2,4,6-Triisopropylbenzenesulfonyl chloride, 98%, Thermo Scientific Chemicals
2,4,6-Triisopropylbenzenesulfonyl chloride, 98%, Thermo Scientific Chemicals
Thermo Scientific Chemicals

2,4,6-Triisopropylbenzenesulfonyl chloride, 98%, Thermo Scientific Chemicals

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500 g
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Catalog number A11458.36
also known as A11458-36
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936.00
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Quantity:
500 g
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Price (USD)/ Each
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2,4,6-Triisopropylbenzenesulfonyl chloride, 98%, Thermo Scientific Chemicals
Catalog numberA11458.36
Price (USD)/ Each
936.00
-
Add to cart
Chemical Identifiers
CAS6553-96-4
IUPAC Name2,4,6-tris(propan-2-yl)benzene-1-sulfonyl chloride
Molecular FormulaC15H23ClO2S
InChI KeyJAPYIBBSTJFDAK-UHFFFAOYSA-N
SMILESCC(C)C1=CC(C(C)C)=C(C(=C1)C(C)C)S(Cl)(=O)=O
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SpecificationsSpecification SheetSpecification Sheet
Appearance (Color)White to pale pink to pale cream
Assay (Titration ex Chloride)≥97.5 to ≤102.5%
Melting Point (clear melt)93-99?C
FormCrystals or powder or crystalline powder
Identification (FTIR)Conforms
2,4,6-Triisopropylbenzenesulfonyl chloride is used for the synthesis of glycerophospholipids as a condensing agent and in the analysis of phosphonolipids in egg yolk by HPLC/MS technique. It acts as a coupling reagent for the synthesis of oligonucleotides and as sulfonates of pyrimidine nucleosides. It also serves as a condensing agent in the synthesis of hydrogen-phosphonate diesters.

This Thermo Scientific Chemicals brand product was originally part of the Alfa Aesar product portfolio. Some documentation and label information may refer to the legacy brand. The original Alfa Aesar product / item code or SKU reference has not changed as a part of the brand transition to Thermo Scientific Chemicals.

Applications
2,4,6-Triisopropylbenzenesulfonyl chloride is used for the synthesis of glycerophospholipids as a condensing agent and in the analysis of phosphonolipids in egg yolk by HPLC/MS technique. It acts as a coupling reagent for the synthesis of oligonucleotides and as sulfonates of pyrimidine nucleosides. It also serves as a condensing agent in the synthesis of hydrogen-phosphonate diesters.

Solubility
Soluble in chloroform.

Notes
Incompatible with strong bases.
RUO – Research Use Only

General References:

  1. 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. Mesityl ene-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).
  2. 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).
  3. Cai, H.; Liu, Q.; Gao, D.; Wang, T.; Chen, T.; Yan, G.; Chen, K.; Xu, Y.; Wang, H.; Li, Y.; Zhu, W. Novel fatty acid binding protein 4 (FABP4) inhibitors: Virtual screening, synthesis and crystal structure determination. Eur. J. Med. Chem. 2015, 90, 241-250.