2944-28-7

Basic information

• Product Name: 1-(phenylamino)anthraquinone
• Synonyms: 1-(phenylamino)anthraquinone;Solvent Red 227;Plasto Red 8350;C.I. SOLVENT RED 227);Disperse red 22 (C.I. 60510);1-Anilinoanthraquinone;1-Phenylamino-9,10-anthracenedione;1-Phenylamino-9,10-anthraquinone
• CAS NO: 2944-28-7
• Molecular Formula: C₂₀H₁₃NO₂
• Molecular Weight: 299.32272
• EINECS: 220-945-4
• Mol File: 2944-28-7.mol

Chemical Properties

• Boiling Point: 503.2°C at 760 mmHg
• Flash Point: 189.6°C
• Appearance: /
• Density: 1.329g/cm³
• Vapor Pressure: 2.97E-10mmHg at 25°C
• Refractive Index: 1.71
• CAS DataBase Reference: 1-(phenylamino)anthraquinone(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(phenylamino)anthraquinone(2944-28-7)
• EPA Substance Registry System: 1-(phenylamino)anthraquinone(2944-28-7)

Safety Data

• Hazardous Substances Data: 2944-28-7(Hazardous Substances Data)

Usage

Uses

Used in Textile Industry:
1-(Phenylamino)anthraquinone is used as a dye for acetate and triacetate fibers due to its pink color and compatibility with these materials. It provides good ironing fastness, light fastness, perspiration fastness, and washing fastness, with ratings of ISO 6-7, 5, 5, and 4-5, respectively. However, it is not commonly used for dyeing polyester fibers.

Preparation

1-Chloroanthraquinone and aniline condensation

Standard(Vinegar fiber)

Ironing Fastness

Fading

Stain

InChI:InChI=1/C20H13NO2/c22-19-14-9-4-5-10-15(14)20(23)18-16(19)11-6-12-17(18)21-13-7-2-1-3-8-13/h1-12,21H

Upstream product

• 82-34-8 1-nitroanthraquinone 
• 62-53-3 aniline 
• 82-44-0 1-chloroanthracene-9,10-dione 
• 30845-78-4 potassium 9,10-dihydro-9,10-dioxoanthracene-1-sulfonate 
• 632-83-7 1-Bromoanthraquinone 
• 108-86-1 bromobenzene 
• 82-45-1 1-amino-9,10-anthracenedione 
• 98-95-3 nitrobenzene 
• 129-43-1 1-hydroxyanthraquinone 
• 591-50-4 iodobenzene 
• 102-07-8 bis(diphenyl)urea 
• 107035-89-2 1-<<(4-methylphenyl)sulfonyl>oxy>-9,10-anthraquinone 
• 17613-65-9 1-phenoxy-anthraquinone 

Downstream Products

• 55099-72-4 1-(2,4-Dinitrophenylazophenylamino)anthraquinone 
• 86133-24-6 1-(4-hydroxymethylphenylamino)anthraquinone 
• 2944-19-6 1-(4-methylanilino)anthraquinone 
• 69658-00-0 1-N-acetylphenylaminoanthraquinone 
• 70557-88-9 1-(4-formylphenylamino)anthraquinone 
• 86133-30-4 6-(4-formylphenylamino)-3-methylanthrapyridone 
• 76787-92-3 1-(2-Cyano-4-nitrophenylazophenylamino)anthraquinone 
• 2944-12-9 1,4-bis(phenylamino)anthracene-9,10-dione 
• 2944-23-2 1-(4-nitro-anilino)-anthraquinone 
• 75839-22-4 1-(2-nitro-4-methylanilino)anthraquinone 
• 37038-06-5 1-(4-bromo-anilino)-anthraquinone 

Relevant articles and documents

Preparation method of 1-(phenylamino) anthraquinone

The invention discloses a preparation method of 1-(phenylamino)anthraquinone. The preparation method comprises the following steps: adding tetramethylurea into a container with a stirrer, starting stirring, refluxing water, adding 1-nitroanthraquinone, dissolving, adding 1,3-diphenylurea, heating to 120-145 DEG C, carrying out a heat preservation reaction for 48 hours, cooling to room temperatureafter the reaction is finished, carrying out suction filtration, washing the filter cake with tetramethylurea, pouring the filtrate into water, separating out a product, and filtering to obtain a 1-(phenylamino) anthraquinone crude product. According to the preparation method of the 1-(phenylamino)anthraquinone, a nucleophilic substitution method is adopted, 1-nitroanthraquinone and 1,3-diphenylurea are used as raw materials, and tetramethylurea is used as a solvent, so that heavy metal pollution is avoided, safety and environmental protection are achieved, and the purity is as high as 97%.

Synthesis and photoluminescent properties of new ceramidine derivatives

A series of new ceramidine derivatives 8a-f has been synthesized in 4-5 steps involving a Wittig reaction of ceramidonine with various triphenylphosphonium bromides. Their UV and photoluminescence (PL) properties are reported. The compounds showed medium to strong PL between 502 and 522 nm at a concentration of 1 × 10-5 M CH2Cl2.

Palladium-catalyzed amination of aromatic halides in water-containing solvent systems: A two-phase protocol

The use of the six-fold sulfonated ligand BINAS-6 1 permits the Pd0-catalyzed amination of aromatic halides in water containing single- or two-phase systems.

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.

KINETIC OF THE REACTION OF 1-BROMOANTRAQUINONE AND ITS AMINO AND SULFO DERIVATIVES WITH ANILINE

The products and the kinetics of the reaction of 1-bromo- and 1-amino-4-bromo-anthraquinones and sodium 1-bromoanthraquinone-3-sulfonate and 1-amino-4-bromoanthraquinone-2-sulfonate with aniline were studied in a mixture of dioxane and a buffer solution of borax and sodium carbonate with pH 10 (1.3:1 by volume) in the presence of copper sulfate and without a catalyst.The products from substitution of the bromine atom by the phenylamino group and also the debromination products are formed, and their ratio depends on the presence of oxygen and of the catalyst.In thenoncatalytic reaction the NH2 group reduces and the SO3(1-) group increases the mobility of the bromine atom; in the catalytic reaction both groups increase the mobility of the bromine atom.The activating effect of the amino group is probably due to the formation of chelate complex involving the copper ions and the amino and carbonyl groups of the anthraquinone ring.

(Tosyloxy)anthraquinones: Versatile Synthons for the Preparation of Various Aminoanthraquinones

Various aminoathraquinones can be easily prepared from (tosyloxy)anthraquinone precursors.Unsymmetrical 1,4-diaminoanthraquinones are prepared via the intermediate monoamino mono(tosyloxy)anthraquinones derived from 1,4-bis(tosyloxy)anthraquinone.The ability to remove tosylate groups sequentially is controlled by the proper selection of solvent and temperature.Hindered 1,4-diamino and 1-aminoanthraquinones are prepared from their corresponding tosyl derivatives, and the amount of steric hindrance present can be succesfully correlated with spectral and color data.The methods described offer advantages over the literature preparations of these compounds.

REACTIVITY OF AMIDINES OF THE ANTHRAQUINONE SERIES.

The introduction of an amidine group into 1-arylamino- and α,α'-diarylaminoanthraquinones fully deactivates the aryl ring attached to the amidine group toward bromination in acetic acid but partly passivates the ring in sulfuric acid solutions.This makes it possible to introduce bromine at the meta position to the amidine group with the para position occupied and subsequently to introduce bromine into the various aryl rings.