86688-08-6

Basic information

• Product Name: R-(+)-2,2-DIBROMO-1,1'-BINAPHTHYL
• Synonyms: R-(+)-2,2-DIBROMO-1,1'-BINAPHTHYL;(1R)-2,2'-dibroMo-1,1'-Binaphthalene;(R)-2,2'-Dibromo-1,1'-binaphthalene;(R)-2,2'-Dibromo-1,1'-binaphthalene, 99%e.e.;(1R)-2,2'-Dibromo-1,1'-binaphthalene, min. 98%
• CAS NO: 86688-08-6
• Molecular Formula: C₂₀H₁₂Br₂
• Molecular Weight: 413.12522
• Mol File: 86688-08-6.mol
• Article Data: 14

Chemical Properties

• Boiling Point: 464.1±30.0 °C(Predicted)
• Appearance: white to light-yellow/solid
• Density: 1.614±0.06 g/cm3(Predicted)
• CAS DataBase Reference: R-(+)-2,2-DIBROMO-1,1'-BINAPHTHYL(CAS DataBase Reference)
• NIST Chemistry Reference: R-(+)-2,2-DIBROMO-1,1'-BINAPHTHYL(86688-08-6)
• EPA Substance Registry System: R-(+)-2,2-DIBROMO-1,1'-BINAPHTHYL(86688-08-6)

Safety Data

• Hazardous Substances Data: 86688-08-6(Hazardous Substances Data)

Usage

General Description

R-(+)-2,2-DIBROMO-1,1'-BINAPHTHYL is a chemical compound with the formula C20H12Br2. It is an optically active dibrominated binaphthyl derivative, which consists of two naphthalene rings connected by a bridge at the 1 and 1' positions. R-(+)-2,2-DIBROMO-1,1'-BINAPHTHYL is widely used as a chiral ligand in asymmetric catalysis and organic synthesis, due to its ability to facilitate enantioselective reactions. It is known for its ability to form stable complexes with various metal ions, particularly palladium, rhodium, and copper. R-(+)-2,2-DIBROMO-1,1'-BINAPHTHYL has found applications in the pharmaceutical industry, agrochemicals, and fine chemical synthesis, where chirality plays a crucial role in determining the properties and activities of the desired compounds.

Upstream product

• 4488-22-6 1,1'-binaphthalene-2,2'-diamine 
• 135-19-3 β-naphthol 
• 580-13-2 2-bromonaphthalene 
• 18741-85-0 (R)-1,1'-binaphthyl-2,2'-diamine 
• 35216-79-6 1-naphthyl-2-naphthol 
• 602-09-5 1,1'-bi-2-naphthol 
• 603-35-0 triphenylphosphine 
• 1034-39-5 dibromotriphenylphosphorane 
• 156568-04-6 2,2'-bis(trimethylsiloxy)-1,1'-bi-2-naphthyl 

Downstream Products

• 76144-87-1 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl 
• 86632-32-8 R-2-bromo-2'-(diphenylphosphino)-1,1'-binaphthyl 
• 76189-55-4 (R)-(+)-2,2'-bis(diphenylphosphino)-1,1'-binaphthalene 
• 130164-89-5 2,2’-bis(diphenylphosphinooxide)-1,1’-binaphthalene 
• 604-53-5 1,1'-bisnaphthalene 
• 18531-96-9 (S)-1,1'-binaphthyl-2,2'-dicarboxylic acid 
• 746-46-3 (R)-1,1'-binaphthyl-2,2'-dicarboxylic acid 
• 194038-54-5 2-bromo-1,1'-binaphthyl-2'-boronic acid 
• 1059502-63-4 2-methyl-2'-[hydroxyl(diphenyl)methyl]-1,1'-binaphthyl 
• 207611-58-3 2-bromo-[1,1']dinaphthyl 
• 1059502-55-4 2-bromo-2'-[hydroxyl(phenyl)methyl]-1,1'-binaphthyl 
• 741264-28-8 2-[hydroxyl(phenyl)methyl]-1,1'-binaphthyl 
• 1059502-60-1 2-methyl-2'-[hydroxyl(phenyl)methyl]-1,1'-binaphthyl 
• 194-59-2 7H-dibenzo[c,g]carbazole 

Relevant articles and documents

Synthesis method of 2, 2 '-bisdiphenylphosphino-1, 1'-binaphthalene

The invention relates to a synthesis method of 2, 2 '-bisdiphenylphosphino-1, 1'-binaphthalene, which is realized by the following steps: step 1, carrying out BUCHERER reaction on 1, 1 '-binaphthyl-2-naphthol to generate 1, 1'-binaphthyl-2, 2 '-diamine; 2, subjecting 1, 1 '-binaphthyl-2, 2'-diamine to a Sandmeyer reaction to generate binaphthyl dibromide; and 3, carrying out a Grignard reaction onthe binaphthyl dibromide and diphenyl phosphine chloride to generate 2, 2 '-bisdiphenylphosphino-1, 1'-binaphthalene (BINAP). Bulk chemical raw materials are used and are low in price and easy to obtain, and the production cost is effectively reduced; the method has the advantages of easily available raw materials, high reaction yield, simple post-treatment, facilitation of industrial amplification, and strong industrial application prospect.

Reconnaissance of reactivity of an Ag(II)SO4 one-electron oxidizer towards naphthalene derivatives

We test divalent silver sulphate, Ag(ii)SO4 as a novel reagent for oxidative coupling of aromatic hydrocarbons under ambient temperature conditions. The applicability of the C(sp2)-C(sp2) coupling protocol is illustrated for naphthalene and its 1-substituted derivatives containing either electron donating (e.g. Me, MeO, or Ph) or electron-withdrawing groups (X = F?I), leading to 4,4′-disubstituted-1,1′-binaphthyls. Coupling of 2-bromo-naphthalene yields a mixture of 2,2′-, 2,7′-, and 7,7′-dibromo-1,1′-binaphthyls together with their trimeric and tetrameric analogues. The coupling of strongly electron-withdrawing 1-CF3-naphthalene provides the 5,5′-disubstituted-1,1′-binaphthyl derivative. The new method does not require the presence of halogen substituents, in contrast to most of the known C-C coupling methods, and it preserves them, if present. Ag(ii)SO4 may be easily electrochemically regenerated from the Ag(i)HSO4 byproduct. However, the C-C coupling method currently suffers from low yields, up to 17%, and it requires further optimization.

A highly diastereoselective route to dinaphtho [c,e][1,2] oxaphosphinines and their application as ligands in homogeneous catalysis

A new and facile method for the synthesis of 6H-dinaphtho[c,e][1,2] oxaphosphinines starting from dinaphthol (BINOL) is described. The ring-opening of an intermediary dinaphtho[2,1-b;1′,2′-d]furan proceeds with extremely high diastereoselectivity and forms the thermodynamically most stable product. The stereochemistry was elucidated by 31P NMR spectroscopy and X-ray structural analysis. Epimerization at the stereogenic P-centre did not take place. DFT calculations were performed to determine the dihedral angles of several dinaphtho[c,e][1,2]oxaphosphinines and to explain the observed loss of stereochemistry during the total synthesis from, the starting enantiopure BINOL. The synthetic potential of 6-chloro-6H-dinaphtho[c,e][1,2]oxaphosphinine was corroborated in its reactions with phenols to afford the corresponding phosphonites. These were successfully applied as ligands in the Rh-catalysed hydroformylation of three terminal olefins.