82-28-0

Basic information

• Product Name: 1-AMINO-2-METHYLANTHRAQUINONE
• Synonyms: 1-AMINO-2-METHYLANTHRAQUINONE;LABOTEST-BB LT00159721;CI 60700;DISPERSE ORANGE 11;TIMTEC-BB SBB003232;1-amino-2-methyl-10-anthracenedione;1-amino-2-methyl-9,10-anthracenedione;1-amino-2-methyl-9,10-anthraquinone
• CAS NO: 82-28-0
• Molecular Formula: C₁₅H₁₁NO₂
• Molecular Weight: 237.25
• EINECS: 201-408-3
• Product Categories: Intermediates of Dyes and Pigments;Aminoanthraquinones;Anthraquinones
• Mol File: 82-28-0.mol

Chemical Properties

• Melting Point: 204-206 °C(lit.)
• Boiling Point: 379.79°C (rough estimate)
• Flash Point: 244.8 °C
• Appearance: red powder
• Density: 1.1469 (rough estimate)
• Vapor Pressure: 2.05E-09mmHg at 25°C
• Refractive Index: 1.5500 (estimate)
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: -0.53±0.20(Predicted)
• Water Solubility: 332.2ug/L(25 oC)
• Stability: Stable. Incompatible with strong oxidizing agents, mineral acids.
• CAS DataBase Reference: 1-AMINO-2-METHYLANTHRAQUINONE(CAS DataBase Reference)
• NIST Chemistry Reference: 1-AMINO-2-METHYLANTHRAQUINONE(82-28-0)
• EPA Substance Registry System: 1-AMINO-2-METHYLANTHRAQUINONE(82-28-0)

Safety Data

• WGK Germany: 3
• RTECS: CB5740000
• F: 10-21
• HazardClass: IRRITANT
• Hazardous Substances Data: 82-28-0(Hazardous Substances Data)

Usage

Uses

Used in Dye Industry:
1-Amino-2-methylanthraquinone is used as a dye for synthetic fibers, furs, and thermoplastic resins, due to its red light orange color and red powder properties.
Used in Imaging Studies:
1-Amino-2-methylanthraquinone is used as a dye in imaging studies, such as confocal transmission imaging microscopy or polymers, under the name Disperse Orange 11.
Used in Environmental Testing:
1-Amino-2-methylanthraquinone is used in environmental testing for dyes and metabolites.
Note: The dyes derived from 1-amino-2-methylanthraquinone that were produced in the United States, C.I. acid blue 47 and C.I. solvent blue 13, were last produced in 1973 and 1974, respectively.

Preparation

2-Methylanthracene-9,10-dione nitrification, then use the method reduction

Air & Water Reactions

Insoluble in water.

Reactivity Profile

1-AMINO-2-METHYLANTHRAQUINONE is incompatible with strong oxidizing agents. Forms salts with mineral acids .

Fire Hazard

Flash point data for 1-AMINO-2-METHYLANTHRAQUINONE are not available; however, 1-AMINO-2-METHYLANTHRAQUINONE is probably combustible.

Safety Profile

Confirmed carcinogen with experimental carcinogenic, neoplastigenic, and tumorigenic data. Mutation data reported. When heated to decomposition it emits toxic fumes of NOx,.

Potential Exposure

1-Amino-2-methylanthraquinone is used almost exclusively as a dye intermediate for the production of a variety of anthraquinone dyes. May be used as a dye for a variety of synthetic fibers, especially acetates, as well as wool, sheepskins, furs, and surface dyeing of thermoplastics. None of the dyes that can be prepared from it are presently produced in commercial quantities.1Amino-2-methylanthraquinone had been produced commercially in the United States since 1948, but production was last reported by a single company in 1970. The potential for exposure is greatest among workers engaged in the dyeing of textiles. 1-Amino-2-methylanthraquinone is not presently used in consumer products according to the CPSC.

