Methanesulfonyl chloride

Structural formula
General
Surname	Methanesulfonyl chloride
other names	Mesyl chloride; Methanesulfonic acid chloride;
Molecular formula	CH 3 ClO 2 S
Brief description	yellowish liquid with a pungent odor
External identifiers / databases
EC number	204-706-1
ECHA InfoCard	100.004.279
PubChem	31297
Wikidata	Q417706
properties
Molar mass	114.55 g mol −1
Physical state	liquid (> 20 ° C)
density	1.48 g cm −3
Melting point	−32 ° C
boiling point	161 ° C (96 Pa); 62 ° C (2 Pa);
Vapor pressure	2.6 h Pa (20 ° C)
solubility	almost insoluble in water
Refractive index	1.4573 (20 ° C)
safety instructions
H and P phrases	H: 290-301-311-330-314-317-335
	P: 280-310-305 + 351 + 338-304 + 340-301 + 330 + 331-303 + 361 + 353
Toxicological data	50 mg kg −1 ( LD 50 , rat , oral )
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions . Refractive index: Na-D line , 20 ° C

Methanesulfonic acid chloride (also mesyl chloride , often abbreviated Ms – Cl) is the acid chloride of methanesulfonic acid .

Manufacturing

By reacting methanesulfonic acid with thionyl chloride .

{\ displaystyle \ mathrm {CH_ {3} SO_ {2} OH + SOCl_ {2} \ rightarrow CH_ {3} SO_ {2} Cl + HCl + SO_ {2}}}

properties

Methanesulfonyl chloride is a yellow, very difficult to ignite liquid with a pungent odor, which is practically insoluble in water, but decomposes in it. It has a dynamic viscosity of 1.97 mPas at 25 ° C.

use

Methanesulfonic acid chloride is often used as a reagent in organic synthesis. As a rule, hydroxyl groups of alcohols cannot be replaced directly in the case of nucleophilic substitutions . Therefore, the alcohol is first reacted with methanesulphonyl chloride to form methanesulphonic acid ester ( mesylate ). The mesylate is a very good leaving group and can usually be substituted by a nucleophile .

Individual evidence

↑ ^a ^b ^c ^d ^e ^f ^g ^h record with methanesulfonyl chloride in the GESTIS database of IFA , accessed on January 8, 2020(JavaScript required) .
^ The Merck Index . An Encyclopaedia of Chemicals, Drugs and Biologicals. 14th edition, 2006, p. 1029, ISBN 978-0-911910-00-1 .
↑ ^a ^b ^c The Merck Index . An Encyclopaedia of Chemicals, Drugs and Biologicals. 9th edition, Merck & Co., 1976, pp. 776, ISBN 0-911910-26-3 .
↑ David R. Lide (Ed.): CRC Handbook of Chemistry and Physics . 90th edition. (Internet version: 2010), CRC Press / Taylor and Francis, Boca Raton, FL, Physical Constants of Organic Compounds, pp. 3-326.

[GESTIS-1] ↑ ^a ^b ^c ^d ^e ^f ^g ^h record with methanesulfonyl chloride in the GESTIS database of IFA , accessed on January 8, 2020(JavaScript required) .

[Merckedex-2] The Merck Index . An Encyclopaedia of Chemicals, Drugs and Biologicals. 14th edition, 2006, p. 1029, ISBN 978-0-911910-00-1 .

[Merck_Index-3] The Merck Index . An Encyclopaedia of Chemicals, Drugs and Biologicals. 9th edition, Merck & Co., 1976, pp. 776, ISBN 0-911910-26-3 .

[CRC90_3_326-4] David R. Lide (Ed.): CRC Handbook of Chemistry and Physics . 90th edition. (Internet version: 2010), CRC Press / Taylor and Francis, Boca Raton, FL, Physical Constants of Organic Compounds, pp. 3-326.