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
Show more names
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
- Formal charge
- 0
- Complexity
- 108
Experimental & physicochemical properties
Color/Form
Oil
Pale yellow
Solubility
Soluble in carbon disulfide
Slightly soluble (decomposes) in water and alcohol; very soluble in ether and dichloromethane.
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
- solubility
- soluble in dichloromethane,Ether
- form
- Liquid
- color
- Clear colorless to light yellow or light brownish to pinkish-purple
- Water Solubility
- DECOMPOSES
- Sensitive
- Moisture Sensitive
- BRN
- 773865 · 773865
- InChI
- 1S/C2H5ClO2S/c1-2-6(3,4)5/h2H2,1H3
- InChIKey
- FRYHCSODNHYDPU-UHFFFAOYSA-N
- SMILES
- CCS(Cl)(=O)=O
- CAS DataBase Reference
- 594 · 594-44-5(CAS DataBase Reference)
- EWG's Food Scores
- 1 · 1
- FDA UNII
- 56 ZOC898A · B56ZOC898A
- NIST Chemistry Reference
- Ethanesulfonyl chloride(594-44-5)
- EPA Substance Registry System
- Ethanesulfonyl chloride (594-44-5)
- UNSPSC Code
- 12352107 · 12352107
- NACRES
- 22 · NA.22
- Symbol(GHS)
- 5 · GHS05,GHS06
- Signal word
- Danger
- Hazard statements
- 302 · H302+H312-H314-H330-H335
- Precautionary statements
- 260 · P260-P280-P301+P312-P303+P361+P353-P304+P340+P310-P305+P351+P338
- target organs
- Respiratory system
- PPE
- Faceshields, Gloves, Goggles, type ABEK (EN14387) respirator filter
- Hazard Codes
- T
- Risk Statements
- 21 · 21/22-23-34-22
- Safety Statements
- 26 · 26-36/37/39-45
- RIDADR
- 2927 · UN 2927 6.1/PG 2
- WGK Germany
- 3 · 3
- RTECS
- 8050000 · KI8050000
- F
- 19 · 19-21
- TSCA
- TSCA listed
- HazardClass
- 6.1 · 6.1
- PackingGroup
- II
- HS Code
- 29049090 · 29049090
- Storage Class
- 6.1 A · 6.1A - Combustible acute toxic Cat. 1 and 2very toxic hazardous materials
- Hazard Classifications
- 2 InhalationAcute · Acute Tox. 2 InhalationAcute Tox. 4 DermalAcute Tox. 4 OralEye Dam. 1Skin Corr. 1BSTOT SE 3
- Hazardous Substances Data
- 594 · 594-44-5(Hazardous Substances Data)
- REACH Registrations
- Active
Safety & regulation
GHS classification
GHS Classification
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
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
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]
Safety & protection
Disposal Methods
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
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
Non-Human Toxicity Excerpts
/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.
Non-Human Toxicity Values
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
- hs_code
- 29049090
- risk_code
- 21/22-23-34-22
- Signal word
- Danger
- Symbol(GHS)
- GHS05,GHS06
- hazard_code
- T
- safety_code
- 26-36/37/39-45
- hazard_class
- 6.1
- Storage Class
- 6.1A - Combustible acute toxic Cat. 1 and 2very toxic hazardous materials
- packing_group
- II
- target organs
- Respiratory system
- Hazard statements
- H302+H312-H314-H330-H335
- REACH Registrations
- Active
- Hazard Classifications
- Acute Tox. 2 InhalationAcute Tox. 4 DermalAcute Tox. 4 OralEye Dam. 1Skin Corr. 1BSTOT SE 3
- Precautionary statements
- P260-P280-P301+P312-P303+P361+P353-P304+P340+P310-P305+P351+P338
- Hazardous Substances Data
- 594-44-5(Hazardous Substances Data)
Chemistry & industry
Uses & manufacturing
Uses
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.
Methods of Manufacturing
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.
Applications
UsesChloroethylsulfone was used in discovery of a selective inhibitor of oncogenic B-raf kinase with potent antimelanoma activity.
Upstream & downstream products
Upstream raw materials
Downstream products
Suppliers100 total
Related reactions
Compound notes
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