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773-64-8 - Mesitylene-2-sulfonyl chloride, 99% - 2,4,6-Trimethylbenzenesulfonyl chloride - A11775 - Alfa Aesar

A11775 Mesitylene-2-sulfonyl chloride, 99%

Numéro de CAS
773-64-8
Synonymes
2,4,6-Trimethylbenzenesulfonyl chloride

Conditionnement Prix ($) Quantité Disponibilité
25g 54,00
100g 149,00
500g 525,00
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Mesitylene-2-sulfonyl chloride, 99%

MDL
MFCD00007434
EINECS
212-257-8

Propriétés chimiques

Formule
C9H11ClO2S
Poids moleculaire
218.70
Point de fusion
53-57°
Point d'ébullition
150°/20mm
Point d'éclair
>110°(230°F)
Sensibilité
Moisture Sensitive
Solubilité
Soluble in toluene (almost transparency).

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

Notes

Moisture Sensitive. Store under inert gas. Incompatible with strong bases. Store away from moisture.

Références bibliographiques

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-Triisopropyl­benzenesulfonyl­ 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.

Mentions de danger et de prudence du SGH

Mentions de danger (UE): H314-H318

Causes severe skin burns and eye damage. Causes serious eye damage.

Mentions de prudence: P260u-P303+P361+P353-P305+P351+P338-P301+P330+P331-P405-P501a

Do not breathe dusts or mists. IF ON SKIN (or hair): Remove/Take off immediately all contaminated clothing. Rinse skin with water/shower. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. IF SWALLOWED: Rinse mouth. Do NOT induce vomiting. Store locked up. Dispose of contents/container in accordance with local/regional/national/international regulations.

Autres références

Beilstein
1107601
Classe de danger
8
Groupe d'emballage
II
Code tarifaire harmonisé
2904.99
TSCA
No
RTECS
DB8930000

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Consulté récemment

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Catalyseurs

Analytique et matériel de laboratoire