4-acetamidobenzene-1-sulfonyl azide

• ChemBase编号: 145939
• 分子式: C8H8N4O3S
• 平均质量: 240.23912
• 单一同位素质量: 240.03171114
• SMILES: CC(=O)Nc1ccc(cc1)S(=O)(=O)N=[N+]=[N-]
• Canonical SMILES: CC(=O)Nc1ccc(cc1)S(=O)(=O)N=[N+]=[N-]
• InChI: InChI=1S/C8H8N4O3S/c1-6(13)10-7-2-4-8(5-3-7)16(14,15)12-11-9/h2-5H,1H3,(H,10,13)
• InChIKey: NTMHWRHEGDRTPD-UHFFFAOYSA-N

名称和登记号

名称

• IUPAC标准名: 4-acetamidobenzene-1-sulfonyl azide
• IUPAC传统名: 4-acetamidobenzenesulfonyl azide
• 别名: 对乙酰氨基苯磺酰叠氮; 4-乙酰氨基苯磺酰叠氮; 4-乙酰胺基 苯磺酰基叠氮; p-ABSA; 4-Acetamidobenzenesulfonyl azide

登记号

• CAS号: 2158-14-7
• MDL号: MFCD00029626
• Beilstein号: 2219568
• PubChem SID: 24865269; 162240139
• PubChem CID: 5129185

理论计算性质

• Acid pKa: 13.31138
• 质子受体: 5
• 质子供体: 1
• LogD (pH = 5.5): 0.3478259
• LogD (pH = 7.4): 0.3478254
• Log P: 0.46187156
• 摩尔折射率: 57.636 cm^3
• 极化性: 21.74883 Å^3
• 极化表面积: 92.67 Å^2
• 可自由旋转的化学键: 2
• 里宾斯基五规则: true

分子性质

理化性质

• 熔点: 104-111 °C; 107-111 °C(lit.); 107-111°C

安全信息

• 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: 26-37; 26-37/39
• 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: 2-8°C

产品相关信息

• 纯度: ≥95.0% (HPLC); 97%
• 级别: purum
• 线性分子式: CH3CONHC6H4SO2N3

详细说明

Sigma Aldrich - 404764

包装
5, 25 g in glass bottle
Application
Hydroazidation Catalyst for Facile Preparation of OrganoazidesDiazo transfer agent.1,2,3
Reagent for synthesis of: Monosaccharide-derived alcohols Non-peptidic NK3 receptor antagonistsReagent for: A late-stage intermolecular C-H olefination Intramolecular isomuenchnone cycloaddition approach to antitumor agents Rhodium-catalyzed carbene cyclization cycloaddition cascade reaction of vinylsulfonates Suzuki-Miyaura cross coupling reaction

Sigma Aldrich - 00245

Other Notes
重氮基转移试剂：用于合成 α-重氮酯7,8
Application
Reagent for synthesis of: Monosaccharide-derived alcohols1 Non-peptidic NK3 receptor antagonists2Reagent for: A late-stage intermolecular C-H olefination3 Intramolecular isomuenchnone cycloaddition approach to antitumor agents4 Rhodium-catalyzed carbene cyclization cycloaddition cascade reaction of vinylsulfonates5 Suzuki-Miyaura cross coupling reaction6

参考文献

• Diazo transfer agent. Recommended as a safer alternative to tosyl azide for diazo transfer reactions, in the presence of a base, e.g. Et₃N or DBU, with active methylene compounds. A further advantage of the reagent is that the by-product sulfonamide is removable by trituration with water: Synth. Commun., 17, 1709 (1987). For illustrative examples, with subsequent cyclization using Rhodium(II) acetate, L15152, as a route to highly substituted furans, see: Tetrahedron, 44, 3343 (1988); Org. Synth. Coll., 9, 422 (1998):
  
• For a further example, see: Org. Synth. Coll., 9, 155 (1998).