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| | Di-tert-Butyl azodicarboxylate Basic information | | Uses |
| | 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 | | solubility | Chloroform (Sparingly), Methanol (Slightly) | | form | Crystals or Crystalline Powder | | color | Yellow | | Water Solubility | Insoluble | | Sensitive | Light Sensitive | | BRN | 1911434 | | InChI | InChI=1S/C10H18N2O4/c1-9(2,3)15-7(13)11-12-8(14)16-10(4,5)6/h1-6H3 | | InChIKey | QKSQWQOAUQFORH-VAWYXSNFSA-N | | SMILES | N(C(OC(C)(C)C)=O)=NC(OC(C)(C)C)=O | | CAS DataBase Reference | 870-50-8(CAS DataBase Reference) |
| 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 |
| | Di-tert-Butyl azodicarboxylate Usage And Synthesis |
| Uses | Di-tert-butyl azodicarboxylate is a reagent used in the preparation of acyl hydrazinedicarboxylates via photoorganocatalytic hydroacylation of dialkyl azodicarboxylates with aldehydes in presence of phenylglyoxylic acid as photocatalyst. | | Chemical Properties | yellow crystals or crystalline powder | | Uses | Utilized in the asymmetric Friedel-Crafts amination via a chiral organocatalyst. | | Uses | Di-tert-butyl azodicarboxylate is a reagent used in the preparation of acyl hydrazinedicarboxylates. It is also used in the electrophilic amination of beta-keto esters catalyzed by an axially chiral guanidine. It serves as a precursor in an enantioselective synthesis of 3,6-dihyropyridazines employing organocatalysts such as L-proline or (S)-2-pyrrolidinyl tetrazole. It is also utilized in the asymmetric Friedel-Crafts amination through a chiral organocatalyst. Further, it acts as a reactant for preparation of hexapeptide key fragments through stereo selective selenocyclization/oxidative deselenylation reactions. In addition to this, it is employed as a starting material in the synthesis of pyrroloisoquinoline template through stereoselective N-acyliminium-mediated cyclization and enolate amination for preparation of peptidomimetic compounds and Barbier-type propargylation reactions. | | General Description | Di-tert-butyl azodicarboxylate is a an acid labile reagent for Mitsunobu reactions allowing facile isolation of products and for the electrophilic amination and hydrazination of enolates and lithium alkyls. | | Purification Methods | The 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]. |
| | Di-tert-Butyl azodicarboxylate Preparation Products And Raw materials |
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