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124-63-0 - Methanesulfonyl chloride, 98% - Mesyl chloride - A13383 - Alfa Aesar

A13383 Methanesulfonyl chloride, 98%

CAS Number
124-63-0
Synonyms
Mesyl chloride

Size Price ($) Quantity Availability
100g 16.18
500g 53.66
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Methanesulfonyl chloride, 98%

MDL
MFCD00007454
EINECS
204-706-1

Chemical Properties

Formula
CH3ClO2S
Formula Weight
114.55
Melting point
-33°
Boiling Point
161°
Flash Point
97°(206°F)
Density
1.477
Refractive Index
1.4520
Sensitivity
Moisture Sensitive
Solubility
Miscible with alcohol, ether and organic solvents. Immiscible with water.

Applications

Methanesulfonyl 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 CH<sub>3</sub>SO<sub>2</sub><Sup>+</sup> group. It is also used to prepare beta-chloro sulfones, methanesulfonamide and heterocyclic compounds containing five membered sultones.

Notes

Moisture sensitive. Store in a cool place. Incompatible with strong bases, oxidizing agents and alcohols. It is a lachrymator and reacts with water.

Literature References

Reagent for conversion of alcohols to their mesylate esters. For mesylation of an acetylenic alcohol followed by displacement with an amine, see Org. Synth. Coll., 9, 46 (1998). In the presence of triethylamine, reaction occurs by way of the sulfene intermediate, which mesylates alcohols of low nucleophilicity including tert-alcohols and 2,2,2-trifluoroethanol: J. Org. Chem., 35, 3195 (1970).

In pyridine, primary alcohols are converted to alkyl chlorides, via nucleophilic displacement by Cl- on the mesylate: Chem. Pharm. Bull., 24, 365 (1976); J. Org. Chem., 48, 657 (1983). In combination with LiCl in collidine, allylic alcohols are converted to chlorides without allylic rearrangement: J. Org. Chem., 36, 3044 (1971).

For use in the symmetrical coupling of aryl mesylates to give biaryls, catalyzed by Dichlorobis(triphenyl­phosphine)­nickel(II)­, 13930, see: J. Org. Chem., 60, 6895 (1995).

Esters of hindered acids have been prepared via the mesyl mixed anhydride and reaction with the alcohol in the presence of DMAP: Synth. Commun., 12, 727 (1982).

Zhan, N.; Palui, G.; Mattoussi, H. Preparation of compact biocompatible quantum dots using multicoordinating molecular-scale ligands based on a zwitterionic hydrophilic motif and lipoic acid anchors. Nat. Protoc 2015, 10 (6), 859-874.

Wang, H.; Cheng, F.; Li, M.; Peng, W.; Qu, J. Reactivity and Kinetics of Vinyl Sulfone-Functionalized Self-Assembled Monolayers for Bioactive Ligand Immobilization. Langmuir 2015, 31 (11), 3413-3421.

GHS Hazard and Precautionary Statements

Hazard Statements: H300-H310-H330-H314-H318

Fatal if swallowed. Fatal in contact with skin. Fatal if inhaled. Causes severe skin burns and eye damage. Causes serious eye damage.

Precautionary Statements: P260-P301+P310-P303+P361+P353-P304+P340-P305+P351+P338-P320-P330-P361-P405-P501a

Do not breathe dust/fume/gas/mist/vapours/spray. IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician. IF ON SKIN (or hair): Remove/Take off immediately all contaminated clothing. Rinse skin with water/shower. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. Specific treatment is urgent (see label). Rinse mouth. Store locked up. Dispose of contents/container in accordance with local/regional/national/international regulations.

Other References

Merck
14,5955
Beilstein
506297
Hazard Class
6.1
Packing Group
I
Harmonized Tariff Code
2904.90
TSCA
Yes
RTECS
PB2790000

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