212378-89-7

Basic information

• Product Name: (1S,2R)-1-(2-(HYDROXY-3,5-DI-TERT-BUTYL&
• Synonyms: (1S,2R)-1-(2-(HYDROXY-3,5-DI-TERT-BUTYL&;(1S,2R)-1-[(3,5-Di-tert-butyl-2-hydroxybenzylidene)amino]-2-indanol 97%
• CAS NO: 212378-89-7
• Molecular Formula: C24H31NO2
• Molecular Weight: 365.514
• Mol File: 212378-89-7.mol

Chemical Properties

• Melting Point: 128-131 °C
• Boiling Point: 496 °C at 760 mmHg
• Flash Point: 330.3 °C
• Appearance: /
• Density: 1.08g/cm³
• Vapor Pressure: 1.18E-10mmHg at 25°C
• Refractive Index: 1.565
• CAS DataBase Reference: (1S,2R)-1-(2-(HYDROXY-3,5-DI-TERT-BUTYL&(CAS DataBase Reference)
• NIST Chemistry Reference: (1S,2R)-1-(2-(HYDROXY-3,5-DI-TERT-BUTYL&(212378-89-7)
• EPA Substance Registry System: (1S,2R)-1-(2-(HYDROXY-3,5-DI-TERT-BUTYL&(212378-89-7)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36/37
• WGK Germany: 3
• Hazardous Substances Data: 212378-89-7(Hazardous Substances Data)

Usage

Uses

Used in Chemical Synthesis:
(1S,2R)-1-(2-(Hydroxy-3,5-di-tert-butyl)benzylidene)amino)-2-indanol is used as a ligand for the preparation of Schiff-base chromium(III) complexes. These complexes serve as catalysts in various chemical reactions, enhancing the efficiency and selectivity of the processes.
Used in Polymer Industry:
In the polymer industry, (1S,2R)-1-(2-(Hydroxy-3,5-di-tert-butyl)benzylidene)amino)-2-indanol is used as a ligand to prepare catalysts for the synthesis of poly(cyclohexene carbonate). This is achieved through the coupling of CO2 and cyclohexene oxide, contributing to the development of environmentally friendly polymers derived from renewable carbon sources.
Used in Asymmetric Synthesis:
(1S,2R)-1-(2-(Hydroxy-3,5-di-tert-butyl)benzylidene)amino)-2-indanol is also used as a ligand in the synthesis of β-hydroxyenol ethers. It is employed in asymmetric hetero-ene reactions between aryl aldehydes and 2-methoxypropene, allowing for the selective formation of enantioenriched products. This application is particularly relevant in the pharmaceutical and agrochemical industries, where enantioselective synthesis is crucial for the production of biologically active compounds.

InChI:InChI=1/C24H31NO2/c1-23(2,3)17-11-16(22(27)19(13-17)24(4,5)6)14-25-21-18-10-8-7-9-15(18)12-20(21)26/h7-11,13-14,20-21,26-27H,12H2,1-6H3/b25-14+/t20-,21+/m1/s1

Upstream product

• 37942-07-7 3,5-di-tert-butyl-2-hydroxybenzaldehyde 
• 136030-00-7 (1R,2S)-1-Amino-2-indanol 
• 7480-35-5 (1S,2R)-1-amino-2-indanol 
• 163061-74-3 (1S,2S)-1-amino-2,3-dihydro-1H-inden-2-ol 

Relevant articles and documents

Enantioselective syntheses of β-amino alcohols catalyzed by recyclable chiral Fe(III) metal complex

An efficient asymmetric desymmetrization of meso-epoxides with anilines catalysed by a series of simple and environmentally benign in situ generated Fe(iii) complexes based on chiral tridentate ligands L1-L7 with achiral and chiral l

Catalytic asymmetric bromochlorination of aromatic allylic alcohols promoted by multifunctional Schiff base ligands

It was found that the tridentate O,N,O-type Schiff base ligand bearing suitable substituents was a highly effective promoter in the catalytic asymmetric bromochlorination reaction, in which the corresponding aromatic bromochloroalcohols with vicinal halogen-bearing stereocenters were formed with perfect regioselectivity, with moderate to excellent enantioselectivities (up to 93% ee), and with good yields and chemoselectivities.

