Reaction
ChemicalBook > CAS DataBase List > (S)-(-)-2,2'-BIS(DI-P-TOLYLPHOSPHINO)-1,1'-BINAPHTHYL

(S)-(-)-2,2'-BIS(DI-P-TOLYLPHOSPHINO)-1,1'-BINAPHTHYL

Reaction
Product Name
(S)-(-)-2,2'-BIS(DI-P-TOLYLPHOSPHINO)-1,1'-BINAPHTHYL
CAS No.
100165-88-6
Chemical Name
(S)-(-)-2,2'-BIS(DI-P-TOLYLPHOSPHINO)-1,1'-BINAPHTHYL
Synonyms
(S)-T-BINAP;(S)-(−(R)-TOL-BINAP;(S)-TOL-BINAP;(S)-4-Me-BINAP;98% (S)-TolBINAP;(S)-(-)-2,2'-Bis(di-p-toL;BisdiptolylphosphinobinaphthylSTolBI;(S)-2,2'-BIS(DI-P-TOLYLPHOSPHINO)-1,1'-&;5-Bromo-37-fluorobenzylamine&hydrochloride
CBNumber
CB0334534
Molecular Formula
C48H40P2
Formula Weight
678.78
MOL File
100165-88-6.mol
More
Less

(S)-(-)-2,2'-BIS(DI-P-TOLYLPHOSPHINO)-1,1'-BINAPHTHYL Property

Melting point:
252-256 °C
alpha 
-160° (c 0.5, C6H6)
Boiling point:
754.4±60.0 °C(Predicted)
storage temp. 
Inert atmosphere,Room Temperature
form 
Powder
color 
White
optical activity
[α]20/D -156°, c = 0.5 in benzene
Water Solubility 
Insoluble in water.
InChIKey
IOPQYDKQISFMJI-UHFFFAOYSA-N
CAS DataBase Reference
100165-88-6(CAS DataBase Reference)
More
Less

Safety

Risk Statements 
36/37/38
Safety Statements 
26-36/37/39
WGK Germany 
3
TSCA 
No
HS Code 
29333990
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
668974
Product name
(S)-(?)-2,2′-Bis(di-p-tolylphosphino)-1,1′-binaphthyl
Purity
97%
Packaging
250mg
Price
$41.3
Updated
2023/06/20
Sigma-Aldrich
Product number
668974
Product name
(S)-(?)-2,2′-Bis(di-p-tolylphosphino)-1,1′-binaphthyl
Purity
97%
Packaging
1g
Price
$113
Updated
2023/06/20
TCI Chemical
Product number
T3153
Product name
(S)-(-)-TolBINAP
Purity
>98.0%(HPLC)
Packaging
1g
Price
$82
Updated
2024/03/01
TCI Chemical
Product number
T3153
Product name
(S)-(-)-TolBINAP
Purity
>98.0%(HPLC)
Packaging
5g
Price
$302
Updated
2024/03/01
Alfa Aesar
Product number
042120
Product name
(S)-(-)-2,2'-Bis(di-p-tolylphosphino)-1,1'-binaphthyl, 98%
Packaging
0.5g
Price
$69.65
Updated
2024/03/01
More
Less

(S)-(-)-2,2'-BIS(DI-P-TOLYLPHOSPHINO)-1,1'-BINAPHTHYL 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 iridium-catalyzed enantioselective C-H bond activation of 2-(alkylamino)-pyridine with alkenes.
  10. Iridium-catalyzed regio-, diastereo-, and enantioselective tert-(hydroxyl)-prenylation of alcohols.
  11. Rhodium-catalyzed cross cyclotrimerization.



Chemical Properties

White powder

Uses

(S)-(-)-2,2'-Bis(di-p-tolylphosphino)-1,1'-binaphthyl is chiral ligand widely used in asymmetric synthesis. It also used as excellent catalysts for asymmetric hydrogenation of alkenes and some cyclic anhydrides. BINAP is used in organic synthesis for enantioselective transformations catalyzed by its complexes of ruthenium, rhodium, and palladium

Uses

(S)-T-BINAP reacts with silver nitrate to form (S)-Tol-BINAP·AgNO3, which can catalyze the enantioselective allylation reaction of aldehydes to form enantiopure secondary alcohols. It may be used as a chiral ligand in the palladium catalyzed asymmetric double carbohydroamination of iodoarenes to form α-aminoamides. It can also catalyze the asymmetric N-allylation reaction of ortho-tert-butylanilide derivatives with diallyl carbonate to form chiral N-allyl ortho-tert-butylanilides.

