3578-32-3

Usage

Chemical Structure

Consists of a benzene ring with a methanol group attached to it, along with an a-[(1-methylethoxy)methyl] side chain.

Uses

Commonly used as a reagent or building block in organic synthesis.
Employed in pharmaceutical research.
Utilized in the manufacturing of various specialty chemicals.
Acts as a solvent in industrial processes.

Odor

Mild and pleasant.

Stability

Relatively stable under typical storage and handling conditions.

Safety Considerations

Should be handled with care.
Proper safety protocols should be followed due to potential irritancy and toxicity in concentrated or high exposure situations.

Upstream product

• 96-09-3 styrene oxide 
• 67-63-0 isopropyl alcohol 
• 683-60-3 sodium isopropylate 
• 52129-03-0 2,2-dimethyl-4-phenyl-1,3-dioxolane 
• 3587-58-4 isopropoxymethyl chloride 
• 100-52-7 benzaldehyde 

Downstream Products

• 844874-58-4 ethyl (2-isopropoxy-1-phenylethoxy)acetate 

Relevant academic research and scientific papers

Influence of Hydrogen Bond Donating Sites in UiO-66 Metal-Organic Framework for Highly Regioselective Methanolysis of Epoxides

A Zr(IV)-based UiO-66 metal-organic framework (MOF) (named 1) was synthesized by employing 1-(aminomethyl)naphthalene-2-ol appended terephthalate linker and Zr(IV) salt via solvothermal method and subsequently characterized. Furthermore, the potential efficiency of activated (named 1′) form of as-synthesized MOF was investigated as an organocatalyst for the ring-opening of epoxide by methanol. The catalytic performance of 1 and 1′ was studied in the methanolysis of styrene oxide as a model substrate and the activity of 1′ was also examined with various alcohols. Under the optimized reaction conditions, the catalytic performance of 1′ reached 96 % conversion of styrene oxide to its corresponding product with 98 % regioselectivity. The reusability and stability of the catalyst were proved by recycling up to four runs in the methanolysis of styrene oxide. The Lewis acidity originating from metal nodes and hydrogen bond donating (HBD) sites in the linker is distributed homogeneously throughout the framework, thus playing crucial role in the activation of epoxide with easy accessibility.

Postsynthetic Oxidation of the Coordination Site in a Heterometallic Metal-Organic Framework: Tuning Catalytic Behaviors

Postsynthetic modification (PSM) in metal-organic frameworks (MOFs) can introduce multiple functionalities and alter the structural function for the desired application. However, the PSM of the coordination site faces the challenges of structural collapse or incompatibility between the original metal site and the newly formed coordination group. Herein, we developed a novel concept of introducing primary and secondary nodes, coexisting in a water-stable, Zr-based heterometallic MOF, [Zr6(μ3-OH)8(OH)8][Cu4I(L1)4]2 (1-SH-a, H2L1 = 6-mercaptopyridine-3-carboxylic acid). The postsynthetic oxidation at the coordination site was successfully achieved in the secondary nodes [Cu4I(L1)4]4-, while the robust primary nodes [Zr6(μ3-OH)8(OH)8]8+ stabilized the whole framework to form [Zr6(μ3-OH)8(OH)8][(Cu0.44ICu0.56II(OH)0.56)4(L2)4]2 (1-SO3H, H2L2 = 6-sulfonicotinic acid). Attempts to directly synthesize 1-SO3H through the reactions of Zr(IV), Cu(II), and H2L2 failed. Furthermore, the PSM of 1-SH-a to form 1-SO3H was utilized to tune the catalytic behaviors toward the styrene oxide ring-opening reaction to give an improved regioselectivity of the primary alcohol (A) of ～99% compared with that of 1-SH-a (～71%).

Creation of Exclusive Artificial Cluster Defects by Selective Metal Removal in the (Zn, Zr) Mixed-Metal UiO-66

The differentiation between missing linker defects and missing cluster defects in MOFs is difficult, thereby limiting the ability to correlate materials properties to a specific type of defects. Herein, we present a novel and easy synthesis strategy for the creation of solely missing cluster defects by preparing mixed-metal (Zn, Zr)-UiO-66 followed by a gentle acid wash to remove the Zn nodes. The resulting material has the reo UiO-66 structure, typical for well-defined missing cluster defects. The missing clusters are thoroughly characterized, including low-pressure Ar-sorption, iDPC-STEM at a low dose (1.5 pA), and XANES/EXAFS analysis. We show that the missing cluster UiO-66 has a negligible number of missing linkers. We show the performance of the missing cluster UiO-66 in CO2 sorption and heterogeneous catalysis.

