| Identification | More | [Name]
Di-tert-Butyl azodicarboxylate | [CAS]
870-50-8 | [Synonyms]
Azodicarboxylic acid di-tert-butyl ester
DI-T-BUTYL AZODICARBOXYLATE
DI-TERT-BUTYL AZODICARBOXYLATE
Di-Tert-ButylAzodicarboxylate(Dbad)
Di-tert-butyl azodicarboxylate 98%
Di-tert-butyl Azodicarboxylate (20% in Toluene)
Di-tert-B-butyl azodicarboxylate, 98%
1,2-Bis(tert-butoxycarbonyl)diazene
Azobis(formic acid tert-butyl) ester
Bis(tert-butoxycarbonyl)diazene
Diazene-1,2-bis(formic acid tert-butyl) ester
Diazene-1,2-dicarboxylic acid di-tert-butyl ester
Diazenedicarboxylic acid bis-tert-butyl ester | [EINECS(EC#)]
212-796-9 | [Molecular Formula]
C10H18N2O4 | [MDL Number]
MFCD00015001 | [Molecular Weight]
230.26 | [MOL File]
870-50-8.mol |
| Chemical Properties | Back Directory | [Appearance]
yellow crystals or crystalline powder | [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) |
| Questions And Answer | Back Directory | [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. |
| Safety Data | Back Directory | [Hazard Codes ]
Xi,F | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin .
R11:Highly Flammable. | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36:Wear suitable protective clothing .
S37/39:Wear suitable gloves and eye/face protection .
S16:Keep away from sources of ignition-No smoking . | [RIDADR ]
1325 | [WGK Germany ]
3
| [Hazard Note ]
Irritant | [HazardClass ]
3 | [PackingGroup ]
II | [HS Code ]
29270000 |
| Hazard Information | Back Directory | [Chemical Properties]
yellow crystals or crystalline powder | [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]. |
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