4169-04-4

Usage

Uses

Used in Semiconductor Industry:
2-Phenoxylpropanol is used as a semiconductor light-emitting nanoparticle for its improved quantum yield. This property allows for enhanced light emission efficiency, making it a valuable component in the development of advanced semiconductor devices and technologies.
Used in Post-Chemical Mechanical Polishing (Post-CMP) Cleaners:
In the semiconductor manufacturing process, 2-Phenoxylpropanol is utilized in post-CMP cleaners to remove residual chemicals and particles from the surface of the wafer after the polishing step. This ensures a clean and smooth surface, which is crucial for the subsequent steps in the fabrication of integrated circuits and other semiconductor devices.

InChI:InChI=1/C9H12O2/c1-8(7-10)11-9-5-3-2-4-6-9/h2-6,8,10H,7H2,1H3

Upstream product

• 42412-84-0 ethyl 2-phenoxypropionate 
• 29279-27-4 t-butyl 2-phenoxypropanothioate 
• 67-63-0 isopropyl alcohol 
• 1529-50-6 trimethylphenoxystannane 
• 75-56-9 methyloxirane 
• 57-55-6 propylene glycol 
• 107-21-1 ethylene glycol 
• 108-95-2 phenol 
• 940-31-8 2-phenoxypropionic acid 
• 122-35-0 2-phenoxypropanoic acid chloride 
• 108-94-1 cyclohexanone 
• 18099-45-1 diborane 
• 1129-46-0 (R)-(+)-2-phenoxypropionic acid 
• 28899-97-0 triphenylbismuth(V) diacetate 

Downstream Products

• 71159-33-6 (+/-)-2-phenoxy-1-propyl acetate 
• 87860-35-3 (S)-2-Methyl-2-phenoxy carbinolcid 
• 64658-22-6 (R)-2-phenoxypropan-1-ol 
• 61687-10-3 2-phenoxy-1-propanol O-methanesulfonate 
• 120-36-5 2-(2,4-dichlorophenoxy)propionic acid 
• 98919-13-2 2-(2,4-dichlorophenoxy)propan-1-ol 
• 3307-39-9 2-(4-chlorophenoxy)propionic acid 
• 63650-24-8 2-(4-chlorophenoxy)-1-propanol 
• 1252084-55-1 2-[2-phenoxypropyl]-1H-isoindole-1,3(2H)-dione 
• 52687-81-7 2-phenoxypropionaldehyde 

Relevant academic research and scientific papers

Development of effective bidentate diphosphine ligands of ruthenium catalysts toward practical hydrogenation of carboxylic acids

Hydrogenation of carboxylic acids (CAs) to alcohols represents one of the most ideal reduction methods for utilizing abundant CAs as alternative carbon and energy sources. However, systematic studies on the effects of metal-to-ligand relationships on the catalytic activity of metal complex catalysts are scarce. We previously demonstrated a rational methodology for CA hydrogenation, in which CA-derived cationic metal carboxylate [(PP)M(OCOR)]+ (M = Ru and Re; P = one P coordination) served as the catalyst prototype for CA self-induced CA hydrogenation. Herein, we report systematic trial- and-error studies on how we could achieve higher catalytic activity by modifying the structure of bidentate diphosphine (PP) ligands of molecular Ru catalysts. Carbon chains connecting two P atoms as well as Ar groups substituted on the P atoms of PP ligands were intensively varied, and the induction of active Ru catalysts from precatalyst Ru(acac)3 was surveyed extensively. As a result, the activity and durability of the (PP)Ru catalyst substantially increased compared to those of other molecular Ru catalyst systems, including our original Ru catalysts. The results validate our approach for improving the catalyst performance, which would benefit further advancement of CA self-induced CA hydrogenation.

TiO2-Supported Re as a General and Chemoselective Heterogeneous Catalyst for Hydrogenation of Carboxylic Acids to Alcohols

TiO2-supported Re, Re/TiO2, was found to promote selective hydrogenation of carboxylic acids having aromatic and aliphatic moieties to the corresponding alcohols. Re/TiO2showed superior results compared to other transition-metal-loaded TiO2and supported Re catalysts for selective hydrogenation of 3-phenylpropionic acid. 3-phenylpropanol was produced in 97 % yield under mild conditions (5 MPa H2at 140 °C). Contrary to typical heterogeneous catalysts, Re/TiO2does not lead to the formation of dearomatized byproducts. The catalyst is recyclable and shows a wide substrate scope in the synthesis of alcohols (22 examples; up to 97 % isolated yield).

Highly Enantioselective Hydrogenation of Amides via Dynamic Kinetic Resolution Under Low Pressure and Room Temperature

High-throughput screening and lab-scale optimization were combined to develop the catalytic system trans-RuCl2((S,S)-skewphos)((R,R)-dpen), 2-PrONa, and 2-PrOH. This system hydrogenates functionalized α-phenoxy and related amides at room temperature under 4 atm H2 pressure to give chiral alcohols with up to 99% yield and in greater than 99% enantiomeric excess via dynamic kinetic resolution.

