4837-38-1

Basic information

• Product Name: Cyclohexanesulfonylchloride
• Synonyms: Cyclohexylsulfonylchloride;NSC 41208
• CAS NO: 4837-38-1
• Molecular Formula: C₆H₁₁ClO₂S
• Molecular Weight: 182.6683
• Mol File: 4837-38-1.mol

Chemical Properties

• Boiling Point: 255.8 °C at 760 mmHg
• Flash Point: 108.5 °C
• Appearance: colorless to yellow liquid
• Density: 1.29 g/cm³
• Vapor Pressure: 0.0256mmHg at 25°C
• Refractive Index: 1.497
• Storage Temp.: 2-8°C
• CAS DataBase Reference: Cyclohexanesulfonylchloride(CAS DataBase Reference)
• NIST Chemistry Reference: Cyclohexanesulfonylchloride(4837-38-1)
• EPA Substance Registry System: Cyclohexanesulfonylchloride(4837-38-1)

Safety Data

• Hazard Codes: C:Corrosive
• Statements: R34:
• Safety Statements: S26:; S36/37/39:; S45:
• RIDADR: UN 3265 8/PG 2
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 4837-38-1(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Cyclohexanesulfonylchloride is used as a key building block for the synthesis of various pharmaceuticals. Its ability to introduce the sulfonyl group into other molecules makes it a valuable component in the development of new drugs with improved therapeutic properties.
Used in Agrochemical Industry:
In the agrochemical industry, Cyclohexanesulfonylchloride is utilized as a crucial intermediate in the synthesis of various agrochemicals. Its reactivity allows for the creation of compounds with enhanced pesticidal or herbicidal activities.
Used in Organic Synthesis:
Cyclohexanesulfonylchloride is employed as a reagent in organic synthesis to introduce the sulfonyl group into other molecules. This functionality is essential for the development of new organic compounds with specific properties and applications.
Used in Research and Development:
In the field of research and development, Cyclohexanesulfonylchloride is used to explore new chemical reactions and pathways. Its reactivity and ability to form diverse compounds make it a valuable tool for discovering novel chemical entities and materials.

InChI:InChI=1/C6H11ClO2S/c7-10(8,9)6-4-2-1-3-5-6/h6H,1-5H2

Upstream product

• 110-82-7 cyclohexane 
• 2550-40-5 1,2-dicyclohexyl disulfide 
• 4251-13-2 thiocyanatocyclohexane 
• 10039-63-1 S-cyclohexyl ethanethioate 
• 1569-69-3 Cyclohexanethiol 
• 98-07-7 Benzotrichlorid 
• 7791-25-5 sulfuryl dichloride 
• 64-19-7 acetic acid 
• 110-86-1 pyridine 
• 141-86-6 2.6-diaminopyridine 
• 97-74-5 bis(dimethylthiocarbamoyl)sulfide 
• 7782-50-5 chlorine 
• 7732-18-5 water 
• 931-51-1 cyclohexylmagnesiumchloride 

Downstream Products

• 90886-59-2 N,N-dimethyl-cyclohexanesulfonamide 
• 5464-06-2 N-phenylcyclohexanesulfonamide 
• 7010-85-7 cyclohexanesulfonic acid methylamide 
• 109450-42-2 1,4-bis-cyclohexanesulfonyloxy-butane 
• 1569-69-3 Cyclohexanethiol 
• 2438-38-2 cyclohexanesulfonamide 
• 5675-01-4 cyclohexanesulfinic acid 
• 368-42-3 cyclohexane-1-sulfonyl fluoride 
• 59427-27-9 C₁₄H₂₆O₆S₂ 
• 24610-65-9 Cyclohexan-sulfonsaeure-(o-tolyl-ester) 
• 25078-02-8 Cyclohexan-sulfonsaeure-(o-methoxy-phenyl-ester) 
• 59427-18-8 Cyclohexansulfonsaeure-<4-tert-butyl-phenylester> 
• 59427-16-6 Cyclohexanesulfonic acid 4-(1-methyl-1-phenyl-ethyl)-phenyl ester 
• 4247-57-8 (1-Chlor-1-cyclohexyl)cyclohexylsulfon 

Relevant articles and documents

High yielding protocol for direct conversion of thiols to sulfonyl chlorides and sulfonamides

In this paper, a new method for oxidative chlorination of thiols to sulfonyl chlorides and sulfonamides using H2O2 in the presence of TMSCl is reported. The excellent yields, short reaction times, excellent efficiencies, low costs, and easy separation of products are the most important advantages of this method.

Sulfonyl halide synthesis by thiol oxyhalogenation using NBS/NCS – iPrOH

A rapid and facile method provides a general route to sulfonyl bromides/chlorides by the oxidation of thiols using NXS – ROH (X?=?Br,Cl, R?=?iPr) as an oxyhalogenation reagent. Control experiments suggest that the alcohol component is the source of oxygen. The proposed method enable the access to structurally diverse sulfonyl bromides and chlorides including challenging examples, inaccessible by other synthetic methods.

