18511-56-3

Usage

Uses

Used in Chemical Industry:
(3,3-Dimethyloxiranyl)methanol is used as a chemical intermediate for the production of glycidyl ethers, glycidyl esters, and glycidyl amine, which are essential components in various industrial applications.
Used in Pharmaceutical Industry:
(3,3-Dimethyloxiranyl)methanol is used as a chemical building block in the synthesis of pharmaceuticals, contributing to the development of new drugs and medications.
Used in Resin Systems, Adhesives, and Coatings Production:
(3,3-Dimethyloxiranyl)methanol is used as a key component in the production of resin systems, adhesives, and coatings, enhancing their properties and performance.
However, it is important to note that (3,3-Dimethyloxiranyl)methanol is classified as a potential human carcinogen, and exposure to high levels of the compound may pose a risk to human health. As a result, efforts are being made to regulate and limit its use and exposure in various industries to ensure safety and minimize potential health risks.

InChI:InChI=1/C5H10O2/c1-5(2)4(3-6)7-5/h4,6H,3H2,1-2H3

Upstream product

• 556-82-1 3-methyl-2-buten-1-ol 
• 620621-16-1 (1R,2R,4R)-2-exo-hydroperoxy-2-endo-(2'-furyl)-1,7,7-trimethylbicyclo[2.2.1]heptane 
• 5369-62-0 (+/-)-3,3-dimethyloxirane-2-carboxaldehyde 
• 107-86-8 3,3-dimethyl acrylaldehyde 

Downstream Products

• 105632-37-9 2,2-dimethyl-3-<<<(E)-2-(phenylsulfonyl)ethenyl>oxy>methyl>oxirane 
• 147910-38-1 2,3-epoxy-3-methyl-1-phenylthiobutane 
• 312736-31-5 benzyl-carbamic acid (3,3-dimethyl-oxiran-2-yl)methyl ester 
• 141700-91-6 [(2R)-3,3-dimethyloxiran-2-yl]methyl 4-nitrobenzoate 
• 208763-43-3 1-(2-Hydroxy-5-methyl-phenyl)-3-methyl-butane-2,3-diol 
• 208763-42-2 1-(2-Hydroxy-5-methyl-phenyl)-1-isopropylsulfanyl-3-methyl-butane-2,3-diol 
• 208763-41-1 Acetic acid 2-acetoxy-1-[(2-hydroxy-5-methyl-phenyl)-isopropylsulfanyl-methyl]-2-methyl-propyl ester 
• 106268-98-8 (S)-(3,3-dimethyloxiran-2-yl)methyl 4-nitrobenzoate 

Relevant academic research and scientific papers

Microencapsulated VO(acac)2: Preparation and Use in Allylic Alcohol Epoxidation

(matrix presented) Microencapsulated VO(acac)2 [MC-VO(acac)2] has been prepared and screened with success as a catalyst for the epoxidation of allylic alcohols using tert-butyl hydroperoxide as oxidant. The reactions are run in hexane at room temperature. The MC-VO(acac)2 is reusable without significant loss of activity.

Click functionalization of magnetite nanoparticles: A new magnetically recoverable catalyst for the selective epoxidation of olefins

A new magnetically recoverable heterogeneous molybdenum catalyst was developed by means of a click chemistry approach. First, silica-coated magnetite nanoparticles were functionalized using a bidentate ligand via thiol–ene click reaction of mercaptopropyl-modified magnetite nanoparticles with acrylic acid. Then, a molybdenum complex was covalently supported on the surface of the clicked silica-coated magnetite nanoparticles. The prepared catalyst was characterized using Fourier transform infrared and inductively coupled plasma optical emission spectroscopies, X-ray diffraction, vibrating sample magnetometry and transmission electron microscopy. The catalytic performance of the prepared heterogeneous catalyst was investigated in the epoxidation of olefins with tert-butyl hydroperoxide as oxidant. This catalyst could be reused for five runs without significant loss of activity and selectivity.

