4288-84-0

Usage

InChI:InChI=1/C6H13ClO2/c1-5(2)9-6(3,8)4-7/h5,8H,4H2,1-3H3

Upstream product

• 67-63-0 isopropyl alcohol 
• 106-89-8 epichlorohydrin 
• 4362-40-7 5-chloromethyl-2,2-dimethyl-1,3-dioxolane 
• 4016-14-2 glycidyl isopropyl ether 
• 68-12-2 N,N-dimethyl-formamide 
• 145119-74-0 Acetic acid 1-chloromethyl-2-isopropoxy-ethyl ester 

Downstream Products

• 1572051-31-0 1-((fluoro(methyl)phosphoryl)oxy)-3-isopropoxypropan-2-yl oleate 
• 5589-51-5 3-isopropoxymethyl-8-methyl-2-oxa-8-aza-5-azonia-spiro[4.5]decane; tetraphenylborate 

Relevant academic research and scientific papers

Readily Scalable Methodology for the Synthesis of Nonsymmetric Glyceryl Diethers by a Tandem Acid-/Base-Catalyzed Process

A useful optimized synthetic methodology has been designed for the synthesis of nonsymmetric glyceryl diethers from epichlorohydrin. A tandem process combining a cheap, heterogeneous, and fully recoverable acid catalyst and alkaline hydroxide is used for the synthesis of a variety of glycerol-derived ethers bearing different alkyl substituents in 1 and 3 positions. Different heterogeneous acid catalysts have been tested for the reaction of epichlorohydrin with several alcohols, the best results being obtained with readily available recoverable and inexpensive montmorillonite-K10 and Nafion NR50. For the second reaction step, potassium hydroxide is used. In all the cases, good yields of the desired glyceryl diethers are obtained in smooth reaction conditions, always with total conversion of epichlorohydrin and without the need of intermediate purification. Scale-up of the tandem process has been carried out with good results.

An epoxide ring-opening reaction by using sol–gel-synthesized palladium supported on a strontium hydroxyl fluoride catalyst

Palladium supported on a strontium hydroxyl fluoride catalyst was synthesized by a one-pot fluorolytic sol–gel method. The prepared catalyst was characterized by various physicochemical techniques. The sol–gel method has led to the formation of a high surface area (57?m2g?1), mesoporous (pore diameter?=?13.0?nm) catalyst with uniform dispersion of Pd nanoparticles of size ～7?nm on the surface of strontium hydroxyl fluoride. The catalyst was used for epoxide alcoholysis, and 100% conversion was obtained with 96% selectivity for β-alkoxy alcohols under mild conditions. The catalyst could be recycled for up to three catalytic cycles without any appreciable decrease in conversion and selectivity, indicating the stability of the catalyst under the reaction conditions. Further, the mechanism of alcoholysis was proposed on the basis of the physicochemical characteristics of the catalyst and on the basis of the products formed during the catalytic reaction.

1,3,2,4-diazadiphosphetidine-based phosphazane oligomers as source of P(III) atom economy reagents: Conversion of epoxides to vic -haloalcohols, vic -dihalides, and alkenes in the presence of halogen sources

1,3,2,4-Diazadiphosphetidines (P1-P3), as easily prepared, stable, and heterogeneous P(III) compounds, were used for the efficient conversion of epoxides to vic-halohydrins, vic-dihalides, or alkenes in the presence of different halogen sources in CH3CN. Of these phosphazanes, P3 is most suitable and contains 4 phosphorous atoms with the advantage of having greater atom economy and its phosphorus oxide byproduct can be easily separated from the reaction mixture by simple filtration. The nitrogen atoms in this molecule can also act as acid scavengers in the reaction.

Synthesis of Di-, Tri-, and tetrasubstituted oxetanes by rhodium-catalyzed O-H insertion and C-C bond-forming cyclization

Oxetanes offer exciting potential as structural motifs and intermediates in drug discovery and materials science. Here an efficient strategy for the synthesis of oxetane rings incorporating pendant functional groups is described. A wide variety of oxetane 2,2-dicarboxylates were accessed in high yields, including functionalized 3-/4-aryl-and alkyl-substituted oxetanes and fused oxetane bicycles. Enantioenriched alcohols provided enantioenriched oxetanes with complete retention of configuration. The oxetane products were further derivatized, while the ring was maintained intact, thus highlighting their potential as building blocks for medicinal chemistry.

Mild organic ammonium tribromide-mediated regioselective ring opening of epoxides with alcohols, water, acetic anhydride, and amines under solvent-free reaction conditions

Organic ammonium tribromide (OATB), N-methylpyrrolidine-2-one hydrotribromide (MPHT) was found to be an efficient catalyst for the regioselective ring opening of epoxides with various nucleophiles under solvent free conditions. This procedure occurs under neutral and mild reaction conditions with out adding any additive and afforded high yields of products.

Facile, high regio- And chemoselective conversion of epoxides to β-chlorohydrins using chlorodiphenylphosphine under solvent-free conditions

A new method is described for the mild and high regioselective conversion of epoxides to β-chlcrohydrins in high yields even in the presence of alcohols, carboxylic acids, oximes, amides, thiols and tetrahydropyranyl ethers using chlorodiphenylphosphine (ClPPh2) under solvent-free and neutral conditions at room temperature and in short reaction times. In addition, some other functional groups such as carbon-carbon double bonds, ester groups and also phenyl ring that are present in the epoxide molecules remain intact in this method.

Alumina-supported molybdenum (VI) oxide: An efficient and recyclable heterogeneous catalyst for regioselective ring opening of epoxides with thiols, acetic anhydride, and alcohols under solvent-free conditions

An efficient and simple protocol for regioselective ring opening of epoxides with thiols, acetic anhydride, and alcohols using 16wt% MoO3 supported on alumina as a recyclable catalyst is described. Copyright

A new dinuclear chiral salen complexes for asymmetric ring opening and closing reactions: Synthesis of valuable chiral intermediates

A new dinuclear chiral Co(salen) complexes bearing group 13 metals have been synthesized and characterized. The easily prepared complexes exhibited very high catalytic reactivity and enantioselectivity for the asymmetric ring opening of epoxides with H2O, chloride ions and carboxylic acids and consequently provide enantiomerically enriched terminal epoxides (>99% ee). It also catalyzes the asymmetric cyclization of ring opened product, to prepare optically pure terminal epoxides in one step. The homogeneous dinuclear chiral Co(salen) have been covalently immobilized on MCM-41. The potential benefits of heterogenization include facilitation of catalyst separation and recyclability requiring very simple techniques. The system described is very efficient.

Regioselective conversion of unsymmetrical terminal epoxides into vicinal chlorohydrins using dimethoxyboron chloride

A highly regioselective synthesis of chlorohydrins by chlorinative cleavage of unsymmetrical epoxides utilizing dimethoxyboron chloride is described. Except for styrene oxide, all the terminal epoxides were regioselectively cleaved following a predominantly SN2-type reaction pathway favouring the formation of primary chlorides. In the case of styrene oxide, a benzylic epoxide, (MeO)2BCl transfers the chlorine at the benzylic position, by following an apparent SN1-type mechanism. CSIRO 2006.

Mild and efficient ring opening of epoxides catalyzed by potassium dodecatungstocobaltate(III)

Efficient ring opening of epoxides under mild conditions is reported. Potassium dodecatungstocobaltate(III) trihydrate was used as an efficient catalyst for the alcoholysis and acetolysis of epoxides. Conversion of epoxides to thiiranes was also performed efficiently in the presence of this catalyst. Springer-Verlag 2005.