1633-82-5

Usage

Uses

Used in Pharmaceutical Industry:
3-Chloropropanesulfonyl chloride is used as an intermediate for the preparation of many enzymatic inhibitors. Its application in this industry is due to its ability to facilitate the synthesis of compounds that can inhibit the activity of certain enzymes, which can be beneficial in the development of drugs targeting specific enzyme-related diseases.
Used in Organic Chemistry:
3-Chloropropanesulfonyl chloride is used as a reagent in the generation and trapping of derived sulfene with imines and glyoxylates in the presence of chinchona alkaloids. This process provides chiral sultams and sultones, which are valuable in the field of organic chemistry for their unique properties and potential applications in various chemical reactions and syntheses.
Overall, 3-Chloropropanesulfonyl chloride is a versatile compound with applications in both the pharmaceutical and organic chemistry industries, primarily due to its role as an intermediate in the synthesis of enzymatic inhibitors and its utility in generating chiral sultams and sultones.

InChI:InChI=1/C3H6Cl2O2S/c4-2-1-3-8(5,6)7/h1-3H2

Upstream product

• 287-27-4 trimethylene sulphide 
• 19721-22-3 3-sulfanylpropanol 
• 1120-71-4 1,3-propanesultone 
• 24308-28-9 1,3-propanesultine 
• 10147-36-1 n-propanesulfonyl chloride 
• 7782-50-5 chlorine 
• 64-19-7 acetic acid 
• 15909-83-8 3-hydroxypropanesulfonic acid 
• 10026-13-8 phosphorus pentachloride 
• 540-54-5 1-Chloropropane 
• 3542-44-7 sodium 3-hydroxypropanesulphonate 

Downstream Products

• 90675-22-2 3-chloro-propane-1-sulfonic acid N'-phenyl-hydrazide 
• 63556-32-1 1-[2-(1,1-dioxo-1λ⁶-isothiazolidin-2-yl)-ethyl]-4-(3-trifluoromethyl-phenyl)-piperazine 
• 21297-87-0 3-Chloro-propane-1-sulfonic acid phenyl ester 
• 140685-47-8 N-benzyloxycarbonyl-3-chloropropanesulfonamide 
• 78472-00-1 3-chloro-propane-1-sulfonic acid dimethylamide 
• 146475-47-0 1-butyl 3-chloro-1-propanesulfonate 
• 1026803-80-4 1-Benzyl-4-(3-chloro-propane-1-sulfonyl)-piperazine 
• 1027546-51-5 1-(3-Chloro-propane-1-sulfonyl)-4-(3-trifluoromethyl-benzyl)-piperazine 
• 1026433-26-0 (2R,3R,4S)-4-Benzo[1,3]dioxol-5-yl-1-{2-[(3-chloro-propane-1-sulfonyl)-propyl-amino]-ethyl}-2-(3-fluoro-4-methoxy-phenyl)-pyrrolidine-3-carboxylic acid ethyl ester 
• 263552-81-4 1,3-dibutyl-7-(3-chloro-propane-1-sulfonyl)-3,7-dihydro-purine-2,6-dione 
• 216487-29-5 N₁-ethyl-3-chloro-1-propanesulfonamide 
• 365565-97-5 3-chloro-propane-1-sulfonic acid [4-(8-methyl-imidazo[1,2-a]pyridin-2-yl)-phenyl]-amide 
• 591249-56-8 2-benzhydryl-1,2-isothiazolidine 1,1-dioxide 
• 692755-50-3 4β-(3-chloropropyl)sulfonamido-4'-tert-butyldimethylsilyloxy-4'-O-demethyl-4-desoxypodophyllotoxin 

Relevant academic research and scientific papers

Structural Engineering and Optimization of Zwitterionic Salts for Expeditious Discovery of Thermoresponsive Materials

This work reported the discovery of N-triflimide (NTf)-based zwitter-ionic liquids (ZILs) that exhibit UCST-type phase transitions in water, and their further structural optimization in finetuning polarity to ultimately afford newfangled thermosensitive materials carrying attractive and biocompatible Tc values that clearly demonstrated the true value of the tunability of ZIL structure. This research established that with non-aromatic, acyclic ZILs as small-molecule thermoresponsive materials, their mixing and de-mixing with water triggered by temperatures are entirely reversible.

Green synthesis method of 3-chloropropyl sulfonyl chloride

The invention discloses a green synthesis method of 3-chloropropyl sulfonyl chloride. The green synthesis method comprises a synthesis route as shown in the specification and specifically comprises the following steps: (1) by taking 1-bromine-3-chloropropane and thiourea as raw materials, preparing in an appropriate temperature and a solvent so as to obtain S-(3-chloropropyl) isothiourea; (2) carrying out a chlorination reaction on the S-(3-chloropropyl) isothiourea obtained in the step (1) under conditions of appropriate catalysts, temperatures and solvents, thereby obtaining 3-chloropropyl sulfonyl chloride. By adopting the mode, the green synthesis method has the characteristics of being gentle in reaction condition, high in yield, simple and convenient to operate and green and environmentally friendly, and large-scale production of the 3-chloropropyl sulfonyl chloride can be achieved.

