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
• Article Data: 9

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

Chemical Properties

Different sources of media describe the Chemical Properties of 82-28-0 differently. You can refer to the following data:
1. red powder
2. 1-Amino-2-methylanthraquinone is a red crystalline substance or powder.

Uses

Different sources of media describe the Uses of 82-28-0 differently. You can refer to the following data:
1. 1-Amino-2-methylanthraquinone was used almost exclusively as a dyeand as an intermediate in the production of dyes. It was used as a dyefor synthetic fibers, furs, and thermoplastic resins. The only dyes derived from 1-amino-2-methylanthraquinone that were produced in the United States were C.I. acid blue 47, last produced in 1973, and C.I. solvent blue 13, last produced in 1974 (IARC 1982, HSDB 2009).
2. Disperse Orange 11 is a dye used in imaging studies including confocal transmission imaging microscopy or polymers. Dyes and metabolites, Environmental Testing

Preparation

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

General Description

Red powder.

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.

Properties and Applications

red light orange

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 
• 871895-69-1 2-methyl-1-(toluene-4-sulfonylamino)-anthraquinone 
• 82-45-1 1-amino-9,10-anthracenedione 
• 555-31-7 aluminum isopropoxide 
• 67-63-0 isopropyl alcohol 
• 110-89-4 piperidine 
• 21172-16-7 3-methyl-anthra[1,9-cd]isoxazol-6-one 
• 82-34-8 1-nitroanthraquinone 
• 111-92-2 dibutylamine 
• 7664-93-9 sulfuric acid 
• 110-86-1 pyridine 
• 7803-57-8 hydrazine hydrate 
• 117-80-6 2,3-Dichloro-1,4-naphthoquinone 
• 108-88-3 toluene 

Downstream Products

• 112128-44-6 1-(4-Chloro-phenyl)-3-(2-methyl-9,10-dioxo-9,10-dihydro-anthracen-1-yl)-urea 
• 62982-43-8 1-(2-Methyl-9,10-dioxo-9,10-dihydro-anthracen-1-yl)-3-phenyl-urea 
• 3225-97-6 1-amino-2-methyl-4-chloroanthraquinone 
• 81-26-5 2,2'-dimethyl-1,1'-bianthraquinone 
• 21810-19-5 1-amino-2-(phenylimino-methyl)-anthraquinone 
• 81-50-5 1-amino-2-methyl-4-bromoanthraquinone 
• 67499-51-8 C₂₃H₁₆BrNO₃ 
• 67499-52-9 6-bromo-4-methyl-1-phenyl-3H-naphtho[1,2,3-de]quinoline-2,7-dione 
• 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 
• 129-35-1 1-chloro-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.

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.

REACTION OF 1-NITROANTRAQUINONE WITH HEXAMETHYLENETETRAMINE

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