124-63-0

Basic information

• Product Name: Methanesulfonyl chloride
• Synonyms: Methane sufonyl chloride;124-63-0;Methanesulfonyl chloride###124-63-0;AKOS BBS-00004350;METHYLSULFOCHLORIDE;METHYLSULFONYL CHLORIDE;MESYL CHLORIDE;METHANESULFONYL CHLORIDE
• CAS NO: 124-63-0
• Molecular Formula: CH3ClO2S
• Molecular Weight: 114.55132
• EINECS: 204-706-1
• Product Categories: Organics;Pharmaceutical Intermediates
• Mol File: 124-63-0.mol

Chemical Properties

• Melting Point: -33°C
• Boiling Point: 60 °C21 mm Hg(lit.)
• Flash Point: >230 °F
• Appearance: Clear/Liquid
• Density: 1.48 g/mL at 25 °C(lit.)
• Refractive Index: n20/D 1.452(lit.)
• Storage Temp.: Store at R.T.
• Water Solubility: Miscible with alcohol, ether and organic solvents. Immiscible with water.
• Sensitive: Moisture Sensitive
• Merck: 14,5955
• BRN: 506297
• CAS DataBase Reference: Methanesulfonyl chloride(CAS DataBase Reference)
• NIST Chemistry Reference: Methanesulfonyl chloride(124-63-0)
• EPA Substance Registry System: Methanesulfonyl chloride(124-63-0)

Safety Data

• Hazard Codes: T+,T,C
• Statements: 24/25-26-34-37-35-22-41
• Safety Statements: 26-28-36/37/39-45-25-28A
• RIDADR: UN 3246 6.1/PG 1
• WGK Germany: 2
• RTECS: PB2790000
• TSCA: Yes
• HazardClass: 6.1
• PackingGroup: I
• Hazardous Substances Data: 124-63-0(Hazardous Substances Data)

Usage

Reactivity Profile

Methanesulfonyl chloride reacts vigorously with water, steam, alkali, methylformamide. Emits toxic fumes of chloride and oxides of sulfur when heated to decomposition. A dangerous storage hazard. Reacts explosively with dimethyl sulfoxide [Buckley, A., J. Chem. Educ., 1965, 42, p. 674]. 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].

Chemical Properties

Colorless to yellow liquid

Purification Methods

Distil the sulfonyl chloride from P2O5 under vacuum. It is a strong IRRITANT.[Beilstein 4 IV 27.]

General Description

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

Health Hazard

TOXIC; inhalation, ingestion or contact (skin, eyes) with vapors, dusts or substance may cause severe injury, burns or death. Contact with molten substance may cause severe burns to skin and eyes. Reaction with water or moist air will release toxic, corrosive or flammable gases. Reaction with water may generate much heat that will increase the concentration of fumes in the air. Fire will produce irritating, corrosive and/or toxic gases. Runoff from fire control or dilution water may be corrosive and/or toxic and cause pollution.

Fire Hazard

Combustible material: may burn but does not ignite readily. Substance will react with water (some violently) releasing flammable, toxic or corrosive gases and runoff. When heated, vapors may form explosive mixtures with air: indoors, outdoors and sewers explosion hazards. Most vapors are heavier than air. They will spread along ground and collect in low or confined areas (sewers, basements, tanks). Vapors may travel to source of ignition and flash back. Contact with metals may evolve flammable hydrogen gas. Containers may explode when heated or if contaminated with water.

Uses

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

InChI:InChI=1/CH3ClO2S/c1-5(2,3)4/h1H3

Synthetic route

Dimethyldisulphide (624-92-0) → methanesulfonyl chloride (124-63-0)

Conditions	Yield
With hydrogenchloride; manganese(IV) oxide; potassium sulfate; water at 60 - 90℃; for 22h; Reagent/catalyst; Temperature; Large scale;	99.81%
With chloro-trimethyl-silane; potassium nitrate In dichloromethane at 50℃; for 8h;	90%

S,S-dimethyl dithiocarbonate (868-84-8) → methanesulfonyl chloride (124-63-0)

