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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%

CAS Number
773-64-8
Synonyms
2,4,6-Trimethylbenzenesulfonyl chloride

Size Price ($) Quantity Availability
25g 44.08
100g 140.27
500g 492.03
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Mesitylene-2-sulfonyl chloride, 99%

MDL
MFCD00007434
EINECS
212-257-8

Chemical Properties

Formula
C9H11ClO2S
Formula Weight
218.70
Melting point
53-57°
Boiling Point
150°/20mm
Flash Point
>110°(230°F)
Sensitivity
Moisture Sensitive
Solubility
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.

Literature 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-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.

GHS Hazard and Precautionary Statements

Hazard Statements: H314-H318

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

Precautionary Statements: P260-P280-P303+P361+P353-P305+P351+P338-P301+P330+P331-P304+P340-P310-P363-P405-P501a

Do not breathe dust/fume/gas/mist/vapours/spray. Wear protective gloves/protective clothing/eye protection/face protection. 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. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. Immediately call a POISON CENTER or doctor/physician. Wash contaminated clothing before reuse. Store locked up. Dispose of contents/container in accordance with local/regional/national/international regulations.

Other References

Beilstein
1107601
Hazard Class
8
Packing Group
II
Harmonized Tariff Code
2904.90
TSCA
No
RTECS
DB8930000

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