142010-87-5

Basic information

• Product Name: (S)-3,3'-Dibromo-2,2'-bis(meth
• Synonyms: (S)-3,3'-Dibromo-2,2'-bis(meth;(S)-3,3'-Dibromo-2,2'-bis(methoxymethoxy)-1,1'-binaphthyl, 97%;(S)-3,3'-Dibromo-bis(methoxymethoxyl)-1,1'-binaphtyl, 99%e.e.
• CAS NO: 142010-87-5
• Molecular Formula: C₂₄H₂₀Br₂O₄
• Molecular Weight: 532.2212
• Mol File: 142010-87-5.mol

Chemical Properties

• Melting Point: 93-95℃
• Appearance: /
• Storage Temp.: 2-8°C
• CAS DataBase Reference: (S)-3,3'-Dibromo-2,2'-bis(meth(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-3,3'-Dibromo-2,2'-bis(meth(142010-87-5)
• EPA Substance Registry System: (S)-3,3'-Dibromo-2,2'-bis(meth(142010-87-5)

Safety Data

• Hazardous Substances Data: 142010-87-5(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
(S)-3,3'-Dibromo-2,2'-bis(meth is employed as a reagent in organic synthesis, facilitating the formation of new chemical bonds and the synthesis of complex organic molecules. Its unique structure and reactivity make it a valuable tool in the creation of a wide range of compounds.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, (S)-3,3'-Dibromo-2,2'-bis(meth is used as a chiral catalyst for asymmetric synthesis. Its ability to selectively catalyze reactions involving chiral molecules contributes to the production of enantiomerically pure compounds, which are essential for the development of effective and safe drugs.
Used in Agrochemical Industry:
Similarly, in the agrochemical industry, (S)-3,3'-Dibromo-2,2'-bis(meth is utilized for asymmetric synthesis of biologically active compounds. Its chiral properties enable the production of enantiomerically pure agrochemicals, which can improve the effectiveness and reduce the environmental impact of these products.
Used as a Chiral Catalyst:
(S)-3,3'-Dibromo-2,2'-bis(meth is used as a chiral catalyst in various chemical reactions, promoting enantioselective processes. Its unique structure allows it to selectively interact with specific enantiomers, leading to the formation of desired chiral products with high enantiomeric purity. This selective catalysis is crucial in the synthesis of optically active compounds for pharmaceutical, agrochemical, and other applications.

Upstream product

• 18531-99-2 (S)-[1,1']-binaphthalenyl-2,2'-diol 
• 74292-20-9 (S)-2,2'-bis(methoxymethoxy)-1,1'-binaphthyl 
• 173831-50-0 rac-2,2'-bis-(methoxymethoxy)-1,1'-binaphthalene 
• 135-19-3 β-naphthol 
• 602-09-5 1,1'-bi-2-naphthol 

Downstream Products

• 756491-46-0 (+/-)-3,3'-bis(3,5-dimethylphenyl)-2,2'-bis(methoxymethoxy)-1,1'-binaphthyl 

Relevant articles and documents

Synthesis, properties, and structures of functionalized peri -xanthenoxanthene

Three types of alkylated peri-xanthenoxanthene (PXX) have been synthesized employing efficient synthetic routes. These heteroaromatic compounds exhibited different electronic and crystal structures according to UV-vis spectra, electrochemical measurements, and X-ray structural analyses. Among them, 1,7-DOPXX has been demonstrated as an active material for organic field-effect transistors with promising mobility and a high on/off ratio simultaneously.

Synthesis of (±)-3,3′-diphenyl-2,2′-binaphthol via different routes using Pd and Ni as catalyst respectively

3,3′-Biphenyl-2,2′-binaphthols (BINOLs) are precursors of phosphoric acids that are widely used as ligands and catalysts in organic reactions. In this report, two routes for the synthesis of (±)-3,3′-diphenyl BINOLs via (±)-3,3′ bis-halogenated BINOLs int

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.

Synthesis of Chiral Indenylcobalt(I) Complexes and Their Evaluation in Asymmetric [2+2+2] Cycloaddition Reactions

The syntheses of two new indenyl-based cobalt(I) complexes were reported and their properties as catalysts in asymmetric cyclotrimerizations evaluated. While one complex was synthesized from a functionalized BINOL derivative by cross-coupling with 2-indenylboronate, the other complex was derived from a known chiral indenyl cobalt(I) complex by exchange of COD for two phosphite ligands, delivering the first chiral indenyl cobalt(I) complex, which can easily be activated thermally. The prepared complexes were tested in asymmetric cyclization reactions of triynes as well as diynes with nitriles to deliver chiral triaryls and heterobiaryls, respectively. While the BINOL-based precatalysts promoted the cyclizations in good yield without selectivity, the bisphosphite cobalt(I) complex induces chirality with up to 80% ee under photochemical as well as under thermal conditions.

Conformationally driven asymmetric induction of a catalytic dendrimer

Nature-s catalysts promote the reactions necessary for life with extremely high specificity by folding into specific shapes capable of communicating remote structural information to an active site. Achieving this objective in synthetic systems has been ha

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.

Design of N-spiro C2-symmetric chiral quaternary ammonium bromides as novel chiral phase-transfer catalysts: Synthesis and application to practical asymmetric synthesis of α-amino acids

A series of C2-symmetric chiral quaternary ammonium bromides 10 and 11 have been designed as a new, purely synthetic chiral phase-transfer catalyst, and readily prepared from commercially available optically pure 1,1′-bi-2-naphthol as a basic c

EXPEDIENT ROUTE TO 3- AND 3,3'-SUBSTITUTED 1,1'-BI-2-NAPHTHOLS BY DIRECTED ortho METALATION AND SUZUKI CROSS COUPLING METHODS

A directed ortho metalation-based route to 3- and 3,3'-substituted binaphthols 2a-c and 3a-c, including chiral materials, is described.Using the Suzuki cross coupling process, dibromo system 3a (E = Br) has been transformed into 3,3'-diaryl binaphthols 5.