Diethyl azodicarboxylate, 97%
|UN#:||UN2810||Hazard Class:||6.1||Packing Group:||III|
|Alternate Name:||Azodicarboxylic acid diethyl ester
Pricing and Availability
|Size||($) Price||Your Price||Quantity||Options||Availability|
|5g||31.00||Enter qty and click checkbox|
|25g||86.10||Enter qty and click checkbox|
|100g||255.00||Enter qty and click checkbox|
|Formula weight:||174.16||Refractive Index:||1.4210|
|Boiling point:||106°/13mm||Sensitivity:||Air Sensitive|
Explosion risk by heating undiluted material.
Dehydrogenating agent and aza-dienophile. Oxidizes alcohols to aldehydes, thiols to disulfides and hydrazo to azo groups: J. Am. Chem. Soc., 88, 2328 (1966). Arylhydroxylamines are converted in high yield to nitroso compounds: Chem. Commun., 199 (1967).
Undergoes pericyclic reactions with alkenes and dienes via both ene and Diels-Alder processes. For further details and references, see: Encyclopedia of Reagents for Organic Synthesis, L. A. Paquette, Ed., Wiley, Chichester (1995), vol. 3, p. 1790.
Secondary and tertiary amines have been dealkylated by reaction with DEAD under mild conditions, followed by acid hydrolysis: J. Org. Chem., 38, 1652 (1973).
In combination with Triphenylphosphine, L02502, is widely used in the Mitsunobu reaction for activation of primary and secondary alcohols by formation of the alkoxyphosphonium salts, which behave as versatile alkylating agents under mild SN2 conditions: reactions normally proceed with inversion of configuration. For reviews, see: Synthesis, 1 (1981); Org. React., 42, 335 (1992); Org. Prep. Proced. Int., 28, 127 (1996); Synlett, 1221 (2003); Eur. J. Org. Chem., 2763 (2004):
For study of the mechanism, see: J. Org. Chem., 67, 1751 (2002).
Details for esterification of (-)-menthol with 4-nitrobenzoic acid with stereoinversion: Org. Synth. Coll., 9, 607 (1998). For an example of its use to convert a secondary alcohol to an amine by reaction with phthalimide followed by hydrazinolysis, see: Org. Synth. Coll., 7, 501 (1990). For dehydration of Boc-L-serine to the cyclic anhydride (2-oxetanone), see: Org. Synth. Coll., 9, 24 (1998).
ɑ-Amination of aldehydes can be effected in the presence of L-proline as an enantioselective catalyst, affording chiral ɑ-amino alcohols and ɑ-amino acids with good ee: Angew. Chem. Int. Ed., 41, 1790 (2002); for a similar reaction with scheme, see Dibenzyl azodicarboxylate, L19347.
|Harmonized Tariff Code:||2927.00|
GHS Hazard and Precautionary Statements
Harmful if swallowed. Harmful in contact with skin. Causes skin irritation. Causes serious eye irritation. May cause respiratory irritation. Combustible liquid.
Keep away from heat/sparks/open flames/hot surfaces. - No smoking. Avoid breathing dust/fume/gas/mist/vapours/spray. Wear protective gloves/protective clothing/eye protection/face protection. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. Store locked up. Dispose of contents/container in accordance with local/regional/national/international regulations.
Risk & Safety
|Heating may cause an explosion. Harmful in contact with skin and if swallowed. Irritating to eyes, respiratory system and skin.|
|In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. Wear suitable protective clothing and gloves. This material and/or its container must be disposed of as hazardous waste.|