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ChemicalBook > CAS DataBase List > (R)-(+)-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl

(R)-(+)-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl

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Product Name
(R)-(+)-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl
CAS No.
76189-55-4
Chemical Name
(R)-(+)-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl
Synonyms
BINAP;RAC-BINAP;(R)-BINAP;RACEMIC-2,2'-BIS(DIPHENYLPHOSPHINO)-1,1'-BINAPHTHYL;(+)-BINAP;(+/-)-BINAP;98% (R)-BINAP;(R)-(+)-BINAP;RACEMIC-BINAP;(R)-BINAP,99%e.e.
CBNumber
CB2186988
Molecular Formula
C44H32P2
Formula Weight
622.69
MOL File
76189-55-4.mol
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(R)-(+)-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl Property

Melting point:
283-286 °C(lit.)
alpha 
240 º (c=0.3, toluene)
Boiling point:
724.3±55.0 °C(Predicted)
refractive index 
235 ° (C=0.3, Toluene)
storage temp. 
Inert atmosphere,Room Temperature
solubility 
Benzene (Slightly), Chloroform (Slightly)
form 
Powder
color 
White to cream-white
optical activity
[α]20/D +222°, c = 0.5% in benzene
Water Solubility 
insoluble
Sensitive 
Air Sensitive
Merck 
14,1223
BRN 
4914063
InChIKey
MUALRAIOVNYAIW-UHFFFAOYSA-N
SMILES
P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC2=CC=CC=C2C=1C1C2=CC=CC=C2C=CC=1P(C1C=CC=CC=1)C1C=CC=CC=1
CAS DataBase Reference
76189-55-4(CAS DataBase Reference)
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Safety

Hazard Codes 
Xi,Xn
Risk Statements 
36/37/38-20/21/22
Safety Statements 
22-24/25-37/39-26-36
WGK Germany 
3
F 
8-10-23
TSCA 
No
HS Code 
29319090
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P304+P340IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P405Store locked up.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
693065
Product name
(R)-BINAP
Packaging
100MG
Price
$18.78
Updated
2024/03/01
Sigma-Aldrich
Product number
693065
Product name
(R)-BINAP
Packaging
500MG
Price
$79.8
Updated
2024/03/01
Sigma-Aldrich
Product number
295817
Product name
(R)-(+)-2,2′-Bis(diphenylphosphino)-1,1′-binaphthalene
Purity
97%
Packaging
1g
Price
$54
Updated
2024/03/01
Sigma-Aldrich
Product number
295817
Product name
(R)-(+)-2,2′-Bis(diphenylphosphino)-1,1′-binaphthalene
Purity
97%
Packaging
5g
Price
$143
Updated
2024/03/01
TCI Chemical
Product number
B1406
Product name
(R)-(+)-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl
Packaging
1g
Price
$88
Updated
2024/03/01
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(R)-(+)-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl Chemical Properties,Usage,Production

