physikochemische Eigenschaften

Color/FormRed needles (from xylene)
Solubilityless than 1 mg/mL at 73 °F (NTP, 1992)
Flash Point · 2 Einträge

greater than 392 °F (NTP, 1992)

Flash point > 200 °C

DecompositionWhen heated to decomposition it emits very toxic fumes of /bromine/ and /nitrogen oxides/.
Melting Point · 2 Einträge

439 °F (NTP, 1992)

221 °C

Physical Description · 2 Einträge

1-amino-2,4-dibromoanthraquinone is an odorless red powder. (NTP, 1992)

Odorless red solid; [CAMEO]

Physikochemische Eigenschaften

Schmelzpunkt
226 °C · 226°C
Siedepunkt
550.4 · 550.4±50.0 °C(Predicted)
Dichte
1.8218 · 1.8218 (rough estimate)
Brechungsindex
1.622 · 1.6220 (estimate)
storage temp.
-20 °C · Amber Vial, -20°C Freezer, Under inert atmosphere
Löslichkeit
Chloroform (Slightly), Ethyl Acetate (Slightly)

Sicherheit und Regulatorisches

GHS-Klassifizierung

GHS Classification · 6 Einträge

Warning

H319 (90.9%): Causes serious eye irritation [Warning Serious eye damage/eye irritation];H351 (13.6%): Suspected of causing cancer [Warning Carcinogenicity]

P203, P264+P265, P280, P305+P351+P338, P318, P337+P317, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 44 reports by companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.;Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website.

Gefahrenhinweise

Regulatory Information · 3 Einträge

Chemical: 9,10-Anthracenedione, 1-amino-2,4-dibromo-

Hazard Traits - Carcinogenicity;Authoritative List - IARC Carcinogens - 2B; NTP RoC - reasonable; Prop 65;Report - regardless of intended function of ingredient in the product

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.)

Other Safety InformationIMAP assessments - 9,10-Anthracenedione, 1-amino-2,4-dibromo-: Human health tier II assessment
Fire HazardsThis chemical is probably combustible. (NTP, 1992)
Health Hazards · 1 Eintrag

SYMPTOMS: Symptoms of exposure to this compound include eye and respiratory tract irritation.;ACUTE/CHRONIC HAZARDS: This compound may cause eye irritation. It may also be irritating to the mucous membranes of the nose and throat. When heated to decomposition it emits toxic fumes of nitrogen oxides and hydrogen bromide. (NTP, 1992)

Hazards SummaryAnthraquinones are toxic by ingestion: vomiting, diarrhea, kidney and liver damage, and coma; Deaths have been reported after children ingested Rhamnus berries; [HSDB] An eye and respiratory tract irritant; [CAMEO] An irritant; [MSDSonline]
Reactive GroupKetones;Aryl Halides;Amines, Aromatic

Sicherheit und Schutzausrüstung

Fire FightingFires involving this chemical can be controlled with a dry chemical, carbon dioxide or Halon extinguisher. A water spray may also be used. (NTP, 1992)
First Aid · 1 Eintrag

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.;SKIN: IMMEDIATELY flood affected skin with water while removing and isolating all contaminated clothing. Gently wash all affected skin areas thoroughly with soap and water. If symptoms such as redness or irritation develop, IMMEDIATELY call a physician and be prepared to transport the victim to a hospital for treatment.;INHALATION: IMMEDIATELY leave the contaminated area; take deep breaths of fresh air. If symptoms (such as wheezing, coughing, shortness of breath, or burning in the mouth, throat, or chest) develop, call a physician and be prepared to transport the victim to a hospital. Provide proper respiratory protection to rescuers entering an unknown atmosphere. Whenever possible, Self-Contained Breathing Apparatus (SCBA) should be used; if not available, use a level of protection greater than or equal to that advised under Protective Clothing.;INGESTION: DO NOT INDUCE VOMITING. If the victim is conscious and not convulsing, give 1 or 2 glasses of water to dilute the chemical and IMMEDIATELY call a hospital or poison control center. Be prepared to transport the victim to a hospital if advised by a physician. If the victim is convulsing or unconscious, do not give anything by mouth, ensure that the victim's airway is open and lay the victim on his/her side with the head lower than the body. DO NOT INDUCE VOMITING. IMMEDIATELY transport the victim to a hospital. (NTP, 1992)

