2-chloroethanesulfonyl chloride Chemical Properties

Melting point:

3 °C

Boiling point:

84-86 °C15 mm Hg(lit.)

Density 

1.56 g/mL at 25 °C(lit.)

vapor pressure 

15 mm Hg ( 84 °C)

refractive index 

n20/D 1.493(lit.)

Flash point:

>230 °F

storage temp. 

Refrigerator

form 

Liquid

color 

Clear slightly yellow to brown

Water Solubility 

Reacts with water.

Sensitive 

Moisture Sensitive

BRN 

1751202

InChI

InChI=1S/C2H4Cl2O2S/c3-1-2-7(4,5)6/h1-2H2

InChIKey

VHCSBTPOPKFYIU-UHFFFAOYSA-N

SMILES

C(S(Cl)(=O)=O)CCl

CAS DataBase Reference

1622-32-8(CAS DataBase Reference)

EPA Substance Registry System

2-Chloro-ethanesulfonyl chloride (1622-32-8)

Safety Information

Hazard Codes 

T+

Risk Statements 

22-26-34-36

Safety Statements 

26-28-36/37/39-45-23

RIDADR 

UN 3390 6.1/PG 1

WGK Germany 

3

RTECS 

KI8060000

F 

10-19

TSCA 

Y

HazardClass 

8

PackingGroup 

II

HS Code 

29049090

Hazardous Substances Data

1622-32-8(Hazardous Substances Data)

Toxicity

mouse,LC50,inhalation,250mg/m3/4H (250mg/m3),Gigiena Truda i Professional'nye Zabolevaniya. Labor Hygiene and Occupational Diseases. Vol. 15(6), Pg. 59, 1971.

MSDS

• Language:English Provider:ACROS
• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

2-chloroethanesulfonyl chloride Usage And Synthesis

Chemical Properties

CLEAR SLIGHTLY YELLOW TO BROWN LIQUID

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.

Application

As a precursor of the bis-electrophilic synthon vinylsulfonyl chloride, 2-chloroethanesulfonyl chloride can react with a wide range of bis-nucleophilic synthons, such as substituted 2-amino alcohols, to generate 7-membered sultams. This compound can be used in lieu of vinylsulfonyl chloride via a domino elimination– amidation reaction[1-2].

General Description

A liquid. Density 1.56 g / cm3. Flash point exceeds 230°F.

Air & Water Reactions

Reacts with water to produce corrosive and toxic gaseous hydrogen chloride.

Reactivity Profile

2-CHLOROETHANESULFONYL CHLORIDE is incompatible with strong oxidizing agents, alcohols, amines, alkali. 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].

References

[1] Qin Zang. “Synthesis of a Library of 1,5,2-Dithiazepine 1,1-Dioxides. Part 1: A One-Pot Sulfonylation/Thia-Michael Protocol.” Heterocycles 86 2 (2012).
[2] Victor O Rogachev, Peter Metz. “Thermal and high pressure intramolecular Diels–Alder reaction of vinylsulfonamides.” Nature Protocols 1 6 (2007): 3076–3087.

2-chloroethanesulfonyl chloride(1622-32-8)Related Product Information

• Ethanesulfonyl chloride
• 2-Chloronicotinyl chloride
• 2-CHLOROETHANESULFONYL CHLORIDE
• CHLOROETHANE
• Dichloroethane
• chloroethanesulfonyl chloride
• CHLOROSULFONYLACETYL CHLORIDE
• 4-CHLORO-1,1-DIOXO-TETRAHYDRO-1LAMBDA6-THIOPHENE-3-SULFONYL CHLORIDE
• 2-chloroethanethiol
• 2-CHLORO-1,1,2,2-TETRAFLUORO-ETHANESULFONYL CHLORIDE