Reaction

  1. (R)-BINAP or (R)-Tol-BINAP can be combined with dichloro(1,5-cyclooctadiene)ruthenium to form precursors to NOYORI CATALYST SYSTEMS. These systems exhibit very high catalytic activity and enantioselectivity in the hydrogenation of a wide range of substrates. NOYORI CATALYST SYSTEMS have been shown to effect highly enantioselective hydrogenation of functionalized ketones where the substituents are dialkylamino, hydroxy, siloxy, carbonyl, ester, amide or thioester.
  2. Useful ligand in asymmetric Heck processes.
  3. Ligand employed in palladium-catalyzed asymmetric arylation of ketones.
  4. Ligand employed in rhodium-catalyzed 1,4-additions to enones.
  5. Ligand employed in palladium-catalyzed hydroamination of styrene derivatives.
  6. Ligand employed in silver-catalyzed asymmetric Sakuri-Hosomi allylation and Mukaiyama aldol reaction.
  7. Ligand employed in rhodium-catalyzed kinetic resolution of enynes.
  8. Ligand employed in asymmetric rhodium-catalyzed hydroboration of cyclopropenes.
  9. Ligand employed in silver-catalyzed a-hydroxylation of stannyl enol ethers.
  10. Ligand employed in palladium-catalyzed synthesis of chiral allenes.
  11. Ligand for palladium-catalyzed enantioselective hetero Michael addition to form b-amino acid derivatives.
  12. Ligand employed in rhodium-catalyzed asymmetric rearrangement of alkynyl alkenyl carbinols.
  13. Ligand employed in rhodium-catalyzed 1,2-addition of aluminium organyl compounds to cyclic enones.
  14. Ligand employed in iridium-catalyzed transfer hydrogenative allylation of benzylic alcohols.
  15. Ligand employed in rhodium-catalyzed asymmetric C-Si bond formation by conjugate silyl transfer using a Si-B linkage.
  16. Ligand employed in the iridium-catalyzed asymmetric cyclopropane-mediated carbonyl allylation of primary alcohols.
  17. Ligand employed in the nickel-catalyzed asymmetric α-arylation of tetralones.
  18. Ligand employed in the copper-catalyzed asymmetric propargylation of ketones.
  19. Ligand employed in the cobalt-catalyzed asymmetric reductive coupling of alkynes with alkenes.
  20. Ligand employed in the rhodium-catalyzed asymmetric 1,4-addition of arylalanes on trisubstituted enones.
  21. Ruthenium-catalyzed asymmetric hydrocyanation of imines.
  22. Palladium-catalyzed asymmetric intermolecular cyclization.





Chemical Properties

white to light yellow crystal powde

Uses

Chiral ligand for metal mediated asymmetric catalysis.

Uses

Useful ligand for transition metal catalyzed asymmetric reactions, including hydrogenation and disilylation. 2,2′-Bis(diphenylphosphino)-1,1′-binaphthyl and its rhodium and ruthenium derivatives are highly selective homogeneous catalysts used for the reduction of aryl ketones, β-keto esters, and α-amino ketones. They have also been used for asymmetric hydrogenation and hydroformylation of olefins, asymmetric Heck reactions, and asymmetric isomerizations of allyls.
Complex with Ag(I) used to catalyze an asymmetric aldol reaction between alkenyl trichloroacetates and aldehydes. Also used with Ag(I) to catalyze an enantioselective hetero-Diels-Alder reaction of azo compounds.

General Description

(R)-(+)-2,2′-Bis(diphenylphosphino)-1,1′-binaphthalene is an axially dissymmetric bis(triaryl)phosphine ligand for asymmetric reactions.

(R)-(+)-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl Preparation Products And Raw materials

Raw materials

Nickel(II) chloride hexahydrate Diphenylphosphine Ethanol N,N-Dimethylformamide (R)-(+)-1,1'-Bi-2-naphthol Trifluoroacetic anhydride 1,2-Bis(diphenylphosphino)ethane Ethyl acetate Dichloromethane Methanol Triphenylphosphine Pyridine Triethylenediamine

Preparation Products

(3S,4R)-4-Acetoxy-3-[(R)-1-(tert-butyldimethylsilyloxy)ethyl]azetidin-2-one
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(R)-(+)-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl Suppliers

Americas 1 Belgium 2 Canada 3 China 375 Europe 4 France 5 Germany 7 India 19 Japan 6 Norway 1 Russia 1 Switzerland 4 The Netherlands 1 Ukraine 2 United Kingdom 13 United States 42 Global 486
TCI Chemicals (India) Pvt. Ltd.
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View Lastest Price from (R)-(+)-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl manufacturers

Shanghai UCHEM Inc.
Product
(R)-(+)-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl 76189-55-4
Price
US $230.00-1005.00/g
Min. Order
1g
Purity
0.98
Supply Ability
25kg
Release date
2023-10-12
Hebei Weibang Biotechnology Co., Ltd
Product
(R)-(+)-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl 76189-55-4
Price
US $0.00-0.00/KG
Min. Order
1KG
Purity
99%
Supply Ability
20 mt
Release date
2023-02-10
Henan Fengda Chemical Co., Ltd
Product
(R)-(+)-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl 76189-55-4
Price
US $10.00-3.00/KG
Min. Order
1KG
Purity
99%
Supply Ability
g-kg-tons, free sample is available
Release date
2024-04-26

