98-09-9 Usage
Description
Benzenesulfonyl chloride is a colorless oily liquid with a pungent odor, insoluble in water, and soluble in ethanol and ether. It is a toxic and corrosive chemical that can cause skin, eye, and mucous membrane irritation, and burns. It has a melting point of approximately 40°F and may emit toxic fumes when heated to high temperatures.
Uses
Used in Liquid Crystals Industry:
Benzenesulfonyl chloride serves as an intermediate for the synthesis of liquid crystals, which are essential components in display technologies.
Used in Pharmaceutical Industry:
Benzenesulfonyl chloride is used as a reagent in the synthesis of alpha-disulfones, sulfonamides, and sulfoante esters, which are important precursors in the development of pharmaceutical compounds.
Used in Food Analysis:
It is widely used to check the assay of thiamine in different food products, helping to ensure the nutritional quality of food items.
Used in Environmental Analysis:
Benzenesulfonyl chloride acts as 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, contributing to environmental monitoring and protection.
Used in Chemical Research:
It is a common reagent used in the Hinsberg test for the detection and distinction of the type of amines as primary, secondary, and tertiary amines, aiding in the identification and classification of amine compounds.
Used in Organic Synthesis:
Benzenesulfonyl chloride reacts with Grignard reagents to form oxindoles from N-unsubstituted indoles, which are valuable intermediates in organic synthesis.
General Description:
Benzenesulfonyl chloride is a colorless to slightly yellow solid that is very irritating to skin, eyes, and mucous membranes. It is 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.
Check Digit Verification of cas no
The CAS Registry Mumber 98-09-9 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 9 and 8 respectively; the second part has 2 digits, 0 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 98-09:
(4*9)+(3*8)+(2*0)+(1*9)=69
69 % 10 = 9
So 98-09-9 is a valid CAS Registry Number.
InChI:InChI=1/C6H5ClO2S/c7-10(8,9)6-4-2-1-3-5-6/h1-5H
98-09-9Relevant articles and documents
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Wittmann et al.
, p. 734 (1969)
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Copper-Catalyzed N-Directed Distal C(sp3)-H Sulfonylation and Thiolation with Sulfinate Salts
Chen, Guang-Le,He, Shi-Hui,Cheng, Liang,Liu, Feng
supporting information, p. 8338 - 8342 (2021/10/25)
We herein report a selective and catalytic C(sp3)-H functionalization approach to access amines bearing organo-sulfonyl and organo-thiol groups. This reaction proceeds through a cascade process of N-radical formation, alkyl radical formation via 1,5-HAT, and C-S bond formation, thereby offering a series of functionalized amines. This method could enable primary, secondary, and tertiary C(sp3)-H sulfonylation and thiolation and also exhibits good functional group tolerance.
Chromoselective Synthesis of Sulfonyl Chlorides and Sulfonamides with Potassium Poly(heptazine imide) Photocatalyst
Antonietti, Markus,Guldi, Dirk M.,Markushyna, Yevheniia,Savateev, Aleksandr,Schü?lbauer, Christoph M.,Ullrich, Tobias
supporting information, p. 20543 - 20550 (2021/08/12)
Among external stimuli used to promote a chemical reaction, photocatalysis possesses a unique one—light. Photons are traceless reagents that provide an exclusive opportunity to alter chemoselectivity of the photocatalytic reaction varying the color of incident light. This strategy may be implemented by using a sensitizer capable to activate a specific reaction pathway depending on the excitation light. Herein, we use potassium poly(heptazine imide) (K-PHI), a type of carbon nitride, to generate selectively three different products from S-arylthioacetates simply varying the excitation light and otherwise identical conditions. Namely, arylchlorides are produced under UV/purple, sulfonyl chlorides with blue/white, and diaryldisulfides at green to red light. A combination of the negatively charged polyanion, highly positive potential of the valence band, presence of intraband states, ability to sensitize singlet oxygen, and multi-electron transfer is shown to enable this chromoselective conversion of thioacetates.
Preparation method for symmetric diaryl disulfide
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Paragraph 0038; 0039; 0040; 0041, (2019/04/17)
The invention discloses a preparation method for symmetric diaryl disulfide. The preparation method comprises the following steps: using aromatic hydrocarbon as shown in a general formula (I) as a rawmaterial and reacting with chlorosulfonic acid to generate aryl chlorosulfonic acid, and reacting with sulfoxide chloride to synthesize aryl sulfonyl chloride as shown in a general formula (II); andpreparing the symmetric diaryl disulfide as shown in a general formula (III) under the action of a reducing agent through a reduction reaction by the aryl sulfonyl chloride as shown in the general formula (II). The disclosed preparation method for the symmetric diaryl disulfide has many advantages of low toxicity of the reaction raw material, short reaction time, cheap reagents and easy acquisition, convenient separation and purification and the like, and has very high application value and industrial production value.