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Chemical Structure| 116-82-5 Chemical Structure| 116-82-5

Structure of 116-82-5

Chemical Structure| 116-82-5

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Product Details of [ 116-82-5 ]

CAS No. :116-82-5
Formula : C14H8BrNO3
M.W : 318.12
SMILES Code : O=C1C2=C(C=CC=C2)C(C3=C(O)C=C(Br)C(N)=C13)=O
English Name :1-Amino-2-bromo-4-hydroxyanthracene-9,10-dione
MDL No. :MFCD00019156
InChI Key :MSSQDESMUMSQEN-UHFFFAOYSA-N
Pubchem ID :8320

Safety of [ 116-82-5 ]

Application In Synthesis of [ 116-82-5 ]

* 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 [ 116-82-5 ]

[ 116-82-5 ] Synthesis Path-Downstream   1~7

  • 1
  • [ 81-49-2 ]
  • [ 116-82-5 ]
YieldReaction ConditionsOperation in experiment
With sulfuric acid; boric acid
With sulfuric acid at 30 - 40℃;
With sulfuric acid at 100 - 110℃;
69.1 g Stage #1: 1-amino-2, 4-dibromoanthraquinone With sulfur trioxide; boric acid at 25 - 90℃; Stage #2: With water at 60℃; 1-3 Example 2: Put 180g of 92% sulfuric acid into a 500ml four-necked bottle, start stirring,Drop into 1-aminoanthraquinone dry product 50g while stirring,After the temperature was raised to 90°C, 62g of bromine was added dropwise, and the drop was completed in 6.5 hours.After the dropwise addition, keep warm for 3 hours to the end point.Cool down to 55°C,Add boric acid 15g,At this temperature, dropwise adding 81.8 g of liquid sulfur trioxide with a heat preservation temperature of 25 ° C,The dropwise addition was completed in 1.5 hours, and then the temperature was raised to 90° C. for 3.5 hours to reach the end point. Cool down to 60°C, add 143g of soft water dropwise at this temperature for 3.5 hours, keep warm for 1 hour and filter after the dropwise addition, wash the filter cake with hot water at 75°C until neutral, and obtain 69.1g of dry intermediate after drying.Content 98.81%.

  • 2
  • [ 116-85-8 ]
  • [ 116-82-5 ]
YieldReaction ConditionsOperation in experiment
92% With bromine at 50 - 60℃; Bio-ionic liquid;
With bromine; acetic acid
33.9 g With bromine In nitrobenzene at 100 - 130℃; for 4h; Inert atmosphere; 6 Preparation of compound 19 31.0 g of 1-amino-4-hydroxyanthrachinone are dissolved in 300 ml of nitrobenzene and heated to 100 °C in an argon atmosphere. During one hour 23.0 g of bromine are dropped into that mixture which is subsequently heated to 130 °C for additional three hours. After cooling down to room temperature the mixture is poured into 100 ml methanol and filtered. The residue is thouroughly washed with methanol and hexane and finally dried at 100 °C in vacuum. By concentrating the mother liquors an additional crop of compound 19 is obtained resulting in an overall yield of 33.9 g.
  • 3
  • [ 116-82-5 ]
  • [ 16375-90-9 ]
  • [ 38920-11-5 ]
  • 4
  • [ 116-82-5 ]
  • [ 28443-52-9 ]
  • [ 38912-95-7 ]
YieldReaction ConditionsOperation in experiment
(i) K2CO3, Py, (ii) /BRN= 1887275/; Multistep reaction;
  • 5
  • [ 116-82-5 ]
  • [ CAS Unavailable ]
  • [ 17418-58-5 ]
YieldReaction ConditionsOperation in experiment
99% With pyridine; sodium carbonate at 150 - 155℃; for 9h; Sealed tube; Large scale; 1-4 Example 4 In a 3000L enamel kettle, 1000kg of phenol, 500kg of 1-amino-2-bromo-4-hydroxyanthraquinone, 180kg of sodium carbonate, and 6kg of pyridine were added. After the addition was completed, the seal was heated to 150-155°C for 3 hours and kept warm Carry out the condensation reaction for 6 hours, take a sample to measure the end point, after the end point, cool to 95100, add 1300kg of water at this temperature, then drop 30kg of 30% liquid alkali, and finally cool to 5052 to filter, wash and prepare Desired Red 60 finished product 485kg, yield 99%, content 99.6%.
With potassium hydroxide In water; N,N-dimethyl-formamide at 120 - 125℃; for 3h;
  • 6
  • [ 10193-30-3 ]
  • [ 81-49-2 ]
  • [ 116-82-5 ]
YieldReaction ConditionsOperation in experiment
With nitrogen; paraformaldehyde In water 2 EXAMPLE 2 EXAMPLE 2 A stirred reactor is charged with 184 parts of sulfuric acid monohydrate and 4.2 parts (0.8 equivalent) of paraformaldehyde are added, with stirring, over about 15 minutes. The mixture is stirred until a clear solution is obtained. This solution is heated to 60°-65° C. and then 59.5 parts of 1-amino-2,4-dibromoanthraquinone (96% pure) are added. The reaction mixture is then heated to 110° C. over 1 hour and stirred at this temperature for a further 4 hours. During the reaction, nitrogen is passed through the reaction mixture, which is subsequently cooled to 60° C. Then 120 parts of water are added and the resultant suspension is filtered. The filter residue is washed with hot water until neutral and the product is dried in vacuo at 80°-90° C. Yield: 48.5 parts (93% of theory) of 1-amino-2-bromo-4-hydroxyanthraquinone. Rf =0.27 (eluant: concentrated formic acid, saturated with 1-bromonaphthalene).
  • 7
  • [ 116-82-5 ]
  • [ 61514-54-3 ]
  • [ 1338810-37-9 ]
YieldReaction ConditionsOperation in experiment
70% With pyridine; copper(l) iodide; trans-bis(triphenylphosphine)palladium dichloride; triethylamine at 75℃; for 8h; Inert atmosphere;
 

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