Carcinogenicity

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

InChI:InChI=1/C15H11NO2/c1-8-6-7-11-12(13(8)16)15(18)10-5-3-2-4-9(10)14(11)17/h2-7H,16H2,1H3

Upstream product

• 129-15-7 1-nitro-2-methylanthraquinone 
• 82-45-1 1-amino-9,10-anthracenedione 
• 110-89-4 piperidine 
• 21172-16-7 3-methyl-anthra[1,9-cd]isoxazol-6-one 
• 7664-93-9 sulfuric acid 
• 871895-69-1 2-methyl-1-(toluene-4-sulfonylamino)-anthraquinone 
• 555-31-7 aluminum isopropoxide 
• 67-63-0 isopropyl alcohol 
• 108-88-3 toluene 
• 85-44-9 phthalic anhydride 
• 117-80-6 2,3-Dichloro-1,4-naphthoquinone 
• 92439-31-1 2-methylanthraquinone-1-sulfonic acid 
• 129-35-1 1-chloro-2-methylanthraquinone 
• 84-54-8 2-methylanthracene-9,10-dione 

Downstream Products

• 6079-34-1 1-benzoylamino-2-methyl-anthraquinone 
• 21810-19-5 1-amino-2-(phenylimino-methyl)-anthraquinone 
• 3225-97-6 1-amino-2-methyl-4-chloroanthraquinone 
• 129-35-1 1-chloro-2-methylanthraquinone 
• 81-50-5 1-amino-2-methyl-4-bromoanthraquinone 
• 81-26-5 2,2'-dimethyl-1,1'-bianthraquinone 
• 67499-52-9 6-bromo-4-methyl-1-phenyl-3H-naphtho[1,2,3-de]quinoline-2,7-dione 
• 67499-51-8 C₂₃H₁₆BrNO₃ 
• 95163-94-3 1-amino-2-methyl-4-(toluene-4-sulfonylamino)-anthraquinone 
• 95636-55-8 1-methoxy-2-(1'-oxo-2'-selenophenylpentyl)anthraquinone 
• 95636-56-9 1-hydroxy-2-(1'-oxo-2'-selenophenylpentyl)anthraquinone 
• 728916-24-3 (2-methyl-10-oxo-9,10-dihydro-anthracen-1-yl)-carbamic acid 4-nitro-phenyl ester 
• 728916-25-4 Carbonic acid allyl ester 4-{(S)-2-allyloxycarbonylamino-2-[4-(2-methyl-9,10-dioxo-9,10-dihydro-anthracen-1-ylcarbamoyloxymethyl)-phenylcarbamoyl]-ethyl}-phenyl ester 
• 129-15-7 1-nitro-2-methylanthraquinone 

Relevant articles and documents

Direct and ketone-sensitized photoconversion of 1-nitro-9,10-anthraquinone to 1-amino-9,10-anthraquinone mediated by donor radicals

The full photoreduction of 1-nitro-2-R-9,10-anthraquinone (R = H: N1, methyl: N2) was studied in benzene, acetonitrile and acetonitrile-water mixtures in the presence of 2-propanol and triethylamine (TEA). The major photoproduct is the fluorescing 1-amino-2-R-AQ (A1, A2). The quantum yield of full reduction increases with the donor concentration, approaching ΦNH2 = 0.1. The intermediates involved are assigned on the basis of spectral and kinetic characteristics. The short-lived triplet state (≤20 ns) of N2 can be intercepted by 2-propanol or TEA, thereby forming the spectroscopically hidden donor radicals and the nitroAQ radicals which absorb at 400 and 540 nm; the latter band is due to the radical anion. The triplet state of N1 was not observed at room temperature, but the radical properties and decay in the nitrosoAQ are similar for N1 and N2. For donors in lower concentrations ΦNH2 is strongly increased in the presence of benzophenone, acetophenone or acetone, approaching 0.22. The results under direct and sensitized conditions are compared and major dependences and the effects of mixtures of acetonitrile with water are outlined.

Novel anthraquinone compounds inhibit colon cancer cell proliferation via the reactive oxygen species/JNK pathway

A series of amide anthraquinone derivatives, an important component of some traditional Chinese medicines, were structurally modified and the resulting antitumor activities were evaluated. The compounds showed potent anti-proliferative activities against eight human cancer cell lines, with no noticeable cytotoxicity towards normal cells. Among the candidate compounds, 1-nitro-2-acyl anthraquinone-leucine (8a) showed the greatest inhibition of HCT116 cell activity with an IC50 of 17.80 μg/mL. In addition, a correlation model was established in a three-dimensional quantitative structure-activity relationship (3D-QSAR) study using Comparative Molecular Field Analysis (CoMFA) and comparative molecular similarity index analysis (CoMSIA). Moreover, compound 8a effectively killed tumor cells by reactive oxygen species (ROS)-JNK activation, causing an increase in ROS levels, JNK phosphorylation, and mitochondrial stress. Cytochrome c was then released into cytoplasm, which, in turn activated the cysteine protease pathway and ultimately induced tumor cell apoptosis, suggesting a potential use of this compound for colon cancer treatment.

