3205-21-8

Basic information

• Product Name: (S)-1-(2'-aminophenyl)ethanol
• Synonyms: (S)-1-(2'-aminophenyl)ethanol
• CAS NO: 3205-21-8
• Molecular Weight: 137.181
• Mol File: 3205-21-8.mol

Chemical Properties

• CAS DataBase Reference: (S)-1-(2'-aminophenyl)ethanol(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-1-(2'-aminophenyl)ethanol(3205-21-8)
• EPA Substance Registry System: (S)-1-(2'-aminophenyl)ethanol(3205-21-8)

Safety Data

• Hazardous Substances Data: 3205-21-8(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
(S)-1-(2'-aminophenyl)ethanol is used as a chiral building block for the synthesis of pharmaceuticals and fine chemicals. Its unique molecular structure allows for the creation of drugs that target specific medical conditions, making it a crucial component in the development of novel treatments.
Used in Organic Synthesis:
As a chiral compound, (S)-1-(2'-aminophenyl)ethanol is utilized in organic synthesis to create a variety of complex molecules with specific properties. Its versatility in this field contributes to the advancement of chemical research and the development of new materials.
Used in Chiral Resolution:
(S)-1-(2'-aminophenyl)ethanol is used as a chiral resolving agent in chromatography, where it plays a vital role in separating racemic mixtures into their individual enantiomers. This ability to differentiate between enantiomers is essential in the pharmaceutical industry, as the biological activity of a compound can vary significantly between its enantiomers.

Upstream product

• 3205-25-2 (S)-1-(2-nitrophenyl)ethanol 
• 577-59-3 2-acetylnitrobenzene 
• 941706-81-6 1-(2-aminophenyl)ethanol 
• 578-54-1 ortho-ethylaniline 
• 314773-77-8 tert-butyl (2-acetylphenyl)carbamate 
• 551-93-9 2-aminoacetophenone 
• 328956-56-5 tert-butyl (2-(1-hydroxyethyl)phenyl)carbamate 
• 1352281-55-0 tert-butyl (S)-(2-(1-hydroxyethyl)phenyl)carbamate 
• 80379-10-8 1-(2-nitrophenyl)ethan-1-ol 
• 552-89-6 2-nitro-benzaldehyde 
• 3205-23-0 Phthalsaeure-((+)-1-(o-nitro-phenyl)-ethylester) 

Downstream Products

• 1445-91-6 (S)-1-phenylethanol 

Relevant articles and documents

Tridentate nitrogen phosphine ligand containing arylamine NH as well as preparation method and application thereof

The invention discloses a tridentate nitrogen phosphine ligand containing arylamine NH as well as a preparation method and application thereof, and belongs to the technical field of organic synthesis. The tridentate nitrogen phosphine ligand disclosed by the invention is the first case of tridentate nitrogen phosphine ligand containing not only a quinoline amine structure but also chiral ferrocene at present, a noble metal complex of the type of ligand shows good selectivity and extremely high catalytic activity in an asymmetric hydrogenation reaction, meanwhile, a cheap metal complex of the ligand can also show good selectivity and catalytic activity in the asymmetric hydrogenation reaction, and is very easy to modify in the aspects of electronic effect and space structure, so that the ligand has huge potential application value. A catalyst formed by the ligand and a transition metal complex can be used for catalyzing various reactions, can be used for synthesizing various drugs, and has important industrial application value.

Redox-driven deracemization of secondary alcohols by sequential ether/O2-mediated oxidation and Ru-catalyzed asymmetric reduction

The deracemization of benzylic alcohols has been achieved using a redox-driven one-pot two-step process. The racemic alcohols were oxidized by bis(methoxypropyl) ether and oxygen to give the ketone intermediates, followed by an asymmetric transfer hydrogenation with a chiral ruthenium catalyst. This compatible oxidation/reduction process gave the enantiomerically enriched alcohols with up to 95% ee values.

Method for synthesizing chiral alcohol through deracemization

The invention relates to a method for synthesizing chiral alcohol (formula I) through deracemization. The preparation method provided by the invention is one-pot asymmetric cascade reaction, and comprises the following steps: 1), with racemic alcohol (formula II) as a raw material and dipropylene glycol dimethyl ether as a solvent, reacting at 120 DEG C for 12 hours, and performing a dehydrogenation reaction to produce intermediate ketone (formula III); and 2), directly adding 2.5mol% of a chiral diamine metal ruthenium complex as a catalyst into a reaction system, with 5 equivalents of sodiumformate as a hydrogen source and a mixed solution of methanol and water as a solvent, reacting at 50 DEG C for 12 hours under the protection of nitrogen, and performing asymmetric transfer hydrogenation to obtain the chiral alcohol (formula I). The method has the advantages of environment-friendly synthesis such as a simple and mild reaction condition, step economy and atomic economy; and in addition, a substrate has a wide application range, the enantioselectivity is high, and the method has a broad application prospect in synthesis of chiral alcohol pharmaceutical intermediates and fine chemical raw materials.

