120523-16-2

Basic information

• Product Name: (R)-4-CHROMANOL
• Synonyms: (R)-4-CHROMANOL;SPECS 131/40242452
• CAS NO: 120523-16-2
• Molecular Formula: C₉H₁₀O₂
• Molecular Weight: 150.17
• Mol File: 120523-16-2.mol
• Article Data: 77

Chemical Properties

• Melting Point: 68-70 °C(Solv: ethyl ether (60-29-7))
• Boiling Point: 266.6±29.0 °C(Predicted)
• Appearance: /
• Density: 1.208±0.06 g/cm3(Predicted)
• PKA: 14.12±0.20(Predicted)
• CAS DataBase Reference: (R)-4-CHROMANOL(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-4-CHROMANOL(120523-16-2)
• EPA Substance Registry System: (R)-4-CHROMANOL(120523-16-2)

Safety Data

• Hazardous Substances Data: 120523-16-2(Hazardous Substances Data)

Usage

General Description

(R)-4-Chromanol, also known as (R)-4-Hydroxy-2H-1-benzopyran, is a chemical compound that belongs to the class of chromanols. It is a chiral molecule, which means it has a non-superimposable mirror image. (R)-4-CHROMANOL is commonly found in natural sources such as fruits, vegetables, and essential oils. (R)-4-Chromanol has been studied for its potential antioxidant and anti-inflammatory properties, as well as its role in promoting cardiovascular health. It is also used in the synthesis of pharmaceuticals and as a precursor in organic chemical reactions. (R)-4-CHROMANOL is of interest in various research fields due to its biological activities and potential therapeutic applications.

Upstream product

• 493-08-3 chromane 
• 1481-93-2 4-hydroxychroman 
• 491-37-2 2,3-dihydro-4H-1-benzopyran-4-one 
• 574014-07-6 (-)-(4S)-[4-2H]-chromane 
• 574014-11-2 (+)-(4R)-[4-2H]-chromane 
• 254-04-6 2H-chromene 
• 574014-06-5 (+/-)-[4-2H]-chromane 
• 180469-85-6 (S)-3,3,3-Trifluoro-2-methoxy-2-phenyl-propionic acid (3S,4S)-3-bromo-chroman-4-yl ester 
• 108-05-4 vinyl acetate 
• 491-38-3 1-benzopyran-4(4H)-one 
• 76-86-8 Triphenylsilyl chloride 
• 766-77-8 Dimethylphenylsilane 
• 574014-04-3 (+)-(3S,4R)-[4-2H]-3-(p-toluenesulfonyloxy)chromane 
• 574014-02-1 (-)-(3S,4R)-[4-2H]-chroman-3-ol 

Downstream Products

• 777056-99-2 C₂₂H₂₈F₂N₂O₃ 
• 1448783-61-6 C₂₅H₃₁F₃N₂O₃ 
• 1448783-62-7 C₂₄H₂₈F₄N₂O₃ 
• 1448783-63-8 C₂₆H₃₁F₂N₃O₃ 
• 1448783-64-9 C₂₆H₃₂F₄N₂O₃ 
• 676134-45-5 N-((1S,2R)-1-(3,5-difluorobenzyl)-2-hydroxy-3-{[(4S)-6-isopropoxy-3,4-dihydro-2H-chromen-4-yl]amino}propyl)acetamide 
• 1448783-65-0 C₂₆H₃₂F₂N₂O₄ 
• 676134-13-7 tert-butyl (1S,2R)-1-(3,5-difluorobenzyl)-2-hydroxy-3-{[(4S)-6-neopentyl-3,4-dihydro-2H-chromen-4-yl]amino}propylcarbamate 
• 1313511-63-5 (R)-(chroman-4-yloxy)triphenylsilane 
• 676134-50-2 tert-butyl (1S,2R)-1-(3,5-difluorobenzyl)-2-hydroxy-3-{[(4S)-6-isopropoxy-3,4-dihydro-2H-chromen-4-yl]amino}propylcarbamate 

Relevant articles and documents

The hydrogenation/transfer hydrogenation network: Asymmetric hydrogenation of ketones with chiral η6-arene/N-tosylethylenediamine- ruthenium(II) catalysts