Design, Synthesis, Molecular Docking, and Biological Evaluation of New Emodin Anthraquinone Derivatives as Potential Antitumor Substances

The emodin anthraquinone derivatives are generally used in traditional Chinese medicine due to their various pharmacological activities. In the present study, a series of emodin anthraquinone derivatives have been designed and synthesized, among which 1,3-dihydroxy-6,8-dimethoxyanthracene-9,10-dione is a natural compound that has been synthesized for the very first time, and 1,3-dimethoxy-5,8-dimethylanthracene-9,10-dione is a compound that has never been reported earlier. Interestingly, while total seven of these compounds showed neuraminidase inhibitory activity in influenza virus with inhibition rate more than 50 %, specific four compounds exhibited significant inhibition of tumor cell proliferation. The further results demonstrate that 1,3-dimethoxy-5,8-dimethylanthracene-9,10-dione showed the best anticancer activity among all the synthesized compounds by inducing highest apoptosis rate to HCT116 cancer cells and arresting their G0/G1 cell cycle phase, through elevation of intracellular level of reactive oxygen species (ROS). Moreover, the binding of 1,3-dimethoxy-5,8-dimethylanthracene-9,10-dione with BSA protein has thoroughly been investigated. Altogether, this study suggests the neuraminidase inhibitory activity and antitumor potential of the new emodin anthraquinone derivatives.

A facile method for preparing substituted 1-aminoanthraquinones

An efficient and simple preparation of α-substituted aminoanthraquinones using 2,2,-dialkoxyethylamines is described.

Process for the preparation of monoaminoanthraquinones

The invention relates to a process for the preparation of monoaminoanthraquinones of the formula STR1 wherein R is a non-ionic substituent and n is 0, 1, 2 or 3, by reduction of corresponding mononitroanthraquinones, which process comprises reacting said mononitroanthraquinones with formaldehyde, in the presence of a base and a catalyst, in an aqueous alcoholic solution.

NUCLEOPHILIC SUBSTITUTION OF HYDROGEN IN AROMATIC SYSTEMS. II. MECHANISM OF AMINATION IN ANTHRAISOXAZOL-6-ONES

The nucleophilic substitution of the C5-H hydrogen atom in anthraisoxazol-6-ones by amines in acetonitrile in the absence of Cu2+, Ag+, Co2+, or Ni2+ cations takes place with the formation of strong hydrogen bond in the sixmembered chelate ring of the product from 1,4-addition of the amine to the isoxazolone at the C5 and =O atoms.The structure of the reaction product is determined by the character of the amine, and (with the absence of readily eliminated groups) substitution of C5-H is suppressed by the competing amination of C3-H and reduction of the heterocycle.The substitution of C5-Hlg by amines under analogous conditions leads to trivial reaction products.In nitromethane C3-H or C3-Hlg is mainly substituted, and C5-H or C5-Hlg is partly substituted, leading to products with trivial structures.In the presence of Cu2+, Ag+, Co2+, Ni2+ cations in acetonitrile only C3-H or C3-Hlg is substituted through the formation of mixed complex of amine and isoxazolone on the cation.

Process for the production of aminoanthraquinone compounds

The present invention concerns a novel process for the reduction of a nitro-anthraquinone compound of formula I: STR1 wherein M IS AN INTEGER 1, 2 OR 3, AND n is an integer 1, 2 or 3, The sum of m + n being 3, 4 or 5, and the rings A and B are either further substituted or unsubstituted, To the corresponding amino-anthraquinone compound which comprises reacting the compound of formula I with hydrazine in aqueous medium. The resulting amino-anthraquinone compounds are in general known and are useful intermediates in the production of anthraquinone dyestuffs.

Water-soluble amine-linked polymeric colorants

Polymeric colorants comprising a hydrocarbon backbone and attached directly thereto through amine linkages, at least one water-solubilizing group and at least one optically chromophoric group are disclosed. In a preferred embodiment, the backbone is a saturated aliphatic hydrocarbon, the chromophore is an anthraquinone chromophore and the solubilizing group is a sulfonate or sulfamate residue.