6781-43-7

Basic information

• Product Name: 1-[4-(1-hydroxyethyl)phenyl]ethanol
• CAS NO: 6781-43-7
• Molecular Formula: C₁₀H₁₄O₂
• Molecular Weight: 166.22
• Mol File: 6781-43-7.mol

Chemical Properties

• Boiling Point: 297.1°Cat760mmHg
• Flash Point: 142.2°C
• Density: 1.096g/cm³
• CAS DataBase Reference: 1-[4-(1-hydroxyethyl)phenyl]ethanol(CAS DataBase Reference)
• NIST Chemistry Reference: 1-[4-(1-hydroxyethyl)phenyl]ethanol(6781-43-7)
• EPA Substance Registry System: 1-[4-(1-hydroxyethyl)phenyl]ethanol(6781-43-7)

Safety Data

• Hazardous Substances Data: 6781-43-7(Hazardous Substances Data)

Upstream product

• 105-05-5 1,4-diethylbenzene 
• 108-22-5 Isopropenyl acetate 
• 1009-61-6 1,4-Diacetylbenzene 
• 912334-66-8 C₁₈H₂₆O₄ 
• 143329-80-0 (R,R)-α,α'-dimethyl-1,4-benzenedimethanol diacetate 
• 108124-68-1 α,α'-dimethyl-1,4-benzenedimethanol diacetate 
• 108673-17-2 rac-1-(4-(1-hydroxyethyl)phenyl)ethan-1-one 
• 17194-87-5 1,4-bis(1'-bromoethyl)benzene 
• 100-41-4 ethylbenzene 
• 100-20-9 terephthaloyl chloride 
• 100-21-0 terephthalic acid 
• 75-16-1 methylmagnesium bromide 
• 623-27-8 terephthalaldehyde, 

Downstream Products

• 108124-68-1 α,α'-dimethyl-1,4-benzenedimethanol diacetate 
• 6781-43-7 (R,R)-1-<4'-(1''-hydroxyethyl)phenyl>ethanol 
• 143394-10-9 (S,S)-α,α'-dimethyl-1,4-benzenedimethanol 
• 143329-80-0 (R,R)-α,α'-dimethyl-1,4-benzenedimethanol diacetate 
• 112710-41-5 meso-α,α’-dimethyl-(1,4-benzene)dimethanol 
• 143329-79-7 meso-α,α’-dimethyl-(1,4-benzene)dimethanol monoacetate 
• 108673-17-2 (R)-1-[4-(1-hydroxyethyl)phenyl]ethan-1-one 
• 51042-58-1 1,4-bis[(E)-2-(4-nitrophenyl)ethenyl]benzene 
• 65614-67-7 4,4'-(1E,1'E)-2,2'-(1,4-phenylene)bis(ethene-2,1-diyl)diphenol 
• 54842-61-4 (E,E)-1,4-bis[2-(4-methoxyphenyl)-ethenyl]benzene 
• 1009-61-6 1,4-Diacetylbenzene 
• 1360861-46-6 C₁₀H₆⁽²⁾H₈O₂ 
• 67-63-0 isopropyl alcohol 
• 912334-66-8 C₁₈H₂₆O₄ 

Relevant articles and documents

Silver-Catalyzed Hydrogenation of Ketones under Mild Conditions

The silver-catalyzed hydrogenation of ketones using H2 as hydrogen source is reported. Silver nanoparticles are generated from simple silver (I) salts and operate at 25 °C under 20 bar of hydrogen pressure. Various aliphatic and aromatic ketones, including natural products were reduced into the corresponding alcohols in high yields. This silver catalyst allows for the selective hydrogenation of ketones in the presence of other functional groups. (Figure presented.).

Selective Room-Temperature Hydrogenation of Carbonyl Compounds under Atmospheric Pressure over Platinum Nanoparticles Supported on Ceria-Zirconia Mixed Oxide

A Pt/CeO2-ZrO2 catalytic system was able to initiate an extremely intense hydrogen spillover providing a huge amount of activated hydrogen (12 mol/mol Pt) at temperatures –50°C - +25°C, which was not observed before. The idea was to use this activated hydrogen for reduction of carbonyl compounds under ambient conditions. Thus, the efficient and selective heterogeneous hydrogenation of carbonyl compounds of different structure, including 5-hydroxymethylfurfural and cinnamaldehyde, to the corresponding alcohols with quantitative yields was successfully performed over the Pt/CeO2-ZrO2 catalysts at room-temperature and atmospheric pressure of H2. The proposed catalysts afforded hydrogenation under significantly milder conditions with a much higher activity and selectivity compared to the commercial catalysts and reported catalytic systems. Hydrogenation of the C=O bond in the presence of a C=C bond proceeded with a high regioselectivity.

Transfer Hydrogenation of Carbonyl Groups, Imines and N-Heterocycles Catalyzed by Simple, Bipyridine-Based MnI Complexes

Utilization of hydroxy-substituted bipyridine ligands in transition metal catalysis mimicking [Fe]-hydrogenase has been shown to be a promising approach in developing new catalysts for hydrogenation. For example, MnI complexes with 6,6′-dihydroxy-2,2′-bipyridine ligand have been previously shown to be active catalysts for CO2 hydrogenation. In this work, simple bipyridine-based Mn catalysts were developed that act as active catalysts for transfer hydrogenation of ketones, aldehydes and imines. For the first time, Mn-catalyzed transfer hydrogenation of N-heterocycles was reported. The highest catalytic activity among complexes with variously substituted ligands was observed for the complex bearing two OH groups in bipyridine. Deuterium labeling experiments suggest a monohydride pathway.

