2325-10-2

Basic information

• Product Name: (S,S)-(-)-HYDROBENZOIN
• Synonyms: (S,S)-(-)-Hydrobenzoin 99%, optical purity ee: 99% (GLC);(S,S)-(-)-Hydrobenzoin;(1S,2S)-(-)-HYDROBENZOIN;(1S,2S)-(-)-1,2-DIPHENYL-1,2-ETHANEDIOL;(S,S)-(-)-HYDROBENZOIN;(S,S)-1,2-DIPHENYL-ETHYLENE GLYCOL;(S,S)-(-)-1,2-DIPHENYL-1,2-ETHANEDIOL;(S,S)-1,2-DIPHENYL-1,2-ETHANEDIOL
• CAS NO: 2325-10-2
• Molecular Formula: C₁₄H₁₄O₂
• Molecular Weight: 214.26
• Mol File: 2325-10-2.mol
• Article Data: 429

Chemical Properties

• Melting Point: 146-149 °C
• Boiling Point: 314.4°C (rough estimate)
• Flash Point: 179.8 °C
• Appearance: White/Crystals
• Density: 1.0781 (rough estimate)
• Vapor Pressure: 3.18E-06mmHg at 25°C
• Refractive Index: -95 ° (C=1, CHCl3)
• Storage Temp.: 2-8°C
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• PKA: 13.38±0.20(Predicted)
• Merck: 14,4777
• BRN: 2330888
• CAS DataBase Reference: (S,S)-(-)-HYDROBENZOIN(CAS DataBase Reference)
• NIST Chemistry Reference: (S,S)-(-)-HYDROBENZOIN(2325-10-2)
• EPA Substance Registry System: (S,S)-(-)-HYDROBENZOIN(2325-10-2)

Safety Data

• Safety Statements: 22-24/25
• WGK Germany: 3
• F: 10
• Hazardous Substances Data: 2325-10-2(Hazardous Substances Data)

Usage

Description

(S,S)-(-)-HYDROBENZOIN, also known as (S,S)-(-)-Hydrobenzoin, is a chiral reagent characterized by its white crystalline powder form. It is a valuable compound in the field of organic chemistry, particularly for its ability to influence the stereochemistry of chemical reactions.

Uses

(S,S)-(-)-HYDROBENZOIN is used as a chiral auxiliary in various chemical reactions for its ability to induce stereoselectivity, leading to the formation of desired enantiomers with high purity.
Used in Pharmaceutical Industry:
(S,S)-(-)-HYDROBENZOIN is used as a building block for the synthesis of complex organic molecules, particularly in the development of pharmaceutical compounds. Its chiral nature allows for the creation of enantiomerically pure drugs, which is crucial for ensuring the desired therapeutic effects and minimizing potential side effects.
Used in Chemical Synthesis:
(S,S)-(-)-HYDROBENZOIN is used as a versatile building block in the synthesis of various organic compounds, including natural products, agrochemicals, and other specialty chemicals. Its unique stereochemistry makes it a valuable asset in the development of novel molecules with specific biological activities.
Used in Research and Development:
(S,S)-(-)-HYDROBENZOIN is employed as a chiral auxiliary in academic and industrial research settings, where it is utilized to study the effects of stereochemistry on reaction outcomes and to develop new synthetic methodologies for the preparation of enantiomerically pure compounds.

InChI:InChI=1/C14H14O2/c15-13(11-7-3-1-4-8-11)14(16)12-9-5-2-6-10-12/h1-10,13-16H/t13-,14-/m0/s1

Upstream product

• 79-21-0 peracetic acid 
• 645-49-8 cis-stilben 
• 103-30-0 (E)-1,2-diphenyl-ethene 
• 530-36-9 2-amino-1,2-diphenylethanol 
• 496-45-7 glyoxal sulfate 
• 588-59-0 stilbene 
• 15951-99-2 1,2-dichloro-1,2-diphenylethane 
• 563-63-3 silver(I) acetate 
• 572-45-2 benzil dioxime 
• 1140-29-0 N-(2-aminoethyl)-N-phenylaniline 
• 60-29-7 diethyl ether 
• 677-22-5 tert-butylmagnesium chloride 
• 119-53-9 2-hydroxy-2-phenylacetophenone 
• 671795-46-3 sec-butylmagnesium bromide 

