60706-63-0

Basic information

• Product Name: 2,3,5,6-TETRAMETHYLBENZENESULFONYL CHLORIDE
• Synonyms: BENZENESULFONYL CHLORIDE, 2,3,5,6-TETRAMETHYL-;2,3,5,6-TETRAMETHYLBENZENESULFONYL CHLORIDE;2,3,5,6-TETRAMETHYLBENZENESULPHONYL CHLORIDE;TIMTEC-BB SBB005823;Benzenesulfonyl chloride, 2,3,5,6-tetramethyl- (7CI, 9CI);2,3,5,6-Tetramethylbenzenesulfonyl chloride,98%;2,3,5,6-Tetramethylbenzenesulfonyl cholride
• CAS NO: 60706-63-0
• Molecular Formula: C₁₀H₁₃ClO₂S
• Molecular Weight: 232.73
• Product Categories: SULFONYLHALIDE
• Mol File: 60706-63-0.mol

Chemical Properties

• Melting Point: 97-101 °C
• Boiling Point: 343.8 °C at 760 mmHg
• Flash Point: 161.7 °C
• Appearance: White to pale cream/Crystalline Powder
• Density: 1.217 g/cm³
• Vapor Pressure: 0.000137mmHg at 25°C
• Refractive Index: 1.528
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Sensitive: Moisture Sensitive
• BRN: 1876644
• CAS DataBase Reference: 2,3,5,6-TETRAMETHYLBENZENESULFONYL CHLORIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 2,3,5,6-TETRAMETHYLBENZENESULFONYL CHLORIDE(60706-63-0)
• EPA Substance Registry System: 2,3,5,6-TETRAMETHYLBENZENESULFONYL CHLORIDE(60706-63-0)

Safety Data

• Hazard Codes: C,Xi
• Statements: 34-29-36
• Safety Statements: 45-36/37/39-26
• RIDADR: 3261
• HazardClass: 8
• PackingGroup: II
• Hazardous Substances Data: 60706-63-0(Hazardous Substances Data)

Usage

InChI:InChI=1/C10H13ClO2S/c1-6-5-7(2)9(4)10(8(6)3)14(11,12)13/h5H,1-4H3

Upstream product

• 95-93-2 1,2,4,5-tetramethylbenzene 

Downstream Products

• 14786-84-6 2,3,5,6-tetramethylthiophenol 
• 92890-85-2 2,3,5,6-tetramethylbenzenesulfonamide 
• 32479-04-2 C₂₃H₂₅N₃O₂S 
• 62533-27-1 2,3,5,6-tetramethylbenzene-1-sulfonyl azide 
• 117678-83-8 1-(3-Durylsulfonyloxy)-6-nitrobenzotriazol 
• 799252-62-3 NC₅H₄CH₂NHSO₂C₆H(CH₃)4 
• 63157-79-9 Bis(2,3,5,6-tetramethylphenyl)disulfide 

Relevant articles and documents

Intermolecular 1,2-Difunctionalization of Alkenes Enabled by Fluoroamide-Directed Remote Benzyl C(sp3)-H Functionalization

A copper-catalyzed remote benzylic C-H functionalization strategy enabling 1,2-difunctionalization of alkenes with 2-methylbenzeneamides and nucleophiles, including alcohols, indoles, pyrroles, and the intrinsic amino groups, is reported, which is charact

Propanolysis of arenesulfonyl chlorides: Nucleophilic substitution at sulfonyl sulfur

We have studied the mechanism of solvolysis of arenesulfonyl chlorides by propan-1-ol and propan-2-ol at 303-323 K. Kinetic profiles were appropriately fit by first-order kinetics. Reactivity increases with electron-donating substituents. Ortho-alkyl substituted derivatives of arenesulfonyl chlorides show increased reactivity, but the origin of this “positive” ortho-effect remains unclear. Likely, ortho-methyl groups restrict rotation around the C-S bond, facilitating the attack of the nucleophile. No relevant reactivity changes have been found with propan-1-ol and propan-2-ol in terms of nucleophile steric effect. The existence of isokinetic relationships for all substrates suggests a single mechanism for the series. Solvolysis reactions of all substrates in both alcohols show isokinetic temperatures (Tiso) close to the working temperature range, which is an evidence of the process being influenced by secondary reactivity factors, likely of steric nature in the TS. Solvation plays a relevant role in this reaction, modulating the reactivity. In some cases, the presence of t-Bu instead of Me in para- position leads to changes in the first solvation shell, increasing the energy of the reaction (ca. 1?kJ·mol?1). The obtained results suggest the same kinetic mechanism of solvolysis of arenesulfonyl chlorides for propan-1-ol and propan-2-ol, as in MeOH and EtOH, where bimolecular nucleophilic substitution (SN2) takes place with nucleophilic solvent assistance of one alcohol molecule and the participation of the solvent network involving solvent molecules of the first solvation shell.

Solvent network at the transition state in the solvolysis of hindered sulfonyl compounds

Alcoholysis rates of unhindered benzenesulfonyl chlorides (X-ArSO2Cl, X = H-; 4-Br-; 4-Me-) are similar in methanol; the same behavior is also observed in ethanol, whereas the reactivity order in iso-propanol is 4 Me- 2Cl) (X = 2,4,6-Me3-3-NO2-; 2,6-Me2-4-tBu-; 2,4,6-Me3-; 2,3,5,6-Me4-; 2,4,6-iPr3-; 2,4-Me2-; 2,4,6-(OMe)3-) in all studied alcohols show a significant increase in reactivity, the so-called positive steric effect. Most of the substrates showed a reaction order b ~ 2 with respect to the nucleophile in methanol and ethanol, and b ~ 3 in iso-propanol. The correlation between reactivity and the Kirkwood function (1/ξ) gives negative sensitivity (U) for all systems. All substrates showed high sensitivity to media nucleophilicity that depends on ΣσX. Obtained results suggest the alcoholysis of benzenesulfonyl chlorides proceeds through SN2 mechanism where the transition state (TS) involves the participation of 2–3 alcohol molecules; such a TS can be cyclic, in the case of unbranched alcohols, or linear, for alcohols with bulkier hydrocarbon groups like iso-propanol. To include the number of alcohol molecules playing such a role in the TS, the following terminology is proposed: cSN2sn for SN2 reactions involving n solvent molecules in a cyclic (c) TS, where “s” stands for the solvent and “n” is either the closest integer or half-integer to the reaction order relative to the solvent or, in computational studies, the proposed number of solvent molecules taking part in the TS, whereas SN2sn is proposed when the TS is not cyclic. Copyright