Well-defined epoxide-containing styrenic polymers and their functionalization with alcohols

Polymers containing electrophilic moieties, such as activated esters, epoxides, and alkyl halides, can be readily modified with a variety of nucleophiles to produce useful functional materials. The modification of epoxide-containing polymers with amines and other strong nucleophiles is well-documented, but there are no reports on the modification of such polymers with alcohols. Using phenyloxirane and glycidyl butyrate as low molecular weight model compounds, it was determined that the acid-catalyzed ring-opening of aryl-substituted epoxides by alcohols to form β-hydroxy ether products was significantly more efficient than that of alkyl-substituted epoxides. An aryl epoxide-type styrenic monomer, 4-vinylphenyloxirane (4VPO), was synthesized in high yield using an improved procedure and then polymerized in a controlled manner under reversible addition-fragmentation chain-transfer (RAFT) polymerization conditions. A successful chain extension with styrene proved the high degree of chain-end functionalization of the poly4VPO-based macro chain transfer agent. Poly4VPO was modified with a library of alcohols and phenols, some of which contained reactive functionalities, e.g., azide, alkyne, allyl, etc., using either CBr4 (in PhCN at 90°C for 2-3 days) or BF3 (in CH2Cl2 at ambient temperature over 30 min) as the catalyst. The resulting β-hydroxy ether-functionalized homopolymers were characterized using size exclusion chromatography, 1H NMR and IR spectroscopy, and thermal gravimetric analysis.

Mesoporous carbon as an efficient catalyst for alcoholysis and aminolysis of epoxides

The ring opening reaction of epoxides by alcohols and amines using mesoporous activated carbon as efficient and environmentally friendly heterogeneous catalyst is reported. Carbon xerogels were synthesized by polymerization of resorcinol and formaldehyde. The surface of the activated carbon was oxidized in liquid phase with HNO3 and then functionalized with H2SO4. Chemical and textural characterization by elemental analysis, pHPZC, TPD, BET and XPS indicates that oxidation in liquid phase is effective in the introduction of strong acid groups in the carbon surface. The functionalization with H2SO4 led to more acid functional groups, as expected. The activated carbons were tested in alcoholysis and aminolysis of epoxides, having been obtained excellent results of conversion and selectivity, both over 95%.

An environmentally benign catalytic method for efficient and selective nucleophilic ring opening of oxiranes by zirconium tetrakis(dodecyl Sulfate)

An operationally simple and environmentally benign protocol for a highly regio- and chemoselective preparation of β-substituted alcohols by means of ring-opening reactions of oxiranes with various aliphatic alcohols, H 2O, NaN3 , and NaCN as nucleophiles in the presence of catalytic amounts of zirconium tetrakis(dodecyl sulfate) as Lewis acid/surfactant-combined catalysts (LASCs) was developed. The high efficiency of the catalyst was confirmed by the high product yields obtained within desired times and, in particularly by the reusability of the ZrIV complex.

Process for preparation of 2-phenyl ethanol

The present invention provides an improved process for preparation of 2-phenyl ethanol. More specifically, the present invention relates to a process for preparing 2-phenyl ethanol by catalytic transfer hydrogenation of styrene oxide, in the presence of a supported transition metal catalyst. The catalyst system comprises of a palladium supported on silica, alumina, clay or charcoal.

PROCESS FOR PREPARATION OF 2-PHENYL ETHANOL

The present invention provides an improved process for preparation of 2-phenyl ethanol. More specifically, the present invention relates to a process for preparing of 2-phenyl ethanol by catalytic transfer hydrogenation of styrene oxide, in the presence of a supported transition metal catalyst. The catalyst system comprises of a palladium supported on silica, alumina, clay or charcoal.

The role of organic fluorine in directing alkylation reactions via lithium chelation

The fluorine of a fluoromethyl group displays a measurable chelation effect to lithium during α-methylation of an ester with lithium diisopropylamide (LDA) and methyl iodide. A series of esters is compared with F, H and O, and the resultant diastereoselectivity is consistent with the intermediate capacity of F to chelate lithium relative to H and O. In a second system which involved comparing a tertiary organic fluorine with hydrogen, no such effect is apparent, most probably due to adverse steric effects. The absolute and relative stereochemistry of the predominant diastereoisomers are confirmed by X-ray crystallography of suitable crystalline derivatives in each case. It is concluded that there is a potential role for organic-bound fluorine to become involved in lithium chelation in well-designed enolate alkylation systems. The diastereoselectivity of alkylation is explored comparing the coordination ability of H, F and OR substituents in the above model.

The First Solvent-directed Regioselective Ketal Reduction of Unsymmetrical Glycols

Borane-dimethyl sulphide/TMSOTf in THF reduces ketals of unsymmetrical vicinal diols with much higher regioselectivity than with CH2Cl2 as solvent.