3391-10-4

Usage

Uses

Used in Chemical Industry:
1-(4-Chlorophenyl)ethanol is used as a reactant for the study of transfer dehydrogenation of various alcohols over heterogeneous palladium catalysts using olefins as hydrogen acceptors. This application is significant in the development of new and efficient methods for converting alcohols into other valuable chemical products.
Used in Pharmaceutical Industry:
Although not explicitly mentioned in the provided materials, 1-(4-Chlorophenyl)ethanol, due to its chemical structure, could potentially be used as an intermediate in the synthesis of various pharmaceutical compounds. Its reactivity and functional groups may be exploited to create new drugs or improve existing ones.
Used in Research and Development:
1-(4-Chlorophenyl)ethanol can be utilized as a model compound in academic and industrial research to study the effects of different catalysts and reaction conditions on the transfer dehydrogenation process. This can contribute to the advancement of knowledge in the field of catalysis and chemical reactions.

InChI:InChI=1/C8H9ClO/c1-6(10)7-2-4-8(9)5-3-7/h2-6,10H,1H3/t6-/m1/s1

Upstream product

• 141-52-6 sodium ethanolate 
• 99-91-2 para-chloroacetophenone 
• 555-31-7 aluminum isopropoxide 
• 75-07-0 acetaldehyde 
• 51833-36-4 4-chlorophenylmagnesium chloride 
• 1073-67-2 4-vinylbenzyl chloride 
• 14804-61-6 1-(1-bromoethyl)-4-chlorobenzene 
• 103966-61-6 1-(4-chlorophenyl)ethyl acetate 
• 104-88-1 4-chlorobenzaldehyde 
• 75-24-1 trimethylaluminum 
• 38111-44-3 phenylzinc(II) bromide 
• 274-07-7 benzo[1,3,2]dioxaborole 
• 623-43-8 methyl crotonate 
• 938-95-4 2-(4-Chloro-phenyl)-propionic acid 

Downstream Products

• 20001-65-4 1-chloro-4-(1-chloroethyl)benzene 
• 14804-61-6 1-(1-bromoethyl)-4-chlorobenzene 
• 99-91-2 para-chloroacetophenone 
• 10017-37-5 tert-butylamine hydrochloride 
• 937-20-2 p-chlorophenacyl chloride 
• 19759-43-4 (S)-1-(4-chlorophenyl)ethyl acetate 
• 19759-43-4 (R)-1-(4-chlorophenyl)ethyl acetate 
• 3391-10-4 (R)-1-(4-chlorophenyl)ethan-1-ol 
• 114200-16-7 1-(p-chlorophenyl)ethyl benzenesulfonate 
• 114200-15-6 1-(p-chlorophenyl)ethyl tosylate 
• 29342-34-5 1-(4-chlorophenyl)-1-nitroethane 
• 25917-49-1 1-(4-chlorophenyl)-2-(p-tolylsulfonyloxy)ethanone 
• 622-98-0 4-chloro(ethylbenzene) 
• 6314-52-9 2-bromo-1-(4-chlorophenyl)ethanol 

Relevant academic research and scientific papers

A new C2-symmetric chiral bisphosphine ligand containing a bioxazole backbone: Highly enantioselective hydrosilylation of ketones

C2-Symmetric (4S,4'S)-2,2'-bis(o-diphenylphosphinophenyl-4,4',5,5'-tetrahydro-4,4'-bi(1,3 -oxazole) (1, Phos-Biox) has been designed and synthesized as a chiral ligand for metal-catalyzed reactions. The Phos-Biox 1 was found to be an efficient

Synthesis and reactivity of BINEPINE-based chiral Fe(II) PNP pincer complexes

A new asymmetric chiral PNP ligand based on the 2,6-diaminopyridine scaffold featuring a R-BINEPINE moiety was prepared. Treatment of anhydrous FeX2 (X = Cl, Br) with 1 equiv of PNP-iPr,BIN at room temperature afforded the coordinatively unsatu

Efficient whole-cell biotransformation in a biphasic ionic liquid/water system

Biocompatible ionic liquids act as a substrate reservoir and an in situ extracting agent in biotransformations with whole cells (see scheme). In the reduction of 4-chloroacetophenone to (R)-1-(4-chlorophenyl)ethanol, high product concentration (82 g Lsup

Ruthenium(II) N,S-heterocyclic carbene complexes and transfer hydrogenation of ketones

A series of ruthenium(II) N,S-heterocyclic carbene (NSHC) complexes Ru IIX(RCOO)(PPh3)2(3-R′BzTh) (BzTh = benzothiazol-2-ylidene; R = Me, R′/X = Bz/Br (4), Pri/I (6), Bui/I (8); R = Et, R′/X = Bz/Br (

Stable electroenzymatic processes by catalyst separation

A study was conducted to demonstrate stable electroenzymatic processes by catalyst separation. The influence of amino acids on the mediator activity by cyclic was determined to investigate the interactions between the mediator and the amino acids. An in p

Syntheses and structures of ruthenium(II) N,S-heterocyclic carbene diphosphine complexes and their catalytic activity towards transfer hydrogenation

Phosphine exchange of [RuIIBr(MeCOO)(PPh3) 2(3-RBzTh)] (3-RBzTh=3-benzylbenzothiazol-2-ylidene) with a series of diphosphines (bis(diphenylphosphino)methane (dppm), 1,2-bis(diphenylphosphino) ethylene (dppv), 1,1′-bis(diph

