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

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

Reaction
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
More
Less

(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)
More
Less

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
More
Less

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.

More
Less

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
More
Less

(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
More
Less

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

Americas 1 Belgium 2 Canada 3 China 377 Europe 4 France 5 Germany 7 India 18 Japan 6 Norway 1 Russia 1 Switzerland 4 The Netherlands 1 Ukraine 2 United Kingdom 13 United States 42 Global 487
Xinxiang Runyu Material Co., Ltd.
Tel
166-166-37336996 15690792173
Fax
0373-7759608
Email
chenxi.song@runvmat.com
Country
China
ProdList
303
Advantage
55
Zhengzhou HQ Material Co., Ltd.
Tel
0371-67759225 13526468238
Fax
+86-37155919558
Email
sales@hqmat.com
Country
China
ProdList
483
Advantage
60
Wuxi Helen Biotechnology Co., Ltd.,
Tel
0510-85629785 18013409632
Fax
0510-85625359
Email
sales@reading-chemicals.com
Country
China
ProdList
14081
Advantage
58
Puyang Huicheng Electronic Material Co. Ltd.
Tel
0393-0393-0393-8910800 15238090375
Fax
0393-8912775
Email
info@huichengchem.com
Country
China
ProdList
563
Advantage
64
BeiJing Greenchem Technology Co.,Ltd.
Tel
131-21959385 15640741633
Fax
010-62925455
Email
chemrocking@bjgreenchem.com
Country
China
ProdList
269
Advantage
58
Shanghai Arbor Chemical Co., Ltd.
Tel
021-60451683 15001705751
Email
market@arborpharmchem.com
Country
China
ProdList
2554
Advantage
58
J & K SCIENTIFIC LTD.
Tel
010-82848833 400-666-7788
Fax
86-10-82849933
Email
jkinfo@jkchemical.com
Country
China
ProdList
94657
Advantage
76
Chemvon Biotechnology Co., Ltd
Tel
021-50790412
Fax
+86-21-50790419
Email
info@chemvon.com
Country
China
ProdList
371
Advantage
57
Meryer (Shanghai) Chemical Technology Co., Ltd.
Tel
021-61259108 18621169109
Fax
86-21-61259102
Email
market03@meryer.com
Country
China
ProdList
40228
Advantage
62
Beijing Donghualituo Techonlogy Development Co.,Ltd.
Tel
010-88425576
Fax
(+86)-10-88425546
Email
sales@dhltchem.com
Country
China
ProdList
793
Advantage
59
More
Less

View Lastest Price from (R)-(+)-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl manufacturers

XINXIANG RUNYU MATERIAL 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
0.99
Supply Ability
500kg
Release date
2021-11-23
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
2024-11-29
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

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