Surface modification of magnetite nanoparticles with molybdenum-dithiocarbamate complex: a new magnetically separable nanocatalyst

Surface modification of silica-coated magnetite nanoparticles (SCMNPs) by anchoring of molybdenum-dithiocarbamate complex resulted in the preparation of a new magnetically separable nanocatalyst for the epoxidation of olefins. The prepared nanocatalyst was characterized by various physicochemical techniques which indicated that the molybdenum complex is successfully supported on the SCMNPs support. This heterogeneous catalyst exhibited good catalytic activity and high selectivity in the epoxidation of olefins with tert-butyl hydroperoxide as oxidant under mild reaction conditions. It can be easily recovered by an external magnetic field and reused up to three times without noticeable deactivation. Graphical abstract: [Figure not available: see fulltext.].

Organocatalyzed Domino [3+2] Cycloaddition/Payne-Type Rearrangement using Carbon Dioxide and Epoxy Alcohols

An unprecedented organocatalytic approach towards highly substituted cyclic carbonates from tri- and tetrasubstituted oxiranes and carbon dioxide has been developed. The protocol involves the use of a simple and cheap superbase under mild, additive- and metal-free conditions towards the initial formation of a less substituted carbonate product that equilibrates to a tri- or even tetrasubstituted cyclic carbonate under thermodynamic control. The latter are conveniently trapped in situ, providing overall a new domino process for synthetically elusive heterocyclic scaffolds. Control experiments provide a rationale for the observed cascade reactions, which demonstrate similarity to the well-known Payne rearrangement of epoxy alcohols.

Rational Design of a Polyoxometalate Intercalated Layered Double Hydroxide: Highly Efficient Catalytic Epoxidation of Allylic Alcohols under Mild and Solvent-Free Conditions

Intercalation catalysts, owing to their modular and accessible gallery and unique interlamellar chemical environment, have shown wide application in various catalytic reactions. However, the poor mass transfer between the active components of the intercalated catalysts and organic substrates is one of the challenges that limit their further application. Herein, we have developed a novel heterogeneous catalyst by intercalating the polyoxometalate (POM) of Na9LaW10O36?32 H2O (LaW10) into layered double hydroxides (LDHs), which have been covalently modified with ionic liquids (ILs). The intercalation catalyst demonstrates high activity and selectivity for the epoxidation of various allylic alcohols in the presence of H2O2. For example, trans-2-hexen-1-ol undergoes up to 96 % conversion and 99 % epoxide selectivity at 25 °C in 2.5 h. To the best of our knowledge, the Mg3Al?ILs?C8?LaW10composite material constitutes one of the most efficient heterogeneous catalysts for the epoxidation of allylic alcohols (including the hydrophobic allylic alcohols with long alkyl chains) reported so far.

Immobilized molybdenum-thiosemicarbazide Schiff base complex on the surface of magnetite nanoparticles as a new nanocatalyst for the epoxidation of olefins

In this work, a new magnetically recoverable nanocatalyst was developed by immobilization of thiosemicarbazide ligand on the surface of silica coated magnetite nanoparticles (SCMNPs) through Schiff base condensation and followed complexation with MoO2(acac)2. Characterization of the prepared nanocatalyst was performed with different physicochemical methods such as Fourier transform infrared (FT-IR) and atomic absorption spectroscopies, X-ray diffraction (XRD), vibrating sample magnetometry (VSM), thermogravimetric analysis (TGA), field-emission scanning electron microscopy (FE-SEM), and transmission electron microscopy (TEM). The prepared catalyst catalyzed the epoxidation of olefins and allyl alcohols with tert-butyl hydroperoxide (TBHP) and cumene hydroperoxide (CHP) quantitatively with excellent selectivity toward the corresponding epoxides under mild reaction conditions.

Oxidation of geraniol and other substituted olefins with hydrogen peroxide using mesoporous, sol-gel-made tungsten oxide-silica mixed oxide catalysts

The preparation of a series of mesoporous tungsten oxide-silica mixed oxides by sol-gel methods under basic conditions is reported. Surface modification with methyl and 3-chloropropyl groups is possible in an amount between 10 and 40 mol% with respect to the silane precursor. The amount of polar organic functional groups controls the surface area, the porosity, and the catalytic activity of the solids in the oxidation of different substrates with hydrogen peroxide. The oxidation of geraniol is studied in detail. The catalysts are active and produce epoxides in good yields. The latter are influenced by the presence of polar organic groups. The preparation method allows the preparation of catalysts that are resistant to leaching and can be recycled several times without appreciable loss of activity.

