88343-72-0

Basic information

• Product Name: clomesone
• Synonyms: clomesone;(Methylsulfonyl)methanesulfonic acid 2-chloroethyl ester;Chlorethyl SOSO;NSC-338947;SRI-6155
• CAS NO: 88343-72-0
• Molecular Formula: C4H9ClO5S2
• Molecular Weight: 236.695
• Mol File: 88343-72-0.mol

Chemical Properties

• Boiling Point: 485.9°C at 760 mmHg
• Flash Point: 247.7°C
• Appearance: /
• Density: 1.533g/cm³
• Vapor Pressure: 4.02E-09mmHg at 25°C
• Refractive Index: 1.491
• CAS DataBase Reference: clomesone(CAS DataBase Reference)
• NIST Chemistry Reference: clomesone(88343-72-0)
• EPA Substance Registry System: clomesone(88343-72-0)

Safety Data

• Hazardous Substances Data: 88343-72-0(Hazardous Substances Data)

Usage

InChI:InChI=1/C4H9ClO5S2/c1-11(6,7)4-12(8,9)10-3-2-5/h2-4H2,1H3

Upstream product

• 124-63-0 methanesulfonyl chloride 
• 107-07-3 2-chloro-ethanol 
• 22317-89-1 (methylsulphonyl)-methanesulphonyl chloride 

Relevant articles and documents

Synthesis, characterization and crystal structure of 2-chloroethyl(methylsulfonyl)methanesulfonate

The aim of this study was to evaluate the structural and vibrational properties and biological activity of 2-chloroethyl(methylsulfonyl)methanesulfonate, CH3SO2CH2SO2OCH2CH2Cl (clomesone). The solid-state molecular structure has been isolated and characterized using experimental (X-ray diffraction) and theoretical (DFT method) methodologies. The molecules are packed through C-H?O bifurcated interactions and Cl?Cl interactions. The experimental investigations are supplemented by quantum chemical calculations and Hirshfeld surface calculations. Furthermore, the infrared and Raman spectra of the solid phase have been obtained, and the observed bands are assigned to the vibrational normal modes. This study is completed using the atoms-in-molecules (AIM) theory and natural bond orbital (NBO) analysis. Finally, we studied the function of clomesone in biofilm formation and investigated a methanesulfonate complex with respect to QS activity.

Synthesis and antineoplastic evaluation of α-substituted alkanesulfonates: Analogues of clomesone

2-Chloroethyl (methylsulfonyl)methanesulfonate (clomesone) is highly effective against certain experimental neoplasma and is now undergoing initial clinical trials. Two groups of analogues have been prepared to explore further the anticancer activity of this type of sulfonates. The first group is comprised of several 2-chloroethyl sulfonates that have electron- attracting groups α to the sulfonate group; among these, the α- chloroethanesulfonate and the (trifluoromethyl)-methanesulfonate caused increases in lifespan of 45 and 72%, respectively, in tests against P388 leukemia in mice. The second group is comprised of several (methylsulfonyl)methanesulfonates that possess alkylating groups other than the 2-haloethyl groups. 2-Hydroxyethyl (methylsulfonyl)methanesulfonate was active against P388 leukemia (increases in lifespan, 66 and 94%), but was less effective than clomesone, which effects cures. The 3-chloropropyl and the propyl derivatives caused modest increases in lifespan. Therefore, several 2-chloroethyl α-substituted methanesulfonates are less effective against P388 leukemia than is the α-(methylsulfonyl) derivative (clomesone), and several substituted alkyl (methylsulfonyl)methanesulfonates are also less effective than is the 2-chloroethyl derivative (clomesone). The synthesis of clomesone was simplified to one operational step from methanesulfonyl chloride.

(Alkylsulfonyl)methanesulfonates as anticancer agents

Compounds of the formula: STR1 wherein R is methyl or other lower alkyl group; X and X' individually are hydrogen or lower alkyl; and R' is a 2-haloethyl group or other halogenated lower alkyl group are useful in the treatment of neoplastic diseases.

2-Chloroethyl (methylsulfonyl)methanesulfonate and related (methylsulfonyl)methanesulfonates. Antineoplastic activity in vivo

2-Haloethyl and ethyl (methylsulfonyl)methanesulfonates were prepared via sulfene intermediates. 2-Chloroethyl (methylsulfonyl)methanesulfonate is highly active against P388 leukemia in vivo; the majority of leukemic mice treated with this compound at 50 mg/kg per day, qd 1-5, survived more than 30 days and about 37% survived for more than 60 days. 2-Fluoroethyl (methylsulfonyl)methanesulfonate is also highly effective against P388 cells in vivo, but it is more toxic. Other (methylsulfonyl)methanesulfonate esters are more active than the analogous methanesulfonates and chloromethanesulfonates.