98327-87-8

Basic information

• Product Name: (+/-)-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl
• Synonyms: (+/-)-(1,1'-BINAPHTHALENE-2,2'-DIYL)BIS(DIPHENYLPHOSPHINE);(+/-)-2,2'-BIS(DIPHENYLPHOSPHINO)-1,1'-BINAPHTHYL;2,2'-BIS(DIPHENYLPHOSPHINO)-1,1'-BINAPHTHYL;(+/-)-2,2'-BIS(DIPHENYLPHOSPHINO)-1,1'-BINAPHTHALENE;(+/-)-BINAP;BINAP;S(-)-2,2'-BIS(DIPHENYLPHOSPHINO)-1,1'-BINAPHTHALENE;S(-)-(1,1'-BINAPHTHALENE-2,2'-DIYL)BIS(DIPHENYLPHOSPHINE)
• CAS NO: 98327-87-8
• Molecular Formula: C₄₄H₃₂P₂
• Molecular Weight: 622.67
• EINECS: 1308068-626-2
• Product Categories: Phosphines;API intermediates;Achiral Phosphine;Aryl Phosphine;BINAP Series
• Mol File: 98327-87-8.mol
• Article Data: 42

Chemical Properties

• Melting Point: 283-286 °C(lit.)
• Boiling Point: 724.3 °C at 760 mmHg
• Flash Point: 419 °C
• Appearance: White to light beige/Powder
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• Solubility: Chloroform (Slightly, Sonicated), Dichloromethane (Slightly, Heated),
• Water Solubility: Soluble in tetrahydrofuran, benzene and dichloromethane. Slightly soluble in ether, methanol and ethanol. Insoluble in water.
• Sensitive: Air Sensitive
• Merck: 14,1223
• BRN: 5321443
• CAS DataBase Reference: (+/-)-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl(CAS DataBase Reference)
• NIST Chemistry Reference: (+/-)-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl(98327-87-8)
• EPA Substance Registry System: (+/-)-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl(98327-87-8)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 22-24/25-37/39-26
• WGK Germany: 3
• F: 8-10-23
• TSCA: No
• Hazardous Substances Data: 98327-87-8(Hazardous Substances Data)

Usage

Chemical Properties

1.1'-Binaphthyl-2.2'-diphemyl phosphine is White to light beige powder

Uses

Different sources of media describe the Uses of 98327-87-8 differently. You can refer to the following data:
1. racemic-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl ( (+/-)-BINAP ) is an essential role in the organic synthesis of enantioselective transformations catalyzed by the complexes of ruthenium, rhodium and palladium. It is also employed in palladium-catalyzed arylamine coupling in the preparation of demethylthiocholchines. used with Cu(II) to catalyze the addition of arylsulfonamides to styrenes and olefins.
2. (^+)-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl plays an essential role in the organic synthesis of enantioselective transformations catalyzed by the complexes of ruthenium, rhodium and palladium. It is also employed in palladium-catalyzed arylamine coupling in the preparation of demethylthiocholchines. It is used with Cu(II) to catalyze the addition of arylsulfonamides to styrenes and olefins.
3. 2,2'-Bis(diphenylphosphino)-1,1'-dinaphthalene is a powerful chiral auxiliary that is used as a homogeneous catalyst in some asymmetric chemical syntheses. 2,2'-Bis(diphenylphosphino)-1,1'-dinaphthalene is utilized for its high enantioselectivity and is used as a ligand to create coordination complexes.

Reactions

Phosphine Ligand Kit component. Useful ligand for palladium-catalyzed carbon-nitrogen bond formation. Useful ligand for rhodium-catalyzed C-C bond formation. Useful ligand for palladium-catalyzed intramolecular acylation of aryl bromides via C-H activation. Used in the preparation of Buchwald third generation precatalyst. Used in methoxy directed Rhodium migration. Used in Nickel catalyzed C-N cross-coupling reactions.

General Description

Racemic version of BINAP.

Purification Methods

Dissolve the enantiomer in toluene, wash it with 30% aqueous NaOH, three times with H2O, dry (Na2SO4), evaporate to ~15% of its volume and add an equal volume of degassed MeOH. Collect the solid, wash it with MeOH and dry it at 80o/0.005mm for 6hours. Recrystallise it from a 1:1 mixture of toluene/EtOH to optical purity (m 241-242o) [Takaya et al. Org Synth 67 20 1989]. [Noyori & Takaya Acc Chem Res 2 3 345 1990, Kitamura et al. Org Synth 71 1 1993, Takaya et al. Org Synth 72 74 1995, Kitamura et al. J Org Chem 57 4053 1992.]

