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Chemical Structure| 69447-36-5

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Product Details of [ 69447-36-5 ]

CAS No. :69447-36-5
Formula : C14H14Se2
M.W : 340.18
SMILES Code : CC1=CC=CC=C1[Se][Se]C2=CC=CC=C2C

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Application In Synthesis of [ 69447-36-5 ]

* 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 [ 69447-36-5 ]

[ 69447-36-5 ] Synthesis Path-Downstream   1~1

  • 1
  • [ 615-37-2 ]
  • [ 69447-36-5 ]
YieldReaction ConditionsOperation in experiment
83% With N,N-diethyl selenoformamide; potassium hydroxide; In water; N,N-dimethyl-formamide; at 110℃; for 12h; General procedure: Symmetrical organic diselenides synthesis: typical experimentalprocedure. CuO nanoparticles (10 mol%) were addedto stirred solution of iodobenzene (2.0 mmol), selenoamide(2.0 mmol) and KOH (3 mmol) in 4 mL DMF/H2O (20:1). The reaction continued at 110 C under atmospheric conditions.After completion of the reaction [about 10 h; TLC(EtOAc/hexane, 1:20) monitoring. CH2Cl2(20 mL) wasadded and the mixture was washed with H2O(2 × 15 mL).The combined organic fractions were dried (Na2SO4) andconcentrated under reduced pressure. The residue was purifiedby preparative chromatography (silica gel), hexane/EtOAc, 20:1] to give the product.
79% With selenium; potassium hydroxide; copper(I) bromide; In ethanol; at 60℃; for 2h;Green chemistry; Add 99mg (1.25mmol) of selenium powder, 84mg (1.5mmol) of potassium hydroxide, 14mg (0.1mmol) of cuprous bromide to the reaction flask, then add 0.5mL of ethanol, and then add 218mg of 2-iodotoluene ( 1mmol) I-3 was added to the reaction flask and reacted at 60C for 2 hours to stop the reaction. Filter, wash the filter cake with 1mL ethanol, combine the filtrate, evaporate the ethanol, add 3mL water, extract twice with ethyl acetate (2mL×2), filter, wash the filter cake with 1mL ethanol, combine the filtrate, evaporate the ethanol, Then add 3 mL of water, extract twice with ethyl acetate (2 mL×2), combine the organic phases, evaporate the ethyl acetate on a rotary evaporator, and separate and purify the residue by column chromatography. The eluent is n-hexane: ethyl acetate = 30:1, collect the eluent containing the target product, and evaporate the eluent to obtain 134 mg of diphenyl diselenide compound II-3 with a yield of 79%. The structure of compound II-3 is characterized as follows:
59% With selenium; hydrazine hydrate; sodium hydroxide; In N,N-dimethyl-formamide; at 153℃; for 30h;Inert atmosphere; General procedure: To a stirred mixture of Se (79 mg, 1.0 mmol, 1.0 eq) and NaOH (40 mg, 1.0 mmol, 1.0 eq) in DMF (1.5 mL) was added NH2NH2*H2O (36 mL, 0.75 mmol, 0.75 eq) under N2. The resulting mixture was stirred for 2 h at 25 C during which it turned a reddish-brown. The alkyl halide was then added, and stirring was continued for 2 - 40 h at 25 - 153 C until reaction completion (Table 2). The reaction mixture was then diluted with water (30 mL), extracted with CH2Cl2 (3 x 30 mL), and washed with brine (30 mL). Combined organic layers were dried (MgSO4) and concentrated in vacuo, forming a sticky residue that was purified by column chromatography (1:50/1:1 EtOAc/hexanes) to yield diorganyl diselenides 1. Spectral data of all compounds were in accordance with the literature information.
35% With selenium; copper(II) oxide; potassium hydroxide; In dimethyl sulfoxide; at 90℃;Inert atmosphere; General procedure: To a stirred solution of Se0 powder (10 mmol, 2.0 equiv.) and aryl iodides (5 mmol, 1.0 equiv.) in dry DMSO (0.5 M) was added CuO nanoparticles (10 mol%) followed by KOH (10 mmol, 2.0 equiv.) under nitrogen atmosphere at 90 C. The progress of the reaction was monitored by TLC. After completing the reaction, the mixture was cooled to room temperature, which was subjected to column chromatographic separation to give pure diselenides (7b-7f). The same procedure was followed for the synthesis of ditellurides (7g).
9% With [2,2]bipyridinyl; selenium; copper(l) iodide; sodium carbonate; magnesium; In N,N-dimethyl-formamide; at 110℃; for 65h;Inert atmosphere; General procedure: To a mixture of selenium (47.4 mg, 0.6 mmol), CuI (5.7 mg, 0.03 mmol), magnesium powder (212-600 m) (14.6 mg, 0.6 mmol), Na2CO3 (31.8 mg, 0.3 mmol), bpy (4.7 mg, 0.03 mmol), and DMF (0.5 mL) was added iodobenzene 1b (61.2 mg, 0.3 mmol), and the mixture was stirred at 110 C for 65 h. After the reaction mixture was diluted with Et2O, the solution was washed with H2O and saturated sodium chloride and dried over anhydrous magnesium sulfate. Chromatography on silica gel (hexane) gave diphenyl diselenide (35.0 mg, 75%). 4c
With [2,2]bipyridinyl; selenium; copper(l) iodide; sodium carbonate; magnesium; In N,N-dimethyl-formamide; at 110℃; To a 50mL round bottomed flask, mixture of selenium (95mg, 1.2mmol), CuI (11.4mg, 0.06mmol) Magnesium powder (29.2mg, 1.2mmol), sodium carbonate (63.6mg, 0.6mmol), 2,2’-bipyridyl (9.4mg, 0.06mmol) and DMF(2mL) was added iodobenzene (122.4mg, 0.6mmol) and the mixture was stirred at 110 ... The reaction progresswas monitored by TLC (EA:Hexane) and GC-MS. After the reaction mixture was diluted with diethyl ether, thesolution was washed with water and saturated sodium chloride and dried over anhydrous sodium sulfate.Chromatography on silica gel afforded pure diphenyldiselenide
With selenium; copper(II) oxide; potassium hydroxide; In dimethyl sulfoxide; at 90℃; for 1h;Inert atmosphere; General procedure: To a stirred solution of Se (0) metal (4.0 mmol) and aryl iodides (2.0mmol) in dry DMSO (3.0 mL) was added CuO (10 mol %) followed by KOH (2.0 equiv)under nitrogen atmosphere at 90 oC. The progress of the reaction wasmonitored by TLC. After the reaction was complete, Et2O (10 mL) wasadded and the mixture was washed successively with water (2×20mL). The organiclayer was separated and dried by adding anhydrous Na2SO4.Evaporation of the solvent under reduced pressure gave almost pure product. Further purication was achieved by columnchromatography on silica gel (ethylacetate: hexane (1:50)) to give pure productin good to excellent yield.
With selenium; copper(II) oxide; potassium hydroxide; In dimethyl sulfoxide; at 90℃; General procedure: To a stirred solution of Se0 powder (10 mmol, 2.0 equiv.) and aryl iodides (5 mmol, 1.0 equiv.) in dry DMSO (0.5 M) was added CuO nanoparticles (10 mol%) followed by KOH (10 mmol, 2.0 equiv.) under nitrogen atmosphere at 90 C. The progress of the reaction was monitored by TLC. After completing the reaction, the mixture was cooled to room temperature, which was subjected to column chromatographic separation to give pure diselenides. The same procedure was followed for the synthesis of ditellurides.[3]

 

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