(S)-(-)-2,2'-BIS(DI-P-TOLYLPHOSPHINO)-1,1'-BINAPHTHYL Preparation Products And Raw materials

Raw materials

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

Preparation Products

More
Less

(S)-(-)-2,2'-BIS(DI-P-TOLYLPHOSPHINO)-1,1'-BINAPHTHYL Suppliers

Belgium 1 China 129 Germany 4 India 5 Japan 3 Norway 1 Russia 1 Switzerland 1 United Kingdom 2 United States 14 Global 161
Alfa Chemistry
Tel
Fax
1-516-927-0118
Email
Info@alfa-chemistry.com
Country
United States
ProdList
24072
Advantage
58
Accela ChemBio Inc.
Tel
+1-858-6993322
Fax
(+1)-858-876-1948
Email
info@accelachem.com
Country
United States
ProdList
17322
Advantage
58
Protheragen-ING
Tel
+16313385890
Email
info@protheragen-ing.com
Country
United States
ProdList
3868
Advantage
58
Aladdin Scientific
Tel
+1-+1(833)-552-7181
Email
sales@aladdinsci.com
Country
United States
ProdList
57505
Advantage
58
Alfa Aesar
Tel
--
Fax
--
Email
tech@alfa.com
Country
United States
ProdList
6814
Advantage
81
3B Scientific Corporation
Tel
--
Fax
--
Email
sales@3bsc.com
Country
United States
ProdList
6962
Advantage
56
Combi-Blocks Inc.
Tel
--
Fax
--
Email
sales@combi-blocks.com
Country
United States
ProdList
6618
Advantage
69
Strem Chemicals, Inc.
Tel
--
Fax
--
Email
info@strem.com
Country
United States
ProdList
4910
Advantage
86
Riedel-de Haen AG
Tel
--
Fax
--
Country
United States
ProdList
6773
Advantage
87
TCI America
Tel
--
Fax
--
Email
sales@tciamerica.com
Country
United States
ProdList
6909
Advantage
75
Matrix Scientific
Tel
--
Fax
--
Email
sales@matrixscientific.com
Country
United States
ProdList
6632
Advantage
80
Waterstone Technology, LLC
Tel
--
Fax
--
Email
sales@waterstonetech.com
Country
United States
ProdList
6786
Advantage
30
Anvia Chemicals, LLC
Tel
--
Fax
--
Email
sales@anviachem.com
Country
United States
ProdList
3933
Advantage
0
3B Scientific Corporation
Tel
--
Fax
--
Email
sales@3bsc.com
Country
United States
ProdList
6718
Advantage
47
More
Less

View Lastest Price from (S)-(-)-2,2'-BIS(DI-P-TOLYLPHOSPHINO)-1,1'-BINAPHTHYL manufacturers

Hebei Weibang Biotechnology Co., Ltd
Product
(S)-(-)-2,2'-BIS(DI-P-TOLYLPHOSPHINO)-1,1'-BINAPHTHYL 100165-88-6
Price
US $0.00-0.00/KG
Min. Order
1KG
Purity
99%
Supply Ability
20 mt
Release date
2022-11-16
Hebei Mojin Biotechnology Co., Ltd
Product
(S)-(-)-2,2'-BIS(DI-P-TOLYLPHOSPHINO)-1,1'-BINAPHTHYL 100165-88-6
Price
US $0.00/KG
Min. Order
1KG
Purity
99%
Supply Ability
50000KG/month
Release date
2023-08-17
XINXIANG RUNYU MATERIAL CO., LTD.
Product
(S)-(-)-2,2'-BIS(DI-P-TOLYLPHOSPHINO)-1,1'-BINAPHTHYL 100165-88-6
Price
US $0.00-0.00/KG
Min. Order
1KG
Purity
0.99
Supply Ability
500kg
Release date
2021-11-29

100165-88-6, (S)-(-)-2,2'-BIS(DI-P-TOLYLPHOSPHINO)-1,1'-BINAPHTHYLRelated Search:

(R)-(+)-TolBINAP Bis(diphenylphosphino)methane 2,2'-BIS(DI-P-TOLYLPHOSPHINO)-1,1'-BINAPHTHYL,rac-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 (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 1,1'-BINAPHTHYL Dichloro{(S)-(-)-2,2'-bis[di(3,5-xylyl)phosphino]-1,1'-binaphthyl}[(1S,2S)-(-)-1,2-diphenylethylenediamine]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) Dichloro{(R)-(+)-2,2'-bis[di(3,5-xylyl)phosphino]-1,1'-binaphthyl}[(1R,2R)-(+)-1,2-diphenylethylenediamine]ruthenium(II) Diacetato{(S)-(-)-2,2'-bis[di(3,5-xylyl)phosphino]-1,1'-binaphthyl}ruthenium(II) Chloro{(R)-(+)-2,2'-bis[di(3,5-xylyl)phosphino]-1,1'-binaphthyl}(p-cymene)ruthenium(II)chloride Dichloro{(R)-(+)-2,2'-bis[di(3,5-xylyl)phosphino]-1,1'-binaphthyl}[(2R)-(-)-1,1-bis(4-methoxyphenyl)-3-methyl-1,2-butanediamine]ruthenium(II) Dichloro{(S)-(-)-2,2'-bis[di(3,5-xylyl)phosphino]-1,1'-binaphthyl}[(2S)-(+)-1,1-bis(4-methoxyphenyl)-3-methyl-1,2-butanediamine]ruthenium(II) Chloro[(R)-(+)-2,2'-bis(di-p-tolylphosphino)-1,1'-binaphthyl](p-cymene)ruthenium(II)chloride Dimethylammoniumdichlorotri(mu-chloro)bis[(R)-(+)-2,2'-bis(di-p-tolylphosphino)-1,1'-binaphthyl]diruthenate(II)

