1-Amino-2-methylanthraquinone

Base Information

• Chemical Name: 1-Amino-2-methylanthraquinone
• CAS No.: 82-28-0
• Deprecated CAS: 507484-51-7
• Molecular Formula: C15H11NO2
• Molecular Weight: 237.258
• Hs Code.: 2922399090
• European Community (EC) Number: 201-408-3
• NSC Number: 667744,39943
• UNII: RHN157F30Q
• DSSTox Substance ID: DTXSID7020057
• Nikkaji Number: J4.610H
• Wikidata: Q27155911
• NCI Thesaurus Code: C44302
• ChEMBL ID: CHEMBL1413787
• Mol file: 82-28-0.mol

Synonyms:1-Amino-2-methyl-9,10-anthraquinone;1-amino-2-methylanthraquinone;disperse orange 11

Chemical Property of 1-Amino-2-methylanthraquinone

Chemical Property:

• Appearance/Colour: red powder
• Vapor Pressure: 2.05E-09mmHg at 25°C
• Melting Point: 204-206 °C(lit.)
• Refractive Index: 1.687
• Boiling Point: 481.1 °C at 760 mmHg
• PKA: -0.53±0.20(Predicted)
• Flash Point: 244.8 °C
• PSA: 60.16000
• Density: 1.335 g/cm³
• LogP: 2.93380
• Storage Temp.: Sealed in dry,Room Temperature
• Water Solubility.: 332.2ug/L(25 oC)
• XLogP3: 3.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 237.078978594
• Heavy Atom Count: 18
• Complexity: 379

Purity/Quality:

99% ^*data from raw suppliers

Disperse Orange 11 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Dyes -> Anthraquinone Dyes
• Canonical SMILES: CC1=C(C2=C(C=C1)C(=O)C3=CC=CC=C3C2=O)N
• Uses: 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). Disperse Orange 11 is a dye used in imaging studies including confocal transmission imaging microscopy or polymers. Dyes and metabolites, Environmental Testing

Technology Process of 1-Amino-2-methylanthraquinone

There total 27 articles about 1-Amino-2-methylanthraquinone which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 95.6%

1-nitro-2-methylanthraquinone (129-15-7) → disperse orange 11 (82-28-0)

Guidance literature:

With sodium tetrahydroborate; In N,N-dimethyl-formamide; at 20 ℃;

DOI:10.3390/molecules25071672

Reference yield: 70.0%

1-nitroanthraquinone (82-34-8) → 1-hydroxyanthraquinone (129-43-1) + 1-amino-9,10-anthracenedione (82-45-1) + disperse orange 11 (82-28-0)

Guidance literature:

In N,N-dimethyl-formamide; for 8h; Heating;

Reference yield: 70.0%

1-nitroanthraquinone (82-34-8) + hexamethylenetetramine (100-97-0) → 1-hydroxyanthraquinone (129-43-1) + 1-amino-9,10-anthracenedione (82-45-1) + disperse orange 11 (82-28-0)

Guidance literature:

In N,N-dimethyl-formamide; for 8h; Heating;

upstream raw materials:

1-nitro-2-methylanthraquinone

2-methyl-1-(toluene-4-sulfonylamino)-anthraquinone

1-amino-9,10-anthracenedione

aluminum isopropoxide

Downstream raw materials:

1-benzoylamino-2-methyl-anthraquinone

1-amino-2-(phenylimino-methyl)-anthraquinone

1-amino-4-anilino-2-methyl-anthraquinone

1-amino-2-methyl-4-chloroanthraquinone

Refernces

CONVENIENT METHOD FOR THE SYNTHESIS OF 2-SUBSTITUTED NAPHTHO<2,3-g>INDOLE-6,11-DIONES

10.1007/BF00962408

The research focuses on the development of a convenient one-step method for the synthesis of 2-substituted naphtho[2,3-g]indole-6,11-diones, which are important compounds in organic chemistry. The purpose of this study was to improve upon the traditional two-step method that typically requires rigorous conditions for direct cyclization of 1-amino-2-acetylenylanthraquinones. The researchers discovered that the cyclization of intermediates could be efficiently catalyzed by a mineral acid, leading to the development of a more convenient one-step method. The process involves the addition of piperidine to 1-amino-2-acetylenylanthraquinone, followed by cyclization in the presence of dilute hydrochloric acid, resulting in the formation of the desired naphtho[2,3-g]indole-6,11-diones.