Bispiperidines as antithrombotic agents

Novel compounds which are inhibitors of the binding of fibrinogen to the Gp IIb/IIIa platelet receptors, and which can be used therepeutically as antithrombotic agents

Quinolinoxy phenylsulphonamides

New phenylsulphonamide of the formula in which STR1 R1 represents a pyridyl, quinolyl or isoquinolyl radical which is unsubstituted or substituted by halogen, alkyl, cycloalkyl, alkoxy, cyano, nitro, halogenoalkyl, halogenoalkoxy, alkoxycarbonyl or alkylsulphonyl, R2 represents hydrogen, cyano, nitro, halogen, alkyl, alkoxy, halogenoalkyl, halogenoalkoxy or alkoxycarbonyl, R3 represents an aryl radical which is unsubstituted or monosubstituted, disubstituted or trisubstituted by halogen, halogenoalkyl, halogenoalkoxy, alkyl, alkoxy, alkylthio, alkylsulphonyl, cyano, nitro or alkoxycarbonyl, the substituents being identical or different, or represents pentafluorophenyl or represents a straight-chain, branched or cyclic alkyl which is unsubstituted or substituted by halogen, aryl, aryloxy, cyano, alkoxycarbonyl, alkoxy, alkylthio or trifluoromethyl, and X represents an --O--, --A--B-- or --B--A-- group where A denotes --O--, STR2 and B denotes --CH2 -- or STR3 where R1 does not represent a pyridyl radical when x represents an --O-- group, and salts thereof are prepared by reacting appropriate amines with sulphonyl halides. The substituted phenylsulphonamides can be employed as active compounds for inhibiting enzymatic reactions and for inhibiting thrombocyte aggregations.

Organic sulfur mechanisms. 24. Preparation and reaction of 2-hydroxyethanesulfonyl chloride, the first hydroxyalkanesulfonyl chloride

2-Hydroxyethanesulfonyl chloride (1a) is readily made by reaction of an aqeous solution of 2-mercaptoethanol (4a) with chlorine.This is the first clearly proved preparation of a compound which is both an alcohol and a sulfonyl chloride.Reactions of 1a with water and alcohols evidently proceed largely by intramolecular cyclization to the transient β-sultone (2a), which then undergoes nucleophilic ring opening to form the products.In the presence of tertiary amines a minor but significant part of the reaction is shown by deuterium labelling to proceed via hydroxymethylsulfene (14), the principal reaction of which is simply to add the alcohol or water; only a small part, if any, of the sulfene (14) loses the hydroxyl group to give the ethenesulfonate derivatives (13 or 22).Aqueous chlorination of 3-mercapto-1-propanol gave 3-chloro-1-propanesulfonyl chloride (5a) and 1,3-propane sultone (2b) with no sign of any 3-hydroxy-1-propanesulfonyl chloride (1b).A mechanism for the aqueous chlorination process invoking a cyclic chlorooxasulfoxonium ion (27) is discussed.

Studies on Sulphochlorination of Paraffins. VII. Studies on the Chlorination of Individual Alkane Sulphochlorides

The products of the chlorination of individual C2-C6 alkane sulphochlorides were studied by means of 13C-n.m.r. spectroscopy.In no case a geminal chloro sulphochloride could be found, and only in very few cases chlorination at vicinal C-H-bonds took place.As in the sulphochlorination of alkane sulphochlorides the C-H-bonds geminal and vicinal to the sulphochloride group are strongly desactivated.The results of 13C-n.m.r. analyses were confirmed by the results of gaschromatographgy of the sulphonic acid dimethyl amides, formed by the reaction of the chlorination mixtures with dimethyl amine.

Studies on Sulphochlorination of Paraffins. VI. Studies on the Sulphochlorination of individual Alkyl Chlorides

The products of sulphochlorination of individual C2-C7 alkyl chlorides were studied by means of 1H- and 13C-n.m.r. spectroscopy.Gaschromatographic determination of the isomers formed was possible after the reaction of the chloroalkane sulphochloride mixture with dimethyl amine in ether.In no case geminal chloroalkane sulphochlorides were formed.Vicinal chlorosulphochlorides are formed,but substitution in greater distance from thechlorine is preferred if possible.Thus higher alkyl chlorides yield only verylittle amounts of vicinal chloroalkane sulphochlorides.The relative rates of sulphochlorination of alkyl chlorides were determined by competitive rections.

N-sulfonyl-N-dihalophenylimidazolidinediones

3-(3' -Dihalophenyl)-1-sulfonylimidazolidine-2,4-5'-diones of the formula: STR1 wherein X is a halogen atom, R1 is a C1 -C12 alkyl group, a C2 -C4 alkenyl group or a halogenated C1 -C4 alkyl group having 1 to 3 halogen atoms, and R2 and R3 are individually a hydrogen atom or a methyl group, which show high microbicidal activities against various fungi and bacteria without any material toxicity to mammals and which plants and can be produced by reacting the corresponding 1-unsubstituted compound with a sulfonyl halide.