Synthesis of a chiral fluorescence active probe and its application as an efficient catalyst in the asymmetric Friedel-Crafts alkylation of indole derivatives with nitroalkenes

Novel chiral Zn(ii) complexes were synthesized and these complexes showed fluorescence behaviour. These chiral Zn(ii) complexes were tested in the asymmetric Friedel-Crafts alkylation reaction of indole derivatives with nitroalkenes. In all the cases, the

Screening of a library of hemisalen ligands in asymmetric H-transfer: Reduction of aromatic ketones in water

A library of chiral hemisalen ligands (30) was realized. The ligands were synthesized by the condensation of salicylaldehyde derivatives with amino-alcohols (amino-indanol or substituted amino-ethanol) and characterized. These ligands associated with ruthenium (II) precursors were tested on the asymmetric transfer hydrogenation (ATH) of aromatic ketones by sodium formate in water. The different substituent pattern on the ligand (electronic and hindrance effects on different positions) as well as the ruthenium precursor were investigated. The best compromise in terms of conversion and chiral induction led to the complex [RuCl2(mesitylene)]2 coordinated to (1S,2R)-1-((E)-(3-(dimethyl(phenyl)silyl)-2-hydroxy-5-methoxy benzylidene) amino)-2,3-dihydro-1H-inden-2-ol (L25). It reduces acetophenone in 95% yield and 91% ee in 18 h at 30°C.

Synthesis of chiral ligands with multiple stereogenic centers and their application in titanium(iv)-catalyzed enantioselective desymmetrization of meso-epoxides

New chiral ligands, (S,R,S)-1, (S,S,S)-1, (S,S,R)-1, (S,R,R)-1, (R,R,R)-1, (R,R,S)-1, (R,S,S)-1, (R,S,R)-1, (S,R,S)-2, (S,S)-3 and (R,S)-4 with diverse stereogenic centers arising from various diastereomeric combinations of aminoalcohol functionality with

Method for Producing Polyhydroxyalkanoates

The invention relates to a process for preparing polyhydroxyalkanoates by polymerization of lactones of the general formula I, where the substituents and the index n have the meanings given in the description, in the presence of at least one catalyst of the formula (II) LIMaXam, where the substituents and indices have the meanings given in the description. The invention further relates to poly-3-hydroxybutyrates which have a novel property profile and are obtainable for the first time by means of this process, and also biodegradable polyester mixtures based on these poly-3-hydroxybutyrates.

Enantioselective synthesis of an atropisomeric diaryl ether

(Chemical Equation Presented) Twisted ethers: Introduction of a bulky alkylsulfinyl substituent ortho to the C-O axis of a diaryl ether imposes a powerful conformational preference (see scheme). The preference persists upon oxidation of the sulfoxide to a sulfone, leading to dynamic thermodynamic resolution of the atropisomeric ether. This is the first enantioselective synthesis of an atropisomeric diaryl ether not forming part of a macrocyclic ring.

Exploring structural diversity in ligand design: The aminoindanol case

A series of enantiopure ligands based on the aminoindanol scaffold, but differing in regio-and stereochemistry has been synthesized. These ligands have been conveniently derivatized and their catalytic efficiency in different enantioselective reactions has been screened to determine privileged candidates with respect to regio- and stereochemistry for each considered process. The nature of the amino substituent has been optimized for specific applications and this has led to the development of an efficient method for the preparation of bulky bicyclic amines by reductive amination.

Enantioselective sulfide oxidation with H2O2: A solid phase and array approach for the optimisation of chiral Schiff base-vanadium catalysts

Two libraries of chiral Schiff base ligands were synthesised and screened in the vanadium-catalysed oxidation of alkyl aryl sulfides with hydrogen peroxide as terminal oxidant. The vanadium-chiral Schiff base complex 10, readily prepared from 3,5-diiodo-salicylaldehyde and (S)-tert-leucinol, was found to be highly enantioselective. Optically active sulfoxides could thus be obtained in good yields with up to 97% ee.