Methanesulfonyl chloride

HCID 31297CAS 124-63-0

Basic information

Standard SMILES
CS(=O)(=O)Cl
InChIKey
QARBMVPHQWIHKH-UHFFFAOYSA-N
Molecular formula
CH3ClO2S
Average molar mass
114.55 g/mol
Monoisotopic mass
113.95422802

Overview

Methanesulfonyl chloride appears as a pale yellow corrosive liquid. More dense than water and insoluble in water. Very toxic by ingestion, inhalation, or skin absorption.

Names & identifiers

Preferred name
Methanesulfonyl chloride
IUPAC
methanesulfonyl chloride
English name
Methanesulfonyl chloride
Molecular formula
CH3ClO2S
Molecular weight
114.55

Names & synonyms

Methanesulfonyl chloride124-63-0Mesyl chlorideMethanesulphonyl chlorideMethyl sulfochlorideMETHYLSULFONYL CHLORIDEChloro methyl sulfoneMethanesulfonic acid chlorideMethanesulfuryl chlorideMethyl sulfonyl chlorideChloromethyl sulfoneDTXSID1021615
Show more names
MSCLMSCMSCICH3SO2ClmethanesulfonylJJHXLMethane sufonyl chloride
METHANE SULFONYL CHLORIDEB17EWY1R7QNSC-15039DTXCID601615RefChem:156944204-706-1MesylchlorideNSC 15039

Database identifiers

CAS
124-63-0
PubChem CID
31297
DTXSID
DTXSID1021615
UNII
B17EWY1R7Q
EC Number
204-706-1
Nikkaji
J2.507K

Properties

Computed structural properties

XLogP
0.4
Topological polar surface area
42.5 Ų
Hydrogen bond donors
0
Hydrogen bond acceptors
2
Rotatable bonds
0
Heavy atoms
5

Experimental & physicochemical properties

Chemical ClassesToxic Gases & Vapors -> Acid Halides
SpringerMaterials PropertiesSchoenflies notation
OdorUnpleasant odor
Density · 3 items

1.4805 at 18 °C/4 °C

Relative density (water = 1): 1.5

1.4805 @ 18°C

Viscosity1.33 centistokes at 25 °C
Color/FormPale yellow liquid

Physicochemical properties

Melting point
-33 °C · -33°C
Boiling point
60 °C/21 · 60 °C/21 mmHg (lit.)
Density
1.48 g/mL · 1.48 g/mL at 25 °C (lit.)
vapor pressure
3.001 · 3.001-8.9hPa at 20-25℃
refractive index
20 · n20/D 1.452(lit.)
Flash point
230 °F · >230 °F

Safety & regulation

GHS classification

GHS Classification · 6 items

Danger

H290 (47.5%): May be corrosive to metals [Warning Corrosive to Metals]

P234, P260, P261, P262, P264, P264+P265, P270, P271, P272, P273, P280, P284, P301+P316, P301+P317, P301+P330+P331, P302+P352, P302+P361+P354, P304+P340, P305+P354+P338, P316, P317, P319, P320, P321, P330, P333+P317, P361+P364, P362+P364, P363, P390, P403+P233, P405, P406, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 314 reports by companies from 27 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Danger

H301: Toxic if swallowed [Danger Acute toxicity, oral]

Hazard information

Hazards IdentificationToxic/poison by inhalation (TIH/PIH)
Regulatory Information · 5 items

Chemical: Methanesulfonyl chloride

Methanesulfonyl chloride is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Methanesulfonyl chloride are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)

SP - indicates a substance that is identified in a proposed Significant New Use Rule.

Status: Active Update: 10-01-2023 https://echa.europa.eu/registration-dossier/-/registered-dossier/13541

Methanesulphonyl chloride: HSNO Approval: HSR004556 Approved with controls

DOT LabelPoison Inhalation Hazard Corrosive
Fire Hazards · 3 items

Excerpt from ERG Guide 156 [Substances - Toxic and/or Corrosive (Combustible / Water-Sensitive)]:

· Combustible material: may burn but does not ignite readily.

Combustible. Gives off irritating or toxic fumes (or gases) in a fire.

Health Hazards · 2 items

Excerpt from ERG Guide 156 [Substances - Toxic and/or Corrosive (Combustible / Water-Sensitive)]:

· TOXIC and/or CORROSIVE; inhalation, ingestion or contact (skin, eyes) with vapors, dusts or substance may cause severe injury, burns or death.

