伯吉斯试剂

• 产品号: L20155
• CAS号: 29684-56-8
• 分子式: C8H18N2O4S
• 分子量: 238.30452
• 纯 度: 96%

产品别名

• 标题: Burgess Reagent
• IUPAC标准名: (methoxycarbonyl)[(triethylazaniumyl)sulfonyl]azanide
• IUPAC传统名: (methoxycarbonyl)(triethylammoniosulfonyl)azanide
• 别名: (Methoxycarbonylsulfamoyl)triethylammonium hydroxide, inner salt; Methyl N-(triethylammoniosulfonyl)carbamate

产品登记号

• MDL号: MFCD00077815
• Beilstein号: 1432131
• CAS号: 29684-56-8

产品性质

• GHS危险声明: H315-H319-H335
• 欧盟危险性物质标志: 刺激性(Irritant) (Xi)
• GHS警示性声明: P261-P305+P351+P338-P302+P352-P321-P405-P501A
• 危险公开号: 36/37/38
• 安全公开号: 26-37
• 保存注意事项: Moisture Sensitive
• TSCA收录: 否
• 纯度: 96%
• 熔点: 72-82°C

参考文献

• Primary amides undergo facile dehydration to nitriles, even in the presence of other functional groups including alcohols: Tetrahedron Lett., 29, 2155 (1988). Aldoximes are also dehydrated to nitriles: Synth. Commun., 30, 1509 (2000); Synlett, 1169 (2000). Formamides afford isonitriles: J. Chem. Soc., Perkin 1, 1015 (1998). 2-Acylamino carbonyl compounds undergo the Robinson-Gabriel cyclodehydration to give oxazoles, avoiding conventional harsh dehydrating agents (e.g. P₂ O₅, POCl₃ or SOCl₂ ): Synlett, 1642 (1999):
  
• Mild, efficient dehydrating agent. Primary alcohols are converted to carbamates, which can be hydrolyzed to primary amines, thus providing a valuable alcohol to amine transformation. Secondary and tertiary alcohols afford olefins in synthetically useful yields: J. Org. Chem., 38, 26 (1973); Org. Synth. Coll., 6, 788 (1988). For further discussion, see: Encyclopedia of Reagents for Organic Synthesis, L. A. Paquette, Ed., Wiley, Chichester (1995), vol. 5, p. 3345.
• Primary amides undergo facile dehydration to nitriles, even in the presence of other functional groups including alcohols: Tetrahedron Lett., 29, 2155 (1988). Aldoximes are also dehydrated to nitriles: Synth. Commun., 30, 1509 (2000); Synlett, 1169 (2000). Formamides afford isonitriles: J. Chem. Soc., Perkin 1, 1015 (1998). 2-Acylamino carbonyl compounds undergo the Robinson-Gabriel cyclodehydration to give oxazoles, avoiding conventional harsh dehydrating agents (e.g. P₂ O₅, POCl₃ or SOCl₂ ): Synlett, 1642 (1999):
  
• The cyclization of 1,2-diacylhydrazines to 1,3,4-oxadiazoles has also been reported: Tetrahedron Lett., 40, 3275 (1999).