Storage Conditions · 1 Eintrag

PRECAUTIONS FOR "CARCINOGENS": Storage site should be as close as practical to lab in which carcinogens are to be used, so that only small quantities required for ... expt need to be carried. Carcinogens should be kept in only one section of cupboard, an explosion-proof refrigerator or freezer (depending on chemicophysical properties ...) that bears appropriate label. An inventory ... should be kept, showing quantity of carcinogen & date it was acquired ... Facilities for dispensing ... should be contiguous to storage area. /Chemical Carcinogens/

Cleanup Methods · 2 Einträge

SRP: Wastewater from contaminant suppression, cleaning of protective clothing/equipment, or contaminated sites should be contained and evaluated for subject chemical or decomposition product concentrations. Concentrations shall be lower than applicable environmental discharge or disposal criteria. Alternatively, pretreatment and/or discharge to a permitted wastewater treatment facility is acceptable only after review by the governing authority and assurance that "pass through" violations will not occur. Due consideration shall be given to remediation worker exposure (inhalation, dermal and ingestion) as well as fate during treatment, transfer and disposal. If it is not practicable to manage the chemical in this fashion, it must be evaluated in accordance with EPA 40 CFR Part 261, specifically Subpart B, in order to determine the appropriate local, state and federal requirements for disposal.

PRECAUTIONS FOR "CARCINOGENS": A high-efficiency particulate arrestor (HEPA) or charcoal filters can be used to minimize amt of carcinogen in exhausted air ventilated safety cabinets, lab hoods, glove boxes or animal rooms ... Filter housing that is designed so that used filters can be transferred into plastic bag without contaminating maintenance staff is avail commercially. Filters should be placed in plastic bags immediately after removal ... The plastic bag should be sealed immediately ... The sealed bag should be labelled properly ... Waste liquids ... should be placed or collected in proper containers for disposal. The lid should be secured & the bottles properly labelled. Once filled, bottles should be placed in plastic bag, so that outer surface ... is not contaminated ... The plastic bag should also be sealed & labelled. ... Broken glassware ... should be decontaminated by solvent extraction, by chemical destruction, or in specially designed incinerators. /Chemical Carcinogens/

Nonfire Spill Response · 1 Eintrag

SMALL SPILLS AND LEAKAGE: If you spill this chemical, you should dampen the solid spill material with 5% acetic acid, then transfer the dampened material to a suitable container. Use absorbent paper dampened with 5% acetic acid to pick up any remaining material. Your contaminated clothing and the absorbent paper should be sealed in a vapor-tight plastic bag for eventual disposal. Wash all contaminated surfaces with 5% acetic acid followed by washing 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.;STORAGE PRECAUTIONS: You should protect this chemical from exposure to light. Keep the container tightly closed under an inert atmosphere, and store under refrigerated temperatures. (NTP, 1992)

Disposal Methods · 5 Einträge

PRECAUTIONS FOR "CARCINOGENS": Carcinogens that are alkylating, arylating or acylating agents per se can be destroyed by reaction with appropriate nucleophiles, such as water, hydroxyl ions, ammonia, thiols & thiosulfate. The reactivity of various alkylating agents varies greatly ... & is also influenced by sol of agent in the reaction medium. To facilitate the complete reaction, it is suggested that the agents be dissolved in ethanol or similar solvents. ... No method should be applied ... until it has been thoroughly tested for its effectiveness & safety on material to be inactivated. For example, in case of destruction of alkylating agents, it is possible to detect residual compounds by reaction with 4(4-nitrobenzyl)-pyridine. /Chemical Carcinogens/