76189-55-4, (R)-(+)-2,2'-Bis(diphenylphosphino)-1,1'-binaphthylRelated Search:

N-(Carboxymethyl)-N-(phosphonomethyl)-glycine Phenformin hydrochloride Phenformin 1,1'-Bis(diphenylphosphino)ferrocene (S)-(-)-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl (S)-(-)-2,2'-BIS(DI-P-TOLYLPHOSPHINO)-1,1'-BINAPHTHYL (S)-(-)-2,2'-Bis[di(3,5-xylyl)phosphino]-1,1'-binaphthyl [(R)-(+)-2,2'-BIS(DIPHENYLPHOSPHINO)-1,1'-BINAPHTHYL]PALLADIUM(II) CHLORIDE,[(S)-(+)-2,2'-BIS(DIPHENYLPHOSPHINO)-1,1'-BINAPHTHYL]PALLADIUM(II)CHLORIDE DICHLORO[(S)-2,2'-BIS-(DIPHENYLPHOSPHINO)-1,1'-BINAPHTHYL]RUTHENIUM(II) HOMOPOLYMER,DICHLORO[(S)-(-)-,2,2'-BIS(DIPHENYLPHOSPHINO)-1,1'-BINAPHTHYL]RUTHENIUM (II) DICHLORO[(S)-(-)-,2,2'-BIS(DIPHENYLPHOSPHINO)-1,1'-BINAPHTHYL]RUTHENIUM (II),DICHLORO[(S)-2,2'-BIS-(DIPHENYLPHOSPHINO)-1,1'-BINAPHTHYL]RUTHENIUM(II) HOMOPOLYMER 1.1'-Binaphthyl-2.2'-diphemyl phosphine (R)-(+)-2,2'-BIS(DIPHENYLPHOSPHINO)-1,1'-BINAPHTHALENECHLORO(P-CYMENE)RUTHENIUM CHLORIDE (R)-(+)-TolBINAP 1,1'-BINAPHTHYL 2,2'-BIS(DIPHENYLPHOSPHINO)-1,1'-BIPHENYL Diphenylphosphine Phosphine Chloro{(R)-(+)-2,2'-bis[di(3,5-xylyl)phosphino]-1,1'-binaphthyl}(p-cymene)ruthenium(II)chloride

