Benzenesulfonyl chloride
- CAS No.
- 98-09-9
- Chemical Name:
- Benzenesulfonyl chloride
- Synonyms
- benzenesulfonyl;Benzenesulphochloride;Phenylsulfonyl chloride;BENZENESULPHONYL CHLORIDE;BENZENE SULFOCHLORIDE;Benzolsulfonylchlorid;bsc-refined;AKOS BBS-00004356;benzolsulfochloride;rcrawastenumberu020
- CBNumber:
- CB6854744
- Molecular Formula:
- C6H5ClO2S
- Molecular Weight:
- 176.62
- MOL File:
- 98-09-9.mol
- MSDS File:
- SDS
- Modify Date:
- 2024/7/24 17:31:20
| Melting point | 13-15 °C (lit.) |
|---|---|
| Boiling point | 251-252 °C (lit.) |
| Density | 1.384 g/mL at 25 °C (lit.) |
| vapor pressure | 0.04 mm Hg ( 20 °C) |
| refractive index |
n |
| Flash point | >230 °F |
| storage temp. | Store below +30°C. |
| solubility | alcohol: soluble |
| form | Liquid |
| color | Clear |
| Water Solubility | may decompose |
| Sensitive | Moisture Sensitive |
| Merck | 14,1072 |
| BRN | 606926 |
| Stability | Stable. Incompatible with water, strong oxidizing agents, strong bases, methyl formamide, dimethyl sulfoxide. |
| LogP | 3.39 at 23℃ |
| CAS DataBase Reference | 98-09-9(CAS DataBase Reference) |
| NIST Chemistry Reference | Benzenesulfonyl chloride(98-09-9) |
| EPA Substance Registry System | Benzenesulfonyl chloride (98-09-9) |
SAFETY
Risk and Safety Statements
| Symbol(GHS) |   GHS05,GHS07 |
|||||||||
|---|---|---|---|---|---|---|---|---|---|---|
| Signal word | Danger | |||||||||
| Hazard statements | H302-H314 | |||||||||
| Precautionary statements | P270-P280-P301+P312-P303+P361+P353-P304+P340+P310-P305+P351+P338 | |||||||||
| Hazard Codes | C | |||||||||
| Risk Statements | 20/22-34-42/43-29-22 | |||||||||
| Safety Statements | 23-26-36/37/39-45 | |||||||||
| RIDADR | UN 2225 8/PG 3 | |||||||||
| WGK Germany | 1 | |||||||||
| RTECS | DB8750000 | |||||||||
| F | 21 | |||||||||
| TSCA | Yes | |||||||||
| HazardClass | 8 | |||||||||
| PackingGroup | III | |||||||||
| HS Code | 29049090 | |||||||||
| Toxicity | LD50 orl-rat: 1960 mg/kg MEPAAX 20,513,69 | |||||||||
| NFPA 704 |
|
Benzenesulfonyl chloride price More Price(20)
| Manufacturer | Product number | Product description | CAS number | Packaging | Price | Updated | Buy |
|---|---|---|---|---|---|---|---|
| Sigma-Aldrich(India) | 8.00470 | Benzenesulfonyl chloride for synthesis | 98-09-9 | 100ML | ₹4010.01 | 2022-06-14 | Buy |
| Sigma-Aldrich(India) | 8.00470 | Benzenesulfonyl chloride for synthesis | 98-09-9 | 500ML | ₹8440 | 2022-06-14 | Buy |
| Sigma-Aldrich(India) | 8.00470 | Benzenesulfonyl chloride for synthesis | 98-09-9 | 2.5L | ₹15390 | 2022-06-14 | Buy |
| Sigma-Aldrich(India) | 108138 | Benzenesulfonyl chloride 99% | 98-09-9 | 100G | ₹1909.55 | 2022-06-14 | Buy |
| Sigma-Aldrich(India) | 12620 | Benzenesulfonyl chloride for HPLC derivatization | 98-09-9 | 100ML | ₹3238.85 | 2022-06-14 | Buy |
Benzenesulfonyl chloride Chemical Properties,Uses,Production
Chemical Properties
Benzenesulfonyl chloride is a colorless oily liquid with a pungent odor. Insoluble in water, soluble in ethanol and ether. Can react with ammonia, amine and alcohol to produce benzenesulfonamide and benzene sulfonate respectively. It is toxic, irritates skin, eyes and mucous membranes, corrosive, and can cause burns. Oral LD50 1960mg/kg in rats.
