53379-98-9

Usage

Physical state

Clear, colorless liquid

Odor

Slightly sweet

Common use

Solvent in industrial and laboratory applications

Additional use

Stabilizer for chlorineand bromine-containing compounds

Intermediate in production

Pharmaceuticals and other organic compounds

Toxicity

Low toxicity

Safety

Generally regarded as safe for use in intended applications

Precaution

Proper handling and safety measures should be followed

Upstream product

• 122-60-1 Phenyl glycidyl ether 
• 67-64-1 acetone 
• 538-43-2 3-phenoxy-1,2-propanediol 
• 77-76-9 2,2-dimethoxy-propane 
• 23737-51-1 solketal tosylate 
• 108-95-2 phenol 
• 591-50-4 iodobenzene 
• 100-79-8 (R,S)-2,2-dimethyl-1,3-dioxolane-4-methanol 

Downstream Products

• 132840-74-5 4-(Cyclohexa-1,4-dienyloxymethyl)-2,2-dimethyl-[1,3]dioxolane 
• 538-43-2 3-phenoxy-1,2-propanediol 
• 132840-81-4 2,2-Dimethyl-4-(6-methyl-cyclohexa-1,4-dienyloxymethyl)-[1,3]dioxolane 
• 132840-82-5 4-(6-Benzyl-cyclohexa-1,4-dienyloxymethyl)-2,2-dimethyl-[1,3]dioxolane 
• 209860-88-8 AFP-172 
• 209860-87-7 tafluprost 
• 1185851-52-8 (5Z)-N-ethyl-7-{(1R,2R,3R,5S)-2-[(1E)-3,3-difluoro-4-(phnoxy)but-1-enyl]-3,5-dihydroxycyclopentyl}hept-5-enamide 

Relevant academic research and scientific papers

Ultrasound Assisted the Synthesis of 1,3-Dioxolane Derivatives from the Reaction of Epoxides or 1,2-Diols with Various Ketones Using Graphene Oxide Catalyst

Abstract: The main objective of this study concerns the sonochemical synthesis of 1,3-dioxolane derivatives using graphene oxide catalyst by applying two methods. In the first method, we described the synthesis of 1,3-dioxolane by ring-opening of epoxides in the presence of ketones catalyzed by graphene oxide (GO) under ultrasonic irradiation. In the second sonochemical procedure, we described the synthesis of 1,3-dioxolane derivatives by the reaction of 1,2-diols with ketones using same GO catalyst. Mild reaction conditions, high yields, short reaction times, reusability of catalyst and easy isolation of the products make the developed methods very useful. Graphic Abstract: [Figure not available: see fulltext.]

A novel convergent synthesis of the potent antiglaucoma agent tafluprost

Tafluprost (AFP-168, 5) is a unique 15-deoxy-15,15-difluoro-16-phenoxy prostaglandin F2α (PGF2α) analog used as an efficacious ocular hypotensive agent in the treatment of glaucoma and ocular hypertension, as monotherapy, or as adjunctive therapy to β-blockers. A novel convergent synthesis of 5 was developed employing Julia-Lythgoe olefination of the structurally advanced prostaglandin phenylsulfone 16, also successfully applied for manufacturing of pharmaceutical grade latanoprost (2), travoprost (3) and bimatoprost (4), with an aldehyde !-chain synthon 17. The use of the same prostaglandin phenylsulfone 16, as a starting material in parallel syntheses of all commercially available antiglaucoma PGF2α analogs 2-5, significantly reduces manufacturing costs resulting from its synthesis on an industrial scale and development of technological documentation. Another key aspect of the route developed is deoxydifluorination of a trans-13,14-en-15-one 30 with Deoxo-Fluor. Subsequent hydrolysis of protecting groups and final esterification of acid 6 yielded tafluprost (5). The main advantages are the preparation of high purity tafluprost (5) and the application of comparatively cheap reagents. The preparation and identification of two other tafluprost acid derivatives, tafluprost methyl ester (32) and tafluprost ethyl amide (33), are also described.

