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Chemical Structure| 635-12-1 Chemical Structure| 635-12-1
Chemical Structure| 635-12-1

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1,4-Anthraquinone is an effective anticancer agent that can block nucleotide transport, inhibit macromolecule synthesis, induce DNA fragmentation, and reduce cancer cell growth and viability, and can be used in leukemia research.

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Product Details of 1,4-Anthraquinone

CAS No. :635-12-1
Formula : C14H8O2
M.W : 208.21
SMILES Code : O=C1C=CC(C2=C1C=C3C=CC=CC3=C2)=O
MDL No. :MFCD00013724

Safety of 1,4-Anthraquinone

GHS Pictogram:
Signal Word:Danger
Hazard Statements:H302-H361-H372-H410
Precautionary Statements:P201-P264-P280-P301+P330+P331-P312
Class:9
UN#:3077
Packing Group:

Application In Synthesis of 1,4-Anthraquinone

* 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 [ 635-12-1 ]

[ 635-12-1 ] Synthesis Path-Downstream   1~2

  • 1
  • [ 635-12-1 ]
  • [ 443-82-3 ]
  • [ 1201813-50-4 ]
YieldReaction ConditionsOperation in experiment
42% 3-Fluoro-o-xylene (1.2 g, 9.7 mmol) was added to a round-bottom flask with a stir bar and dissolved in 30 mL dichloroethane. N-Bromosuccinimide (7.0 g, 39 mmol) and a small scoop of AIBN (2,2'-azobis(2-methylpropionitrile)) were added, a reflux condenser was attached, and the mixture was refluxed for 6 hr, at which point analysis by GC-MS showed the predominant component to be the tribrominated product. After cooling, water and dichloromethane were added, and the organic layer was separated, then washed with water and dilute hydrochloric acid, dried over magnesium sulfate, and rinsed through a thin pad of silica gel using dichloromethane as an eluent. Removal of solvent yielded 3.4 g of the product mixture. To a 100 mL round-bottom flask equipped with a condenser and stir bar, 12 mL dimethylformamide was added, followed by 0.54 g (2.07 mmol) of the tribrominated product from above and 0.43 g (2.1 mmol) 1,4-anthraquinone. Nitrogen was bubbled through the solution for 20 minutes, then 2.1 g (12 mmol) potassium iodide was added, and the reaction was heated at HO0C for 3 days. The reaction was allowed to cool and the precipitate was collected by filtration, then rinsed sequentially with water, acetone and diethyl ether. The resulting solid was air-dried, yielding 0.29 g (0.88 mmol, 42percent) of 1-fluoropentacenequinone as a light brown solid.
42% Example 19 - Synthesis of 6,13-Bis(3,3,4,4,5,5,6,6,6-nonafluorohexyldiisopropyl- silylethynyl)- 1 -fluoropentaceneSynthesis of l-Fluoropentacene-6,13-dione3-Fluoro-o-xylene (1.2 g, 9.7 mmol) was added to a round-bottom flask with a stir bar and dissolved in 30 mL dichloroethane. N-Bromosuccinimide (7.0 g, 39 mmol) and a small scoop of AIBNu were added, a reflux condenser was attached, and the mixture was refluxed for 6 hr, at which point analysis by GC-MS showed the predominant component to be the tribrominated product. After cooling, water and dichloromethane were added, and the organic layer was separated, then washed with water and dilute hydrochloric acid, dried over MgSO4, and rinsed through a thin pad of silica gel using dichloromethane as an eluant. Removal of solvent yielded 3.4 g of a product mixture. To a 100 mL round-bottom flask equipped with a condenser and stir bar, 12 mL dimethylformamide was added, followed by 0.54 g (2.07 mmol) of the tribrominated product from above and 0.43 g (2.1 mmol) 1,4- anthraquinone. Nitrogen was bubbled through the solution for 20 minutes, then 2.1 g (12 mmol) potassium iodide was added, and the reaction was heated at H0°C for 3 days. The reaction was allowed to cool, and the precipitate was collected by filtration, then rinsed sequentially with water, acetone and diethyl ether. The resulting solid was air-dried, yielding 0.29 g (0.88 mmol, 42percent) of l-fluoropentacene-6,13-dione (or 1-fluoropentacenequinone) as a light brown solid.
  • 2
  • [ 635-12-1 ]
  • [ 13361-34-7 ]
  • C25H25NO3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With ammonium acetate; acetic acid; In toluene; at 100 - 115℃; for 18h;Dean-Stark; Inert atmosphere; l,4-Anthracenedione (6 gm, 28.5 mmol) and toluene (40 mL) are mixed in a clean 250 mL 2 neck round bottom flask equipped with Dean-Stark condenser and nitrogen inlet. 2-Ethylhexyl cyanoacetate (4.4 gm, 22.3 mmol), ammonium acetate (153 mg, 2.0 mmol), and acetic acid (2.8 mL) are added sequentially at 25-30C. The reaction mixture is refluxed for approximately 18 hours at 100-1 l5C. The water is periodically removed from Dean-Stark condenser during the reaction. The reaction is monitored by TLC (ethyl acetate/hexane). After the complete consumption of l,4-anthracenedioneby TLC, the reaction mixture is cooled to room temperature. The toluene layer is washed with water (2x25 mL) followed by saturated sodium bicarbonate solution (25 mL) and again with water (25 mL). The organic layer is evaporated under reduced pressure at 45-50C to obtain crude product as pale brown semisolid. The crude product is purified by column chromatography by eluting with ethyl acetate in hexane to afford pure product.
 

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