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Chemical Structure| 81-41-4 Chemical Structure| 81-41-4

Structure of 81-41-4

Chemical Structure| 81-41-4

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Product Details of [ 81-41-4 ]

CAS No. :81-41-4
Formula : C16H8N4O2
M.W : 288.26
SMILES Code : O=C(C1=C2C=CC=C1)C3=C(N)C(C#N)=C(C#N)C(N)=C3C2=O
English Name :1,4-Diamino-9,10-dioxo-9,10-dihydroanthracene-2,3-dicarbonitrile
MDL No. :MFCD00053082

Safety of [ 81-41-4 ]

Application In Synthesis of [ 81-41-4 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 81-41-4 ]

[ 81-41-4 ] Synthesis Path-Downstream   1~5

  • 1
  • [ 81-42-5 ]
  • [ 81-41-4 ]
  • [ 65596-11-4 ]
YieldReaction ConditionsOperation in experiment
77% 2 Example 2 Example 2 80.0 g (0.26 mol) of 1,4-diamino-2,3-dichloroanthraquinone (calculated as 100%) in 480 g of Solvesso 150 were reacted similarly to Example 1. In the further reaction of the resulting 1,4-diaminoanthraquinone-2,3-disulfonic acid, 64 g of 1,4-diaminoanthraquinone-2,3-dinitrile having a purity of 90% were obtained, which corresponds to a yield of 77%.
  • 2
  • [ CAS Unavailable ]
  • [ 81-42-5 ]
  • [ 81-41-4 ]
YieldReaction ConditionsOperation in experiment
With sulfuric acid; N-benzyl-N,N,N-triethylammonium chloride; dihydrogen peroxide In potassium sulfite; water 21 EXAMPLE 21 EXAMPLE 21 In a mixture of 35.6 parts of benzyltriethylammonium chloride and 27.0 parts of water was charged 5.50 parts of 1,4-diamino-2,3-dichloroanthraquinone, 90.9% in purity and was charged 6.43 parts of anhydrous potassium sulfite under well stirring. After pressure in the system was adjusted to 280 Torr, the mixture was heated to 85° to 90° C. to carry out reaction for 6 hours until the starting material almost disappeared, during which 11.7 parts of water was distilled out of the system at nearly a constant rate. pH in the system showed 9.8 to 8.5. Then, the mixture was cooled to 60° C and 10.52 parts of 25% aqueous sodium cyanide solution was charged therein. pH of the system was controlled to 9.5 to 10.0 with 30% aqueous sulfuric acid solution. The mixture was heated keeping pH unchanged to 65° to 70° C. to carry out reaction until 1,4-diaminoanthraquinone-2,3-disulfonic acid disappeared according to chromatography. While the reaction mixture was cooled at 25° C., excess sodium cyanide was decomposed with 6.1 parts of 35% aqueous hydrogen peroxide, followed by filtration and the resultant wet cake was washed thrice with 20 parts of warm water and dried to obtain 4.77 parts of 1,4-diaminoanthraquinone-2,3-dinitrile, 93.3% in purity. The filtrate and the first used wash water recovered were combined to obtain 80 parts of mixture.
  • 3
  • [ 81-42-5 ]
  • [ 81-41-4 ]
YieldReaction ConditionsOperation in experiment
With sodium hydroxide; phosphoric acid; N-benzyl-N,N,N-triethylammonium chloride; dihydrogen peroxide; sodium sulfite In water 2 EXAMPLE 2 EXAMPLE 2 To a mixture composed of 55.6 parts of benzyltriethylammonium chloride and 55.6 parts of water were added 5.0 parts of 1,4-diamino-2,3-dichloroanthraquinone and 7.18 parts of anhydrous sodium sulfite. With thorough stirring, the reaction system was adjusted to a pH of 9.2 with a 28% aqueous solution of sodium hydroxide. The mixture was heated to 90° to 95° C., and the reaction was carried out until the chromatographic analysis showed that the starting material was substantially consumed. During the reaction, the reaction system was kept at a pH of 9.0 to 9.2 with a 28% aqueous solution of sodium hydroxide. Then, 0.5 part of diatomaceous earth was added to the reaction mixture, followed by filtration at 70° C. The filter cake was washed with 28 parts of warm water, and the washings were combined with the filtrate. The filtrate and washings were cooled to 25° C., and 3.2 parts of sodium cyanide was added thereto. The reaction mixture was heated to 60° to 65° C. while keeping the reaction system at a pH of 9.4 to 9.8 with a 43% aqueous solution of phosphoric acid. The reaction was carried out until the chromatographic analysis showed that the 1,4-diaminoanthraquinone-2,3-disulfonic acid was consumed. Excess sodium cyanide was decomposed with a 35% aqueous solution of hydrogen peroxide. After filtration, the filter cake was washed thoroughly with warm water and dried to obtain 4.2 parts of 1,4-diamino-2,3-dicyanoanthraquinone. The chromatographic analysis showed that this product was a single substance.
  • 4
  • [ 81-42-5 ]
  • [ 95-50-1 ]
  • [ 81-41-4 ]
YieldReaction ConditionsOperation in experiment
With sulfuric acid; N-benzyl-N,N,N-triethylammonium chloride; sodium sulfite In water; nitrobenzene 12 EXAMPLE 12 EXAMPLE 12 To a mixture composed of 32.6 parts of benzyltriethylammonium chloride and 32.6 parts of water were added 5.0 parts of 1,4-diamino-2,3-dichloroanthraquinone, 0.6 part of boric acid, and 50 parts of 1,2-dichlorobenzene. With thorough stirring, 7.18 parts of anhydrous sodium sulfite was added. The mixture was heated to 90° to 95° C., and the reaction was carried out until the chromatographic analysis showed that the starting material was substantially consumed. During the reaction, the pH of the reaction system was 7.5 to 8.5. The 1,2-dichlorobenzene was removed from the reaction mixture by steam distillation, the distillate was separated, and the water layer was returned to the reaction system. 0.5 part of diatomaceous earth was added to the reaction system, followed by filtration at 70° C. The filter cake was washed with 16.3 parts of warm water, and the washings were combined with the filtrate. The filtrate and washings were cooled to 25° C., and 3.2 parts of sodium cyanide and 0.1 part of nitrobenzene were added thereto. The reaction mixture was heated to 60° to 65° C. while keeping at a pH of 9.4 to 9.8 with a 50% aqueous solution of sulfuric acid. The reaction was carried out until the chromatographic analysis showed that the 1,4-diaminoanthraquinone-2,3-disulfonic acid was consumed. After proceeding the same post-treatment as in Example 2, there was obtained 4.2 parts of 1,4-diamino-2,3-dicyanoanthraquinone.
  • 5
  • [ 81-42-5 ]
  • [ 75-12-7 ]
  • [ 81-41-4 ]
YieldReaction ConditionsOperation in experiment
89% With sodium acetate; acetic anhydride for 12h; Reflux; 12 Embodiment 12 The process operation of the embodiment 1 the same, material and proportion is 1,4-diamino -2,3-dichloro ethyltetrahydroanthraquinone with acetic anhydride, anhydrous acetic acid sodium, catalyst AEO-9 (fatty alcohol polyoxyethylene ethers), formamide is the molar ratio of 1:4:3: 0.2 : 4, the m-dichlorobenzene as a reaction solvent, to make 1,4-diamino -2,3-di-cyano ethyltetrahydroanthraquinone, yield 89%, purity 96.7% (high performance liquid chromatography, measuring area law ).
 

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