Conversion of thiols into sulfonyl halogenides under aerobic and metal-free conditions

An environmentally benign, metal-free synthesis of sulfonyl chlorides and bromides from thiols in the presence of ammonium nitrate, an aqueous solution of HCl and HBr and oxygen as a terminal oxidant was developed. The reactivity of various substituted thiophenols, benzylic-, aliphatic- and heteroaromatic thiols was examined. Ammonium nitrate served as a source of nitrogen oxides (NO/NO2), which are the crucial players in a redox-catalytic cycle. Sulfonyl chlorides and bromides were isolated without extraction and "filtered" over a short pad of silica gel; the use of solvents was greatly reduced in comparison with traditional isolation and purification. A "one-pot" protocol for the conversion of thiol into sulfonamide is also demonstrated. Scale-up experiments on the preparation of sulfonyl chloride and bromide are shown. A possible reaction pathway is discussed.

METHOD FOR PRODUCING SULFONYL CHLORIDE COMPOUNDS

PROBLEM TO BE SOLVED: To provide a production method which enables safe and simple production of sulfonyl chloride compounds in high yields, which are useful as intermediates for medicines, agrochemicals, functional materials, and the like. SOLUTION: Provided is a method for producing sulfonyl chloride compounds comprising oxidation of thiols or disulfides in the presence of an oxidizing agent to produce sulfonyl chloride compounds. As the oxidizing agent is used sodium hypochlorite, and the reaction is performed with the pH of the reaction system adjusted to a neutral or acidic value of pH 7 or less. COPYRIGHT: (C)2015,JPOandINPIT

An efficient method for the preparation of sulfonyl chlorides: Reaction of disulfides or thiols with sodium hypochlorite pentahydrate (NaOCl·5H2O) crystals

The reaction of disulfides or thiols with sodium hypochlorite pentahydrate in acetic acid efficiently provided the corresponding sulfonyl chlorides in high yields.

Oxyhalogenation of thiols and disulfides into sulfonyl chlorides/bromides using oxone-KX (X = Cl or Br) in water

A simple and rapid method for efficient synthesis of sulfonyl chlorides/bromides by oxyhalogenation of thiols and disulfides with oxone-KX (X = Cl or Br) using water as the solvent is described. This journal is the Partner Organisations 2014.

Oxidation of disulfides with electrophilic halogenating reagents: Concise methods for preparation of thiosulfonates and sulfonyl halides

The reaction of aromatic or benzylic disulfides with 2.5 equiv of Selectfluor in acetonitrile/water (10:1) at room temperature efficiently produced the corresponding thiosulfonates. Conversely, the reaction of disulfides with 6.5 equiv of Selectfluor or thiosulfonates with 4.5 equiv of Selectfluor in refluxing acetonitrile/water (10:1) provided sulfonyl fluorides in high yields. Accufluor and FP-T300 are also effective in preparing sulfonyl fluorides from disulfides under the similar reaction conditions. Sulfonyl chlorides or sulfonyl bromides were effectively obtained from the reaction of disulfides with 6 equiv of either N-chlorosuccinimide or N-bromosuccinimide in acetonitrile/water (10:1) at room temperature. Some other electrophilic chlorinating or brominating reagents are also able to be used instead of N-chlorosuccinimide or N-bromosuccinimide for the syntheses of sulfonyl halides from disulfides. These reactions of disulfides with electrophilic halogenating reagents are convenient methods to prepare thiosulfonates and sulfonyl halides.

One-pot tandem reactions for direct conversion of thiols and disulfides to sulfonic esters, alcohols to bis(indolyl)methanes and synthesis of pyrroles catalyzed by N-chloro reagents

A convenient synthesis of sulfonic esters from thiols and disulfides has been described. In situ preparation of sulfonyl chlorides from thiols is accomplished by oxidation with Chloramin-T, tetra-butylammonium chloride (t-Bu4NCl) and water. The sulfonyl chlorides are then further allowed to react with phenol derivatives in the same reaction vessel. Also, a facile synthesis of bis(indolyl)methanes from alcohols using TCCA/KBr/wet-SiO2, and N-substituted pyrroles by reaction of hexane-2,5-dione with primary amines has been accomplished under mild condition with excellent yields.

One-pot tandem reactions for direct conversion of thiols and disulfides to sulfonic esters, and Paal-Knorr synthesis of pyrrole derivatives catalyzed by TCCA

A convenient synthesis of sulfonic esters from thiols and disulfides is described. In situ preparation of sulfonyl chlorides from thiols is accomplished by oxidation with trichloroisocyanuric acid (TCCA), tetra-butylammonium chloride (t-Bu4NCl), and water. The sulfonyl chlorides are then further allowed to react with phenol derivatives in the same reaction vessel. Also, a facile synthesis of N-substituted pyrroles by the reaction of hexane-2,5-dione with primary amines has been accomplished using TCCA as a catalyst under mild condition with excellent yields.

Trichloroisocyanuric acid (TCCA) and N-chlorosuccinimide (NCS) as efficient reagents for the direct oxidative conversion of thiols and disulfides to sulfonyl chlorides

Trichloroisocyanuric acid (TCCA) and N-chlorosuccinimide (NCS) were found to be mild and efficient reagents for the direct oxidative conversion of sulfur compounds to the corresponding arenesulfonyl chlorides in good-to-excellent yields through the oxidative chlorination. The overall process is simple and practical, and it provides convenient access to a variety of aryl or heteroarylsulfonyl chlorides. The mild reaction conditions and the broad substrate scope render this method attractive and complementary to existing syntheses of aryl or heteroarylsulfonyl chlorides. Copyright