189518-78-3

Basic information

• Product Name: R-3,3'-diiodo-2,2'-bis(MethoxyMethoxy)1,1'-Binaphthalene
• Synonyms: (1R)-3,3'-Diiodo-2,2'-bis(MethoxyMethoxy)-1,1'-binaphthalene;(R)-3,3'-Diiodo-2,2'-bis(methoxymethoxy)-1,1'- binaphthalene, 99%e.e.;R-3,3'-diiodo-2,2'-bis(MethoxyMethoxy)1,1'-Binaphthalene
• CAS NO: 189518-78-3
• Molecular Formula: C24H20I2O4
• Molecular Weight: 626.22214
• Mol File: 189518-78-3.mol

Chemical Properties

• Melting Point: 45-47 °C
• Boiling Point: 590.255 °C at 760 mmHg
• Flash Point: 310.775 °C
• Appearance: /
• Density: 1.735 g/cm³
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• CAS DataBase Reference: R-3,3'-diiodo-2,2'-bis(MethoxyMethoxy)1,1'-Binaphthalene(CAS DataBase Reference)
• NIST Chemistry Reference: R-3,3'-diiodo-2,2'-bis(MethoxyMethoxy)1,1'-Binaphthalene(189518-78-3)
• EPA Substance Registry System: R-3,3'-diiodo-2,2'-bis(MethoxyMethoxy)1,1'-Binaphthalene(189518-78-3)

Safety Data

• Hazardous Substances Data: 189518-78-3(Hazardous Substances Data)

Usage

Uses

Used in Asymmetric Synthesis:
R-3,3'-diiodo-BINOL is employed as a chiral catalyst in various organic transformations, particularly in asymmetric reduction reactions and carbon-carbon bond forming reactions. Its application is crucial for achieving high enantioselectivity, which is essential for the production of enantiomerically pure compounds, a critical factor in the pharmaceutical industry where the biological activity of enantiomers can differ significantly.
Used in Organic Chemistry Research:
In the field of organic chemistry, R-3,3'-diiodo-BINOL serves as a valuable tool for researchers. It aids in the development of new synthetic methods and the exploration of reaction mechanisms, contributing to the advancement of knowledge in organic chemistry and its applications.
Used in Pharmaceutical Industry:
The high optical purity and enantioselectivity induced by R-3,3'-diiodo-BINOL make it a preferred catalyst in the synthesis of pharmaceutical compounds. This ensures that the final drug products have the desired stereochemistry, which is often directly related to their therapeutic efficacy and safety.
Used in the Synthesis of Complex Molecules:
R-3,3'-diiodo-BINOL is utilized in the creation of complex organic molecules with high stereochemical control. This is particularly relevant in the synthesis of natural products and the development of new pharmaceutical agents, where the stereochemistry of the molecule can influence its biological activity.

Upstream product

• 173831-50-0 rac-2,2'-bis-(methoxymethoxy)-1,1'-binaphthalene 
• 602-09-5 1,1'-bi-2-naphthol 
• 18531-94-7 (R)-1,1'-Bi-2-naphthol 
• 135-19-3 β-naphthol 
• 107-30-2 chloromethyl methyl ether 
• 74292-20-9 (S)-2,2'-bis(methoxymethoxy)-1,1'-binaphthyl 
• 18531-99-2 (S)-[1,1']-binaphthalenyl-2,2'-diol 