Upstream product

• 204862-91-9 2-(diphenylphosphinyl)-2'-(diphenylphosphanyl)-1,1'-binaphthalene 
• 74866-28-7 2,2'-dibromo-1,1'-binaphthyl 
• 1079-65-8 Bromodiphenylphosphin 
• 141807-44-5 (+/-)-2,2'-bis(trifluoromethanesulfonyloxy)-1,1-binaphthyl 
• 128544-05-8 (R)-(-)-1,1'-bi-2-naphthol triflate 
• 1079-66-9 chloro-diphenylphosphine 
• 602-09-5 1,1'-bi-2-naphthol 
• 4559-70-0 Diphenylphosphine oxide 
• 18531-99-2 (S)-[1,1']-binaphthalenyl-2,2'-diol 
• 108-86-1 bromobenzene 
• 829-85-6 diphenylphosphane 
• 126613-06-7 (S)-2,2'-bis((trifluoromethanesulfonyl)oxy)-1,1'-binaphthyl 
• 41593-58-2 diphenylphosphineborane 
• 1499-21-4 Diphenylphosphinic chloride 

Downstream Products

• 303975-55-5 ethyl 4-[4-[4-(7-methoxyheptyloxy)-3,5-dimethylphenyl]piperazin-1-yl]benzoate 
• 303975-65-7 4-[4-(4-phenylpiperidin-1-yl)phenyl]piperazine-1-carboxylic acid tert-butyl ester 
• 130164-89-5 2,2’-bis(diphenylphosphinooxide)-1,1’-binaphthalene 
• 192817-79-1 ethyl 2-(morpholin-4-yl)-benzoate 
• 258528-21-1 5-(benzylamino)-8-fluoro-3,4-dihydro-1(2H)-naphthalenone 
• 250732-89-9 N-Hexyl-4-methyl-4-(3-N-diphenylmethylideneaminophenyl)piperidine 
• 488816-52-0 2-[4-(1,3-dihydro-isoindol-2-yl)-pyrimidin-2-ylamino]-benzoic acid 
• 396076-30-5 (4R,10aR)-7-(benzhydrylidene-amino)-4-methyl-3,4,10,10a-tetrahydro-1H-pyrazino[1,2-a]indole-2-carboxylic acid tert-butyl ester 
• 370882-83-0 (1S,5S)-benzyl 6-(5,6-dichloropyridin-3-yl)-3,6-diazabicyclo[3.2.0]heptane-3-carboxylate 
• 289707-51-3 4-(4-anilinophenoxy)-7-methoxy-N-(3-morpholinopropyl)quinoline-6-carboxamide 
• 285548-84-7 7-t-butyl-5-[(4-methoxy-phenyl)-amino]-3,3,6-trimethyl-2,3-dihydro-benzofuran 
• 298185-30-5 ethyl 4-(1-isopropyl-4,4-dimethyl-1,2,3,4-tetrahydroquinolin-6-ylamino)benzoate 

Relevant articles and documents

The Trityl-Cation Mediated Phosphine Oxides Reduction

Reduction of phosphine oxides into the corresponding phosphines using PhSiH3 as a reducing agent and Ph3C+[B(C6F5)4]? as an initiator is described. The process is highly efficient, reducing a broad range of secondary and tertiary alkyl and arylphosphines, bearing various functional groups in generally good yields. The reaction is believed to proceed through the generation of a silyl cation, which reaction with the phosphine oxide provides a phosphonium salt, further reduced by the silane to afford the desired phosphine along with siloxanes. (Figure presented.).

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.

Chemoselective Reduction of Phosphine Oxides by 1,3-Diphenyl-Disiloxane

Reduction of phosphine oxides to the corresponding phosphines represents the most straightforward method to prepare these valuable reagents. However, existing methods to reduce phosphine oxides suffer from inadequate chemoselectivity due to the strength of the P=O bond and/or poor atom economy. Herein, we report the discovery of the most powerful chemoselective reductant for this transformation to date, 1,3-diphenyl-disiloxane (DPDS). Additive-free DPDS selectively reduces both secondary and tertiary phosphine oxides with retention of configuration even in the presence of aldehyde, nitro, ester, α,β-unsaturated carbonyls, azocarboxylates, and cyano functional groups. Arrhenius analysis indicates that the activation barrier for reduction by DPDS is significantly lower than any previously calculated silane reduction system. Inclusion of a catalytic Br?nsted acid further reduced the activation barrier and led to the first silane-mediated reduction of acyclic phosphine oxides at room temperature.