Downstream Products

• 451-40-1 phenyl benzyl ketone 
• 947-91-1 Diphenylacetaldehyde 
• 103-30-0 (E)-1,2-diphenyl-ethene 
• 15951-99-2 1,2-dichloro-1,2-diphenylethane 
• 13440-24-9 1,2-dibromo-1,2-diphenylethane 
• 119-53-9 2-hydroxy-2-phenylacetophenone 
• 38270-63-2 2-benzhydryl-4,5-diphenyl-[1,3]dioxolane 
• 100-52-7 benzaldehyde 
• 103-29-7 1,1'-(1,2-ethanediyl)bisbenzene 
• 6067-45-4 4,4'-dinitrobenzil 
• 27797-53-1 4,5-diphenyl-[1,3]-dioxolan-2-one 
• 3682-07-3 1,2-diacetoxy-1,2-diphenylethane 
• 5876-79-9 2,4,5-triphenyl-1,3-dioxolane 
• 17601-71-7 α,α'-bis-benzoyloxy-bibenzyl 

Relevant articles and documents

Osmium Replica of Mesoporous Silicate MCM-48: Efficient and Reusable Catalyst for Oxidative Cleavage and Dihydroxylation Reactions

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A stereoselective, tandem [2+2] photocycloaddition-hydrolysis route to aldol-type adducts

Photocycloadditions of aromatic aldehydes 2a-e with cyclic ketene silyl acetals 1a-e have been investigated. Regio-and exo-selective formation of the bicyclic 2-alkoxyoxetanes 3 was observed in high yields. Hydrolysis of the acid-labile oxetanes 3 with neutral water was efficiently achieved to give aldol-type adducts 4 (threo-selective formations).

Catalytic asymmetric dihydroxylation of alkenes using silica gel supported cinchona alkaloid

Immobilization of 3,6-bis(9-O-dihydroquinyl)pyridazine and 3,6-bis(9-O-dihydroquinidyl) pyridazine on silica gel support has been reported. The use of immobilized auxiliary has lead to comparable rate with that of the homogeneous catalytic AD of alkenes, however with lower ee.

A free ligand for the asymmetric dihydroxylation of olefins utilizing one-phase catalysis and two-phase separation

A free cinchona alkaloid derivative, which can be recovered and reused in the same way as the reported soluble polymer-supported cinchona alkaloid-derived ligands, was applied to the homogeneous asymmetric dihydroxylation of olefins. The molar ratio of ligand/olefin was 5%, being much lower than that required for the corresponding soluble polymer-supported ligands (10-25%). Yields of 82-93% and ees of 89-99% have been obtained.

A novel chemoentrapment approach for supportless recycling of a catalyst: Catalytic asymmetric dihydroxylation

A simple method of recycling a metal catalyst through chemoentrapment in an aqueous layer using ethyl vinyl ether has been developed. Using this new methodology, a highly efficient, filtration-free recycling of osmium for catalytic asymmetric dihydroxylation was accomplished. By means of the formation of a water-soluble OsO42- using EVE, AD reactions of mono- and disubstituted olefins with 1 mol % of OsO4 proceeded for up to 9 cycles without any loss of yields and enantioselectivities.

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Osmium-catalyzed asymmetric dihydroxylation of olefins using chiral isoxazolidine ligands

Chiral isoxazolidines, which are readily obtained by 1,3-dipolar cycloadditions of nitrones with olefins, are found to be effective chiral ligands for osmium-catalyzed asymmetric dihydroxylations of olefins.

A Solid-to-Solid Asymmetric Dihydroxylation Procedure for Kilogram-Scale Preparation of Enantiopure Hydrobenzoin

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Unexpectedly superior enantioselectivity for trans-stilbene cis-dihydroxylation over anchored triosmium carbonyl species in confined Al-MCM-41 channels

Superior enantioselectivity in the dihydroxylation of trans-stilbene catalysed by anchored triosmium carbonyl species without using a chiral modifier is observed inside sterically congested MCM-41 channels; this effect is more pronounced through the introduction of surface Al sites into the silicate. The Royal Society of Chemistry 2005.

(S)-Tetrahydro-5-oxo-2-furancarboxylic Acid: A Chiral Derivatizing Reagent for Asymmetric Alcohols

The use of (S)-tetrahydro-5-oxo-2-furancarboxylic (TOF) acid as a potential derivatizing reagent for the determination of the enantiomeric composition of chiral alcohols was investigated.A series of chiral alcohols of widely varying structural type were derivatized with this acid and compared with two widely used acids (S)-α-acetoxypropanoic and (S)-α-methoxy-α-(trifluormethyl)phenylacetic.The resolution of the diastereomeric esters was measured on five different cappillary gas chromatographic (CGC) columns and one high-performance liquid chromatographic (HPLC) column.The 13C NMR spectra of these derivatives were recorded and examined for possible correlations between configuration and carbon chemical shift values.The chromatographic data provide a starting point for the selection of a derivatizing agent and column combination applicable to the CGC analysis of chiral alcohol enantiomeric purity, and the HPLC data allow selection of a derivatizing agent and solvent system for the HPLC analytical or preparative resolution of a chiral alcohol.The 13C NMR data provide information applicable to the assignment of the configuration to the resolved diastereomers.