PRECAUTIONS FOR "CARCINOGENS": ... Small quantities of ... some carcinogens can be destroyed using chem reactions ... but no general rules can be given. ... As a general technique ... treatment with sodium dichromate in strong sulfuric acid can be used. The time necessary for destruction ... is seldom known ... but 1-2 days is generally considered sufficient when freshly prepd reagent is used. ... Carcinogens that are easily oxidizable can be destroyed with milder oxidative agents, such as saturated soln of potassium permanganate in acetone, which appears to be a suitable agent for destruction of hydrazines or of compounds containing isolated carbon-carbon double bonds. Concn or 50% aqueous sodium hypochlorite can also be used as an oxidizing agent. /Chemical Carcinogens/

PRECAUTIONS FOR "CARCINOGENS": HEPA (high-efficiency particulate arrestor) filters ... can be disposed of by incineration. For spent charcoal filters, the adsorbed material can be stripped off at high temp & carcinogenic wastes generated by this treatment conducted to & burned in an incinerator. ... LIQUID WASTE: ... Disposal should be carried out by incineration at temp that ... ensure complete combustion. SOLID WASTE: Carcasses of lab animals, cage litter & misc solid wastes ... should be disposed of by incineration at temp high enough to ensure destruction of chem carcinogens or their metabolites. /Chemical Carcinogens/

PRECAUTIONS FOR "CARCINOGENS": ... Incineration may be only feasible method for disposal of contaminated laboratory waste from biological expt. However, not all incinerators are suitable for this purpose. The most efficient type ... is probably the gas-fired type, in which a first-stage combustion with a less than stoichiometric air:fuel ratio is followed by a second stage with excess air. Some ... are designed to accept ... aqueous & organic-solvent solutions, otherwise it is necessary ... to absorb soln onto suitable combustible material, such as sawdust. Alternatively, chem destruction may be used, esp when small quantities ... are to be destroyed in laboratory. /Chemical Carcinogens/

For more Disposal Methods (Complete) data for 1-AMINO-2,4-DIBROMOANTHRAQUINONE (6 total), please visit the HSDB record page.

Toxikologische Informationen

Interactions · 1 Eintrag

... The reactive oxygen species (ROS) mechanism for photoinduced acute toxicity of 1-amino-2,4-dibromoanthraquinone (ADBAQ) to Daphnia magna was clarified by experiment and theoretical calculation. The results of the present study show that ADBAQ exhibited high toxicity to D. magna under simulated solar radiation (SSR), with a median effective concentration of 1.23 +/- 0.19 nM (mean +/- standard deviation). The photomodified ADBAQ (mixtures of ADBAQ and its photoproducts) was less phototoxic than the intact ADBAQ. The SSR-only or ADBAQ-only treatments did not affect the ROS level in D. magna, whereas increased ROS levels were observed in the presence of SSR and ADBAQ ... The antioxidants, including vitamin C, vitamin E, and beta-carotene, decreased the photoinduced oxidative damage to D. magna, probably by scavenging ROS ...

Environmental Fate · 3 Einträge

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 6,600(SRC), determined from a structure estimation method(2), indicates that 1-amino-2,4-dibromoanthraquinone is expected to be immobile in soil(SRC). Volatilization of 1-amino-2,4-dibromoanthraquinone from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 1.8X10-13 atm-cu m/mole(SRC), using a fragment constant estimation method(3). 1-Amino-2,4-dibromoanthraquinone is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 1.4X10-9 mm Hg(SRC), determined from a fragment constant method(4). Biodegradation data were not available(SRC, 2009).