Downstream Products

• 1352522-61-2 3,3'-bis(1-phenyl-1H-1,2,3-triazol-4-yl)-1,1'-binaphthyl-2,2'-diyl (1-pyrrolidinyl)phosphonite 
• 1352522-63-4 3,3'-bis(1-phenyl-1H-1,2,3-triazol-4-yl)-1,1'-binaphthyl-2,2'-diyl (1-pyrrolidinyl)phosphonate 
• 1352522-87-2 3,3'-bis(1-(p-methoxyphenyl)-1H-1,2,3-triazol-4-yl)-1,1'-binaphthyl-2,2'-diyl (1-pyrrolidinyl)phosphonite 
• 1352522-88-3 3,3'-bis(1-(p-methoxyphenyl)-1H-1,2,3-triazol-4-yl)-1,1'-binaphthyl-2,2'-diyl (1-pyrrolidinyl)phosphonate 
• 1352522-91-8 3,3'-bis(1-(p-bromophenyl)-1H-1,2,3-triazol-4-yl)-1,1'-binaphthyl-2,2'-diyl (1-pyrrolidinyl)phosphonite 
• 1352522-94-1 3,3'-bis(1-(p-bromophenyl)-1H-1,2,3-triazol-4-yl)-1,1'-binaphthyl-2,2'-diyl (1-pyrrolidinyl)phosphonate 
• 1352522-95-2 3,3'-bis(1-(p-fluorophenyl)-1H-1,2,3-triazol-4-yl)-1,1'-binaphthyl-2,2'-diyl (1-pyrrolidinyl)phosphonite 
• 1352522-98-5 3,3'-bis(1-(p-fluorophenyl)-1H-1,2,3-triazol-4-yl)-1,1'-binaphthyl-2,2'-diyl (1-pyrrolidinyl)phosphonate 
• 1352523-00-2 3,3'-bis(1-(2,4,5-trichlorophenyl)-1H-1,2,3-triazol-4-yl)-1,1'-binaphthyl-2,2'-diyl (1-pyrrolidinyl)phosphonite 
• 1352523-02-4 3,3'-bis(1-(2,4,5-trichlorophenyl)-1H-1,2,3-triazol-4-yl)-1,1'-binaphthyl-2,2'-diyl (1-pyrrolidinyl)phosphonate 
• 361342-51-0 (R)-3,3'-bis(9-anthracenyl)-1,1'-binaphthyl-2,2'-diyl hydrogenphosphate 
• 1309446-13-6 (R_a)-3,3’-bis(2,4,6-tricyclohexylphenyl)-[1,1’-binaphthalene]-2,2’-diol 

Relevant articles and documents

Self-assembly of chiral BINOL cagesviaimine condensation

Condensation of an (S)- or (R)-BINOL-derived dialdehyde and tris(2-aminoethyl)amine produced chiral [2+3] imine cages, which were further reduced to furnish more stable chiral amine cages and applied in the enantioselective recognition of (1R,2R)- and (1S

Synthesis of tetra(BINOL) substituted spirobifluorenes

A series of tetra(BINOL) substituted spirobifluorenes (1, 12-15) has been prepared via fourfold Sonogashira cross-coupling reaction from 2,2′,7,7′-tetraiodospirobifluorene (3) and 2,2′bis(methoxymethoxy)-3-ethynyl-1,1′-binaphthyl (10) or 2,2′bis(methoxymethoxy)-3-ethynyl-3′-[(trimethylsilyl)ethynyl]-1, 1′-binaphthyl (11), respectively. Whereas the deprotection of the readily available fully methoxymethyl ether protected precursors 12 and 13 proved to be difficult in the case of the sterically shielded spirobifluorenes 14, 15, not further substituted tetra(BINOL) 1 could be obtained in good yield after acidic hydrolysis. This chiral spirobifluorene closely reassembles the structure of copper(I) or silver(I) complexes of a bis(BINOL) substituted 2,2-bipyridine (2) and can also form two clefts with the BINOL groups orientated in a fashion potentially useful for the cooperative molecular recognition of chiral substrates.

Design and synthesis of a chiral halogen-bond donor with a sp3-hybridized carbon-iodine moiety in a chiral fluorobissulfonyl scaffold

The first example of a chiral halogen-bond donor with a sp3-hybridized carbon-iodine moiety in a fluorobissulfonyl scaffold is described. The binaphthyl backbone was designed as a chiral source and the chiral halogen-bond donor (R)-1 was synthesized from

A crown ether-derived chiral 1, 1 '-linked -2, 2' - naphthol. Preparation method and application thereof