Convenient method for the transformation of epoxide to aldehyde and acetonide mediated by Cr-PLM

Chromium-pillared montmorillonite (Cr-PLM) could be synthesized and efficiently utilized for styrene oxide transformations. The target aldehyde product could be quantitatively achieved from the isomerization of styrene oxide by using 10 wt% of Cr-PLM under reflux temperature for 15 min. The acetonide product could be achieved in excellent yield from the reaction of styrene oxide and acetone by using 10 wt% of Cr-PLM under room temperature for 20 min. The catalyst could be recovered and reused at least five times without loss of activity.

Ullmann C[sbnd]O coupling of sterically hindered secondary alcohols using excess amount of strongly coordinating monodentate ligands

A new effective copper catalyzed C[sbnd]O coupling reaction using excess amount of strongly coordinating monodentate ligands was successfully developed. Among the DMAP-type monodentate ligands, 4-pyrrolidinopyridine afforded the best results. The developed reaction is widely applicable for the synthesis of various hindered or acyclic secondary alkyl-aryl ethers. In this study, a novel and remarkable acceleration of the coupling reaction using excess amount of monodentate ligands was discovered.

Iron oxide-pillared clay catalyzed the synthesis of acetonides from epoxides

FeOx-pillared clays (FeOx-pillared bentonite, FeOx-pillared hectorite and FeOx-pillared taeniolite) were synthesized by the intercalation of FeCl3 into clay interlayers and calcination. The synthesize

Iron oxide-pillared clay catalyzed the synthesis of acetonides from epoxides

FeOx-pillared clays (FeOx-pillared bentonite, FeOx-pillared hectorite and FeOx-pillared taeniolite) were synthesized by the intercalation of FeCl3 into clay interlayers and calcination. The synthesize

Gold-catalysed activation of epoxides: Application in the synthesis of bicyclic ketals

Gold-catalysed generation of diol equivalents from epoxides and their intramolecular reaction with Ca≡C bonds to generate bicyclic ketals is presented. This reaction essentially involves the formation of an acetonide, which subsequently cyclises on the alkyne intramolecularly under gold catalysis conditions. This method could be extended to make optically pure bicyclic ketals. Deuterium incorporation experiments were carried out to ascertain the mechanism of the reaction. Sequential activation of epoxide and alkyne moieties by a gold catalyst in acetone as solvent has been achieved. This strategyhas been employed to synthesise bicyclic ketals from epoxy alkynes. Copyright

Investigation of the catalytic activity of an electron-deficient vanadium(IV) tetraphenylporphyrin: A new, highly efficient and reusable catalyst for ring-opening of epoxides

In this work, the catalytic activity of high-valent tetraphenylporphyrinatovanadium(IV) trifluoromethanesulfonate, [V IV(TPP)(OTf)2], in the nucleophilic ring-opening of epoxides is reported. This new V(IV) catalyst was used as an efficient catalyst for alcoholysis with primary (methanol, ethanol and n-propanol), secondary (iso-propanol) and tertiary alcohols (tert-butanol), hydrolysis and acetolysis of epoxides with acetic acid and also for the conversion of epoxides to 1,2-diacetates with acetic anhydride, conversion of epoxides to thiiranes with ammonium thiocyanate and thiourea, and for conversion of epoxides to acetonides with acetone. The catalyst was reused several times without loss of its activity.

Catalytic conversion of epoxides to 1,3-dioxolanes with phosphomolybdic acid (PMA) in solution and under solvent-free conditions

The fast and efficient conversion of epoxides into 2,2-dimethyl-1,3- dioxolanes was studied with catalytic amounts of phosphomolybdic acid (PMA) (0.1-0.2 mol %) at room temperature in solution and under solvent-free conditions. The products were obtained in high to excellent yields within 1-2 min. Copyright Taylor & Francis Group, LLC.

Ring-opening reactions of epoxides catalyzed by molybdenum(VI) dichloride dioxide

Transformation of epoxides to β-alkoxy alcohols, acetonides, and α-alkoxy ketones is achieved by using molybdenum(VI) dichloride dioxide (MoO2Cl2) as a catalyst. Alcohol, aldehyde, oxime, tosyl, and tert-butyldimethylsilyl functional groups are tolerated during the methanolysis and acetonidation of the functionalized epoxides. No polymerization product is observed with any of the epoxides. Direct conversion of epoxides devoid of sensitive functional groups into the corresponding α-methoxy ketone is achieved in a single step by using the MoO2Cl 2/Oxone system. Georg Thieme Verlag Stuttgart.