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Dodecylbenzenesulfonyl azide

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Dodecylbenzenesulfonyl azide Basic information
Dodecylbenzenesulfonyl azide Chemical Properties
  • Density 1.051 g/mL at 25 °C
  • refractive index n20/D1.510
  • Flash point:>110℃
  • solubility solubility pentane, acetone, and most organic solvents.
  • form viscous liquid.
  • CAS DataBase Reference79791-38-1(CAS DataBase Reference)
Safety Information
Dodecylbenzenesulfonyl azide Usage And Synthesis
  • Usesdiazo-transfer reagent for activated methylene groups.
  • Preparationprepared by addition of granular sodium azide (1.3 equiv) to a mixture of isomeric sulfonyl chlorides (from a commercial mixture of isomers of p-dodecylbenzenesulfonic acid) in acetone solution.
  • ReactionsReagent for Diazo-function Transfer.
    The title reagent has been called a safer diazo-transfer reagent, and is a mixture of 12 or more isomeric p-dodecylbenzenesulfonyl azides, ranging by HPLC from 24% to 1% in area and giving essentially a single spot by TLC.
    The title reagent has been shown to be very useful for the synthesis of various crystalline diazocarbonyl compounds such as diazobarbituric and diazoisopropylidenemalonic acids, derivatives and homologs of diazoacetoacetic acid, and 9-diazoanthrone (eq 1).
    Reagent for Diazo-function Transfer: Dodecylbenzenesulfonyl azide
    Formation of noncrystalline byproduct dodecylsulfonamides facilitates the workup procedure and isolation of the target crys- talline diazo compounds from the reaction mixture.
  • storageDodecylbenzenesulfonyl azide is the safest of the usual are nesulfonyl azides (tosyl azide, etc.) employed in diazo-transfer processes;appropriate care should be taken,as with all azides. Use in a fume hood.
  • Purification Methodselution through short column containing silica gel G with methylene chloride-hexane (1:4) as eluant.
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