81-41-4

Basic information

• Product Name: 1,4-DIAMINO-2,3-DICYANO-9,10-ANTHRAQUINONE
• Synonyms: 1,4-DIAMINO-2,3-DICYANOANTHRAQUINONE;1,4-DIAMINO-9,10-ANTHRAQUINONE-2,3-DICARBONITRILE;1,4-diamino-9,10-dihydro-9,10-dioxo-3-anthracenedicarbonitrile;3-Anthracenedicarbonitrile,1,4-diamino-9,10-dihydro-9,10-dioxo-2;diaminodicyanoanthraquinone;1,4-diamino-9,10-dihydro-9,10-dioxoanthracene-2,3-dicarbonitrile;1,4-diamino-9,10-dioxo-9,10-dihydroanthracene-2,3-dicarbonitrile;2:3 DICYANO 1,4 DIAMINO AQ
• CAS NO: 81-41-4
• Molecular Formula: C₁₆H₈N₄O₂
• Molecular Weight: 288.26
• EINECS: 201-347-2
• Product Categories: Intermediates of Dyes and Pigments;Aminoanthraquinones;Anthraquinones;Dicyanopyrazines, etc. (Building Blocks for Phthalonitriles & Naphthalonitriles);Functional Materials;Phthalonitriles & Naphthalonitriles
• Mol File: 81-41-4.mol

Chemical Properties

• Melting Point: >300℃
• Boiling Point: 695.6 °C at 760 mmHg
• Flash Point: 374.5 °C
• Appearance: /
• Density: 1.57 g/cm³
• Vapor Pressure: 3.36E-19mmHg at 25°C
• Refractive Index: 1.758
• CAS DataBase Reference: 1,4-DIAMINO-2,3-DICYANO-9,10-ANTHRAQUINONE(CAS DataBase Reference)
• NIST Chemistry Reference: 1,4-DIAMINO-2,3-DICYANO-9,10-ANTHRAQUINONE(81-41-4)
• EPA Substance Registry System: 1,4-DIAMINO-2,3-DICYANO-9,10-ANTHRAQUINONE(81-41-4)

Safety Data

• Statements: 23/24/25
• Safety Statements: 26-36/37/39
• RIDADR: 3276
• Hazardous Substances Data: 81-41-4(Hazardous Substances Data)

Usage

Uses

Used in Textile Industry:
1,4-Diamino-2,3-dicyano-9,10-anthraquinone is used as a key intermediate for manufacturing CI Disperse Blue 60, a widely used dye in the textile industry. This dye is known for its excellent color strength, lightfastness, and washfastness properties, making it ideal for coloring synthetic fibers such as polyester, nylon, and acrylic.
Used in Plastics and Polymer Industry:
In the plastics and polymer industry, 1,4-diamino-2,3-dicyano-9,10-anthraquinone is used as a precursor for the synthesis of pigments and dyes that impart color to various types of plastics and polymers. These pigments and dyes are valued for their stability, resistance to heat and light, and ability to provide vibrant colors to the final products.
Used in Ink Industry:
1,4-Diamino-2,3-dicyano-9,10-anthraquinone is also utilized in the ink industry as a starting material for the production of high-performance dyes used in ink formulations. These dyes are known for their excellent color yield, resistance to fading, and compatibility with various printing processes, making them suitable for use in digital, offset, and screen printing applications.
Used in Paint Industry:
In the paint industry, 1,4-diamino-2,3-dicyano-9,10-anthraquinone is employed as a precursor for the synthesis of pigments that provide color to various types of paints and coatings. These pigments are valued for their durability, resistance to weathering, and ability to maintain their color over time, making them ideal for use in architectural, automotive, and industrial coatings.

