2,4,6-trimethylbenzene-1-sulfonyl chloride

• ChemBase ID: 87829
• Molecular Formular: C9H11ClO2S
• Molecular Mass: 218.70044
• Monoisotopic Mass: 218.01682827
• SMILES: S(=O)(=O)(c1c(cc(cc1C)C)C)Cl
• Canonical SMILES: Cc1cc(C)cc(c1S(=O)(=O)Cl)C
• InChI: InChI=1S/C9H11ClO2S/c1-6-4-7(2)9(8(3)5-6)13(10,11)12/h4-5H,1-3H3
• InChIKey: PVJZBZSCGJAWNG-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2,4,6-trimethylbenzene-1-sulfonyl chloride
• IUPAC Traditional name: 2,4,6-trimethylbenzenesulfonyl chloride
• Synonyms: 2,4,6-Trimethylbenzenesulfonyl chloride; 2-Mesitylenesulfonyl chloride; Mesitylene-2-sulphonyl chloride; 2,4,6-Trimethylbenzenesulphonyl chloride; 2,4,6-Trimethylbenzene sulfonyl chloride; 2-MESITYLENESULFONYL CHLORIDE; 2,4,6-TriMethylbenzene-1-sulfonyl chloride; Mesitylene-2-sulfonyl chloride; 2,4,6-三甲基苯磺酰氯; 均三甲苯基磺酰氯; 均三甲苯-2-磺酰氯

Database IDs

• CAS Number: 773-64-8
• EC Number: 212-257-8
• MDL Number: MFCD00007434
• Beilstein Number: 1107601
• PubChem SID: 24897176; 24883017; 162074869
• PubChem CID: 13046

CALCULATED PROPERTIES

• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 3.459813
• LogD (pH = 7.4): 3.459813
• Log P: 3.459813
• Molar Refractivity: 55.3758 cm^3
• Polarizability: 21.671684 Å^3
• Polar Surface Area: 34.14 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 53-57°C; 54-56.5 °C; 55-57 °C(lit.); 55-57°C
• Boiling Point: 150°C/20mm
• Flash Point: >110°C(230°F); 113 °C; 113°C; 235.4 °F

Safety Information

• Storage Warning: Corrosive/Moisture Sensitive/Store under Argon; Moisture Sensitive
• RTECS: DB8930000
• 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: 22-26-27-36/37/39-45; 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: ≥99.0% (T); 97%; 98%; 99%
• Grade: coupling reagent (in polynucleotide synthesis); puriss.
• Linear Formula: (CH3)3C6H2SO2Cl

DETAILS

MP Biomedicals - 02151610

White to off-white crystals.
Coupling reagent for polynucleotide synthesis.
Sulfonating agent for carbohydrates.

Sigma Aldrich - M7707

Application
Coupling reagent in polynucleotide synthesis.1
Packaging
5, 25, 100 g in glass bottle

Sigma Aldrich - 63932

Other Notes
Reagent for intramolecular lactamizations and lactonizations1,2; Reagent for protecting guanidino groups3; For the protection of tryptophan4

REFERENCES

• 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.
• Selective reagent for sulfonylation of carbohydrates: J. Chem. Soc., Perkin 1, 1373 (1974).