Reaction
ChemicalBook > CAS DataBase List > (R)-(+)-TolBINAP

(R)-(+)-TolBINAP

Reaction
Product Name
(R)-(+)-TolBINAP
CAS No.
99646-28-3
Chemical Name
(R)-(+)-TolBINAP
Synonyms
(R)-TOL-BINAP;(R)-T-BINAP;98% (R)-TolBINAP;(R)-p-tolyl-BINAP;(R)-(+)-2,2'-Bis(di-p-toL;phosphino)-1,1'-binaphthyL;2,2'-bis(di-p-tolylphosphino)-1,1'-binaphthalene;(R)-(+)-2,2'-BIS(DI-P-TOLYLPHOSPHINO)1,1-BINAPHTHYL;(R)-2,2’-Bis(di-p-tolylphosphino)-1,1’-binaphthalene;(R)-(+)-2,2'-BIS(DI-P-TOLYLPHOSPHINO)-1,1'-BINAPHTHYL
CBNumber
CB7334533
Molecular Formula
C48H40P2
Formula Weight
678.8
MOL File
99646-28-3.mol
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(R)-(+)-TolBINAP Property

Melting point:
255-257 °C
alpha 
+156° (c 0.5, C6H6)
Boiling point:
754.4±60.0 °C(Predicted)
storage temp. 
Inert atmosphere,Room Temperature
form 
Powder
color 
White to cream
optical activity
[α]20/D +162°, c = 0.5 in benzene
Water Solubility 
Insoluble in water.
λmax
223nm(EtOH)(lit.)
CAS DataBase Reference
99646-28-3(CAS DataBase Reference)
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Safety

Hazard Codes 
Xi
Risk Statements 
36/37/38
Safety Statements 
37/39-26
WGK Germany 
3
TSCA 
No
HS Code 
29310099
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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
668966
Product name
(R)-(+)-2,2′-Bis(di-p-tolylphosphino)-1,1′-binaphthyl
Purity
97%
Packaging
250mg
Price
$37.2
Updated
2023/06/20
Sigma-Aldrich
Product number
668966
Product name
(R)-(+)-2,2′-Bis(di-p-tolylphosphino)-1,1′-binaphthyl
Purity
97%
Packaging
1g
Price
$134
Updated
2023/06/20
TCI Chemical
Product number
T3152
Product name
(R)-(+)-TolBINAP
Purity
>98.0%(HPLC)
Packaging
1g
Price
$72
Updated
2024/03/01
TCI Chemical
Product number
T3152
Product name
(R)-(+)-TolBINAP
Purity
>98.0%(HPLC)
Packaging
5g
Price
$216
Updated
2024/03/01
Alfa Aesar
Product number
042119
Product name
(R)-(+)-2,2'-Bis(di-p-tolylphosphino)-1,1'-binaphthyl, 98%
Packaging
0.5g
Price
$70.65
Updated
2024/03/01
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(R)-(+)-TolBINAP Chemical Properties,Usage,Production

Reaction

  1. Useful ligand for palladium-catalyzed carbon-oxygen bond formation.
  2. Ligand for palladium-catalyzed α-arylation of ketones.
  3. Ligand for Cu-catalyzed asymmetric conjugate reduction.
  4. Ligand for Cu-catalyzed asymmetric dienolate addition to aldehydes.
  5. Enantioselective conjugate reduction of lactones and lactams.
  6. Ligand used in the enantioselective cycloaddition of allenylsilanes with α-Imino esters.
  7. Catalytic Aldol reaction to ketones.
  8. Ligand with rhodium catalyses [2+2+2] cycloaddition reaction of alkenes and alkynes.
  9. Ligand used in the copper-catalyzed asymmetric conjugate addition of alkyl Grignard reagents on α,β-unsaturated esters.
  10. Ligand used in the copper-catalyzed asymmetric synthesis of cyclopropanes via tandem conjugate addition and intramolecular enolate trapping. 


Chemical Properties

White to cream powder

Uses

(R)-(+)-2,2'-Bis(di-p-tolylphosphino)-1,1'-binaphthyl is used as chiral catalyst ligand. (R)-T-BINAP complexes derived from rhodium precursors are used for the asymmetric hydroformylation of vinyl acetate. It is a catalysts used for reductive amination of ketones, Pt dications for cation trapping, Rh(I)-catalyst for hydrogenation of acetamidoacrylic acid derivatives.

