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Mesitylene-2-sulfonyl chloride, 99%, Thermo Scientific Chemicals
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Catalog number A11775.14
also known as A11775-14
Price (USD)/ Each
63.60
-
Quantity:
25 g
Price (USD)/ Each
63.60
Mesitylene-2-sulfonyl chloride, 99%, Thermo Scientific Chemicals
Catalog numberA11775.14
Price (USD)/ Each
63.60
-
Chemical Identifiers
CAS773-64-8
IUPAC Name2,4,6-trimethylbenzene-1-sulfonyl chloride
Molecular FormulaC9H11ClO2S
InChI KeyPVJZBZSCGJAWNG-UHFFFAOYSA-N
SMILESCC1=CC(C)=C(C(C)=C1)S(Cl)(=O)=O
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Specifications
Specification Sheet
Specification SheetAppearance (Color)White
FormCrystals or powder or crystalline powder
Assay (GC)≥98.5%
Identification (FTIR)Conforms
Melting Point (clear melt)50.0-56.0?C
Mesitylene-2-sulfonyl chloride is used as reagent for intramolecular lactamizations and lactonization. It also acts as a reagent for protecting guanidino groups and tryptophan. It is used as coupling reagent in polynucleotide synthesis
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
Mesitylene-2-sulfonyl chloride is used as reagent for intramolecular lactamizations and lactonization. It also acts as a reagent for protecting guanidino groups and tryptophan. It is used as coupling reagent in polynucleotide synthesis
Solubility
Soluble in toluene (almost transparency).
Notes
Moisture Sensitive. Store under inert gas. Incompatible with strong bases. Store away from moisture.
Mesitylene-2-sulfonyl chloride is used as reagent for intramolecular lactamizations and lactonization. It also acts as a reagent for protecting guanidino groups and tryptophan. It is used as coupling reagent in polynucleotide synthesis
Solubility
Soluble in toluene (almost transparency).
Notes
Moisture Sensitive. Store under inert gas. Incompatible with strong bases. Store away from moisture.
RUO – Research Use Only
General References:
- Chi-Hua Wang; Saul G. Cohen. Mercaptan Catalysis in Thermoneutral Free Radical Exchange.J. Am. Chem. Soc. 1957, 79 (8),1924-1929.
- Adeleh Kiania; Batool Akhlaghiniaa; Hamed Rouhi-Saadabada & Mehdi Bakavolia.Journal of Sulfur Chemistry. 2014, 35 119-127.
- Selective reagent for sulfonylation of carbohydrates: J. Chem. Soc., Perkin 1, 1373 (1974).
- For reviews of the use of hindered sulfonyl chlorides as condensing agents for the formation of the phosphate link of oligonucleotides, 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). Compare 2,4,6-Triisopropyl benzenesulfonyl chloride, A11458.
- Reagent for protection of the guanidino function of arginine residues as mesitylenesulfonyl (Mts) derivatives in peptide synthesis: J. Chem. Soc., Chem. Commun., 482 (1978); Chem. Pharm. Bull., 26, 3752 (1978); Int. J. Pept. Prot. Res., 14, 169 (1979). Deprotection can be effected with triflic acid in TFA in the presence of thioanisole as a cation scavenger: J. Chem. Soc., Chem. Commun., 1063 (1980).
- The indole nitrogen, e.g. in tryptophan residues, may also be protected as the Mts amide, stable to dilute alkali, hydrazine hydrate, TFA, 4N HCl in dioxane, or HBr in AcOH, but cleaved by MsOH, or TfOH in TFA: Chem. Pharm. Bull., 32, 2660 (1984). See Appendix 6.