117-79-3

Basic information

• Product Name: 2-AMINOANTHRAQUINONE
• Synonyms: B-ANTHRAQUINONYLAMINE;AKOS NCG-0048;ANTHRAQUINONYLAMINE;2-AMINOANTHRAQUINONE;TIMTEC-BB SBB000619;.beta.-Aminoanthraquinone;10-Anthracenedione,2-amino-9;2-AAQ
• CAS NO: 117-79-3
• Molecular Formula: C₁₄H₉NO₂
• Molecular Weight: 223.23
• EINECS: 204-208-4
• Product Categories: Intermediates of Dyes and Pigments;Aminoanthraquinones;Anthraquinones;C13 to C14;Carbonyl Compounds;Ketones;Building Blocks;C13 to C14;Carbonyl Compounds;Chemical Synthesis;Organic Building Blocks
• Mol File: 117-79-3.mol

Chemical Properties

• Melting Point: 292-295 °C (dec.)(lit.)
• Boiling Point: 364.52°C (rough estimate)
• Flash Point: 283°C
• Appearance: deep brown powder
• Density: 1.1814 (rough estimate)
• Vapor Pressure: 4.12E-09mmHg at 25°C
• Refractive Index: 1.4700 (estimate)
• Solubility: ethanol: soluble(lit.)
• PKA: 0.97±0.20(Predicted)
• Water Solubility: 163ug/L(25 oC)
• Stability: Stable. Incompatible with strong oxidizing agents.
• BRN: 745903
• CAS DataBase Reference: 2-AMINOANTHRAQUINONE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-AMINOANTHRAQUINONE(117-79-3)
• EPA Substance Registry System: 2-AMINOANTHRAQUINONE(117-79-3)

Safety Data

• Hazard Codes: Xn
• Statements: 40
• Safety Statements: 36/37/39
• WGK Germany: 3
• RTECS: CB5120000
• TSCA: Yes
• PackingGroup: II
• Hazardous Substances Data: 117-79-3(Hazardous Substances Data)

Usage

Uses

Used in Dye Industry:
2-Aminoanthraquinone is used as a dye intermediate for the production of various dyes, including CI Vat Red 10. It plays a crucial role in the synthesis of these dyes, contributing to their color and properties.
Used in Pharmaceutical Industry:
2-Aminoanthraquinone is used as a pharmaceutical intermediate, aiding in the synthesis of various pharmaceutical compounds. Its unique chemical properties make it a valuable component in the development of new drugs.
Used in Supercapacitor Fabrication:
2-Aminoanthraquinone is used in the fabrication of high-performance electrodes for supercapacitors based on chemically modified graphene hydrogels. Its incorporation enhances the performance and efficiency of these energy storage devices.
Used in Surface Assembly:
2-Aminoanthraquinone is used in the preparation of ordered assemblies of organic and biological molecules on gold(111) surfaces. This application allows for the creation of well-organized structures with specific properties and functions, useful in various scientific and technological fields.

Air & Water Reactions

Insoluble in water.

Reactivity Profile

2-AMINOANTHRAQUINONE may react with strong oxidizing agents. Forms salts with mineral acids. Can be acylated or alkylated on the nitrogen atom and nitrated or sulgonated in the ring .

Hazard

Questionable carcinogen.

Health Hazard

ACUTE/CHRONIC HAZARDS: 2-AMINOANTHRAQUINONE may be absorbed through the skin and may cause irritation. It is a positive animal carcinogen. When heated to decomposition 2-AMINOANTHRAQUINONE emits toxic fumes of carbon monoxide, carbon dioxide and nitrogen oxides.

Fire Hazard

Flash point data for 2-AMINOANTHRAQUINONE are not available; however, 2-AMINOANTHRAQUINONE is probably combustible.

Safety Profile

Confirmed carcinogen with experimental carcinogenic, neoplastigenic, and tumorigenic data. Moderately toxic via intraperitoneal route. Mutation data reported. When heated to decomposition it emits toxic NO,. See also AMINES.

