2-Chloroethanesulfonyl chloride

Base Information

• Chemical Name: 2-Chloroethanesulfonyl chloride
• CAS No.: 1622-32-8
• Molecular Formula: C2H4Cl2O2S
• Molecular Weight: 163.025
• Hs Code.: 29049090
• European Community (EC) Number: 216-594-1
• UN Number: 3385
• UNII: AET6VQ5A3Q
• DSSTox Substance ID: DTXSID5061825
• Nikkaji Number: J78.119C
• Wikipedia: 2-Chloroethanesulfonyl_chloride
• Wikidata: Q4596871
• Mol file: 1622-32-8.mol

Synonyms:2-Chloroethanesulfonyl chloride;1622-32-8;(2-Chloroethyl)sulphonyl chloride;Ethanesulfonyl chloride, 2-chloro-;2-Chloroethylsulfonyl chloride;2-Chloro-ethanesulfonyl chloride;2-Chloroethane sulfochloride;2-chloroethane-1-sulfonyl chloride;beta-Chloroethanesulfonyl chloride;C2H4Cl2O2S;ETHANESULFONYLCHLORIDE, 2-CHLORO-;HSDB 6420;2-chloro-1-ethanesulfonyl chloride;EINECS 216-594-1;AET6VQ5A3Q;chloroethanesulfonyl chloride;BRN 1751202;MFCD00007461;4-04-00-00036 (Beilstein Handbook Reference);Chloroethylsulfonylchloride;UNII-AET6VQ5A3Q;2-Chloroethanesulfochloride;chloroethyl sulfonylchloride;Chloroethylsulfonyl chloride;chloroethylsulphonyl chloride;2-chloroethylsulfonylchloride;SCHEMBL51350;Chloroethane sulfonyl chloride;2-chloroethansulfonyl chloride;2-chloroethylsulphonyl chloride;2-Chloroethane sulfonylchloride;2-chloro-ethansulfonyl chloride;2-chloroethanesulphonyl chloride;2-chloroethariesulfonyl chloride;2-Chloroethane sulfonyl chloride;2-chloroethane-sulfonyl chloride;beta-Chloroethylsulfonyl chloride;DTXSID5061825;2-chloro-1-ethanesulfonylchloride;Chloroethanesulfonyl chloride, 2-;2-chloro-1-ethanesulphonyl chloride;2-chloroethanesulfonic acid chloride;AMY11389;STR04242;.beta.-Chloroethanesulfonyl chloride;2-chloro-1-ethane sulfonyl chloride;STK503664;2-Chloroethanesulfonyl chloride, 96%;AKOS000120369;beta-chloro-ethanesulfonic acid chloride;BP-31052;LS-65688;BB 0259383;CS-0007583;FT-0600441;EN300-17588;A24440;Q4596871;W-107963;Z56965859;2-Chloroethanesulfonyl chloride, purum, >=97.0% (AT);F0001-0582;2-Chloro-ethanesulfonylchlorid;2-Chloroethylsulfonylchloride

Chemical Property of 2-Chloroethanesulfonyl chloride

Chemical Property:

• Appearance/Colour: Clear slightly yellow to brown liquid
• Vapor Pressure: 15 mm Hg ( 84 °C)
• Melting Point: 3 °C
• Refractive Index: n20/D 1.493(lit.)
• Boiling Point: 202.4 °C at 760 mmHg
• Flash Point: 76.2 °C
• PSA: 42.52000
• Density: 1.547 g/cm³
• LogP: 1.87460
• Storage Temp.: Refrigerator
• Sensitive.: Moisture Sensitive
• Water Solubility.: Reacts with water.
• XLogP3: 1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 161.9309059
• Heavy Atom Count: 7
• Complexity: 121
• Transport DOT Label: Poison Inhalation Hazard Dangerous When Wet

Purity/Quality:

98% ^*data from raw suppliers

2-Chloroethanesulfonyl Chloride ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T+
• Hazard Codes: T+
• Statements: 22-26-34-36
• Safety Statements: 26-28-36/37/39-45-23

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Toxic Gases & Vapors -> Acid Halides
• Canonical SMILES: C(CCl)S(=O)(=O)Cl
• Uses: 2-Chloroethanesulfonyl chloride was used in one-pot sulfonylation/intramolecular thia-Michael protocol for the synthesis of 1,5,2-dithiazepine 1,1-dioxides. It was also used in synthesis of vinyl sulfonamides with a furan, carbocyclic, semi cyclic or acyclic 1,3-diene moiety.

Technology Process of 2-Chloroethanesulfonyl chloride

There total 27 articles about 2-Chloroethanesulfonyl chloride which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 90.0%

sodium 2-hydroxyethanesulfonate (1562-00-1) → 2-Chloroethanesulfonyl chloride (1622-32-8)

Guidance literature:

With thionyl chloride; In dichloromethane; N,N-dimethyl-formamide; at 20 - 60 ℃;

Reference yield: 54.0%

2-hydroxyethanesulfonic acid (107-36-8) → 2-Chloroethanesulfonyl chloride (1622-32-8)

Guidance literature:

With phosphorus pentachloride; for 4h; Heating; Sealed tube;

DOI:10.1007/s10593-019-02609-z

Reference yield: 40.0%

2-chloroethanamine hydrochloride (870-24-6) → 2-Chloroethanesulfonyl chloride (1622-32-8)

Guidance literature:

With chlorosulfonic acid; In acetonitrile; at 80 ℃; for 18h;

upstream raw materials:

2,2'-thiobis-ethanol

thiophosphoric acid S-(2-chloro-ethyl) ester O,O'-diethyl ester

chloroethane

2-chloroethyl sulfenyl chloride

Downstream raw materials:

Vinyl sulfonic acid methyl ester

ethenesulfonic acid ethyl ester

vinyl sulfonamide

ethylenesulfonyl fluoride

Refernces

A new approach for the ortho-substitution of anilines and for the synthesis of indolines

10.1016/j.tetlet.2004.04.111

The study presents a new method for the ortho-substitution of anilines and the synthesis of indolines. The process begins with a radical addition of a xanthate to a vinyl sulfanilide, leading to the formation of a dihydrobenzoisothiazole dioxide structure. This intermediate loses sulfur dioxide upon heating to yield a 2-substituted aniline. In some instances, the presence of DBU during heating induces the formation of an indoline. The vinyl sulfanilides are prepared from 2-chloroethylsulfonyl chloride and anilines. The xanthates used in the radical addition can be benzylic, tertiary, or substituted with electrophilic groups like nitriles, ketones, or ketoesters. The study explores various substituents on the nitrogen and the aromatic ring, finding that electron-withdrawing groups facilitate the formation of indolines. The method is notable for its use of readily available starting materials and reagents, and its potential to access compounds that are difficult to obtain through classical approaches.