(methoxycarbonyl)[(triethylazaniumyl)sulfonyl]azanide

• ChemBase编号: 148030
• 分子式: C8H18N2O4S
• 平均质量: 238.30452
• 单一同位素质量: 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

名称和登记号

名称

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

登记号

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

理论计算性质

• Acid pKa: 1.1242826
• 质子受体: 4
• 质子供体: 0
• LogD (pH = 5.5): 1.8463699
• LogD (pH = 7.4): 1.8463877
• Log P: -0.3106675
• 摩尔折射率: 57.967 cm^3
• 极化性: 22.84542 Å^3
• 极化表面积: 69.67 Å^2
• 可自由旋转的化学键: 4
• 里宾斯基五规则: true

分子性质

理化性质

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

安全信息

• 保存注意事项: Moisture Sensitive
• 欧盟危险性物质标志: 刺激性(Irritant) (Xi)
• 德国WGK号: 3
• 危险公开号: 36/37/38
• 安全公开号: 26-36; 26-37
• TSCA收录: 否
• GHS危险品标识: GHS07
• GHS警示词: Warning
• GHS危险声明: H315-H319-H335
• GHS警示性声明: P261-P305 + P351 + P338; P261-P305+P351+P338-P302+P352-P321-P405-P501A
• 个人保护装置: dust mask type N95 (US), Eyeshields, Gloves
• 保存温度: -20°C

产品相关信息

• 纯度: ≥97.0% (HPLC); 96%; 97%
• 级别: purum
• 运输包装: wet ice
• 线性分子式: CH3O2CNSO2N(C2H5)3

详细说明

Sigma Aldrich - 365483

Application
用于仲醇和叔醇、二元醇、氨基醇、糖类等化合物的强效脱水剂，包括与环氧化合物反应。1,2
包装
1 g in glass bottle

Sigma Aldrich - 64942

Other Notes
用于仲醇和叔醇顺利脱水生成烯烃的试剂1,2；将伯醇转化为 N-烷基化聚氨酯3；将伯胺化学选择性地转化为腈4；环化脱水生成杂环化合物5

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).