Hazards Summary · 1 item

Highly corrosive to skin; [Quick CPC] It is tear drawing and corrosive to the skin and respiratory tract; [ICSC] May form hydrogen chloride gas on contact with water or moisture, although experiments at Argonne National Laboratory have shown essentially no reaction with water; Highly toxic by ingestion, inhalation, and skin absorption; [CAMEO] Slowly hydrolyzed by water forming hydrochloric acid; A lachrymator; Corrosive to tissue; [EPA OHM/TADS] Hydrolyzed by water evolving acidic gas; Causes burns; Inhalation may cause corrosive injuries to upper respiratory tract and lungs; Highly toxic by ingestion, inhalation, and skin absorption; [Aldrich MSDS]

Safety & protection

Fire Fighting · 2 items

Excerpt from ERG Guide 156 [Substances - Toxic and/or Corrosive (Combustible / Water-Sensitive)]:

Use water spray, powder, foam, carbon dioxide.

First Aid Measures · 4 items

Fresh air, rest. Refer immediately for medical attention.

Wear protective gloves when administering first aid. Remove contaminated clothes. Rinse skin with plenty of water or shower. Refer immediately for medical attention.

Rinse with plenty of water for several minutes (remove contact lenses if easily possible). Refer immediately for medical attention.

Rinse mouth. Do NOT induce vomiting. Refer immediately for medical attention.

Accidental Release Measures · 2 items

· CALL 911. Then call emergency response telephone number on shipping paper. If shipping paper not available or no answer, refer to appropriate telephone number listed on the inside back cover.

· ELIMINATE all ignition sources (no smoking, flares, sparks or flames) from immediate area.

First Aid · 2 items

Excerpt from ERG Guide 156 [Substances - Toxic and/or Corrosive (Combustible / Water-Sensitive)]:

General First Aid:

Safe StorageSeparated from food and feedstuffs and incompatible materials. Dry. Well closed. Keep in a well-ventilated room. Store in an area without drain or sewer access.
Exposure Control and Personal Protection · 2 items

· Wear positive pressure self-contained breathing apparatus (SCBA).

TIH (Toxic Inhalation Hazard) - Term used to describe gases and volatile liquids that are toxic when inhaled. Some are TIH materials themselves, e.g., chlorine, and some release TIH gases when spilled in water, e.g., chlorosilanes. [ERG 2016].

Toxicology

Ecotoxicity Values · 4 items

LC50 Menidia beryllina (inland silverside, length 40-100 mm) 15 mg/L/96 hr; static, 20 °C, pH 7.6-7.9, hardness 55 mg/L CaCO3

LC50 Menidia beryllina (inland silverside) 15 mg/L/96 hr; static bioassay in synthetic seawater at 23 °C, mild aeration applied after 24 hr.

LC50 Lepomis macrochirus (bluegill sunfish) 11 mg/L/96 hr; static bioassay in freshwater at 23 °C, mild aeration applied after 24 hr

LC50 Lepomis macrochirus (bluegill, length 33-75 mm) 11 mg/L/96 hr; static, 23 °C, pH 7.6-7.9, hardness 55 mg/L CaCO3

Environmental Fate · 3 items

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 6.1(SRC), determined from a structure estimation method(2), indicates that methanesulfonyl chloride is expected to have very high mobility in soil(SRC). Volatilization of methanesulfonyl chloride from moist soil surfaces is expected to be an important fate process(SRC) given an estimated Henry's Law constant of 4.4X10-5 atm-cu m/mole(SRC), using a fragment constant estimation method(3). Methanesulfonyl chloride is expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 3.1 mm Hg(SRC), determined from a fragment constant method(4). Biodegradation data were not available(SRC, 2007).

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 6.1(SRC), determined from a structure estimation method(2), indicates that methanesulfonyl chloride is not expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is expected(3) based upon an estimated Henry's Law constant of 4.4X10-5 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). Using this Henry's Law constant and an estimation method(3), volatilization half-lives for a model river and model lake are 15 hours and 11 days, respectively(SRC). According to a classification scheme(5), an estimated BCF of 1.9(SRC), from an estimated log Kow of 1.3(SRC) and a regression-derived equation(6), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Methanesulfonyl chloride hydrolyzes slowly in water(7). Biodegradation data were not available(SRC, 2007).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), methanesulfonyl chloride, which has an estimated vapor pressure of 3.1 mm Hg at 25 °C(SRC), determined from a fragment constant method(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase methanesulfonyl chloride is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC); the half-life for this reaction in air is estimated to be 150 days(SRC), calculated from its rate constant of 1.1X10-12 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). Methanesulfonyl chloride does not contain chromophores that absorb at wavelengths >290 nm and therefore is not expected to be susceptible to direct photolysis by sunlight(4).