InChI:InChI=1/C16H8N4O2/c17-5-9-10(6-18)14(20)12-11(13(9)19)15(21)7-3-1-2-4-8(7)16(12)22/h1-4H,19-20H2

Upstream product

• 60345-96-2 1,4-Diamino-9,10-dioxo-9,10-dihydroanthracen-2-carbonsaeuremethylester 
• 143-33-9 sodium cyanide 
• 81-42-5 1,4-diamino-2,3-dichloroanthraquinone 
• 4095-85-6 1,4-diamino-9,10-dioxo-9,10-dihydro-anthracene-2-sulfonic acid 
• 98-47-5 3-Nitrobenzenesulfonic acid 
• 107-98-2 1-methoxy-2-propanol 
• 127-68-4 sodium 3-nitrobenzenesulfonate 
• 95-50-1 1,2-dichloro-benzene 
• 77287-34-4 formamide 

Downstream Products

• 128-81-4 NSC 115447 
• 84425-48-9 4,11-diamino-2-isopropyl-naphth[2,3-f]isoindole-1,3,5,10-tetraone 
• 3176-88-3 4,11-diamino-2-butyl-naphth[2,3-f]isoindole-1,3,5,10-tetraone 

Relevant articles and documents

Preparation method of 1,4-diamido-2,3-dicyano anthraquinone

The invention relates to a preparation method of 1,4-diamido-2,3-dicyano anthraquinone. The preparation method comprises steps as follows: 1,4-diamido-2,3-dichloroanthraquinone is taken as a raw material and is heated to reflux with a high-boiling-point polar solvent as a reaction medium and formamide as a cyanation reagent in the presence of a phase transfer catalyst, a dehydrating agent and an acid-binding agent, a product is cooled, filtered, washed with water and dried, and 1,4-diamido-2,3-dicyano anthraquinone is prepared. The technical scheme has the characteristics of low environmental toxicity, low environmental protection pressure and simplicity in technological operation; the prepared 1,4-diamido-2,3-dicyano anthraquinone reaches the same level of the prior art when used for preparing disperse turquoise blue S-GL.

Preparation of 1,4-diaminoanthraquinone-2,3-disulfonic acid and 1,4-diaminoanthraquinone-2,3-dinitrile

1,4-Diaminoanthraquinone-2,3-disulfonic acid (I) is prepared by reacting 1,4-diamino-2,3-dihaloanthraquinone (II) with boric acid in an inert organic solvent and further reacting the resulting reaction product (IIa) with an aqueous sulfite solution, by a method in which the inert organic solvent used is a nonpolar solvent having a boiling point of ≥130° C. and a density of ≤0.95 g/cm3, and 1,4-diaminoanthraquinone-2,3-dinitrile (III) is prepared by reacting the 1,4-diaminoanthraquinone-2,3-disulfonic (I) with a cyanide.

Preparation of 1,4-diamino-2,3-dicyanoanthraquinone

1,4-Diaminoanthraquinone-2-sulfonic acid or salts thereof are reacted with cyanide ions at pH 8-11 in the presence of oxidizing agents in a mixture of water and 1-methoxy-2-propanol, 2-methoxy-1-propanol, N,N-dimethylformamide, N,N-dimethylacetamide, N,N-dimethylpropionamide, dimethyl sulfoxide, dioxane, N-methylpyrrolidone or mixtures thereof, the ratio water: organic liquid being ≥3:1, the reaction proceeding at higher concentrations than in a purely aqueous medium and producing appreciably purer products in a high space-time yield.

Process for the preparation of 1,4-diamino-2,3-dicyanoanthraquinones

There is disclosed a process for the preparation of 1,4-diamino-2,3-dicyanoanthraquinones by reacting compounds of formula STR1 wherein X1 and X2 are hydroxyl, halogen, acetate or sulfato ester, or, when taken together, are an oxygen atom attached by a double bond to the boron atom, R is a substituent and n is 0, 1 or 2, with an inorganic cyanide in a polar aprotic solvent and in the presence of an oxidizing agent, and subsequently hydrolyzing the reaction product.

Process for preparing 1,4-diaminoanthraquinone-2,3-disubstituted compound

1,4-Diaminoanthraquinone-2,3-disulfonic acid or salt thereof and 1,4-diaminoanthraquinone-2,3-dinitrile which are intermediate of anthraquinone dyes are economically prepared by allowing 1,4-diamino-2,3-dihalogenoanthraquinone to react with alkalimetal sulfite in aqueous solution in the presence of quaternary ammonium or phosphonium compound, while water is being removed, to obtain 1,4-diaminoanthraquinone-2,3-disulfonic acid or salt thereof and, if necessary, cyanogenating the reaction mixture above without removing the disulfonic acid or salt thereof produced above to obtain 1,4-diaminoanthraquinone-2,3-dinitrile. The quaternary ammonium or phosphonium compound is recovered from and re-used for the reactions above.