Transformation of Alkynes into Chiral Alcohols via TfOH-Catalyzed Hydration and Ru-Catalyzed Tandem Asymmetric Hydrogenation

A novel full atom-economic process for the transformation of alkynes into chiral alcohols by TfOH-catalyzed hydration coupled with Ru-catalyzed tandem asymmetric hydrogenation in TFE under simple conditions has been developed. A range of chiral alcohols was obtained with broad functional group tolerance, good yields, and excellent stereoselectivities.

Hydrogenation of Carbonyl Derivatives with a Well-Defined Rhenium Precatalyst

The first efficient and general rhenium-catalyzed hydrogenation of carbonyl derivatives was developed. The key to the success of the reaction was the use of a well-defined rhenium complex bearing a tridentate diphosphinoamino ligand as the catalyst (0.5 mol %) at 70 °C in the presence of H2 (30 bar). The mechanism of the reaction was investigated by DFT(PBE0-D3) calculations.

Molecularly Defined Manganese Pincer Complexes for Selective Transfer Hydrogenation of Ketones

For the first time an easily accessible and well-defined manganese N,N,N-pincer complex catalyzes the transfer hydrogenation of a broad range of ketones with good to excellent yields. This cheap earth abundant-metal based catalyst provides access to useful secondary alcohols without the need of hydrogen gas. Preliminary investigations to explore the mechanism of this transformation are also reported.

Mechanistic basis for the enantioselectivity of the anaerobic hydroxylation of alkylaromatic compounds by ethylbenzene dehydrogenase

The enantioselectivity of reactions catalyzed by ethylbenzene dehydrogenase, a molybdenum enzyme that catalyzes the oxygen-independent hydroxylation of many alkylaromatic and alkylheterocyclic compounds to secondary alcohols, was studied by chiral chromatography and theoretical modeling. Chromatographic analyses of 22 substrates revealed that this enzyme exhibits remarkably high reaction enantioselectivity toward (S)-secondary alcohols (18 substrates converted with > 99% ee). Theoretical QM:MM modeling was used to elucidate the structure of the catalytically active form of the enzyme and to study the reaction mechanism and factors determining its high degree of enantioselectivity. This analysis showed that the enzyme imposes strong stereoselectivity on the reaction by discriminating the hydrogen atom abstracted from the substrate. Activation of the pro(S) hydrogen atom was calculated to be 500 times faster than of the pro(R) hydrogen atom. The actual hydroxylation step (i.e., hydroxyl group rebound reaction to a carbocation intermediate) does not appear to be enantioselective enough to explain the experimental data (the calculated rate ratios were in the range of only 2-50 for pro(S): pro(R)-oriented OH rebound).

Varying the ratio of formic acid to triethylamine impacts on asymmetric transfer hydrogenation of ketones

Asymmetric transfer hydrogenation (ATH) is frequently carried out in the azeotropic mixture of formic acid (F) and triethylamine (T), where the F/T molar ratio is 2.5. This study shows that the F/T ratio affects both the reduction rate and enantioselectivity, with the optimum ratio being 0.2 in the ATH of ketones with the Ru-TsDPEN catalyst. Under such conditions, a range of substrates have been reduced, affording high yields and good to excellent enantioselectivities. In comparison with the common azeotropic F-T system, the reduction is faster. This protocol improves both the classic azeotropic and the aqueous-formate system when using water-insoluble ketones.

Bifunctional rhenium complexes for the catalytic transfer-hydrogenation reactions of ketones and imines

The silyloxycyclopentadienyl hydride complexes [Re(H)(NO)(PR 3)(C5H4OSiMe2tBu)] (R=iPr (3a), Cy (3b)) were obtained by the reaction of [Re(H)(Br)(NO)(PR3) 2] (R=iPr, Cy) with Li[C5H4OSiMe 2tBu]. The ligand-metal bifunctional rhenium catalysts [Re(H)(NO)(PR3)(C5H4OH)] (R=iPr (5a), Cy (5b)) were prepared from compounds 3a and 3b by silyl deprotection with TBAF and subsequent acidification of the intermediate salts [Re(H)(NO)(PR 3)(C5H4O)][NBu4] (R=iPr (4a), Cy (4b)) with NH4Br. In nonpolar solvents, compounds 5a and 5b formed an equilibrium with the isomerized trans-dihydride cyclopentadienone species [Re(H)2(NO)(PR3)(C5H4O)] (6a,b). Deuterium-labeling studies of compounds 5a and 5b with D2 and D 2O showed H/D exchange at the HRe and HO positions. Compounds 5a and 5b were active catalysts in the transfer hydrogenation reactions of ketones and imines with 2-propanol as both the solvent and H2 source. The mechanism of the transfer hydrogenation and isomerization reactions was supported by DFT calculations, which suggested a secondary-coordination-sphere mechanism for the transfer hydrogenation of ketones. The Re-al deal: Bifunctional rhenium complexes [Re(H)(NO)(PR 3)(C5H4OH)] (R=Cy, iPr) of Shvo-type were prepared and used as catalysts for the transfer hydrogenation of ketones and imines. TOFs up to 1164 h-1 were obtained for ketones and up to 79 h-1 for imines. DFT calculations suggested a secondary-coordination- sphere mechanism for the transfer hydrogenation of ketones.

Hydrogenation of aryl ketones using palladium nanoparticles on single-walled carbon nanotubes in an ionic liquid

Single-walled carbon nanotubes (SWNTs) are used as supporting materials for palladium (Pd) nanoparticles generated in situ in ionic liquid (IL); Pd nanocatalysts on SWNTs exhibit superior reactivity for hydrogenation of aryl ketones in IL under mild conditions (1 atm of H2 (g) and room temperature) and can be reused above 10 times without any loss of catalytic activity.