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)

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

• Language:English Provider:ACROS
• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

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

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.

Uses

Utilized in the asymmetric Friedel-Crafts amination via a chiral organocatalyst.

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(870-50-8)Related Product Information

• Di-tert-butyl dicarbonate
• tert-Butanol
• Dimethyl succinate
• tert-Butyl peroxybenzoate
• Butylparaben
• Buprofezin
• Butyl acetate
• 2-Butoxyethanol
• butyl rubber
• Diisopropyl azodicarboxylate
• Isobutyl chloroformate
• Tris(trimethylsilyl)phosphate
• Butyl acrylate
• Diisobutyl phthalate
• Cyhalofop-butyl
• Diethyl azodicarboxylate
• Dibenzyl azodicarboxylate
• Bis(4-chlorobenzyl) azodicarboxylate