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 6,600(SRC), determined from a structure estimation method(2), indicates that 1-amino-2,4-dibromoanthraquinone is expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(3) based upon an estimated Henry's Law constant of 1.8X10-13 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). According to a classification scheme(5), an estimated BCF of 380(SRC), from an estimated log Kow of 5.31(6) and a regression-derived equation(7), suggests the potential for bioconcentration in aquatic organisms is high(SRC). 1-Amino-2,4-dibromoanthraquinone is not expected to undergo hydrolysis in the environment due to the lack of functional groups that hydrolyze under environmental conditions(3). Biodegradation data were not available(SRC, 2009).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), 1-amino-2,4-dibromoanthraquinone, which has an estimated vapor pressure of 1.4X10-9 mm Hg at 25 °C(SRC), determined from a fragment constant method(2), is expected to exist solely in the particulate phase in the ambient atmosphere. Particulate-phase 1-amino-2,4-dibromoanthraquinone may be removed from the air by wet or dry deposition(SRC). 1-Amino-2,4-dibromoanthraquinone contains chromophores that absorb at wavelengths >290 nm(3) and therefore may be susceptible to direct photolysis by sunlight(SRC).

Adverse Effects · 1 Eintrag

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.;IARC Carcinogen - Class 3: Chemicals are not classifiable by the International Agency for Research on Cancer.;NTP Carcinogen - Reasonably anticipated to be a human carcinogen.

Ongoing Test Status · 1 Eintrag

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=81-49-2]

Effluent Concentrations1-Amino-2,4-dibromoanthraquinone was detected in the raw wastewater from a dye manufacturing plant in 4 of 8 samples at concentrations of 92-170 ppb in samples taken July 1976 and not detected in 9 final effluent samples(1).
Medical Surveillance · 1 Eintrag

PRECAUTIONS FOR "CARCINOGENS": Whenever medical surveillance is indicated, in particular when exposure to a carcinogen has occurred, ad hoc decisions should be taken concerning ... /cytogenetic and/or other/ tests that might become useful or mandatory. /Chemical Carcinogens/

Regulatorische Informationen

Regulatory Information · 3 Einträge

Chemical: 9,10-Anthracenedione, 1-amino-2,4-dibromo-

Hazard Traits - Carcinogenicity;Authoritative List - IARC Carcinogens - 2B; NTP RoC - reasonable; Prop 65;Report - regardless of intended function of ingredient in the product

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.)

Sicherheitsdaten

tsca
TSCA listed
RTECS-Nr.
CB5500000
risk_code
36/37/38
safety_code
26-36/37/39
Giftige Stoffe Daten
81-49-2(Hazardous Substances Data)

Chemie und Industrie

Verwendung und Herstellung

Uses · 3 Einträge

Intermediate in the production of anthraquinone dyes; [HSDB]

Intermediate in the production of 1-amino-2-bromo-4-hydroxyanthraquinone (bromo pink)

Aminoanthraquinones are key products for essentially all classes of anthraquinone dyes. /Aminoanthraquinones/

U.S. ProductionProduction volumes for non-confidential chemicals reported under the Inventory Update Rule. [Table#5301]
Methods of Manufacturing1-Amino-2,4-dibromoanthraquinone is prepared from 1-aminoanthraquinone by bromination in dilute mineral acids.
General Manufacturing Information9,10-Anthracenedione, 1-amino-2,4-dibromo-: ACTIVE
Anwendungen · 2 Einträge

BeschreibungDas 1-Amino-2,4-dibromanthrachinon bildet rote, verfilzte, wasserunlösliche Nadeln. Es findet Anwendung bei der Synthese von Anthrachinonfarbstoffen.

VerwendenADBAQ and other aminoanthraquinones are key intermediates in the production of almost all anthraquinone dyes (HSDB 2009). Anthraquinones, including ADBAQ, are widely used as starting material for the manufacture of vat dyes, which are a class of water-insoluble dyes that can easily be reduced to a water-soluble and usually colorless form. In this form, they are readily impregnated into fibers and textiles. Oxidation then produces an insoluble colored form that is remarkably fast to washing, light, and chemicals. Vat dyes typically are used with cotton, wool, and cellulose acetate (NTP 1996).

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Hebei Chuanghai Biotechnology Co., Ltd+86-17732866630 · [email protected]
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