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Chemical Structure| 21792-52-9 Chemical Structure| 21792-52-9

Structure of 21792-52-9

Chemical Structure| 21792-52-9

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Product Details of [ 21792-52-9 ]

CAS No. :21792-52-9
Formula : C10H6
M.W : 126.15
SMILES Code : C#CC1=CC=CC=C1C#C
MDL No. :MFCD28164040
InChI Key :CBYDUPRWILCUIC-UHFFFAOYSA-N
Pubchem ID :140862

Safety of [ 21792-52-9 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H227-H302
Precautionary Statements:P501-P210-P280-P370+P378-P403+P235

Application In Synthesis of [ 21792-52-9 ]

* 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 [ 21792-52-9 ]

[ 21792-52-9 ] Synthesis Path-Downstream   1~1

  • 1
  • [ 126-33-0 ]
  • [ 91-14-5 ]
  • [ 107-21-1 ]
  • [ 21792-52-9 ]
YieldReaction ConditionsOperation in experiment
With potassium hydroxide; hydrogen bromide; bromine; In water; EXAMPLE 2 In Example 2, diethynylbenzene was prepared from divinylbenzene using potassium hydroxide in place of sodium hydroxide. A three-necked, five-liter, round-bottom flask, equipped with an air-driven teflon paddle stirrer, a 250 ml vapor-bypass dropping funnel and a Y adapter provided with a pot thermometer, a gas inlet side arm and a condenser was charged with 700 ml of tetramethylene sulfone (about 880 grams) (Aldrich, 99%) and 274 grams (2.11 mole) of divinylbenzene (Dow Chemical Co.). The mixture was stirred and cooled to 20 C. with an ice water bath. Liquid bromine was added dropwise over 11/2 hours so as to maintain the temperature at 20-28 C. with no loss of Br2 vapor from the system. A total of 634 gms. (3.96 moles) of bromine was added, and the dark reaction mixture was allowed to stand overnight. The mixture was stirred an additional two hours at room temperature, then 41.6 grams of polyethylene glycol (PEG-400; Aldrich) was added, (about 2% of the mixture by weight) and the stirred mixture was cooled to 1720 -18 C. To this was then added dropwise a 60% KOH solution (1375 grams of KOH pellets (85% KOH) in 916 grams distilled water, 20.9 moles KOH, 2290 grams of solution amounting to a 160 mole % excess) over about one hour while maintaining the temperature in the 18-27 C. range with ice-bath cooling. The reaction exotherm is confined to the reaction of the first half of the KOH addition, which coincides with the removal of the first two moles of HBr. The removal of the second two moles of HBr leading to the acetylenic formation is endothermic. The reaction mixture was then heated to 80 C. for two hours. The system was rearranged for steam distillation, and the reaction mixture was then steam distilled at about 110 C. for about 11/2 hours to yield about two liters of distillate. The top layer of diethynylbenzene was separated (146.7 grams) and was dried over Na2 SO4 in a dark bottle. The remainder of the steam distillate (aqueous layer) was extracted with 250 ml of ether and dried over Na2 SO4. When evaporated, 2.1 grams of product was yielded. Steam distillation was continued to yield another liter of steam distillate which was extracted with 250-350 ml of ether. The dried ether extract (Na2 SO4) was evaporated to yield 11 grams of product. The solution in the flask, upon standing overnight at ambient temperature, separated into two layers. The bottom aqueous layer was separated and discarded; the remainder was steam distilled to afford two more distillates of about one liter each. The first of these was extracted with 300 Ml of ether and after drying over Na2 SO4, yielded 18.93 grams of oily product. The pot residue was discarded. The total of product fractions totalled 182.6 grams, corresponding to a yield of 68.7%. An analysis of the principal fraction by gas liquid chromatography produced the following results:
 

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