Potential Exposure

2-Aminoanthraquinone is used as a dye intermediate; in the industrial synthesis of anthraquinone and pharmaceuticals. 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. Because AAQ is used on a commercial scale solely by the dye industry, the potential for exposure to the compound is greatest for workers at dye manufacturing facilities. However, no additional data are available on the number of facilities using AAQ. The Consumer Product Safety Commission staff believes that trace amounts of unreacted AAQ may possibly be present in some dyes based on this chemical and in the final consumer product. Exposure even to trace amounts may be a cause for concern. This concern is based on experience with other dyes derived from aromatic amines.

Carcinogenicity

2-Aminoanthraquinone is reasonably anticipated to be a human carcinogen based on sufficient evidence of carcinogenicity from studies in experimental animals.

Shipping

UN3143 Dyes, solid, toxic, n.o.s. or Dye intermediates, solid, toxic, n.o.s., Hazard Class: 6.1; Labels: 6.1-Poisonous materials, Technical Name Required.

Incompatibilities

Keep away from strong oxidizing and reducing agents. Incompatible with oxidizers (chlorates, nitrates, peroxides, permanganates, perchlorates, chlorine, bromine, fluorine, etc.); contact may cause fires or explosions. Keep away from alkaline materials, strong bases, strong acids, oxoacids, epoxides

InChI:InChI=1/C14H9NO2/c15-8-5-6-11-12(7-8)14(17)10-4-2-1-3-9(10)13(11)16/h1-7H,15H2

Upstream product

• 605-27-6 2-nitroanthraquinone 
• 3274-22-4 2-acetamidoanthraquinone 
• 82-27-9 2-amino-1-chloroanthraquinone 
• 142-71-2 copper diacetate 
• 131-08-8 sodium anthraquinone-2-sulfonate 
• 121-69-7 N,N-dimethyl-aniline 
• 110-86-1 pyridine 
• 84-65-1 9,10-phenanthrenequinone 
• 108-86-1 bromobenzene 
• 49545-73-5 2-azidoanthracene-9,10-dione 
• 75-05-8 acetonitrile 
• 133286-54-1 2-(dibenzylamino)anthraquinone 
• 7664-93-9 sulfuric acid 
• 131-09-9 2-chloroanthracene-9,10-dione 

Downstream Products

• 6871-96-1 6-(9,10-dioxo-9,10-dihydro-[2]anthrylamino)-3-methyl-3H-naphtho[1,2,3-de]quinoline-2,7-dione 
• 6337-15-1 ethyl-(anthraquinon-2-yl)carbamate 
• 3274-22-4 2-acetamidoanthraquinone 
• 52869-18-8 N-(9,10-dioxo-9,10-dihydroanthracen-2-yl)benzamide 
• 387384-95-4 2-(4-nitro-benzylidenamino)-anthraquinone 
• 6417-48-7 1,5-bis-(9,10-dioxo-9,10-dihydro-[2]anthrylamino)-anthraquinone 
• 119959-50-1 N-(9,10-dioxo-9,10-dihydro-[2]anthryl)-N'-phenyl-thiourea 
• 80549-11-7 4-nitro-benzoic acid-(9,10-dioxo-9,10-dihydro-[2]anthrylamide) 
• 42983-73-3 1-chloro-2-acetylaminoanthraquinone 
• 6470-85-5 (9,10-dioxo-9,10-dihydro-[2]anthryl)-carbamoyl chloride 
• 109931-72-8 2-(4-nitro-anilino)-anthraquinone 
• 103391-21-5 N,N'-bis-(9,10-dioxo-9,10-dihydro-[2]anthryl)-benzamidine 
• 143210-98-4 2-chloro-N-(9,10-dioxo-9,10-dihydroanthracen-2-yl)acetamide 
• 55868-86-5 N-(2-Anthraquinonyl)-p-methylbenzenesulfonamide 

Relevant articles and documents

Non-reductive conversion of 1-nitro-9,10-anthraquinone to 1-amino-9,10-anthraquinones

Heating 1-nitro-9,10-anthraquinone 2 with ureas 4 in N,N,N',N'-tetramethylurea (TMU) at around 130 °C resulted in the displacement of the nitro group by the amino groups, leading to the corresponding aminoanthraquinones 5 in good yields.