Conditions	Yield
With water; chlorine at 5 - 10℃; for 0.25h;	95%

Chloromethyltrimethylsilane (2344-80-1) → Chloro(chloromethyl)dimethylsilane (1719-57-9) + sulfate de bis-(dimethylchloromethylsilyle) (20991-92-8) + methanesulfonyl chloride (124-63-0)

Conditions	Yield
With chlorosulfonic acid at 50 - 80℃;	A n/a B 92% C n/a

[(methylthio)methyl]-benzene (766-92-7) → methanesulfonyl chloride (124-63-0)

Conditions	Yield
With hydrogenchloride; iodosylbenzene for 0.0833333h; Chlorination; oxidation;	91%
With hydrogenchloride; iodosylbenzene for 0.0833333h;	91 % Chromat.

N-chlorodimesylamine (71954-24-0) + diphenyl phenylphosphonate (3049-24-9) → N-Mesyl-triphenoxyphosphinimid (102173-66-0) + methanesulfonyl chloride (124-63-0)

Conditions	Yield
In dichloromethane for 18h;	A 82% B n/a

S-Methylisothiourea sulfate (867-44-7) → methanesulfonyl chloride (124-63-0)

Conditions	Yield
With tert-butylhypochlorite In water; acetonitrile at 0 - 20℃;	79%
In diethyl ether; water at 0 - 20℃; for 0.5h; Green chemistry;	0.808 g

methane (34557-54-5) → dichloromethane (75-09-2) + methanesulfonyl chloride (124-63-0)

Conditions	Yield
With sulfur dioxide; chlorine at 25℃; under 2250.23 Torr; for 1h; Concentration; Wavelength; Irradiation;	A n/a B 69%

N-chlorodimesylamine (71954-24-0) → N-Mesyl-trichlorphosphinimid (29651-24-9) + methanesulfonyl chloride (124-63-0)

Conditions	Yield
With phosphorus trichloride In dichloromethane; chloroform for 12h;	A 61% B n/a

methane (34557-54-5) → tetrachloromethane (56-23-5) + methylene chloride (74-87-3) + dichloromethane (75-09-2) + chloroform (67-66-3) + methanesulfonyl chloride (124-63-0)

Conditions	Yield
With hydrogenchloride; sulfur dioxide; chlorine at 63 - 67℃; under 6750.68 Torr; Photolysis;	A n/a B n/a C n/a D n/a E 55%

methane (34557-54-5) → dichloromethane (75-09-2) + chloroform (67-66-3) + methanesulfonyl chloride (124-63-0)

Conditions	Yield
With sulfur dioxide; chlorine at 65℃; under 2250.23 Torr; for 1h; Temperature; Irradiation;	A n/a B n/a C 54.9%

(dichloromethyl)trimethylsilane (5926-38-5) → methanesulfonyl chloride (124-63-0) + C3H7Cl3O3SSi (107716-52-9) + C3H7Cl3O3SSi (107716-51-8) + C6H14Cl4O4SSi2 (107716-53-0)

Conditions	Yield
at 90 - 100℃; Further byproducts given;	A n/a B 51% C n/a D n/a

methanesulfonic acid (75-75-2) → methanesulfonyl chloride (124-63-0)

Conditions	Yield
With 1,3,5-trichloro-2,4,6-triazine; triethylamine In acetone for 20h; Heating;	47%
With thionyl chloride at 95℃;
With phosphorus trichloride at 80℃;

methane (34557-54-5) → methanesulfonyl chloride (124-63-0)

Conditions	Yield
With sulfur dioxide; chlorine at -10 - 110℃; for 2h; Product distribution / selectivity; Sealed reactor;	47%
With sulfuryl dichloride; sulfur trioxide; dihydrogen peroxide; rhodium(III) chloride; urea In sulfuric acid at 60℃; under 36201.3 Torr; for 12h;	1.9 mmol

methane (34557-54-5) → chloroform (67-66-3) + methanesulfonyl chloride (124-63-0)

Conditions	Yield
With sulfur dioxide; chlorine at 25℃; under 2250.23 Torr; for 1h; Temperature; Irradiation;	A n/a B 43.3%

methylsulphinyl chloride (676-85-7) → methanesulfonyl chloride (124-63-0)

Conditions	Yield
With chlorine	13.5%

methyl thiocyanate (556-64-9) → methanesulfonyl chloride (124-63-0)