Process for the preparation of 1,4-diamino-2,3-dicyanoanthraquinone

The invention relates to a process for the preparation of 1,4-diamino-2,3-dicyanoanthraquinone, starting from 1,4-diaminoanthraquinones, or salts thereof, of the formula STR1 wherein n is 0, 1 or 2. To introduce the two cyanide radicals, the starting material is treated, in the presence of an oxidizing agent, with a compound which donates cyanide ions. The process comprises using as solvent a mixture of a carboxamide, an N-alkylated carboxamide or a lactam and water, which mixture contains more than 10% by weight of water. 1,4-Diamino-2,3-dicyanoanthraquinone is an important intermediate for the synthesis of textile dyes.

Process for producing anthraquinone compounds

A process for producing 1,4-diaminoanthraquinone-2,3-disulfonic acid or a salt thereof which comprises reacting a 1,4-diamino-2,3-dihalogenoanthraquinone with a sulfonating agent in an aqueous medium in the presence of at least one of a quaternary ammonium compound and a quaternary phosphonium compound and optionally, in the presence of an inert organic solvent is disclosed. A process for producing 1,4-diamino-2,3-dicyanoanthraquinone which comprises further reacting the thus obtained 1,4-diaminoanthraquinone-2,3-disulfonic acid or salt thereof with a cyanogenation agent is also disclosed.

Process for the preparation of 1,4-diamino-anthraquinone-2-sulphonic acid

1,4-Diamino-anthraquinone-2-sulphonic acid is obtained in a simple manner, in good yield and good purity, by reacting 1-amino-4-bromo-anthraquinone-2-sulphonic acid with ammonia in water in the presence of copper catalysts at an elevated temperature, under a partial pressure of ammonia of at least 5 bar.

35. Ueber die Dicyanierung der 1,4-Diaminoanthrachinone und die Reactivitaet der 1,4-Diamino-9,10-dioxo-9,10-dihydroanthracen-2,3-dicarbonitrile gegenueber nucleophilen Reagenzien

The reaction of 1-amino-9,10-dioxo-4-phenylamino-9,10-dihydroanthracene-2-sulfonic acid (1, R=C6H5) with cyanide in water yields a mixture of 1-amino-9,10-dioxo-4-phenylamino-9,10-dihydroanthracene-2-carbonitrile (3, R=C6H5) and 1-amino-4-(phenylamino)anthraquinone (4, R=C6H5) under the usual reaction conditions (Scheme 1).In dimethylsulfoxide, however, a second cyano group is introduced, and 1-amino-9,10-dioxo-4-phenylamino-9,10-dihydroanthracene-2,3-dicarbonitrile (7) is formed (Scheme 2).The cyano groups are very reactive towards nucleophiles.The cyano group in 2-position can be substituted by hydroxide and aliphatic amines (Schemes 5 and 6).The cyano group in 3-position can be eliminated by aliphatic amines and hydrazine (Scheme 7).Nucleophilic attack at the cyano C-atom of the 2-cyano group by suitable reagents leads to ring formation, yielding e.g. 2-(Δ2-1,3-oxazolin-2-yl)-, 2-(benzimidazol-2-yl)- and 2-(1H-tetrazol-5-yl)anthraquinones (Schemes 8 and 10).

Process for the preparation of 1,4-diamino-2,3-dicyano-anthraquinones

2,3-Dicyano-anthraquinones of the formula STR1 wherein R denotes hydrogen, alkyl or cycloalkyl, are obtained in good yields and high purity by reacting compounds of the formula STR2 wherein X denoted hydrogen or the sulphonic acid group, with cyanides in formamide or N-methylformamide as solvents, and if appropriate oxidizing agents and heavy metal catalysts.