Solvent-free, microwave assisted oxidation of alcohols with 4-hydroxypyridinium chlorochromate functionalized silica gel

4-Hydroxypyridinium chlorochromate functionalized silica gel was found to be an efficient and reusable oxidant for the very fast oxidation of primary and secondary alcohols to the corresponding carbonyl compounds under solventfree conditions and microwave irradiation in excellent yields.

A triazine-phosphite polymeric ligand bearing cage-like P,N-ligation sites: An efficient ligand in the nickel-catalyzed amination of aryl chlorides and phenols

A novel P,N-ligand was introduced for efficient Ni-catalyzed amination of aryl chlorides. Reaction of cyanuric acid (1,3,5-triazine-2,4,6-triol) and trichlorophosphine (PCl3) resulted in the production of a new porous material (TPPM) containing triazine rings with phosphite moieties in a sheet morphology. Cavities in the prepared compound create sites on the surface of the material with appropriate ligation character to coordinate with metals for catalytic purposes. The nickel-catalyzed amination of aryl chlorides and of phenols in their 2,4,6-triaryloxy-1,3,5-triazine (TAT) protected form were efficiently accomplished in the presence of this easily prepared and reusable P,N-ligand under mild reaction conditions. More importantly, TPPM was reusable for 5 iterations following this protocol without significantly decreasing in its activity.

DEVICE FOR DETECTING AN ANALYTE

Devices for detecting an analyte comprising a redox active analyte sensitive material on a working electrode and computer assisted signal acquisition and processing.

Carbon-carbon cleavage of aryl diamines and quinone formation using sodium periodate: a novel application

A first novel synthetic utility of sodium periodate for aryl diamine carbon-carbon cleavage is described. Aryl 1,2-diamine compounds were successfully converted into corresponding nitriles, while the developed method is also useful for the preparation of quinones from corresponding aryl 1,4-diamine compounds. The advantages of this protocol are shorter reaction time and mild reaction conditions to obtain moderate to good yields.

A novel application of (Diacetoxyiodo)benzene for carbon-carbon cleavage of aryl diamines and synthesis of quinones

A novel synthetic utility of hypervalent iodine reagent, (diacetoxyiodo)benzene for diamino aryl carbon-carbon cleavage is described. 1,2-Diamino aryl compounds were successfully converted into the corresponding nitriles, while the developed method was also useful for the preparation of quinones from corresponding 1,4-diamino aryl compounds. The advantages of this protocol are shorter reaction times and mild reaction conditions to obtain moderate to good yields.

Chemoselective reduction of azides with sodium sulfide hydrate under solvent free conditions

Sodium sulfide hydrate has been employed for an efficient reduction of a variety of azides to the primary amines in good-to-excellent yields under solvent-free system and without perturbing many active functionalities such as ether, carbonyl, sulfonyl, and nitro.

Synthesis of 2,6-Dihydronaphthindol-6-ones

The reaction of 1-aminoanthraquinone with benzyl chloride in KOH-DMSO system afforded 3,11b-dibenzyl-2-phenyl-2,3,7,11b-tetrahydroanthraoxazin-7-one (5; 78percent yield), whose structure was determined by single-crystal X-ray diffraction.The reaction of compound 5 with aluminium chloride gave 1-phenyl-2,6-dihydronaphthindol-6-one (52percent yield) having strong fluorescence.

Substituent Effects in Anthrasemiquinones

Electron spin resonance spectra have been obtained from series of 2-substituted anthrasemiquinones and of 3-substituted 1,8-dihydroxyanthrasemiquinones.The proton splittings are consistently assigned by means of linear correlation plots between splitting constants and a substituent-dependent paramater.All lines in the plots of he two series of compounds obey the following linear equation aRi = AixR + aHi where aHi and aRi are the splitting constants at position i before and after the substituent has been added.Ai is the slope of the line for the splittings from position i and xR is a constant characteristic of the substituent R. xR is comparable to the Hammett ? parameter.Electron-donating substituents at C-2 are shown to increase the spin densities at the positions 1 > 6 > 8, and to decrease them at the positions 4 > 3 > 7 > 5, with the strength of the effect indicated.Electron-withdrawing substituents have the opposite effect.Preliminary Hueckel molecular-orbital calculations qualitatively predict the observed correlations, solely by changing the parameter for the resonance integral.