1199631-29-2

Basic information

• Product Name: (S)-3,3'-bis(4-Methoxyphenyl)-[1,1'-Binaphthalene]-2,2'-diol
• Synonyms: (S)-3,3'-bis(4-Methoxyphenyl)-[1,1'-Binaphthalene]-2,2'-diol;(S)-3,3'-Bis(4-methoxyphenyl)-[1,1'-binaphthalene]-2,2'- diol, 99%e.e.
• CAS NO: 1199631-29-2
• Molecular Formula: C34H26O4
• Molecular Weight: 498.56784
• Mol File: 1199631-29-2.mol

Chemical Properties

• Boiling Point: 624.7±55.0 °C(Predicted)
• Appearance: /
• Density: 1.251±0.06 g/cm3(Predicted)
• PKA: 8.20±0.50(Predicted)
• CAS DataBase Reference: (S)-3,3'-bis(4-Methoxyphenyl)-[1,1'-Binaphthalene]-2,2'-diol(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-3,3'-bis(4-Methoxyphenyl)-[1,1'-Binaphthalene]-2,2'-diol(1199631-29-2)
• EPA Substance Registry System: (S)-3,3'-bis(4-Methoxyphenyl)-[1,1'-Binaphthalene]-2,2'-diol(1199631-29-2)

Safety Data

• Hazardous Substances Data: 1199631-29-2(Hazardous Substances Data)

Usage

Uses

Used in Chemical Synthesis Industry:
(S)-BINOL is utilized as a chiral ligand for [asymmetric synthesis and catalysis] because of its capacity to form stable complexes with metals, facilitating the production of enantiomerically pure compounds which are essential in creating biologically active pharmaceuticals.
Used in Pharmaceutical Research:
In the pharmaceutical sector, (S)-BINOL is employed as a reagent for [the development of enantiomerically pure drugs] due to its ability to induce chirality in synthesized molecules, which is crucial for ensuring the desired biological activity and minimizing side effects.
Used in Biomedical Research:
(S)-BINOL is studied as a compound with [potential antioxidant and anti-inflammatory properties], making it a subject of interest for research into new therapeutic agents that could treat a variety of diseases and conditions.
Overall, (S)-BINOL's applications cut across multiple industries, underscoring its importance in both the creation of novel chemical entities and the advancement of medical treatments.

Upstream product

• 173831-50-0 rac-2,2'-bis-(methoxymethoxy)-1,1'-binaphthalene 
• 142010-87-5 (±)?3,3'?dibromo?2,2'?bis(methoxymethyl)?1,1'?binaphthalene 
• 602-09-5 1,1'-bi-2-naphthol 
• 104-92-7 1-bromo-4-methoxy-benzene 
• 18531-94-7 (R)-1,1'-Bi-2-naphthol 
• 171364-79-7 2-(4-methoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 5720-07-0 4-methoxyphenylboronic acid 
• 189518-78-3 (Ra)-3,3’-diiodo-2,2’-bis(methoxymethoxy)-1,1’-binaphthalene 
• 756491-45-9 (+/-)-3,3'-bis(4-methoxyphenyl)-2,2'-bis(methoxymethoxy)-1,1'-binaphthyl 

Relevant articles and documents

Chiral Bronsted acid catalyzed enantioselective Mannich-type reaction

Mannich-type reaction of ketene silyl acetals with aldimines proceeded catalytically by means of a phosphoric acid diester, derived from (R)-BINOL, as a chiral Bronsted acid to afford β-amino esters with good diastereoselectivity in favor of the syn isomer and high enantioselectivity (up to 96% ee). The highest enantioselectivity was achieved by the phosphoric acid diester bearing 4-nitrophenyl groups on the 3,3′-positions of BINOL. The N-2-hydroxyphenyl group of aldimine was found to be essential for the present Mannich-type reaction. In combination with these experimental investigations, two possible monocoordination and dicoordination pathways were explored using density functional theory calculations (BHandHLYP/6-31G*). The present reaction proceeds via a dicoordination pathway through the zwitterionic and nine-membered cyclic transition state (TS) consisting of the aldimine and the phosphoric acid. The re-facial selectivity was also well-rationalized theoretically. The nine-membered cyclic structure and aromatic stacking interaction between the 4-nitrophenyl group and N-aryl group would fix the geometry of aldimine on the transition state, and the si-facial attacking TS is less favored by the steric hindrance of the 3,3′-aryl substituents.