Conditions	Yield
With water; chlorine
With water; chlorine

methyl magnesium iodide (917-64-6) → methanesulfonyl chloride (124-63-0)

Conditions	Yield
With sulfuryl dichloride; diethyl ether at 10℃;

dimethylsulfide (75-18-3) → methanesulfonyl chloride (124-63-0)

Conditions	Yield
With water; chlorine

Methanesulfenyl chloride (5813-48-9) → methanesulfonyl chloride (124-63-0)

Conditions	Yield
With diethyl ether; nitric acid at -15℃;

2-methylisothiourea sulphate (14527-26-5, 867-44-7) → methanesulfonyl chloride (124-63-0)

Conditions	Yield
With water; chlorine at 10 - 15℃;

Methanesulfonic anhydride (7143-01-3) → methanesulfonyl chloride (124-63-0)

Conditions	Yield
With hydrogenchloride at 105℃;

1-Heptene (592-76-7) + methanedisulfonyl chloride (5799-68-8) → 1,3-dichlorooctane (5799-71-3) + 3-chloro-octanesulfonyl chloride (5799-72-4) + methanesulfonyl chloride (124-63-0)

Conditions	Yield
With dibenzoyl peroxide In benzene Heating;

α,α-Dichlor-dimethylsulfid (64258-22-6) → methanesulfonyl chloride (124-63-0)

Conditions	Yield
With water; chlorine In acetic acid

methylsulphinyl chloride (676-85-7) → methanethiosulfonic acid S-methyl ester (2949-92-0) + dimethylsulfide (75-18-3) + S-methyl methanethiosulfinate (13882-12-7) + methyl methanesulfinyl sulfone (14128-56-4) + Zinc methanesulfinate (19186-23-3) + methanesulfonyl chloride (124-63-0)

Conditions	Yield
With zinc In various solvent(s) at -30℃; for 1.5h; Mechanism; Product distribution; var. solv., var. time, var. temp.;	A 7 % Spectr. B 1 % Spectr. C 3 % Spectr. D 1 % Spectr. E 5 % Spectr. F 9 % Spectr.

methylsulphinyl chloride (676-85-7) → methanethiosulfonic acid S-methyl ester (2949-92-0) + dimethylsulfide (75-18-3) + S-(chloromethyl) methanesulphonothioate (22224-96-0) + methanesulfonyl chloride (124-63-0)

Conditions	Yield
triethylamine In diethyl ether at 22 - 24℃; for 24h; Product distribution; other amines;	A 6 % Spectr. B 5 % Spectr. C 27 % Spectr. D 3 % Spectr.

dimethyl sulfoxide (67-68-5) → methanethiosulfonic acid S-methyl ester (2949-92-0) + dimethylsulfone (67-71-0) + hydrochloric acid, dimethyl sulphoxide (26394-12-7) + methanesulfonyl chloride (124-63-0)

Conditions	Yield
With chlorine In dichloromethane at -0.1℃;
With chlorine In dichloromethane at -0.1℃; Further byproducts given;

Tetrahydro-pyran-4-ol (2081-44-9) + methanesulfonyl chloride (124-63-0) → 4-oxanyl methanesulfonate (134419-59-3)

Conditions	Yield
With triethylamine In dichloromethane at 0 - 20℃; for 2.5h;	100%
With triethylamine In dichloromethane at 0 - 20℃; for 2.5h;	100%
With triethylamine In dichloromethane at 0℃; for 1.5h;	100%

methanol (67-56-1) + methanesulfonyl chloride (124-63-0) → Methyl methanesulfonate (66-27-3)

Conditions	Yield
Stage #1: methanol With triethylamine In dichloromethane at 25℃; Stage #2: methanesulfonyl chloride In dichloromethane at 0 - 20℃;	100%
With pyridine; diethyl ether at -30℃;
With triethylamine

propan-1-ol (71-23-8) + methanesulfonyl chloride (124-63-0) → propyl methanesulfonate (1912-31-8)

Conditions	Yield
With triethylamine In dichloromethane at 0 - 20℃; for 1h;	100%
With pyridine 1.) from -20 deg C to 30 deg C, 2.) room temp., 2 h;	65%
With pyridine at 0℃;

