Benzenesulfonyl chloride
C6H5ClO2S
benzenesulfonyl chloride
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Identification
- CAS Number
- 98-09-9
- EC Number
- 202-636-6
- UN Number
- 2225
- PubChem CID
- 7369
Physical-chemical properties
- Molecular Formula
- C6H5ClO2S
- Molar Mass
- 176.62 g/mol
- IUPAC Name
- benzenesulfonyl chloride
Chemical Identifiers
- InChI
- InChI=1S/C6H5ClO2S/c7-10(8,9)6-4-2-1-3-5-6/h1-5H
- InChI Key
- CSKNSYBAZOQPLR-UHFFFAOYSA-N
Overview
Benzenesulfonyl chloride (CAS 98-09-9) is an aromatic sulfonyl chloride compound with high reactivity toward nucleophiles and versatile synthetic applications. This colorless to pale yellow liquid represents a fundamental building block in organic synthesis, featuring a benzene ring directly attached to a sulfonyl chloride functional group. The compound exhibits characteristic properties of both aromatic systems and acyl chloride derivatives, making it an invaluable reagent in pharmaceutical, agrochemical, and specialty chemical manufacturing. With its molecular formula C6H5ClO2S and molecular weight of 176.62 g/mol, benzenesulfonyl chloride demonstrates exceptional electrophilic character due to the electron-withdrawing nature of the sulfonyl group. The compound requires careful handling due to its corrosive properties and classification under ADR Class 8. It readily hydrolyzes in the presence of moisture, releasing hydrogen chloride gas, necessitating storage under anhydrous conditions. Safety protocols must include appropriate ventilation and protective equipment to prevent inhalation or skin contact. Like other reactive chlorides in its chemical family, including benzene-1,4-dicarbonyl chloride, benzenesulfonyl chloride demands respect for its aggressive nature toward organic materials and biological tissues. Primary industrial applications include the synthesis of sulfonamide pharmaceuticals, where it serves as a key intermediate in drug development. The compound also finds extensive use in the production of dyes, pigments, and polymer additives. Additionally, it functions as a protecting group reagent in complex organic syntheses, particularly in peptide chemistry and advanced material science applications. OYSI maintains reliable supply chains for benzenesulfonyl chloride to support European chemical manufacturing operations.
Safety & Classification
No Hazard Classification
This substance is not classified as hazardous according to CLP Regulation (EC) No 1272/2008.
Transport (ADR)
| UN Number | 2225 |
| ADR Class | 8 |
| Packing Group | III |
| Tunnel Code | E |
| Proper Shipping Name | Benzensulfonylchlorid |
| Marine Pollutant | No |
Frequently Asked Questions
What is benzenesulfonyl chloride?
Benzenesulfonyl chloride is an organic chemical compound with the molecular formula C6H5ClO2S and CAS number 98-09-9. It belongs to the family of sulfonyl chlorides, featuring a benzene ring attached to a sulfonyl chloride functional group (-SO2Cl). This compound has a molecular weight of 176.62 g/mol and serves as an important intermediate in organic synthesis and pharmaceutical manufacturing.
What are the physicochemical properties of benzenesulfonyl chloride?
Benzenesulfonyl chloride is a colorless to pale yellow liquid at room temperature with a pungent, irritating odor. It has a boiling point of approximately 251°C and a density of about 1.38 g/cm³. The compound is highly reactive with water, undergoing hydrolysis to form benzenesulfonic acid and hydrochloric acid. It is soluble in organic solvents like benzene and chloroform but reacts vigorously with water and alcohols.
What is benzenesulfonyl chloride used for?
Benzenesulfonyl chloride is primarily used as a reagent in organic synthesis for introducing benzenesulfonyl groups into molecules. It serves as a key intermediate in pharmaceutical manufacturing, particularly in the synthesis of sulfonamide drugs and other medicinal compounds. Additionally, it is used in the production of dyes, pesticides, and various specialty chemicals. The compound is also employed in analytical chemistry for derivatization reactions and protein modification studies.
How to handle benzenesulfonyl chloride safely?
Benzenesulfonyl chloride requires careful handling due to its corrosive nature and reactivity with moisture. Essential personal protective equipment includes chemical-resistant gloves, safety goggles, and protective clothing. Work should be conducted in a well-ventilated area or under a fume hood to avoid inhalation of vapors. Avoid contact with water, alcohols, and other nucleophiles as this can cause violent reactions and release of toxic gases like hydrogen chloride.
How to store benzenesulfonyl chloride correctly?
Benzenesulfonyl chloride must be stored in a cool, dry place away from moisture and heat sources. Use tightly sealed containers made of compatible materials like glass or PTFE-lined vessels. Keep the chemical away from water, alcohols, amines, and other nucleophilic substances to prevent unwanted reactions. Storage areas should be well-ventilated and equipped with appropriate spill containment measures. Maintain temperatures below 25°C for optimal stability.
What to do in case of contact with benzenesulfonyl chloride?
Benzenesulfonyl chloride contact requires immediate action due to its corrosive properties. For skin contact, immediately remove contaminated clothing and rinse affected area with copious amounts of water for at least 15 minutes. In case of eye contact, flush thoroughly with water and seek immediate medical attention. If inhaled, move the person to fresh air immediately. For ingestion, do not induce vomiting and seek emergency medical care. Always consult a physician after any significant exposure.
How to dispose of benzenesulfonyl chloride properly?
Benzenesulfonyl chloride disposal must comply with local and national hazardous waste regulations. The compound should never be poured down drains or released into the environment. Small quantities can be carefully hydrolyzed under controlled conditions to form less hazardous products, but this should only be done by trained personnel. Larger quantities require disposal through licensed hazardous waste contractors. Always consult local environmental authorities for specific disposal requirements and approved facilities.
How to transport benzenesulfonyl chloride?
Benzenesulfonyl chloride is classified under ADR Class 8 (Corrosive substances), Packing Group III for transportation purposes. It must be packaged in UN-approved containers suitable for corrosive liquids and properly labeled with appropriate hazard markings. Transportation requires compliance with ADR regulations including proper documentation, vehicle placarding, and driver training. Packages must be secured to prevent damage during transit and protected from temperature extremes and moisture exposure.
Is benzenesulfonyl chloride subject to special regulations?
Benzenesulfonyl chloride is regulated under various chemical safety frameworks including REACH regulation in Europe, requiring registration for commercial use. While not classified as a Substance of Very High Concern (SVHC), it must comply with CLP regulation for classification and labeling. Users must follow standard industrial chemical handling protocols and may need to report usage depending on quantities. Always check current regulatory status and local requirements before handling or using this chemical.
Where to buy benzenesulfonyl chloride in Europe?
Benzenesulfonyl chloride is available through specialized chemical distributors across Europe, including OYSI, a trusted European supplier of technical chemicals. OYSI provides this compound to qualified industrial and research customers with proper documentation and safety data sheets. As a regulated chemical, purchases typically require verification of intended use and appropriate handling capabilities. Contact OYSI directly for availability, specifications, and technical support for your specific application requirements.
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Data Sources
Classification per CLP Regulation (EC) No 1272/2008. Data from ECHA and PubChem.