Thermo Scientific™ p-Toluenesulphonyl chloride ≥98%

p-Toluenesulfonyl chloride (TsCl), with the molecular formula C₇H₇ClO₂S, is a white crystalline or powdered compound widely used in organic synthesis as a sulfonating and dehydrating agent. It is a derivative of toluene containing a sulfonyl chloride group, making it an essential intermediate for the production of numerous chemicals, dyes, saccharin, and other derivatives.

Key Features:

• Chemical Formula: C₇H₇ClO₂S
• Molecular Weight: 190.64 g/mol
• Purity: ≥97.5% (assay by GC)
• Appearance: White crystalline powder or crystals.
• Melting Point: 64.0–72.0°C
• Storage: Ambient conditions in a tightly sealed container, as it is moisture-sensitive.

Applications:

1. Organic Synthesis:

• Tosylation of Alcohols:
  • Converts alcohols into toluenesulfonate esters, which serve as excellent leaving groups in nucleophilic substitution reactions.
• Carboxylic Acid Esterification:
  • In the presence of alcohol, TsCl facilitates the formation of esters from carboxylic acids.
• N-Tosylation:
  • Blocks imidazole groups in histidine and arginine residues during peptide synthesis. Tosyl groups can be removed using HF.

2. Catalyst and Dehydrating Agent:

• Dehydrates ureas to carbodiimides, a crucial intermediate in organic synthesis.

3. Industrial Applications:

• Used in the production of dyes and saccharin.
• As a flow-promoting agent in paints and adhesives.
• As a plasticizer for polyamides and a gloss enhancer in plastic film preparations.
• Serves as an antistatic agent in industrial processes.

4. Specialized Reactions:

• Promotes the synthesis of epoxides from 1,2-diols in the presence of strong bases.
• Converts 1,3-diols to oxetanes under specific conditions.

Chemical Properties:

• Solubility:
  • Soluble in alcohol, benzene, and ether.
  • Insoluble in water.
• Functional Groups:
  • Sulfonyl chloride, facilitating nucleophilic substitution and leaving group reactions.
• Reactivity:
  • Reacts readily with alcohols, amines, and carboxylic acids to form sulfonate esters, sulfonamides, and esters, respectively.

Handling and Storage:

• Moisture Sensitivity:
  • TsCl is highly reactive with moisture; it should be stored in tightly sealed containers to prevent degradation.
• Incompatibilities:
  • Avoid contact with strong oxidizing agents and strong bases to prevent unwanted reactions.
• Storage Conditions:
  • Store at ambient temperature, away from moisture and direct sunlight.

Packaging Options:

• 250 g: Catalog No. A14547.30
• 500 g: Catalog No. A14547.36
• 1,000 g (1 kg): Catalog No. A14547.0B
• 5,000 g (5 kg): Catalog No. A14547.0I

Notable References:

1. Tosylation of Primary and Secondary Alcohols:
   • J. Org. Chem., 51, 2386 (1986).
2. Epoxide Formation:
   • Synthesis, 706 (1977).
3. N-Tosylation for Peptide Synthesis:
   • Bull. Chem. Soc. Jpn., 42, 1466 (1969).

Key Specifications:

Safety Notes:

• Hazards:
  • Moisture-sensitive and reactive.
• Storage Recommendations:
  • Store in a dry environment to maintain integrity and prevent degradation.
• Recommended Use:
  • Suitable for laboratory research and industrial synthesis.