41870-82-0

Usage

Uses

Used in Pharmaceutical Synthesis:
2-Amino-1-(4-chlorophenyl)ethan-1-ol is used as a key raw material in the production of various pharmaceuticals. Its unique structure allows it to be a versatile building block in the synthesis of a range of medicinal compounds, contributing to the development of new drugs with specific therapeutic properties.
Used in Research Chemicals:
In the field of scientific research, 2-Amino-1-(4-chlorophenyl)ethan-1-ol serves as an essential component in the synthesis of research chemicals. It aids researchers in exploring the properties and potential applications of new chemical entities, furthering the understanding of chemical reactions and mechanisms.
Used in Organic Compound Production:
2-Amino-1-(4-chlorophenyl)ethan-1-ol is also utilized in the production of organic compounds. Its chemical properties make it a valuable intermediate in the synthesis of various organic substances, which can be used in a wide array of applications across different industries.
Used in Medicine:
Due to its structural similarity to amphetamines, 2-Amino-1-(4-chlorophenyl)ethan-1-ol may have potential applications in medicine. It could be used in the development of new therapeutic agents, particularly in areas where its unique properties can offer advantages over existing treatments.
Used in Industry:
The unique chemical properties of 2-Amino-1-(4-chlorophenyl)ethan-1-ol may also find applications in various industrial processes. Its use could be beneficial in the development of new materials, catalysts, or other industrial chemicals, contributing to advancements in a range of sectors.

Upstream product

• 104-88-1 4-chlorobenzaldehyde 
• 89979-04-4 1-(4-chlorophenyl)-2-nitroethanol 
• 1073-67-2 4-vinylbenzyl chloride 
• 536-38-9 4-chlorobenzoylmethyl bromide 
• 861929-21-7 rac-2-azido-1-(4-chlorophenyl)ethanol 
• 2788-86-5 4-Chlorostyrene oxide 
• 127118-87-0 C₁₀H₈ClNO₃ 
• 122-01-0 4-chloro-benzoyl chloride 
• 13312-83-9 4-chloromandelonitrile 
• 99074-23-4 cyano(4-chlorophenyl)methyl acetate 
• 13014-48-7 4-chlorobenzoyl cyanide 

Downstream Products

• 3876-10-6 5-(4-chloro-phenyl)-4,5-dihydro-oxazol-2-ylamine 
• 3920-06-7 2-anilino-5-(p-chlorophenyl)-2-oxazoline 
• 17528-87-9 2-(4-chlorophenyl)-2-chloroethylamine hydrochloride 
• 68215-54-3 (E)-2-(4-chlorophenyl)ethenyl isothiocyanate 
• 68215-48-5 2-(4-chlorophenyl)-2-chloroethyl isothiocyanate 
• 184003-09-6 1-[(E)-2-(4-Chloro-phenyl)-vinyl]-3-(4-hydroxy-3-methoxy-benzyl)-thiourea 
• 875305-45-6 [rac]-(4-tert-butyl-benzyl)-[2-(4-chloro-phenyl)-2-hydroxy-ethyl]-amine 
• 69776-87-0 5-(4-chlorophenyl)oxazolidin-2-one 
• 98156-99-1 N-dichloroacetyl-5-(p-chlorophenyl)-2,2-dimethyl-1,3-oxazolidine 
• 98156-98-0 rac-5-(4-chlorophenyl)-2,2-dimethyloxazolidine 
• 939757-24-1 rac-tert-butyl [2-(4-chlorophenyl)-2-hydroxyethyl]carbamate 

Relevant academic research and scientific papers

Chiral-Organotin-Catalyzed Kinetic Resolution of Vicinal Amino Alcohols

A highly efficient kinetic resolution of racemic amino alcohols has been achieved for the first time with a chiral tin catalyst. A chiral organotin compound with 3,4,5-trifluorophenyl groups at the 3,3′-positions of the binaphthyl framework enabled this transformation with excellent yield and high enantioselectivity. The process tolerates aryl- and alkyl-substituted amino alcohols and a variety of other substrates, affording the corresponding products in high enantioselectivity and with s factors up to >500.

Synthesis, molecular modelling and CYP24A1 inhibitory activity of novel of (E)-N-(2-(1H-imidazol-1-yl)-2-(phenylethyl)-3/4-styrylbenzamides

CYP24A1 (25-hydroxyvitamin D-24-hydroxylase) is a useful enzyme target for a range of medical conditions including cancer, cardiovascular and autoimmune disease, which show elevated CYP24A1 levels and corresponding reduction of calcitriol (the biologically active form of vitamin D). A series of (E)-N-(2-(1H-imidazol-1-yl)-2-(phenylethyl)-3/4-styrylbenzamides have been synthesised using an efficient synthetic route and shown to be potent inhibitors of CYP24A1 (IC50 0.11–0.35?μM) compared with the standard ketoconazole. Molecular modelling using our CYP24A1 homology model showed the inhibitors to fill the hydrophobic binding site, forming key transition metal interaction between the imidazole nitrogen and the haem Fe3+ and multiple interactions with the active site amino acid residues.

