Ethanesulfonyl chloride

HCID 11667

Basic information

CAS
594-44-5
Standard SMILES
CCS(=O)(=O)Cl
InChIKey
FRYHCSODNHYDPU-UHFFFAOYSA-N
Molecular formula
C2H5ClO2S
Average molar mass
128.58 g/mol
Monoisotopic mass
127.96987808

Names & identifiers

Preferred name
Ethanesulfonyl chloride
IUPAC
ethanesulfonyl chloride
English name
Ethanesulfonyl chloride
Molecular formula
C2H5ClO2S
Molecular weight
128.58

Names & synonyms

ETHANESULFONYL CHLORIDEEthylsulfonyl chlorideEthylsulfochloride1-Ethanesulfonyl chlorideEthanesulphonyl chlorideTL 77ethylsulfuryl chlorideEINECS 209-842-5NSC 8649UNII-B56ZOC898AEthane sulfochlorideBRN 0773865
Show more names
ethanesulflonyl chloridetl771,2-Ethane-disulfonicethylsulfurylchlorideTirofiban Impurity 72Ethyl sulfone chloride
B56ZOC898AHSDB 7487NSC-8649DTXSID0060486EC 209-842-54-04-00-00034 (Beilstein Handbook Reference)ETHANESULPHONYL CHLORIDE [HSDB]1-Ethanesulfonyl chloride(ChemID)

Database identifiers

CAS
594-44-5
PubChem CID
11667
DTXSID
DTXSID0060486
UNII
B56ZOC898A
EC Number
209-842-5
Nikkaji
J53.955D

Properties

Computed structural properties

XLogP
0.8
Topological polar surface area
42.5 Ų
Hydrogen bond donors
0
Hydrogen bond acceptors
2
Rotatable bonds
1
Heavy atoms
6

Experimental & physicochemical properties

Chemical ClassesToxic Gases & Vapors -> Acid Halides
SpringerMaterials PropertiesBoiling point
Color/Form · 2 items

Oil

Pale yellow

Solubility · 2 items

Soluble in carbon disulfide

Slightly soluble (decomposes) in water and alcohol; very soluble in ether and dichloromethane.

Boiling Point177.5 °C
DecompositionWhen heated to decomposition it emits very toxic fumes of /hydrogen chloride and sulfur oxide/.

Physicochemical properties

Melting point
-70 °C · -70°C
Boiling point
177 °C · 177 °C (lit.)
Density
1.357 g/mL · 1.357 g/mL at 25 °C (lit.)
refractive index
20 · n20/D 1.452(lit.)
Flash point
182 °F · 182 °F
storage temp.
2 · Inert atmosphere,2-8°C

Safety & regulation

GHS classification

GHS Classification · 4 items

Danger

H302 (96.6%): Harmful if swallowed [Warning Acute toxicity, oral]

P260, P261, P262, P264, P270, P271, P280, P284, P301+P317, P301+P330+P331, P302+P352, P302+P361+P354, P304+P340, P305+P354+P338, P316, P317, P319, P320, P321, P330, P361+P364, P362+P364, P363, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 58 reports by companies from 11 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Hazard information

Regulatory Information · 2 items

Status: Active Update: 06-01-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/11864

Ethanesulphonyl chloride: Does not have an individual approval but may be used under an appropriate group standard

Hazards Summary · 1 item

A lachrymator; All rats exposed to 1273 ppm died within 30 to 130 minutes; 4-hr LC50 (rat) = approximately 86 ppm; Rats exposed to lethal concentrations have lacrimation, salivation, gasping, and pulmonary hemorrhage; [HSDB] Reacts violently with water; A corrosive substance that can cause injury to the skin, eyes, and respiratory tract; Inhalation may cause chemical pneumonitis; Effects in high-dose animal studies include acute pulmonary edema; [MSDSonline]

Hazard Classes and CategoriesAcute Tox. 4 (96.6%)
Skin, Eye, and Respiratory Irritations/Ethanesulfonyl chloride is a/ lachrymator ...