  • (S)-TOL-BINAP
  • (R)-TOL-BINAP
  • (S)-(-)-2,2'-BIS(DI-P-TOLYLPHOSPHINO)-1,1'-BINAPHTHYL
  • (R)-(+)-2,2'-BIS(DI-P-TOLYLPHOSPHINO)1,1-BINAPHTHYL
  • (S)-2,2'-BIS(DI-P-TOLYLPHOSPHINO)-1,1'-&
  • (S)-(-)-2,2'-Bis(di-p-tolylphosphino)-1,1'-binaphthyl, 98+%
  • (S)-(-)-2,2'-Bis(di-p-tolylphosphino)-1,1'-binaphthyl,98%(S)-Tol-BINAP
  • (S)-(-)-2,2''-BIS(DI-P-TOLYLPHOSPHINO)-1,1''-BINAPHTHYL (S)-TOL-BINAP
  • (S)-(-)-2,2''-Bis-[bis-(p-tolylphosphino)]-1,1''-binaphthyl
  • PHOSPHINE, 1,1''-(1S)-[1,1''-BINAPHTHALENE]-2,2''-DIYLBIS[1,1-BIS(4-METHYLPHENYL)-
  • (S)-T-BINAP
  • (S)-Tol-BINAP, (S)-(-)-2,2μ-p-tolyl-phosphino)-1,1μ-binaphthyl
  • BisdiptolylphosphinobinaphthylSTolBI
  • (S)-(-)-2,2'-Bis(di-p-tolylphosphino)-1,1'-binaphthyl, (S)-p-Tol-BINAP
  • (S)-(-)-2,2'-Bis(di-p-tolylphosphino)-1,1'-binaphthyl, 99% (S)-p-Tol-BINAP
  • (S)-2,2'-Bis[bis(4-methylphenyl)phosphino]-1,1'-binaphthyl
  • (S)-4-Me-BINAP
  • 1,1'-(1S)-[1,1'-Binaphthalene]-2,2'-diylbis[1,1-bis(4-methylphenyl)phosphine
  • 98% (S)-TolBINAP
  • (S)-(-)-2,2'-Bis(di-p-tolylphosphino)-1,1'-binaphthyl 97%
  • (R)-2,2,-bis(di-p-tolylphosphino)-1,1,-binaphthalene
  • 1,1'-(1S)-[1,1'-Binaphthalene]-2,2'-diylbis[bis(4- methylphenyl)phosphine]
  • (S)-2,2'-Bis(di-p-tolylphosphino)-1,1'-binaphthalene
  • (S)-(-)-2,2'-Bis(di-p-toL
  • Phosphine, (1S)-[1,1'-binaphthalene]-2,2'-diylbis[bis(4-methylphenyl)-
  • High purity CAS 100165-88-6 (S)-(-)-2,2'-BIS(DI-P-TOLYLPHOSPHINO)-1,1'-BINAPHTHYL in stock
  • 5-Bromo-37-fluorobenzylamine&hydrochloride
  • (S)-(&#8722
  • )-2,2′-Bis(di-p-tolylphosphino)-1,1′-binaphthyl
  • (S)-(-)-2,2'-Bis(di-p-tolylphosphino)-1,1'-binaphthyl
  • 1,1'-(1S)-[1,1'-Binaphthalene]-2,2'-diylbis[1,1-bis(4-methylphenyl)phosphine
  • (S)-2,2’-Bis(di-p-tolylphosphino)-1,1’-binaphthalene
  • Phosphine, (1S)-[1,1'-binaphthalene]-2,2'-diylbis[bis(4-methylphenyl)-
  • (S)-2,2'-Bis(di-p-tolylphosphino)-1,1'-binaphthyl (S-tol-Binap)
  • 100165-88-6
  • BINAPs
  • Asymmetric Synthesis
  • Privileged Ligands
  • Chiral Catalysts, Ligands, and Reagents
  • BINAP Series
  • Chiral Phosphine