Uses

(R)-T-BINAP complexes derived from rhodium precursors are used for the asymmetric hydroformylation of vinyl acetate. It may be employed as chiral catalyst for allylation of N-tosyl α-imino esters.

General Description

BINAP is based on a bis naphthalene backbone with different phosphine derivatives. 2,2′-bis(di-p-tolylphosphino)-1,1′-binaphthyl (p-Tol-BINAP)·AgF complex catalyzed asymmetric Mukaiyama-type aldol reaction is reported.

(R)-(+)-TolBINAP Preparation Products And Raw materials

Raw materials

Nickel(II) chloride hexahydrate Ethanol N,N-Dimethylformamide (R)-(+)-1,1'-Bi-2-naphthol Trichlorosilane Sodium Trifluoromethanesulfonic anhydride 4-Bromotoluene Tetrahydrofuran Ethyl acetate 1,2-Dichloroethane Diethyl phosphite Triphenylphosphine Pyridine Triethylenediamine Magnesium

Preparation Products

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(R)-(+)-TolBINAP Suppliers

Belgium 1 China 121 Germany 3 India 4 Japan 4 Norway 1 Russia 1 Switzerland 1 United Kingdom 2 United States 14 Global 152
SIGMA-RBI
Tel
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Fax
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Country
Switzerland
ProdList
6896
Advantage
91
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View Lastest Price from (R)-(+)-TolBINAP manufacturers

XINXIANG RUNYU MATERIAL CO., LTD.
Product
(R)-(+)-TolBINAP 99646-28-3
Price
US $0.00-0.00/kg
Min. Order
1kg
Purity
99%
Supply Ability
200
Release date
2023-09-21
Zhuozhou Wenxi import and Export Co., Ltd
Product
(R)-Tol-BINAP 99646-28-3
Price
US $15.00-10.00/KG
Min. Order
1KG
Purity
99%+ HPLC
Supply Ability
Monthly supply of 1 ton
Release date
2021-06-27
Career Henan Chemical Co
Product
(S)-(-)-2,2'-BIS(DI-P-TOLYLPHOSPHINO)-1,1'-BINAPHTHYL 99646-28-3
Price
US $1.00/kg
Min. Order
1kg
Purity
98%
Supply Ability
100KG
Release date
2018-12-21

99646-28-3, (R)-(+)-TolBINAPRelated Search:

(R)-(+)-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl (S)-(-)-2,2'-BIS(DI-P-TOLYLPHOSPHINO)-1,1'-BINAPHTHYL Bis(diphenylphosphino)methane DICHLORO[(R)-(+)-2,2'-BIS(DIPHENYLPHOSPHINO)-1,1'-BINAPHTHYL]RUTHENIUM (II) (S)-(-)-2,2'-Bis[di(3,5-xylyl)phosphino]-1,1'-binaphthyl DICHLORO[(R)-(+)-2,2'-BIS(DIPHENYLPHOSPHINO)-1,1'-BINAPHTHYL]RUTHENIUM (II) (R)-(+)-2,2'-BIS(DIPHENYLPHOSPHINO)-1,1'-BINAPHTHALENECHLORO(P-CYMENE)RUTHENIUM CHLORIDE R-(+)-1,2-BIS(DIPHENYLPHOSPHINO)PROPANE (R)-DM-BINAP (R)-(+)-2-[2-(DIPHENYLPHOSPHINO)PHENYL]-4-(1-METHYLETHYL)-4,5-DIHYDROOXAZOLE 1,1'-BINAPHTHYL rac-2,2'-Bis(di-p-tolylphosphino)-1,1'-binaphthyl ,2,2'-BIS(DI-P-TOLYLPHOSPHINO)-1,1'-BINAPHTHYL Chloro[(S)-(-)-2,2'-bis(di-p-tolylphosphino)-1,1'-binaphthyl](p-cymene)ruthenium(II)chloride Chloro[(R)-(+)-2,2'-bis(di-p-tolylphosphino)-1,1'-binaphthyl](p-cymene)ruthenium(II)chloride Diacetato[(R)-(+)-2,2'-bis(di-p-tolylphosphino)-1,1'-binaphthyl]ruthenium(II) Dimethylammoniumdichlorotri(mu-chloro)bis[(S)-(-)-2,2'-bis(di-p-tolylphosphino)-1,1'-binaphthyl]diruthenate(II) Diacetato[(S)-(-)-2,2'-bis(di-p-tolylphosphino)-1,1'-binaphthyl]ruthenium(II) Dimethylammoniumdichlorotri(mu-chloro)bis[(R)-(+)-2,2'-bis(di-p-tolylphosphino)-1,1'-binaphthyl]diruthenate(II)

