偶氮二甲酸二乙酯

• 产品号: L19348
• CAS号: 1972-28-7
• 分子式: C6H10N2O4
• 分子量: 174.1546
• 纯 度: 97%

产品别名

• 标题: Diethyl azodicarboxylate
• IUPAC标准名: N-[(ethoxycarbonyl)imino]ethoxyformamide
• IUPAC传统名: diethyl azodicarboxylate
• 别名: Azodicarboxylic Acid Diethyl Ester; DEAD

产品登记号

• MDL号: MFCD00009103
• CAS号: 1972-28-7
• Beilstein号: 908662
• EC号: 217-821-7

产品性质

• 纯度: 97%
• 沸点: 106°C/13mm
• 密度: 1.106
• 闪点: 85°C(185°F)
• 折射率: 1.4210
• GHS危险声明: H302-H312-H315-H319-H335-H227
• 欧盟危险性物质标志: X
• GHS警示性声明: P210-P305+P351+P338-P302+P352-P321-P405-P501A
• 危险公开号: 5-21/22-36/37/38
• 安全公开号: 26-36/37-60
• 保存注意事项: Air Sensitive
• TSCA收录: 否
• 联合国危险货物等级: 6.1
• 联合国危险货物编号: UN2810
• 联合国危险货物包装类别(PG): III

参考文献

• 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.
• See also Di-tert-butyl azodicarboxylate, L00294, and Diisopropyl azodicarboxylate, L10386.
• 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.
• 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 S_N2 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).
• Explosion risk by heating undiluted material.
• Secondary and tertiary amines have been dealkylated by reaction with DEAD under mild conditions, followed by acid hydrolysis: J. Org. Chem., 38, 1652 (1973).