(methoxycarbonyl)[(triethylazaniumyl)sulfonyl]azanide

• ChemBase ID: 148030
• Molecular Formular: C8H18N2O4S
• Molecular Mass: 238.30452
• Monoisotopic Mass: 238.09872807
• SMILES: CC[N+](CC)(CC)S(=O)(=O)[N-]C(=O)OC
• Canonical SMILES: COC(=O)[N-]S(=O)(=O)[N+](CC)(CC)CC
• InChI: InChI=1S/C8H18N2O4S/c1-5-10(6-2,7-3)15(12,13)9-8(11)14-4/h5-7H2,1-4H3
• InChIKey: YSHOWEKUVWPFNR-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (methoxycarbonyl)[(triethylazaniumyl)sulfonyl]azanide
• IUPAC Traditional name: (methoxycarbonyl)(triethylammoniosulfonyl)azanide
• Synonyms: Burgess reagent; Methyl N-(triethylammoniosulfonyl)carbamate; (Methoxycarbonylsulfamoyl)triethylammonium hydroxide, inner salt; (Methoxycarbonylsulfamoyl)triethylammonium hydroxide, inner salt; Burgess Reagent; Burgess reagent; N-(三乙基氨磺酰)氨基甲酸甲酯; 伯吉斯试剂; (甲氧基羰基氨磺酰基)三乙基氢氧化铵， 内盐; 伯吉斯试剂

Database IDs

• CAS Number: 29684-56-8
• MDL Number: MFCD00077815
• Beilstein Number: 1432131
• PubChem SID: 24862529; 24883653; 162242210
• PubChem CID: 9566069

CALCULATED PROPERTIES

• Acid pKa: 1.1242826
• H Acceptors: 4
• H Donor: 0
• LogD (pH = 5.5): 1.8463699
• LogD (pH = 7.4): 1.8463877
• Log P: -0.3106675
• Molar Refractivity: 57.967 cm^3
• Polarizability: 22.84542 Å^3
• Polar Surface Area: 69.67 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: ~73 °C (dec.); 72-82°C; 76-79 °C(lit.)

Safety Information

• Storage Warning: Moisture Sensitive
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-36; 26-37
• TSCA Listed: 否
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338; P261-P305+P351+P338-P302+P352-P321-P405-P501A
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Storage Temperature: -20°C

Product Information

• Purity: ≥97.0% (HPLC); 96%; 97%
• Grade: purum
• Shipped in: wet ice
• Linear Formula: CH3O2CNSO2N(C2H5)3

DETAILS

Sigma Aldrich - 365483

Application
Powerful dehydration agent for compounds such as secondary and tertiary alcohols, diols, amino alcohols, sugars, etc., including reactions with epoxides.1,2
Packaging
1 g in glass bottle

Sigma Aldrich - 64942

Other Notes
Reagent used for the smooth dehydration of secondary and tertiary alcohols to olefins1,2; Primary alcohols are transformed into N-alkylated urethanes3; Primary amides are chemoselectively converted into nitriles4; Cyclodehydration to heterocycles5

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).