4-nitro-phenol (100-02-7) + methanesulfonyl chloride (124-63-0) → p-nitrophenyl methanesulfonate (20455-07-6)

Conditions	Yield
With triethylamine In dichloromethane at 0 - 20℃; for 0.75h;	100%
With triethylamine In dichloromethane at 0 - 20℃;	98%
With triethylamine In ethyl acetate at 0 - 20℃; for 0.166667h; Green chemistry;	97%

n-Pent-4-enyl alcohol (821-09-0) + methanesulfonyl chloride (124-63-0) → 4-pentenyl mesylate (64818-35-5)

Conditions	Yield
With triethylamine In dichloromethane at -15℃; for 1h; Green chemistry;	100%
With triethylamine In dichloromethane at -5℃; for 0.666667h;	98%
With triethylamine In dichloromethane at 0 - 20℃; for 91312.5h; Inert atmosphere;	98%

Upstream product

• 8042-47-5 Mineral oil 
• 75-75-2 Methanesulfonic acid 
• 62-56-6 Thiocarbamide 
• 624-92-0 Dimethyl disulfide 
• 7719-09-7 Thionyl chloride 

Downstream Products

• 78110-38-0 Aztreonam 
• 83506-93-8 2-Amino-4,5-difluorobenzoic acid 
• 51803-78-2 Nimesulide 
• 756520-78-2 2-(Methanesulfonylamino)phenylboronic acid 
• 60282-87-3 Gestodene 
• 66104-22-1 Pergolide 
• 105889-45-0 Cefcapene pivoxil 
• 83799-24-0 Fexofenadine 
• 3056-17-5 Stavudine 
• 32305-98-9 (-)-DIOP 
• 66852-54-8 Halobetasol propionate 
• 22373-75-7 (4S)-HYDROXY-3-METHYL-2-(2-PROPENYL)-2-CYCLOPENTENE-1-ONE 
• 35410-28-7 11beta,17,21-trihydroxypregna-1,4-diene-3,20-dione 21-methanesulphonate 
• 1120-71-4 1,3-Propanesultone 
• 99724-19-3 3-N-Boc-aminopyrrolidine 
• 62-50-0 Ethyl methanesulfonate 
• 55-98-1 Busulfan 
• 74397-12-9 LIMAPROST 
• 7151-76-0 4-(METHANESULFONYLAMINO)BENZOIC ACID 
• 37045-73-1 N-(3-Aminophenyl)methanesulfamide 
• 110588-57-3 SAPERCONAZOLE 
• 122536-76-9 (S)-3-(Boc-amino)pyrrolidine 
• 77087-34-4 (4S)-4-hydroxy-3-methyl-2-prop-2-ynyl-cyclopent-2-en-1-one 
• 2707-37-1 9-Fluoro-11,17,21-trihydroxy-16-methylpregna-1,4-diene-3,20-dione21-phosphate piperazine salt 
• 61478-28-2 (2S,4S)-(-)-N-BOC-4-Diphenylphosphino-2-diphenylphosphinomethyl-pyrrolidine 
• 15722-48-2 OLSALAZINE 
• 66-27-3 Methyl methanesulfonate 
• 4455-15-6 ETHYL METHANESULFONYLACETATE 
• 51264-14-3 Amsacrine 
• 156517-64-5 (3S,4S)-(-)-1-BENZYL-3,4-BIS(DIPHENYLPHOSPHINO)PYRROLIDINE 
• 28547-13-9 3-(METHANESULFONYLAMINO)BENZOIC ACID 
• 89-57-6 5-Aminosalicylic acid 
• 53250-82-1 4-(Methylsulfonamido)aniline 
• 3144-09-0 Methanesulfonamide 
• 84449-90-1 Raloxifene 

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Vibrational spectra of Methanesulfonyl chloride (cas 124-63-0) and Methanesulfonyl chloride (cas 124-63-0)-d309/10/2019

The i.r. and Raman spectra of methanesulfonyl chloride and methanesulfonyl chloride-d3 have been recorded in the liquid state, and consistent assignments of the fundamental frequencies of the two isotopic compounds have been given. The normal coordinate calculation based on a modified Urey—Brad...detailed