Safety & protection

Disposal Methods · 1 item

SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational exposure or environmental contamination. Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in soil or water; effects on animal, aquatic, and plant life; and conformance with environmental and public health regulations.

Preventive Measures · 1 item

SRP: Contaminated protective clothing should be segregated in such a manner so that there is no direct personal contact by personnel who handle, dispose, or clean the clothing. Quality assurance to ascertain the completeness of the cleaning procedures should be implemented before the decontaminated protective clothing is returned for reuse by the workers. Contaminated clothing should not be taken home at end of shift, but should remain at employee's place of work for cleaning.

Toxicology

Adverse EffectsDermatotoxin - Skin burns.
Human Toxicity Excerpts/SIGNS AND SYMPTOMS/ /Ethanesulfonyl chloride is a/ lachrymator ...
Non-Human Toxicity Excerpts · 3 items

/LABORATORY ANIMALS: Acute Exposure/ A single dermal application of 2000 mg/kg to rabbits killed two of three animals. No deaths occurred following a dermal application of 200 mg/kg to rabbits.

/LABORATORY ANIMALS: Acute Exposure/ Acute (4-hr) inhalation studies indicated an LC50 of approximately 86 ppm in the rat. Clinical signs included eye irritation, lacrimation, salivation, and gasping. Decedents exhibited pulmonary hemorrhage. All rats died within 30 to 130 min during an exposure to 1273 ppm.

/LABORATORY ANIMALS: Acute Exposure/ Ethanesulfonyl chloride is corrosive to rabbit skin and eyes, and the vapor caused irritation of the eyes and respiratory tract. In rabbits, irritation of the eye 20 to 30 sec after instillation did not reduce the conjunctival necrosis, corneal opacity, or iridial changes. Corneal opacity persisted through 7 days.

Toxicity DataLCLo (rat) = 410 mg/m3/4h
Non-Human Toxicity Values · 2 items

LD50 rat oral 360 mg/kg

LC50 rat inhalation 86 ppm/4 hr

Safety data

F
19-21
PPE
Faceshields, Gloves, Goggles, type ABEK (EN14387) respirator filter
wgk
3
tsca
TSCA listed
rtecs
KI8050000
ridadr
UN 2927 6.1/PG 2

Chemistry & industry

Uses & manufacturing

Uses · 3 items

Used to make sulfonyl-substituted imides, methide lithium salts, and pentafluoroethanesulfonyl fluoride, a fluorinated surfactant; [HSDB]

Intermediate in the syntheses of new, low-cost, non-fluorinated, sulfonyl-substituted imide and methide lithium salts.

Intermediate in the preparation of the fluorinated surfactant pentafluoroethanesulfonyl fluoride.

U.S. ProductionProduction volumes for non-confidential chemicals reported under the Inventory Update Rule. [Table#7143]
Methods of Manufacturing · 2 items

Alkanesulfonyl chlorides are manufactured from mercaptans or disulfides and chlorine using a loop reactor having an ejector, wherein mercaptan or disulfide is dispersed or dissolved into circulating aqueous solvent before the ejector and alowed to react with chlorine supplied through the aspirator of the ejector.

Mercaptans or disulfide in aqueous solvents are reacted with chlorine gas in dark to produce alkanesulfonyl chloride without chloro chain byproducts. Thus, ... ethyl mercaptan was reacted with ... chlorine gas over 4 hours in /the/ dark in ... pure water keeping the reaction temperature under 20 °C to give ethanesulfonyl chloride.

General Manufacturing InformationEthanesulfonyl chloride: ACTIVE

Applications

UsesChloroethylsulfone was used in discovery of a selective inhibitor of oncogenic B-raf kinase with potent antimelanoma activity.

Suppliers100 total

国药集团化学试剂有限公司86-21-63210123 · [email protected]
梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
邹平创新药业有限公司13561560789 · [email protected]
河北创海生物科技有限公司+86-86-13131129325 · [email protected]

Related reactions

704 records

Compound notes

Loading…