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

• ChemBase ID: 89771
• Molecular Formular: C15H23ClO2S
• Molecular Mass: 302.85992
• Monoisotopic Mass: 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

NAMES AND DATABASE IDS

Names

• IUPAC name: 2,4,6-tris(propan-2-yl)benzene-1-sulfonyl chloride
• IUPAC Traditional name: 2,4,6-triisopropylbenzenesulfonyl chloride
• Synonyms: 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; 2,4,6-三异丙基苯磺酰氯

Database IDs

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

CALCULATED PROPERTIES

• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 5.6545763
• LogD (pH = 7.4): 5.6545763
• Log P: 5.6545763
• Molar Refractivity: 82.8246 cm^3
• Polarizability: 32.682453 Å^3
• Polar Surface Area: 34.14 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: ethanol: soluble50 mg/mL, clear
• Melting Point: 92-94 °C(lit.); 94-97°C; 94-99°C; 95-97 °C
• Partition Coefficient: 5.555

Safety Information

• Storage Warning: Corrosive/Moisture Sensitive/Store under Argon; Moisture Sensitive
• European Hazard Symbols: Corrosive (C)
• UN Number: 3261; UN3096
• German water hazard class: 3
• Hazard Class: 8
• Packing Group: 2; II
• Risk Statements: 34
• Safety Statements: 20-26-36/37/39-45; 26-36/37/39-45
• TSCA Listed: 否
• GHS Pictograms: GHS05
• GHS Signal Word: Danger
• GHS Hazard statements: H314; H314-H318
• GHS Precautionary statements: P260-P303+P361+P353-P305+P351+P338-P301+P330+P331-P405-P501A; P280-P305 + P351 + P338-P310
• Personal Protective Equipment: 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

Product Information

• Purity: ≥97.0% (AT); 95+%; 97%; 98%
• Grade: purum
• Linear Formula: [(CH3)2CH]3C6H2SO2Cl

DETAILS

Sigma Aldrich - 119490

Packaging
25, 100 g in glass bottle
Application
Used to prepare coupling reagents for the synthesis of oligonucleotides.1,2,3

Sigma Aldrich - 92077

Other Notes
Starting material for the preparation of 2,4,6-triisopropylbenzenesulfonylhydrazide (TPSH); a convenient source of di-imine1

REFERENCES

• 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).