The chiral 1, 1 '-linked -2, 2' - naphthol, 1 1-linked '- and -2 2 naphthol protected by methoxymethyl ether are prepared by reaction of iodine, palladium catalyzed' - Suzuki coupling, hydrolysis, amidation and deprotection. The crown ether-derived chiral 1, 1 '-coupling -2, 2' - naphthol has chirality and steric hindrance, may be a enantiomer, may be a racemate, or may be a racemic mixture of enantiomers. When the chiral 1, 1 '- linked -2 and 2' - naphthol optical purity ≥ 85% ee derived from the crown ether is excellent in effect in asymmetric catalytic reaction, especially asymmetric Michael addition reaction of alkenyl boronic acid and α, β - unsaturated ketone, the optical purity of the product can reach 90%, and high catalytic reaction activity and high activity are achieved 99%. Stereoselectivity.

Gold-Catalyzed [3+2]-Annulations of α-Aryl Diazoketones with the Tetrasubstituted Alkenes of Cyclopentadienes: High Stereoselectivity and Enantioselectivity

This work reports gold-catalyzed [3+2]-annulations of α-diazo ketones with highly substituted cyclopentadienes, affording bicyclic 2,3-dihydrofurans with high regio- and stereoselectivity. The reactions highlights the first success of tetrasubstituted alkenes to undergo [3+2]-annulations with α-diazo carbonyls. The enantioselective annulations are also achieved with high enantioselectivity using chiral forms of gold and phosphoric acid. Our mechanistic analysis supports that cyclopentadienes serve as nucleophiles to attack gold carbenes at the more substituted alkenes, yielding gold enolates that complex with chiral phosphoric acid to enhance the enantioselectivity.

Br?nsted Acid Catalyzed Stereoselective Polymerization of Vinyl Ethers

Isotactic poly(vinyl ether)s (PVEs) have recently been identified as a new class of semicrystalline thermoplastics with a valuable combination of mechanical and interfacial properties. Currently, methods to synthesize isotactic PVEs are limited to strong

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.

Chiral Metallacycles as Catalysts for Asymmetric Conjugate Addition of Styrylboronic Acids to α,β-Enones

Introducing self-assembly strategies into the construction of catalysts has been proven to have great advantages in asymmetric catalysis. We constructed two chiral metalla-triangles by highly efficient coordination-driven self-assembly from a chiral 3,3′-dipyridyl-substituted BINOL donor. They were successfully applied in asymmetric conjugate addition of a series of α,β-unsaturated ketones with trans-styrylboronic acids. The use of these metalla-triangles as supramolecular catalysts is obviously conducive to the enhancement of catalytic activity and stereoselectivity in the presented addition reactions. Under induction of the chiral metalla-triangles, an array of α,β-enones were converted to chiral ?,I-unsaturated ketones in medium to quantitative yields (40-98%) with high enantioselectivities (87-96% ee).

Br?nsted Acid-Catalyzed Enantioselective Cycloisomerization of Arylalkynes

The first example of an enantioselective carbocyclization of an alkyne-containing substrate catalyzed by chiral Br?nsted acids was achieved. The use of the 2-hydroxynaphthyl substituent on the alkyne as a directing group constituted the key parameter enabling both efficient regioselective protonation of the carbon–carbon triple bond and chiral induction. The key cationic intermediate could be depicted either as a cationic vinylidene ortho-quinone methide or a stabilized vinyl cation. Atropoisomeric phenanthrenes derivatives were produced in high yields and good enantioselectivities under mild, metal-free reaction conditions in the presence of chiral N-triflylphosphoramide catalysts. The carbenic nature of the cationic intermediate was also exploited to describe an example of alkyne/alkane cycloisomerization.

Rhodium-Catalyzed Reaction of Silacyclobutanes with Unactivated Alkynes to Afford Silacyclohexenes

A Rh-catalyzed reaction of silacyclobutanes (SCBs) with unactivated alkynes has been developed to form silacyclohexenes with high chemoselectivity. Good enantioselectivity at the stereogenic silicon center was achieved using a chiral phosphoramidite ligand. The resulting silacyclohexenes are useful scaffolds for synthesizing structurally attractive silacyclic compounds.