Discovery and Redesign of a Family VIII Carboxylesterase with High (S)-Selectivity toward Chiral sec-Alcohols

Highly enantioselective lipase has been widely utilized in the preparation of versatile enantiopure chiral sec-alcohols through kinetic or dynamic kinetic resolution. Lipase is intrinsically (R)-selective, and it is difficult to obtain (S)-selective lipase. Recent crystal structures of a family VIII carboxylesterase have revealed that the spatial array of its catalytic triad is the mirror image of that of lipase but with a catalytic triad that is distinct from lipase. We, therefore, hypothesized that the family VIII carboxylesterase may exhibit (S)-enantioselectivity toward sec-alcohols similar to (S)-selective serine protease, whose catalytic triad is also spatially arrayed as its mirror image. In this study, a homologous enzyme (carboxylesterase from Proteobacteria bacterium SG_bin9, PBE) of a known family VIII carboxylesterase (pdb code: 4IVK) was prepared, which showed not only moderate (S)-selectivity toward sec-alcohols such as 3-butyn-2-ol and 1-phenylethyl alcohol but also (R)-selectivity toward particular sec-alcohols among the substrates explored. Furthermore, the (S)-selectivity of PBE has been significantly improved by rational redesign based on molecular modeling. Molecular modeling identified a binding pocket composed of Ser381, Ala383, and Arg408 for the methyl substituent of (R)-1-phenylethyl acetate and suggested that larger residues may increase the enantioselectivity by interfering with the binding of the slow-reacting enantiomer. As predicted, substituting Ser381with larger residues (Phe, Tyr, and Trp) significantly improved the (S)-selectivity of PBE toward all sec-alcohols explored, even the substrates toward which the wild-type PBE exhibits (R)-selectivity. For instance, the enantioselectivity toward 3-butyn-2-ol and 1-phenylethyl alcohol was improved from E = 5.5 and 36.1 to E = 2001 and 882, respectively, by single mutagenesis (S381F).

PQXdpap: Helical Poly(quinoxaline-2,3-diyl)s Bearing 4-(Dipropylamino)pyridin-3-yl Pendants as Chirality-Switchable Nucleophilic Catalysts for the Kinetic Resolution of Secondary Alcohols

Helically chiral poly(quinoxaline-2,3-diyl)s bearing 4-(dipropylamino)pyridin-3-yl pendants at the 5-position of the quinoxaline ring (PQXdpap) exhibited high catalytic activities and moderate to high selectivities (up to s = 87) in the acylative kinetic resolution of secondary alcohols. The solvent-dependent helical chirality switching of PQXdpap between pure toluene and a 1:1 mixture of toluene and 1,1,2-trichloroethane enabled the preparation of either compound of a pair of enantiomerically pure alcohols (>99% ee) from a single catalyst.

Rhizopus arrhizus mediated SAR studies in chemoselective biotransformation of haloketones at ambient temperature

We have demonstrated a green chemistry approach using the fungus Rhizopus arrhizus for the reductive dehalogenation and synthesis of chiral secondary carbinols and halohydrins of pharmaceutical importance in mild, inexpensive, and environmental friendly process at ambient temperature. In the present study, we have succeeded in unravelling the relationship between the position of the substituent group in the structure of substrate and bioreduction activity of the fungus Rhizopus arrhizus. The asymmetric reduction of the carbonyl group to corresponding chiral halohydrin takes place with good yield and excellent enantiomeric excess (≥92%) when the substituent halogen is on the aromatic nucleus. However, novel results concerning reductive dehalogenation are obtained when halogen is incorporated in the alkyl side chain. Thus, the fungus Rhizopus arrhizus has great potential to bring chemoenzymatic biotransformation of halo ketones. Various influential processing parameters such as microbe selection, temperature, pH, etc. were also investigated to optimize the growth of biocatalyst.

Synthesis, characterization and catalytic performance in enantioselective reactions by mesoporous silica materials functionalized with chiral thiourea-amine ligand

Chiral heterogeneous catalysts have been synthesized by grafting of silyl derivatives of (1R, 2R)- or (1S, 2S)-1,2-diphenylethane-1,2-diamine on SBA-15 mesoporous support. The mesoporous material SBA-15 and so-prepared chiral heterogeneous catalysts were characterized by a combination of different techniques such as X-ray diffractometry (XRD), Fourier transform infrared (FT-IR), thermogravimetric analysis (TGA), field emission scanning electron microscopy (FESEM), and Brunauer–Emmett–Teller (BET) surface area. Results showed that (1R, 2R)- and (1S, 2S)-1,2-diphenylethane-1,2-diamine were successively immobilized on SBA-15 mesoporous support. Chiral heterogeneous catalysts and their homogenous counterparts were tested in enantioselective transfer hydrogenation of aromatic ketones and enantioselective Michael addition of acetylacetone to β-nitroolefin derivatives. The catalysts demonstrated notably high catalytic conversions (up to 99%) with moderate enantiomeric excess (up to 30% ee) for the heterogeneous enantioselective transfer hydrogenation. The catalytic performances for enantioselective Michael reaction showed excellent activities (up to 99%) with poor enantioselectivities. Particularly, the chiral heterogeneous catalysts could be readily recycled for Michael reaction and reused in three consecutive catalytic experiments with no loss of catalytic efficacies.