Rapid synthesis of 3,3′ bis-arylated BINOL derivatives using a C-H borylation in situ suzuki-miyaura coupling sequence

The increased interest in BINOL derived catalysts for asymmetric transformations has encouraged us to disclose a rapid and scalable method of preparing 3,3′ bis-arylated BINOL derivatives 1 using a one-pot CH borylation/Suzuki-Miyaura coupling sequence. T

Expedient BINOL derivative arylations

A dramatic improvement of our previous methodology based on a Suzuki-Miyaura cross-coupling to access 3,3′-disubstituted H8-BINOLs using microwave heating is reported herein. These new conditions represent a large gain in term of atom-economy, reaction time, catalyst loading, and excess of reagents employed.

Hypercrosslinking chiral Br?nsted acids into porous organic polymers for efficient heterogeneous asymmetric organosynthesis

Here, we developed a construction strategy for directly immobilizing the axially chiral phosphoric acid into hypercrosslinked polymers by a one-pot Friedel-Crafts alkylation reaction. The obtained chiral polymers have high porosity, excellent stability and tailorable catalytic centers, and display excellent activity, enantioselectivity and recyclability for asymmetric transfer hydrogenation.

Photocatalyzed E→Z Contra-thermodynamic Isomerization of Vinyl Boronates with Binaphthol

The photocatalytic contra-thermodynamic E→Z isomerization of vinyl boronates by using a binaphthol catalyst is disclosed. The reaction, based on the transient formation of a suitable chromophore with a BINOL derivative as the catalyst, allowed geometrical isomerization in good-to-excellent Z/E ratio and excellent-to-quantitative yields. The mechanism of this E→Z contra-thermodynamic isomerization was studied, and the formation of a transient chromophore species is suggested.

Efficient synthesis of 3,3'-diaryl binaphthol through a one-step method

The invention relates to a class of catalysis reactions of binaphthol and halogenated aromatic hydrocarbons, particularly to efficient preparation of 3,3'-diaryl binaphthol and 3-Bulkyaryl binaphtholthrough a one-step method, and belongs to the technical field of asymmetric catalysis. A purpose of the present invention is to provide a simple and practical method for preparing 3,3'-diaryl binaphthol through a one-step reaction of inexpensive BINOL and a brominated aromatic hydrocarbon reagent, and is further to provide a simple and rapid method for conveniently preparing 3-aryl binaphthol withhigh steric hindrance.

ASYMMETRIC-SYNTHESIS CATALYST BASED ON CHIRAL BROENSTED ACID AND METHOD OF ASYMMETRIC SYNTHESIS WITH THE CATALYST

A compound usable as an asymmetric synthesis catalyst which can be easily synthesized without using any metal such as a lanthanoid group element; a method of asymmetric synthesis with the compound; and a chiral compound obtained by the asymmetric synthesis method. A Broensted acid is used as a catalyst in asymmetric synthesis, the chiral Broensted acid being represented by formula (1) below or formula (3) below. The asymmetric synthesis method employs the catalyst. Asymmetric synthesis with the catalyst gives a chiral compound.

Asymmetric allylboration of aldehydes and ketones using 3,3′-disubstitutedbinaphthol-modified boronates

Allylboronates derived from 3,3′-disubstituted 2,2′-binaphthols react with aldehydes and ketones to give the expected allylated products with up to >99:1 er. Highest selectivities were observed for aromatic ketones. The bis(trifluoromethyl) derivative is particularly outstanding in terms of reactivity, selectivity, and robustness.