The reaction mechanism of chiral hydroxylation of p -OH and p -NH 2 substituted compounds by ethylbenzene dehydrogenase

Ethylbenzene dehydrogenase (EbDH; enzyme commission (EC) number: 1.17.99.2) is a unique biocatalyst that hydroxylates alkylaromatic and alkylheterocyclic compounds to (S)-secondary alcohols under anaerobic conditions. The enzyme exhibits a high promiscuity catalyzing oxidation of over 30 substrates, inter alia, para-substituted alkylphenols and alkylanilines. Secondary alcohols with OH and NH2 substituents in the aromatic ring are highly valuable synthons for many biologically active compounds in the fine chemical industry. EbDH hydroxylates most of the studied compounds highly enantioselectively, except for five substrates that harbour OH and NH2 groups in the para position, which exhibit a significant decrease in the percent enantiomeric excess (% ee). This phenomenon is inconsistent with the previously suggested enzyme mechanism, but it may be linked to a stabilization of the carbocation intermediate by deprotonation of the OH or NH2 substituent in the active site that yields a transient quinone (imine) ethide species. This would initiate an alternative reaction pathway involving the addition of a water molecule to a C=C double bond. This hypothesis was cross-validated by density functional theory (DFT) cluster modelling of the alternative reaction pathway with 4-ethylphenol, as well as by experimental assessment of the pH dependency of enantiomeric excesses. The results reported herein suggest that the alternative reaction pathway may significantly contribute to the overall reaction if the carbocation intermediates are stabilized by deprotonation.

Enzymatic kinetic resolution of tert-butyl 2-(1-Hydroxyethyl) phenylcarbamate, a key intermediate to chiral organoselenanes and organotelluranes

The enzymatic kinetic resolution of tert-butyl 2-(1-hydroxyethyl) phenylcarbamate via lipase-catalyzed transesterification reaction was studied. We investigated several reaction conditions and the carbamate was resolved by Candida antarctica lipase B (CAL

Asymmetric hydrogenation of aromatic ketones by chiral (1S,2S)-DPEN-Ru(II)Cl2(TPP)2 encapsulated in SBA-16

Chiral complex (1S,2S)-DPEN-RuCl2(TPP)2 (DPEN = 1,2-diphenylethylenediamine; TPP = triphenylphosphine) was successfully encapsulated in the mesoporous cage of SBA-16 modified with phenyltrimethoxysilane. This was verified by ICP, powder XRD, N2 adsorption, FTIR, DRS and TEM analysis. The encapsulated chiral Ru complex gave high catalytic activity and excellent enantioselectivity like its homogeneous counterpart in asymmetric hydrogenation of various aromatic ketones. The encapsulated complex also showed high stability and could be recycled without significant loss of activity and enantioselectivity.

An enantiopure galactose oxidase model: synthesis of chiral amino alcohols through oxidative kinetic resolution catalyzed by a chiral copper complex

An enantiopure galactose oxidase (GO) enzyme model has been synthesized from readily available (R)-BINAM and Cu(OTf)2, and the enantiopure GO model has been effectively used in situ as an efficient chiral catalyst for the synthesis of chiral amino alcohols through oxidative kinetic resolution (OKR), where molecular oxygen is used as the sole oxidant. Under the proposed catalytic conditions, both ortho- and para-substituted amino alcohols were resolved with good to excellent enantiomeric excesses through oxidative kinetic resolution.

A molybdenum-catalyzed oxidative system forming oxazines (hetero-Diels-Alder adducts) from primary aromatic amines, hydrogen peroxide, and conjugated dienes

The development of a new molybdenum-catalyzed procedure for the formation of oxazines-hetero-Diels-Alder adducts - from primary aromatic amines, hydrogen peroxide, and conjugated dienes is presented. The method is based on a molybdenum-peroxo complex, which in the presence of hydrogen peroxide as the terminal oxidant selectively catalyzes the oxidation of primary aromatic amines to the corresponding dienophilic nitroso compounds. The molybdenum-peroxo catalyst is under the present reaction conditions not reactive toward conjugated dienes and substituents attached to the aromatic nuclei of the primary aromatic amines. Several oxazines are synthezised following this new procedure using primary aromatic amines having either electron-withdrawing or electron-donating substituents and 1,3-cyclohexadiene as the standard diene. The scope of the new procedure is also demonstrated by the preparation of several oxazines using different alkyland phenyl-substituted conjugated dienes and 4-chloroaniline as precursor for the dienophile. Moderate diastereomeric excesses are found when the reaction is carried out with 1-(2-aminophenyl)-ethanol and 1,3-cyclohexadiene or (E)-1-phenyl-1,3-butadiene. The stereochemical and electronic factors governing the reaction course are briefly discussed.

Enantioselective Addition of Chiral Organotitanium Derivatives to Aldehydes

Alkoxy- and aryloxy-organotitanum compounds 2-4 derived from (S)-2-methyl-1-butanol, (R)-2-butanol, (-)-menthol, quinine, cinchonine, and (S)-1,1'-binaphthol are added to aromiatic aldehydes to give optically active alcohols 5-10 in enantioselectivities of up to 88percent e.e., with nucleophilic transfer of methyl, phenyl, and 1-naphthyl groups.The Tables 1-3 list the effects of varying the reagents, the substrates, and the reaction conditions of the new asymmetric synthesis.