Burgess Reagent

• Catalog No.: L20155
• CAS Number: 29684-56-8
• M. F.: C8H18N2O4S
• M. W.: 238.30452
• Purity: 96%

SYNONYMS

• Title: 伯吉斯试剂
• IUPAC name: (methoxycarbonyl)[(triethylazaniumyl)sulfonyl]azanide
• IUPAC Traditional name: (methoxycarbonyl)(triethylammoniosulfonyl)azanide
• Synonyms: (Methoxycarbonylsulfamoyl)triethylammonium hydroxide, inner salt; Methyl N-(triethylammoniosulfonyl)carbamate

DATABASE IDS

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

PROPERTIES

• GHS Hazard statements: H315-H319-H335
• European Hazard Symbols: Irritant (Xi)
• GHS Precautionary statements: P261-P305+P351+P338-P302+P352-P321-P405-P501A
• Risk Statements: 36/37/38
• Safety Statements: 26-37
• Storage Warning: Moisture Sensitive
• TSCA Listed: 否
• Purity: 96%
• Melting Point: 72-82°C

REFERENCES

• 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).