Adverse EffectsDermatotoxin - Skin burns.
Exposure RoutesThe substance can be absorbed into the body by inhalation, by ingestion and through the skin.
Signs and Symptoms · 4 items

Cough. Sore throat. Burning sensation. Laboured breathing. Shortness of breath.

Redness. Pain. Blisters.

Redness. Pain. Severe burns.

See Inhalation.

ICSC Environmental DataThe substance is harmful to aquatic organisms.

Regulatory information

TSCA Requirements · 2 items

Section 8(a) of TSCA requires manufacturers of this chemical substance to report preliminary assessment information concerned with production, exposure, and use to EPA as cited in the preamble in 51 FR 41329.

Pursuant to section 8(d) of TSCA, EPA promulgated a model Health and Safety Data Reporting Rule. The section 8(d) model rule requires manufacturers, importers, and processors of listed chemical substances and mixtures to submit to EPA copies and lists of unpublished health and safety studies. Methanesulfonyl chloride is included on this list.

Safety data

PPE
Faceshields, Gloves, Goggles, type ABEK (EN14387) respirator filter
wgk
2
tsca
TSCA listed
rtecs
PB2790000
ridadr
UN 3246
hs_code
29049095

Chemistry & industry

Uses & manufacturing

Uses · 6 items

Used as an intermediate in the production of drugs, flame retardants, and other chemicals; Also used as a stabilizer, catalyst, curing agent, and chlorinating agent; Has been detected in air samples at a pulp mill that used chlorine-containing bleaching agents; [HSDB]

Pulp and Paper Processing [Category: Industry]

Intermediate; flame-resistant products; stabilizer for liquid sulfur trioxide; biological chemicals.

Chemical intermediate for busulfan (human antineoplastic agent)

Chemical intermediate for glucocorticoids used in human medicine

Chemical intermediate for antiinflammatory agents in human medicine

U.S. Production · 5 items

2023: 500,000 - <1,000,000 lb

(1979) PROBABLY GREATER THAN 2.27X10+6 GRAMS

(1981) PROBABLY GREATER THAN 2.27X10+6 GRAMS

This chemical is listed as a High Production Volume (HPV) (65FR81686). Chemicals listed as HPV were produced in or imported into the U.S. in >1 million pounds in 1990 and/or 1994. The HPV list is based on the 1990 Inventory Update Rule. (IUR) (40 CFR part 710 subpart B; 51FR21438).

Production volumes for non-confidential chemicals reported under the Inventory Update Rule. [Table#5456]

Industry UsesIntermediate
Methods of Manufacturing · 2 items

Made commercially by ... the sulfochlorination of methane.

Prepared from sulfur trioxide and methane

Formulations/PreparationsGrade: 98%, 99%+
General Manufacturing Information · 2 items

Pesticide, Fertilizer, and Other Agricultural Chemical Manufacturing

Methanesulfonyl chloride: ACTIVE

Applications · 4 items

UsesMethanesulfonyl chloride is used as a reagent for conversion of alcohols to mesylate esters such as methanesulfonate, which is an intermediate in substitution reactions, elimination reactions, reductions, and rearrangement reactions viz. Beckmann rearrangement. It is an electrophile and acts as a source of CH3SO2+ group. It is also used to prepare beta-chloro sulfones, methanesulfonamide and heterocyclic compounds containing five membered sultones.

UsesMethanesulfonyl chloride can be used for the mesylation of primary alcohols to synthesize the corresponding methanesulfonates. It may also be used for the conversion of amines to the corresponding sulfonamides.

UsesIn the synthesis of photographic and agricultural chemicals, pharmaceutical intermediates. As a stabilizer; catalyst; curing and chlorinating agent; precursor to methanesulfonic acid.

General DescriptionA pale yellow corrosive liquid. More dense than water and insoluble in water. Very toxic by ingestion, inhalation, or skin absorption.

Related reactions

19,505 records

Linked notes

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