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
• Article Data: 37

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

General Description

R-3,3'-diiodo-2,2'-bis(MethoxyMethoxy)1,1'-Binaphthalene, also known as R-3,3'-diiodo-BINOL, is a chemical compound with the molecular formula C24H18I2O4. It is a chiral compound with two chiral centers, making it useful in asymmetric synthesis. R-3,3'-diiodo-BINOL is often utilized as a catalyst in various organic transformations, such as asymmetric reduction reactions and carbon-carbon bond forming reactions. R-3,3'-diiodo-2,2'-bis(MethoxyMethoxy)1,1'-Binaphthalene is known for its high optical purity and its ability to induce high enantioselectivity in various reactions. Its unique structure and properties make it a valuable tool in the field of organic chemistry for synthesizing complex molecules with high stereochemical control.

Upstream product

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

Downstream Products

• 215433-52-6 (R)-3,3′-bis(4-biphenyl)-2,2′-dihydroxy-1,1′-dinaphthyl 
• 882992-52-1 (R,R)-(-)-(2,6-diphenyl-3,5-dioxa-4-phospha-cyclohepta[2,1-a;3,4-a']dinaphthalen-4-yl) bis(1-phenylethyl)amine 
• 882992-52-1 (R,S,S)-(-)-(2,6-diphenyl-3,5-dioxa-4-phospha-cyclohepta[2,1-a;3,4-a']dinaphthalen-4-yl) bis(1-phenylethyl)amine 
• 1309446-13-6 (R_a)-3,3’-bis(2,4,6-tricyclohexylphenyl)-[1,1’-binaphthalene]-2,2’-diol 
• 1217901-32-0 (R)-3,3’-bis(4-t-butylphenyl)-[1,1’-binaphthalene]-2,2’-diyl hydrogen phosphate 

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

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

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.

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.