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

A13383 Methanesulfonyl chloride, 98%

Numéro CAS
124-63-0
Synonymes
Mesyl chloride

Dimensions Prix ($) Quantité Disponibilité
100g 16,18
500g 53,66
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Methanesulfonyl chloride, 98%

MDL
MFCD00007454
EINECS
204-706-1

Propriétés chimiques

Formule
CH3ClO2S
Poids formulaire
114.55
Point de fusion
-33°
Point d'ébullition
161°
Point d'éclair
97°(206°F)
Densité
1.477
Indice de réfraction
1.4520
Sensibilité
Moisture Sensitive
Solubilité
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.

Références bibliographiques

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.

Mentions de danger et de prudence du SGH

Mentions de danger (UE): 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.

Mentions de prudence: 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.

Autres références

Merck
14,5955
Beilstein
506297
Classe de danger
6.1
Groupe d'emballage
I
Code tarifaire harmonisé
2904.90
TSCA
Yes
RTECS
PB2790000

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