  • (R)-TOL-BINAP
  • (R)-(+)-2,2'-BIS(DI-P-TOLYLPHOSPHINO)1,1-BINAPHTHYL
  • (R)-p-tolyl-BINAP
  • (R)-(+)-2,2'-Bis(di-p-toL
  • phosphino)-1,1'-binaphthyL
  • (R)-(+)-2,2''-BIS(DI-P-TOLYLPHOSPHINO)-1,1''-BINAPHTHYL (R)-TOL-BINAP
  • PHOSPHINE, 1,1''-(1R)-[1,1''-BINAPHTHALENE]-2,2''-DIYLBIS[BIS(4-METHYLPHENYL)-
  • (R)-T-BINAP
  • (R)-Tol-BINAP, (R)-(+)-2,2μ-Bis(di-p-tolylphosphino)-1,1μ-binaphthyl
  • (R)-TolBINAP,99%e.e. 1,1'-(1R)-[1,1'-Binaphthalene]-2,2'-diylbis[bis(4-methylphenyl)phosphine]
  • (R)-(+)-2,2'-Bis(di-p-tolylphosphino)-1,1'-binaphthyl, (R)-p-Tol-BINAP
  • (R)-(+)-2,2'-Bis(di-p-tolylphosphino)-1,1'-binaphthyl, 95+%
  • (R)-(+)-2,2'-Bis(di-p-tolylphosphino)-1,1'-binaphthyl,98%(R)-Tol-BINAP
  • 98% (R)-TolBINAP
  • (R)-(+)-2,2'-Bis(di-p-tolylphosphino)-1,1'-binaphthyl,98%
  • (R)-(+)-2,2'-Bis(di-p-tolylphosphino)-1,1'-binaphthyl, 99% (R)-p-Tol-BINAP
  • (R)-(+)-2,2'-Bis(di-p-tolylphosphino)-1,1'-binaphthyl 97%
  • 1,1'-(1R)-[1,1'-Binaphthalene]-2,2'-diylbis[bis(4- methylphenyl)phosphine]
  • (R)-(+)-2,2'-Bis-[bis-(p-tolylphosphino)]-1,1'-binaphthyl
  • (R)-(+)-2,2'-BIS(DI-P-TOLYLPHOSPHINO)-1,1'-BINAPHTHYL
  • Phosphine, (1R)-[1,1'-binaphthalene]-2,2'-diylbis[bis(4-methylphenyl)-
  • (r)-(+)-2,2'-bis(di-p-tolylphosphino)-1,1'-binaphthyl, 95+%
  • (R)-2,2’-Bis(di-p-tolylphosphino)-1,1’-binaphthalene
  • (1R)-[1-[2-(bis-p-tolylphosphanyl)-1-naphthyl]-2-naphthyl]-bis(p-tolyl)phosphane
  • 1,1'-(1R)-[1,1'-Binaphthalene]-2,2'-diylbis[bis(4-methylphenyl)phosphine
  • 2,2'-bis(di-p-tolylphosphino)-1,1'-binaphthalene
  • (R)-(+)-2,2'-Bis(di-p-tolylphosphino)-1,1'-binaphthyl (R-tol-Binap)
  • 99646-28-3
  • 10165-88-6
  • C48H4OP2
  • Privileged Ligands
  • Chiral Catalysts, Ligands, and Reagents
  • BINAPs
  • Asymmetric Synthesis
  • Chiral Phosphine
  • BINAP Series