Uses
Benzenesulfonyl chloride reacts with Grignard reagents to form oxindoles from N-unsubstituted indoles. It is widely used to check the assay of thiamine in different food products. It is involved in the synthesis of alpha-disulfones, sulfonamides and sulfoante esters as precursor. It is a derivatization reagent for the determination of various amines in waste water and surface water at the sub-ppb level by gas chromatography-mass spectrometry. It is common reagent used in Hinsberg test for detection and distinguishing the type of amines as primary, secondary and tertiary amines.
Production Methods
The most convenient method for the production of benzenesulfonyl chlorides is the chlorosulfonation reaction of benzene or substituted benzene with chlorosulfuric acid. Sulfonation and formation of the sulfonyl chlo- ride take place in one reaction sequence:
Ar-H+Cl-SO3H→ArSO3H+HCl
ArSO3H+Cl-SO3H=ArSO2Cl+H2SO4
Sulfone is formed in a side reaction of the chlorosulfonation. The amount of sulfone formation can be reduced by diluting with a solvent, by using a large excess of chlorosulfuric acid, or by adding sulfone-inhibiting substances, e.g., alkali metal and ammonium salts, acetic acid, phosphoric acid, dimethylformamide, or amidosulfuric acid.
For industrial chlorosulfonation the chlorosulfuric acid is introduced into a cast-steel or enameled steel vessel and 10 – 25 mol% of the aromatic compound is stirred in at 25 – 30 ℃, whereupon sulfonation of the aromatic compound and HCl formation occur. The formation of sulfonyl chloride is initiated by heating the reactants to 50 – 80 ℃. The reaction is exothermic. The sulfonyl chloride is isolated by draining the reaction mass onto water and simultaneous cooling. Excess chlorosulfuric acid is decomposed, and the sulfonyl chloride either precipitates or separates as an organic liquid phase. The quality of the chlorosulfuric acid affects the yield.
Other chlorinating agents, such as phosgene, thionyl chloride, sulfuryl chloride, or phosphorus pentachloride, can be used instead of chlorosulfu- ricacid. When thionyl chloride is used the sulfonyl chloride is obtained from the sulfonic acid in high yield and without formation of sulfuric acid.
General Description
A colorless to slightly yellow solid that melts at approximately 40°F. Very irritating to skin, eyes and mucous membranes. May emit toxic fumes when heated to high temperatures. Used to make dyes and other chemicals.
Air & Water Reactions
Insoluble and stable in cold water [Merck]. Decomposes in hot water to produce corrosive and toxic hydrochloric acid and benzenesulfonic acid. Rate of reaction decreases as temperature decreases.
Reactivity Profile
Benzenesulfonyl chloride is incompatible with strong oxidizing agents and bases, including amines. Corrodes metals in the presence of water due to slow formation of hydrochloric acid and benzenesulfonic acid [USCG, 1999]. May react vigorously or explosively if mixed with diisopropyl ether or other ethers in the presence of trace amounts of metal salts [J. Haz. Mat., 1981, 4, 291].
Health Hazard
May be fatal if inhaled, swallowed or absorbed through skin. Contact may cause skin and eye burns. Irritating to eyes, skin and mucous membranes. INGESTION: May cause abdominal spasm and vomiting.
Safety Profile
Poison by intraperitoneal route. Adangerous storage hazard. It may explode in a sealedbottle. Explosive reaction with dimethyl sulfoxide. Reactsvigorously with methyl formamide. When heated todecomposition it emits toxic fumes of Cl- and SO
Potential Exposure
It is used as a chemical intermediate for benzenesulfonamides, thiophenol, glybuzole (hypoglycemic agent), N-2-chloroehtylamides, benzonitrile; for its esters-useful as insecticides, and miticides.
Shipping
UN2225 Benzene sulfonyl chloride, Hazard class: 8; Labels: 8—Corrosive material.
Purification Methods
Distil the sulfonyl chloride, then treat it with 3mole % each of toluene and AlCl3, and allow it to stand overnight. The sulfonyl chloride is distilled off at 1mm pressure and then carefully fractionally distilled at 10mm in an all-glass column. [Adams & Marvel Org Synth Coll Vol I 84 1941, Jensen & Brown J Am Chem Soc 80 4042 1958, Beilstein 11 IV 49.] It is TOXIC.
Incompatibilities
Violent reaction with strong oxidizers, dimethyl sulfoxide, and methyl formamide. It is very reactive with bases and many organic compounds. Incompatible with ammonia, aliphatic amines. Water contact forms hydrochloric and chlorosulfonic acids. Aqueous solutions of this chemical are strong acids that react violently with bases. Attacks metals in presence of moisture.
Benzenesulfonyl chloride Preparation Products And Raw materials
Raw materials
Preparation Products
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