Chiral η6-arene/N-tosylethylenediamine-Ru(II) complexes, known as excellent catalysts for asymmetric transfer hydrogenation of aromatic ketones in basic 2-propanol, can be used for asymmetric hydrogenation using H2 gas. Active catalysts are generated from RuCl[(S,S)-TsNCH(C6H5)CH(C6H5)NH2](η6-p-cymene) in methanol, but not 2-propanol, or by combination of Ru[(S,S)-TsNCH(C6H5)CH(C6H5)NH](η6-p-cymene) and CF3SO3H or other non-nucleophilic acids. This method allows, for the first time, asymmetric hydrogenation of simple ketones under acidic conditions. Hydrogenation of base-sensitive 4-chromanone and its derivatives with the S,S catalyst proceeds in methanol with a substrate-to-catalyst molar ratio of 1000-3000 (10 atm) to 7000 (100 atm), giving (S)-4-chromanols with 97% ee quantitatively. The reaction can be achieved even on a 2.4 kg scale. The mechanistic rationale for the catalytic efficiency is presented. Copyright

Enantioselective acylation of chroman-4-ols catalysed by lipase from Pseudomonas cepecia (Amano PS)

Lipase Amano PS catalysed acylation of (±)-chroman-4-ols using vinyl acetate as the acyl donor in n-hexane gave (R)-(+)-chroman-4-ol acetates and (S)-(-)-chroman-4-ols in high enantiomeric excess. The relationship between the position of the substituents in the chroman-4-ol to the ee and the spatial characteristics of the enzyme active site are proposed.

An improved method for chiral oxazaborolidine-catalyzed reduction of 4- chromanone analogs and MK-0499

Addition of isopropanol to the stoichiometric reduction of ketones 4 - 8 using oxazaborolidine-borane complex 3 or the oxazaborolidine-catalyzed reduction of 4-chromanone analogs (1, 7 - 9) enhances the enantioselectivity of the reduction.

Structural Effects on the Enantioselective Acetylation of 4-Hydroxychromans Catalyzed by Microbial Lipases

Kinetic resolutions of a series of racemic 4-hydroxychromans by the Candida cylindracea lipase catalysed acetylation are described.Correlation between structure (conformation) and enantioselectivity is discussed.

Practical access to (S)-heterocyclic aromatic acetates via CAL-B/Na2CO3-deacylation and Mitsunobu reaction protocol

Herein, we report the preparation of enantiomerically pure forms of 2,3-dihydrobenzofuran-3-ol (1), chroman-4-ol (2), thiochroman-4-ol (3), 1-(furan-2-yl) ethanol (5) and 1-(thiophen-2-yl) ethanol (6), through a kinetic resolution catalysed by Candida antarctica lipase B/Na2CO3 hydrolysis sequence in organic media. The (R)-furnished alcohols and the (S)-remained acetates are recovered enantiopures (ee?>99%, E???200, Conv = 50%). Those ideal enzymatic kinetic resolution (EKRs) are well incorporated to the Mitsunobu inversion protocol in a one pot procedure to give (S)-heterocyclic acetates (1a–3a) in good to high enantiomeric excess (88%–92% ee). Whilst, the (S)-heteroaromatic acetates (5a and 6a) are given with moderate enantiomeric excess (51%–62% ee). All the (S)-acetates are given in good isolated chemical yields (>80%) allowing to overcome the maximum of 50% yield which could be usually reached in a regular kinetic resolution processes.

Dynamic Kinetic Resolution of Alcohols by Enantioselective Silylation Enabled by Two Orthogonal Transition-Metal Catalysts

A nonenzymatic dynamic kinetic resolution of acyclic and cyclic benzylic alcohols is reported. The approach merges rapid transition-metal-catalyzed alcohol racemization and enantioselective Cu-H-catalyzed dehydrogenative Si-O coupling of alcohols and hydrosilanes. The catalytic processes are orthogonal, and the racemization catalyst does not promote any background reactions such as the racemization of the silyl ether and its unselective formation. Often-used ruthenium half-sandwich complexes are not suitable but a bifunctional ruthenium pincer complex perfectly fulfills this purpose. By this, enantioselective silylation of racemic alcohol mixtures is achieved in high yields and with good levels of enantioselection.