  • (R)-(+)-BINAP, (R)-(+)-1,1'-Binaphthalene-2,2'-diylbis(diphenylphosphane)
  • (R)-(+)-2,2'-Bis(diphenylphosphino)-1,1'-binaphthalene 97%
  • (<i>R</i>)-(+)-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl
  • R(+)-2,2'-BIS(DIPHENYLPHOSPHINO)-1,1'-BINAPHTHALENE
  • (R)-(+)-2,2'-BIS(DIPHENYLPHOSPHINO)-1,1'-BINAPHTHYL
  • (R)-(+)-2,2BIS(DIPHENYLPHOSPHINO)-1,1-BINAPHTHYL
  • (R)-2,2'-BIS(DIPHENYLPHOSPHINO)-1,1'-BINAPHTHYL
  • (R)-(+)-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl,(R)-BINAP
  • (R)-(+)-2,2`-Bis(Diphenylphosphino)-1,1`-Binaphthy
  • (R)-(+)-2,2'-Bis(diphenyphosphino)-1,1'-binaphthy
  • (R)-(+)-2,2'-Bis(diphenylphosp
  • (R)-2,2'-bis(diphenylphosphino)-1,1'-binaphthyl (BINAP)
  • (R)-(+)-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl,98%(R)-BINAP
  • (R)-(+)-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl, 99+%
  • R-(+)-BINAP/R-(+)-1,1''-BINAPHTHYL-2.2''-DIPHEMYL PHOSPHINE
  • R-(+)-2,2''-BIS(DIPHENYLPHOSPHINO)-1,1''-BIPHENYL
  • (R)-(+)-BINAP (R)-(＋)-2,2'-bis(diphenylphosphino)-1,1'-binaphthyl
  • (R)-(+)-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl ,98%
  • (R)-(+)-2,2′-Bis(diphenylphosphino)-1,1′-binaphthalene,(R)-(+)-(1,1′-Binaphthalene-2,2′-diyl)bis(diphenylphosphine), (R)-(+)-BINAP
  • (R)-(+)-2,2'-Bis(dip
  • R-(+)-1.1'-Binaphthyl-2.2'-dipheMyl phosphine R-BINAP
  • 1,1'-[(1R)-[1,1'-binaphthalene]-2,2'-diyl]bis[1,1-diphenyphosphine]
  • (R)-Bis(diphenylphosphino)-1,1'-binaphthyl
  • (R)-(+)-BINAP, (R)-(+)-1,1'-Binaphthalene-2,2'-diylbis(dip
  • R-(-)2,-Bis(diphenylphosphino)-1,-binaphthyl
  • (R)-(+)-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl, 99% (R)-BINAP
  • (+)-(1R)-[1,1'-Binaphthalene]-2,2'-diylbis[diphenylphosphine]
  • 1,1'-[(1R)-[1,1'-Binaphthalene]-2,2'-diyl]bis[1,1-diphenyl-phosphine
  • 98% (R)-BINAP
  • (R)-(+)-2,2'-Bis(diphenyL
  • R-BINAP 76189-55-4 (R)-(+)-BINAP
  • (R)-(+)-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl 76189-55-4
  • (R)-(+)-2,2'-Bis(diphenylphosphino)-1
  • (+/-)-2,2'-Bis(diphenylphosphino)-1,1'-dinaphthalene (BINAP)
  • (+/-)-BINAP
  • BINAP
  • (R)-(+)-BINAP
  • (R)-BINAP
  • S(-)-2,2'-BIS(DIPHENYLPHOSPHINO)-1,1'-BINAPHTHALENE
  • S-(-)-1,1'-BINAPHTHYL-2,2'-DIPHENYL PHOSPHINE
  • S(-)-(1,1'-BINAPHTHALENE-2,2'-DIYL)BIS(DIPHENYLPHOSPHINE)
  • R-(+)-1,1'-BINAPHTHYL-2,2'-DIPHENYL PHOSPHINE
  • R(+)-(1,1'-BINAPHTHALENE-2,2'-DIYL)BIS(DIPHENYLPHOSPHINE)
  • RACEMIC-2,2'-BIS(DIPHENYLPHOSPHINO)-1,1'-BINAPHTHYL
  • RACEMIC-BINAP
  • RAC-2,2'-BIS(DIPHENYLPHOSPHINO)-1,1'-BINAPHTHYL
  • RAC-2,2-BIS(DIPHENYLPHOSPHINO)-1,1-BINAPHTHYL
  • RAC-BINAP
  • PHOSPHINE, [1,1''-BINAPHTHALENE]-2,2''-DIYLBIS[DIPHENYL-, (R)
  • (R)-(+)-2,2'-Bis(diphenylphosphino)-1,1'-biphthyl
  • (R)-BINAP,99%e.e.
  • (R)-(+)-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl for synthesis
  • (+/-)-(1,1'-BINAPHTHALENE-2,2'-DIYL)BIS(DIPHENYLPHOSPHINE)
  • (+/-)-2,2'-BIS(DIPHENYLPHOSPHINO)-1,1'-BINAPHTHALENE
  • (R)-(+)-2,2''-BIS(DIPHENYPHOSPHINO)-1,1''-BINAPHTHYL
  • PHOSPHINE, 1,1''-[(1R)-[1,1''-BINAPHTHALENE]-2,2''-DIYL]BIS[1,1-DIPHENYL-
  • R(+)-1,1''-BIS(DIPHENYLPHOSPHINO)-1,1-BINAPHTHALENE
  • 1,3-Di(1-adamantyl)imidazolinium Tetrafluoroborate