Olefin epoxidation with ionic liquid catalysts formed by supramolecular interactions

This work demonstrated that the specific ionic liquids (ILs) have been designed via the supramolecular complexation between 18-crown-6 (CE) and ammonium peroxoniobate (NH4-Nb). The resultant ILs have been characterized by elemental analysis, FT-IR, Raman, NMR, DSC, conductivity measurement and MALDI-TOF, etc. The IL (CE-1) consisting of CE and ammonium peroxoniobate can be further coordinated with GLY to generate a new IL (CE-2), which showed both high catalytic activity in epoxidation with H2O2 and good recyclability. The characterization of 93Nb NMR spectra revealed that the peroxoniobate anions has demonstrated a structural evolution in the presence of hydrogen peroxide, in which Nb[dbnd]O species can be easily oxidized into the catalytically active niobium?peroxo species. Especially, the supramolecular complexation can provide suitable hydrophobicity, which ensured that the hydrophobic olefins and allylic alcohols were easily accessible to the catalytically active anions, and thus facilitated the epoxidation reaction. Notably, the supramolecular IL catalysts in this work exhibited a huge advantage of the easy availability, as compared with the previously reported peroxoniobate-based ILs. As far as we know, this is the first example of the highly selective epoxidation of olefins and allylic alcohols by using supramolecular ILs as catalysts.

Synthesis, characterization and immobilization of a novel mononuclear vanadium (V) complex on modified magnetic nanoparticles as catalyst for epoxidation of allyl alcohols

The 2,4,6-tris(2-pyridyl)-1,3,5-triazine (tptz) undergoes hydrolysis in the presence of VO(SO4) in an alkaline solution, affording mainly the bis(2-pyridyl carbonyl)amid) VO2 complex, designated as [VO2(bpca)]. Single-crystal X-ray crystallography revealed that the coordination of V in complex is a distorted square-pyramid coordinated with three nitrogen of bis(2-pyridyl carbonyl)amid) ligand and two binding oxygen atoms. The prepared complex which successfully supported on modified Fe3O4 nanoparticles using tetraethylorthosilicate (TEOS) and (3-aminopropyl)trimethoxysilane(APTMS)was designated as Fe3O4@SiO2@APTMS@[VO2(bpca)] complex (nanocatalyst). The complex and nanocatalyst were characterized by means of FT-IR, XRD, VSM, SEM and TEM. The catalytic activity of [VO2(bpca)] complex and Fe3O4@SiO2@APTMS@complex as catalysts 1 and 2 were evaluated by the epoxidation of geraniol, 3-methyl-2-buten-1-ol, trans-2-hexen-1-ol and 1-octen-3-ol with 70–98% conversions and 95–100% selectivities. Based on the obtained results, the heterogeneity and reusability of the catalyst seems promising. In addition, the in vitro antibacterial activity of [VO2 (bpca)] complex have also been evaluated and compared to the activities of other vanadium complexes, tptz ligand and two standard antibacterial drugs, Nalidixic acid and Vancomycin.

A Ni-containing decaniobate incorporating organic ligands: Synthesis, structure, and catalysis for allylic alcohol epoxidation

An organic-inorganic hybrid polyoxoniobate, Na8{Ni[Ni(en)]2Nb10O32}·28H2O (1) (en = ethanediamine), has been synthesized and characterized. It represents the first example of a trinuclear nickel-containing polyoxoniobate. The catalysis of 1 for allylic alcohol epoxidation was investigated at room temperature in aqueous solution, and was found to catalyze the epoxidation of 3-methyl-2-buten-1-ol with high conversion (98%) and selectivity (94%). Furthermore, magnetic measurements showed that the compound exhibits ferromagnetic interactions.