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Di-tert-Butyl azodicarboxylate

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Di-tert-Butyl azodicarboxylate Basic information
Di-tert-Butyl azodicarboxylate Chemical Properties
  • Melting point:89-92 °C(lit.)
  • Boiling point:287.1±9.0 °C(Predicted)
  • Density 1.06±0.1 g/cm3(Predicted)
  • storage temp. 2-8°C
  • form Crystals or Crystalline Powder
  • color Yellow
  • Water Solubility Insoluble
  • Sensitive Light Sensitive
  • BRN 1911434
  • InChIKeyQKSQWQOAUQFORH-VAWYXSNFSA-N
  • CAS DataBase Reference870-50-8(CAS DataBase Reference)
Safety Information
  • Hazard Codes Xi,F
  • Risk Statements 36/37/38-11
  • Safety Statements 26-36-37/39-16
  • RIDADR 1325
  • WGK Germany 3
  • Hazard Note Irritant
  • HazardClass 3
  • PackingGroup II
  • HS Code 29270000
MSDS
Di-tert-Butyl azodicarboxylate Usage And Synthesis
  • Chemical Propertiesyellow crystals or crystalline powder
  • Purification MethodsThe tert-butyl ester has the advantage over the ethyl ester (below) in being a solid and more acid labile. It crystallises from ligroin and is best purified by covering the dry solid (22g) with pet ether (b 30-60o, 35-40 mL) heating to boiling and adding ligroin (b 60-90o) until the solid dissolves. On cooling, large lemon yellow crystals of the ester separate (~ 20g), m 90.7-92o. Evaporation of the filtrate gives a further crop of crystals [Carpino & Crowley Org Synth 44 18 1964]. This reagent is useful in the Mitsunobu reaction [Mitsunobu Synthesis 1 1981, Gennari et al. J Am Chem Soc 108 6394 1986, Evans et al. J Am Chem Soc 108 6394 1986, Hughes Org React 42 335 1992, Dodge et al. Org Synth 73 110 1996, Hughes Org Prep Proc Int 28 127 1996, Ferguson & Marcelle J Am Chem Soc 128 4576 2006, see also DEAD and DIAD below].
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