CATALYSTS AND PROCESSES FOR THE HYDROGENATION OF AMIDES

There is provided a process for the reduction of one or more amide moieties in a compound comprising contacting the compound with hydrogen gas and a transition metal catalyst in the presence or absence of a base under conditions for the reduction an amide bond. The presently described processes can be performed at low catalyst loading using relatively mild temperature and pressures, and optionally, in the presence or absence of a base or high catalyst loadings using low temperatures and pressures and high loadings of base to effect dynamic kinetic resolution of achiral amides.

An efficient catalyst for ring opening of epoxides with phenol and thiophenol under solvent-free conditions

An efficient and rapid procedure for ring opening reaction of various epoxides with phenol and thiophenol derivatives was developed. The procedure can be obtained at room temperature under solvent-free condition in presence of (C4H12N2)2[BiCl6] Cl·H2O (1 mol %). This catalyst can be reused several times without significant loss of activity.

Straightforward heterogeneous palladium catalyzed synthesis of aryl ethers and aryl amines via a solvent free aerobic and non-aerobic dehydrogenative arylation

Aryl ethers have been prepared from cyclohexanone derivatives and various alcohols in the presence of a catalytic amount of palladium on charcoal. The formation of an enol ether followed by an aerobic or non-aerobic dehydrogenation reaction, seem to be the key steps of this transformation. In addition, this new method was also adapted for the synthesis of arylamines.

Heterogeneous palladium-catalyzed synthesis of aromatic ethers by solvent-free dehydrogenative aromatization: Mechanism, scope, and limitations under aerobic and non-aerobic conditions

Starting from cyclohexanone derivatives and alcohols, both non-aromatic precursors, aryl ethers could be synthesized in good yields and with good selectivities in the presence of a catalytic amount of Pd/C, in one step, without added solvent, in a reaction vessel open to air. For less reactive substrates, the addition of 1-octene in a closed system under non-aerobic conditions improved the conversion. In addition, the catalyst could be recycled several times with no decrease in the yield of the aryl ether. The process was also used with tetralone derivatives and polyols. Several reactions were performed to propose a mechanism for this transformation. The formation of an enol ether followed by a dehydrogenation reaction seem to be the key steps of this reaction. Aryl ethers were prepared in good yields and with good selectivities in a solvent-free and heterogeneous catalytic dehydrogenative alkylation of cyclohexanones with various alcohols. Three different complementary routes were used, and for the first time, non-aerobic, safe conditions could be used. Moreover, the catalyst could be recycled several times with no decrease in the yield of the aryl ether. Copyright

One-pot synthesis of aryloxypropanediols from glycerol: Towards valuable chemicals from renewable sources

Glycerol offers an easy and green route for the synthesis of aryloxypropanediols of known pharmacological activity. Glycerol is selectively converted to aryloxypropanediols in a one-pot reaction, through in situ formed glycerol carbonate, under benign and solvent-free conditions. Catalyst and unreacted reagent can be recycled.

α-Aroyloxyaldehydes: Scope and limitations as alternatives to α-haloaldehydes for NHC-catalysed redox transformations

α-Aroyloxyaldehydes are readily prepared bench stable synthetic intermediates. Their ability to act as α-haloaldehyde surrogates for NHC-promoted redox esterifications and in [4+2] cycloadditions is described.

One-pot alkoxylation of phenols with urea and 1,2-glycols

A one-pot epoxide-free alkoxylation process has been developed for phenolic compounds. The process involves heating phenols and urea in 1,2-glycols at 170-190 °C using Na2CO3/ZnO as co-catalysts under atmospheric conditions. During the course of this new alkoxylation reaction, a five-membered ring cyclic carbonate intermediate, ethylene carbonate (EC) or propylene carbonate (PPC), was produced in-transit as the key intermediate and was subsequently consumed by phenols to form alkoxylated ether alcohols as final products in excellent yields. For instance, phenol, bisphenol A (BPA), hydroquinone and resorcinol were converted into their respective mono-alkoxylated ether alcohols on each of their phenolic groups in 80-95% isolated yields. In propoxylation of phenols, this approach shows great product selectivity favoring production of high secondary alcohols over primary alcohols in isomeric ratios of nearing 95/5. Since ammonia (NH3) and carbon dioxide (CO2) evolving from the reaction can be re-combined in theory into urea for re-use, the overall net-alkoxylation by this approach can be regarded as a simple condensation reaction of phenols with 1,2-glycols giving off water as its by-product. This one-pot process is simple, safe and environmentally friendlier than the conventional alkoxylated processes based on ethylene oxide (EO) or propylene oxide (PO). Moreover, this process is particularly well-suited for making short chain-length alkoxyether alcohols of phenols.