Computational Design of Enantiocomplementary Epoxide Hydrolases for Asymmetric Synthesis of Aliphatic and Aromatic Diols

The use of enzymes in preparative biocatalysis often requires tailoring enzyme selectivity by protein engineering. Herein we explore the use of computational library design and molecular dynamics simulations to create variants of limonene epoxide hydrolas

Engineering Homochiral Metal-Organic Frameworks by Spatially Separating 1D Chiral Metal-Peptide Ladders: Tuning the Pore Size for Enantioselective Adsorption

The reaction of the chiral dipeptide glycyl-L(S)-glutamate with CoII ions produces chiral ladders that can be used as rigid 1D building units. Spatial separation of these building units with linkers of different lengths allows the engineering of homochiral porous MOFs with enhanced pore sizes, pore volumes, and surface areas. This strategy enables the synthesis of a family of isoreticular MOFs, in which the pore size dictates the enantioselective adsorption of chiral molecules (in terms of their size and enantiomeric excess).

Manganese-promoted, titanocene-catalyzed stereoselective pinacol coupling of aldehydes

Aromatic and aliphatic aldehydes undergo pinacol coupling when treated with Mn/Me3SiCl in the presence of Cp2TiCl2 as catalyst. Good yields of bis-silyl pinacol ethers are obtained with varying degrees of diastereoselectivity. Enantioselective pinacolization has been achieved using an enantiomerically enriched catalyst.

Sodium borohydride reduction of aldehydes and ketones in the recyclable ionic liquid [bmim]PF6

In our exploration of the new ionic liquid solvents as possible replacements for classical organic solvents, we have found that the reduction of aldehydes and ketones with NaBH4 in the ionic liquid [bmim]PF6 can be achieved. The ionic liquid can be recycled, and in some cases the product alcohol may be distilled directly from the ionic liquid eliminating classical organic solvents entirely.

Conjugated polymers as photoredox catalysts: A new catalytic system using visible light to promote aryl aldehyde pinacol couplings

The conjugated polymer poly-(p)-phenylene (PPP) was synthesized and used as a photoredox catalyst to promote pinacol coupling of aryl-aldehydes with visible light. The reaction required the use of a sacrificial electron donor (Et3N), and was accelerated by the addition of Lewis and Bronsted acids. A distinct advantage of this photocatalytic system is the robust nature of the system, which is not overly sensitive to impurities, oxygen, or temperature, and proceeds cleanly with few side reactions. As a comparison with the PPP system, the reactivity of Ru(bpy)3Cl2, a popular photoredox catalyst was compared. The PPP system was superior to the Ru(bpy)3Cl2 for the pinacol couplings in both rate and yield.

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Ni2P Nanoalloy as an Air-Stable and Versatile Hydrogenation Catalyst in Water: P-Alloying Strategy for Designing Smart Catalysts

Non-noble metal-based hydrogenation catalysts have limited practical applications because they exhibit low activity, require harsh reaction conditions, and are unstable in air. To overcome these limitations, herein we propose the alloying of non-noble metal nanoparticles with phosphorus as a promising strategy for developing smart catalysts that exhibit both excellent activity and air stability. We synthesized a novel nickel phosphide nanoalloy (nano-Ni2P) with coordinatively unsaturated Ni active sites. Unlike conventional air-unstable non-noble metal catalysts, nano-Ni2P retained its metallic nature in air, and exhibited a high activity for the hydrogenation of various substrates with polar functional groups, such as aldehydes, ketones, nitriles, and nitroarenes to the desired products in excellent yields in water. Furthermore, the used nano-Ni2P catalyst was easy to handle in air and could be reused without pretreatment, providing a simple and clean catalyst system for general hydrogenation reactions.

A convenient pinacol coupling of diaryl ketones with B2pin2viapyridine catalysis

A convenient, pyridine-boryl radical-mediated pinacol coupling of diaryl ketones is developed. In contrast to the conventional pinacol coupling that requires sensitive reducing metal, the current method employs a stable diboron reagent and pyridine Lewis base catalyst for the generation of a ketyl radical. The newly developed process is operationally simple, and the desired diols are produced with excellent efficiency in up to 99% yield within 1 hour. The superior reactivity of diaryl ketone was observed over monoaryl carbonyl compounds and analyzed by DFT calculations, which suggests the necessity of both aromatic rings for the maximum stabilization of the transition states.