Use of a Catalytic Chiral Leaving Group for Asymmetric Substitutions at sp3-Hybridized Carbon Atoms: Kinetic Resolution of β-Amino Alcohols by p-Methoxybenzylation

A catalytic strategy was developed for asymmetric substitution reactions at sp3-hybridized carbon atoms by using a chiral alkylating agent generated in situ from trichloroacetimidate and a chiral phosphoric acid. The resulting chiral p-methoxybenzyl phosphate selectively reacts with β-amino alcohols rather than those without a β-NH functionality. The use of an electronically and sterically tuned chiral phosphoric acid enables the kinetic resolution of amino alcohols through p-methoxybenzylation with good enantioselectivity.

Direct catalytic synthesis of unprotected 2-amino-1-phenylethanols from alkenes by using iron(II) phthalocyanine

Aryl-substituted amino alcohols are privileged scaffolds in medicinal chemistry and natural products. Herein, we report that an exceptionally simple and inexpensive FeII complex efficiently catalyzes the direct transformation of simple alkenes into unprotected amino alcohols in good yield and perfect regioselectivity. This new catalytic method was applied in the expedient synthesis of bioactive molecules and could be extended to aminoetherification.

One-pot combination of enzyme and Pd nanoparticle catalysis for the synthesis of enantiomerically pure 1,2-amino alcohols

One-pot combinations of sequential catalytic reactions can offer practical and ecological advantages over classical multi-step synthesis schemes. In this context, the integration of enzymatic and chemo-catalytic transformations holds particular potential for efficient and selective reaction sequences that would not be possible using either method alone. Here, we report the one-pot combination of alcohol dehydrogenase-catalysed asymmetric reduction of 2-azido ketones and Pd nanoparticle-catalysed hydrogenation of the resulting azido alcohols, which gives access to both enantiomers of aromatic 1,2-amino alcohols in high yields and excellent optical purity (ee >99%). Furthermore, we demonstrate the incorporation of an upstream azidolysis and a downstream acylation step into the one-pot system, thus establishing a highly integrated synthesis of the antiviral natural product (S)-tembamide in 73% yield (ee >99%) over 4 steps. Avoiding the purification and isolation of intermediates in this synthetic sequence leads to an unprecedentedly low ecological footprint, as quantified by the E-factor and solvent demand.

Regio-selective synthesis of 1,2-aminoalcohols from epoxides and chlorohydrins

A simple and efficient procedure for the regio-selective synthesis of 1,2-aminoalcohols from terminal epoxides and chlorohydrins by using NaHMDS as the source of amine is reported. The wider scope and utility of this method is demonstrated.

Indole, indazole and indoline derivatives as CETP inhibitors

The present invention relates to compounds of formula (I): wherein —X—Y—, R1 to R11 and n are as defined in the description and claims, and pharmaceutically acceptable salts thereof. The compounds are useful for the treatment and/or prevention of diseases which are mediated by CETP inhibitors.

Analogues of capsaicin with agonist activity as novel analgesic agents: Structure-activity studies. 4. Potent, orally active analgesics

Structural features of three regions of the capsaicin molecule necessary for agonist properties were delineated by a previously reported modular approach. These in vitro agonist effects were shown to correlate with analgesic potency in rodent models. Comb

Synthesis of 2-Aryl-2,3-dihydro-oxazolopyrrolopyridin-5-one and 2-Aryl-2,3-dihydro-oxazolopyrrolopyridin-5-one

A variety of 2-aryl-2,3-dihydro-oxazolopyrrolopyridin-5-one and 2-aryl-2,3-dihydro-oxazolopyrrolopyridin-5-one were prepared. The absolute configuration of the chiral centers were studied thoroughly from which the structural and stereoformulea of these compounds were deduced by using nmr and microanalysis technique.

Determination des pKa et reaction d'ouverture acide de quelques alkyl-2 et aryl-2 aziridines

Some 2-para substituted aryl aziridines (with pY = CH3O-, CH3-, H-, and Cl-) have been prepared.Their ring opening reaction in acidic medium has been studied and compared with those of two aliphatic aziridines : 2 methyl- and 2,2 dimethyl-aziridine.In aqueous solvent, the addition of HCl, HBr, and HI to the aromatic aziridines leads exclusively to the secondary halogen product, due to the nucleophilic attack on the benzylic carbon.The hydrolysis reaction competes with the addition reaction and is very important for the para methoxy 2-phenyl aziridine.In ethyl alcohol (anhydrous solvent), the hydrohalogenation reaction leads exclusively to halogeno amine with a secondary halogen.The solvolysis reaction, leading to amino-ether, is far less important than in water (excepted for the para methoxy 2-phenyl aziridine).In both solvents, the importance of the solvolysis depends on the HX concentration, as well as the nucleophilic strength of the halogen.The pKa values of these aziridines have been measured, as well as those of 2-phenyl 1-amino 2-ethanol.A linear plot is obtained for the pKa versus ?+p of Brown ; the slopes are respectively -2.8 and 0.Therefore the aromatic aziridines seem to have a behavior similar to that of anilines.