2,4,6-tris(propan-2-yl)benzene-1-sulfonyl chloride

• ChemBase编号: 89771
• 分子式: C15H23ClO2S
• 平均质量: 302.85992
• 单一同位素质量: 302.11072866
• SMILES: S(=O)(=O)(c1c(cc(cc1C(C)C)C(C)C)C(C)C)Cl
• Canonical SMILES: CC(c1cc(cc(c1S(=O)(=O)Cl)C(C)C)C(C)C)C
• InChI: InChI=1S/C15H23ClO2S/c1-9(2)12-7-13(10(3)4)15(19(16,17)18)14(8-12)11(5)6/h7-11H,1-6H3
• InChIKey: JAPYIBBSTJFDAK-UHFFFAOYSA-N

名称和登记号

名称

• IUPAC标准名: 2,4,6-tris(propan-2-yl)benzene-1-sulfonyl chloride
• IUPAC传统名: 2,4,6-triisopropylbenzenesulfonyl chloride
• 别名: 2,4,6-三异丙基苯磺酰氯; 2,4,6-triisopropylbenzenesulfonyl chloride; Trisyl chloride; 2,4,6-Tris(prop-2-yl)benzenesulphonyl chloride; 2,4,6-Tris(isopropyl)benzenesulphonyl chloride 98+%; 2,4,6-Triisopropylbenzenesulfonyl chloride

登记号

• CAS号: 6553-96-4
• EC号: 229-479-6
• MDL号: MFCD00007433
• Beilstein号: 1218575
• PubChem SID: 24847399; 162076627; 24889600
• PubChem CID: 81042

理论计算性质

• 质子受体: 2
• 质子供体: 0
• LogD (pH = 5.5): 5.6545763
• LogD (pH = 7.4): 5.6545763
• Log P: 5.6545763
• 摩尔折射率: 82.8246 cm^3
• 极化性: 32.682453 Å^3
• 极化表面积: 34.14 Å^2
• 可自由旋转的化学键: 4
• 里宾斯基五规则: false

分子性质

理化性质

• 溶解度: ethanol: soluble50 mg/mL, clear
• 熔点: 92-94 °C(lit.); 94-97°C; 94-99°C; 95-97 °C
• 分配系数: 5.555

安全信息

• 保存注意事项: Corrosive/Moisture Sensitive/Store under Argon; Moisture Sensitive
• 欧盟危险性物质标志: 腐蚀性(Corrosive) (C)
• 联合国危险货物编号: 3261; UN3096
• 德国WGK号: 3
• 联合国危险货物等级: 8
• 联合国危险货物包装类别(PG): 2; II
• 危险公开号: 34
• 安全公开号: 20-26-36/37/39-45; 26-36/37/39-45
• TSCA收录: 否
• GHS危险品标识: GHS05
• GHS警示词: Danger
• GHS危险声明: H314; H314-H318
• GHS警示性声明: P260-P303+P361+P353-P305+P351+P338-P301+P330+P331-P405-P501A; P280-P305 + P351 + P338-P310
• 个人保护装置: Eyeshields, Faceshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges
• RID/ADR: UN 3261 8/PG 2

产品相关信息

• 纯度: ≥97.0% (AT); 95+%; 97%; 98%
• 级别: purum
• 线性分子式: [(CH3)2CH]3C6H2SO2Cl

详细说明

Sigma Aldrich - 119490

包装
25, 100 g in glass bottle
Application
用于制备寡核苷酸合成所用的偶联剂。1,2,3

Sigma Aldrich - 92077

Other Notes
作为原料用于制备 2,4,6-三异丙基苯磺酰基肼 (TPSH)；二酰亚胺的便捷来源1

参考文献

• Hindered sulfonyl chlorides have found use as condensing agents for the formation of the phosphate link of oligonucleotides. For reviews, see: Angew. Chem. Int. Ed., 11, 451 (1972); Synthesis, 222 (1975); Chem. Rev., 77, 183 (1977). For reviews of oligonucleotide synthesis by the phosphotriester method, see: Heterocycles, 7, 1197 (1977); Tetrahedron, 34, 3143 (1978). For use as a condensing agent in the synthesis of H-phosphonate diesters, see: Nucleosides Nucleotides, 7, 23 (1988). More hindered in comparison with, e.g. Mesitylene-2-sulfonyl chloride, A11775, and so has less tendency to react with the free 5'-hydroxyl group of sugars: J. Am. Chem. Soc., 88, 829 (1966).
• For examples of the utility of the triisopropylbenzenesulfonyl group in the protection of OH groups, see: J. Am. Chem. Soc., 117, 5693, 5776 (1995): (first synthesis of a digitalis saponin and asymmetric synthesis of (-) and (+)-strychnine, respectively).