15121-11-6

Basic information

• Product Name: 4-(chloromethyl)-1,3,2-dioxathiolane 2-oxide
• Synonyms: 4-(chloromethyl)-1,3,2-dioxathiolane 2-oxide;1,2-Ethanediol, 1-chloromethyl-, cyclic sulfite;1,2-Propanediol, 3-chloro-, cyclic sulfite (ester);1,3,2-Dioxathiolane, 4-(chloromethyl)-, 2-oxide;3-Chloro-1,2-propanediol cyclic sulfite (ester);Ai3-27589;Einecs 239-175-5
• CAS NO: 15121-11-6
• Molecular Formula: C₃H₅ClO₃S
• Molecular Weight: 156.588
• EINECS: 239-175-5
• Mol File: 15121-11-6.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 167.5°C
• Flash Point: 103.3°C
• Appearance: /
• Density: 1.414 (estimate)
• Vapor Pressure: 0.041mmHg at 25°C
• Refractive Index: 1.566
• CAS DataBase Reference: 4-(chloromethyl)-1,3,2-dioxathiolane 2-oxide(CAS DataBase Reference)
• NIST Chemistry Reference: 4-(chloromethyl)-1,3,2-dioxathiolane 2-oxide(15121-11-6)
• EPA Substance Registry System: 4-(chloromethyl)-1,3,2-dioxathiolane 2-oxide(15121-11-6)

Safety Data

• Hazardous Substances Data: 15121-11-6(Hazardous Substances Data)

Usage

Safety Profile

Poison by intravenous route. See also SULFITES. Experimental reproductive effects. When heated to decomposition it emits very toxic fumes of Cland SOx.

InChI:InChI=1/C3H5ClO3S/c4-1-3-2-6-8(5)7-3/h3H,1-2H2

Upstream product

• 96-24-2 3-monochloro-1,2-propanediol 
• 56-81-5 glycerol 
• 556-52-5 oxiranyl-methanol 
• 106-89-8 epichlorohydrin 
• 7719-09-7 thionyl chloride 

Downstream Products

• 109821-98-9 4-o-tolyloxymethyl-[1,3,2]dioxathiolane-2-oxide 
• 82019-13-4 4-phenoxymethyl-1,3,2-dioxathiolane 2-oxide 
• 114097-31-3 5-phenoxy-[1,3,2]dioxathiane-2-oxide 
• 623-81-4 diethyl sulphite 
• 538-43-2 3-phenoxy-1,2-propanediol 
• 556-52-5 oxiranyl-methanol 
• 115798-86-2 5-o-tolyloxy-[1,3,2]dioxathiane-2-oxide 

Relevant articles and documents

Chemo- and Regioselective Functionalization of Polyols through Catalytic C(sp3)-C(sp3) Kumada-Type Coupling of Cyclic Sulfate Esters

This contribution describes a copper-catalyzed, C(sp3)-C(sp3) cross-coupling reaction of cyclic sulfate esters, a distinct class of electrophilic derivatives of polyols, with alkyl Grignard reagents to afford functionalized alcohol products in good yields. The method is operationally simple and highlights the potential of cyclic sulfate esters as highly reactive substrates in catalytic, chemoselective polyol transformations.

Reactions of 4-chloromethyl-1,3,2-dioxathiolane 2-oxides with sodium phenoxide. A reinvestigation

The reactions of 4-chloromethyl-1,3,2-dioxathiolane 2-oxides with PhONa in EtOH are accompanied by ring opening under the action of the ethoxide ion rather than leading to a rearrangement of the starting molecule as has been assumed previously. Under conditions precluding competition with other nucleophiles, the phenoxide anion smoothly replaces the chlorine atom in chloromethyl-substituted cyclic sulfites.