74866-28-7

Basic information

• Product Name: 2,2'-DIBROMO-1,1'-BINAPHTHYL
• Synonyms: 2,2'-DIBROMO-1,1'-BINAPHTHYL;2,2'-DIBROMO-1,1'-DINAPHTHYL;RACEMIC-2,2'-DIBROMO-1,1'-BINAPHTHYL;rac-2,2'-Dibromo-1,1'-binaphthyl,;rac-2,2'-Dibromo-1,1'-binaphthyl,99%;2,2'-Dibromo-1,1'-binapthyl;racemic-2,2'-Dibromo-1,1'-binaphthyl,99%;1,1'-Bi(2-bromonaphthalene)
• CAS NO: 74866-28-7
• Molecular Formula: C₂₀H₁₂Br₂
• Molecular Weight: 412.12
• EINECS: 1312995-182-4
• Product Categories: Aryl;C13 to C37+;Halogenated Hydrocarbons
• Mol File: 74866-28-7.mol
• Article Data: 14

Chemical Properties

• Melting Point: 178-183 °C
• Boiling Point: 178-183°C
• Flash Point: 178-183°C
• Appearance: white to off-white/Powder
• Density: 1.614 g/cm³
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: soluble in Toluene
• Water Solubility: Sparingly Soluble in water.
• CAS DataBase Reference: 2,2'-DIBROMO-1,1'-BINAPHTHYL(CAS DataBase Reference)
• NIST Chemistry Reference: 2,2'-DIBROMO-1,1'-BINAPHTHYL(74866-28-7)
• EPA Substance Registry System: 2,2'-DIBROMO-1,1'-BINAPHTHYL(74866-28-7)

Safety Data

• Hazard Codes: Xn
• Statements: 36/37/38-22
• Safety Statements: 26-36/37/39
• WGK Germany: 3
• Hazardous Substances Data: 74866-28-7(Hazardous Substances Data)

Usage

Uses

The synthesis of this class of compounds relies on the lithiation of racemic 2,2'-dibromo-1,1'-binaphthyl with t-BuLi followed by addition of Ph 2 PCl.

Purification Methods

Purify the binaphthyl by chromatography through a silica gel column (70-230mesh) using hexane as eluent. It gives pale yellow crystals from EtOH with m 187.3-187.9o. The R-(+)-enantiomer [86688-08-6] crystallises from hexane with m 157-157.5o and [] D +32.9o (c 1, pyridine) [Brown et al. J Org Chem 50 4345 1985]. [Okamoto et al. J Am Chem Soc 103 69711981, Beilstein 5 III 2465.]

Upstream product

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

Downstream Products

• 100165-87-5 2,2'-bis(di-p-tolylphosphino)-1,1'-binaphthyl dioxide 
• 139139-84-7 (+/-)-2,2'-bis(dicyclohexylphosphinyl)-1,1'-binaphthyl 
• 139139-84-7 (R)-(-)-2,2'-bis(dicyclohexylphosphinoyl)-1,1'-binaphthyl 
• 139139-84-7 (S)-(+)-2,2'-bis(dicyclohexylphosphinoyl)-1,1'-binaphthyl 
• 100165-89-7 (+/-)-2,2'bis-1,1'-binaphtyl 
• 194-65-0 1,1'-binaphthothiophene 
• 188-57-8 (R)-(-)-dinaphtho<2,1-c:1',2'-e><1,2>dithiin 
• 149639-52-1 (+/-)-7-phenyldinaphtho<2,1-b;1',2'-d>phosphole 
• 76144-87-1 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl 
• 130164-89-5 2,2’-bis(diphenylphosphinooxide)-1,1’-binaphthalene 
• 18531-96-9 1,1'-binaphthyl-2,2'-dicarboxylic acid 
• 613-33-2 (4,4'-dimethyl-1,1'-biphenyl) 

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.