ChemicalBook > CAS DataBase List > 1.1'-Binaphthyl-2.2'-diphemyl phosphine

1.1'-Binaphthyl-2.2'-diphemyl phosphine

Product Name
1.1'-Binaphthyl-2.2'-diphemyl phosphine
CAS No.
98327-87-8
Chemical Name
1.1'-Binaphthyl-2.2'-diphemyl phosphine
Synonyms
BINAP;RAC-BINAP;2,2-Bis-(diphenylphosphino)-1,1-napthalene;2,2'-Bis(diphenylphosphanyl)-1,1'-binaphthalene;[1-(2-diphenylphosphanyl-1-naphthyl)-2-naphthyl]-diphenyl-phosphane;1,1'-binaphthyl-2,2'-bisdiphenylphosphine;RACEMIC-2,2'-BIS(DIPHENYLPHOSPHINO)-1,1'-BINAPHTHYL;(à)-BINA;(+/-)-BINAP;racemic-2,2
CBNumber
CB3186990
Molecular Formula
C44H32P2
Formula Weight
622.69
MOL File
98327-87-8.mol
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1.1'-Binaphthyl-2.2'-diphemyl phosphine Property

Melting point:
283-286 °C(lit.)
Boiling point:
724.3±55.0 °C(Predicted)
storage temp. 
Keep in dark place,Inert atmosphere,Room temperature
solubility 
Chloroform (Slightly, Sonicated), Dichloromethane (Slightly, Heated),
form 
Powder
color 
White to light beige
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
InChIKey
MUALRAIOVNYAIW-UHFFFAOYSA-N
CAS DataBase Reference
98327-87-8(CAS DataBase Reference)
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Safety

Hazard Codes 
Xi
Risk Statements 
36/37/38
Safety Statements 
22-24/25-37/39-26
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
481084
Product name
2,2′-Bis(diphenylphosphino)-1,1′-binaphthalene
Purity
97%
Packaging
5g
Price
$120
Updated
2024/03/01
Sigma-Aldrich
Product number
481084
Product name
2,2′-Bis(diphenylphosphino)-1,1′-binaphthalene
Purity
97%
Packaging
25g
Price
$357
Updated
2024/03/01
TCI Chemical
Product number
B2383
Product name
(+/-)-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl
Purity
>97.0%(GC)
Packaging
5g
Price
$131
Updated
2024/03/01
TCI Chemical
Product number
B2383
Product name
(+/-)-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl
Purity
>97.0%(GC)
Packaging
25g
Price
$394
Updated
2024/03/01
Alfa Aesar
Product number
H26226
Product name
(±)-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl, 98%
Packaging
5g
Price
$157
Updated
2024/03/01
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1.1'-Binaphthyl-2.2'-diphemyl phosphine Chemical Properties,Usage,Production

Chemical Properties

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

Uses

  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.
  2. It is also employed in palladium-catalyzed arylamine coupling in the preparation of demethylthiocholchines.
  3. used with Cu(II) to catalyze the addition of arylsulfonamides to styrenes and olefins.

Uses

(^+)-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.

Uses

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.

  1. Useful ligand for palladium-catalyzed carbon-nitrogen bond formation.
  2. Useful ligand for rhodium-catalyzed C-C bond formation.
  3. Useful ligand for palladium-catalyzed intramolecular acylation of aryl bromides via C-H activation.
  4. Used in the preparation of Buchwald third generation precatalyst.
  5. Used in methoxy directed Rhodium migration.
  6. 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.]

1.1'-Binaphthyl-2.2'-diphemyl phosphine Preparation Products And Raw materials

Raw materials

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

Preparation Products

3-MORPHOLINOPHENOL 3-MORPHOLINOPHENYLBORONIC ACID PINACOL ESTER 3-Morpholinobenzaldehyde
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View Lastest Price from 1.1'-Binaphthyl-2.2'-diphemyl phosphine manufacturers

WUHAN FORTUNA CHEMICAL CO., LTD
Product
1.1'-Binaphthyl-2.2'-diphemyl phosphine 98327-87-8
Price
US $0.00/G
Min. Order
100G
Purity
98%min
Supply Ability
30kg/month
Release date
2023-02-09
Jinan Finer Chemical Co., Ltd
Product
(+/-)-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl 98327-87-8
Price
US $0.00/Kg/Bag
Min. Order
1g
Purity
99%
Supply Ability
10mt/year
Release date
2021-07-23
Hebei Weibang Biotechnology Co., Ltd
Product
1.1'-Binaphthyl-2.2'-diphemyl phosphine 98327-87-8
Price
US $0.00-0.00/KG
Min. Order
1KG
Purity
99%
Supply Ability
20 mt
Release date
2024-11-18

98327-87-8, 1.1'-Binaphthyl-2.2'-diphemyl phosphineRelated Search:

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  • (+/-)-(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
  • Racemic-2,2’-bis(diphenylphosphino)-1,1’-binaphthy
  • RACEMIC-2,2''-BIS(DIPHENYLPHOSPHINO)-1,1''-BINAPHTHYL BINAP
  • RAC-2,2''-BIS(DIPHENYLPHOSPHINO)-1,1''-BINAPHTHYL / RAC-BINAP
  • 2,2'-Bis-(diphenylphosphino)-1,1'-binaphthyl (Racemic BINAP)
  • (+/-)-2,2'-BIS-(DIPHENYLPHOSPHINO) -1,1'-BINAPHTHALINE PURISS
  • (BINAP) Racemic-2,2'-bis(diphenylphosphino)-1,1'-binaphthyl
  • racemic-2,2’-Bis(diphenylphosphino)-1,1
  • racemic-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl,98%rac-BINAP
  • RACEMIC-2,2''-BIS(DIPHENYLPHOSPHINO)-1,1''-BINAPHTHYL/RAC BINAP
  • (+/-)-BINAP
  • BINAP
  • S(-)-2,2'-BIS(DIPHENYLPHOSPHINO)-1,1'-BINAPHTHALENE
  • S(-)-(1,1'-BINAPHTHALENE-2,2'-DIYL)BIS(DIPHENYLPHOSPHINE)
  • S-(-)-1,1'-BINAPHTHYL-2,2'-DIPHENYL PHOSPHINE
  • R(+)-(1,1'-BINAPHTHALENE-2,2'-DIYL)BIS(DIPHENYLPHOSPHINE)
  • R-(+)-1,1'-BINAPHTHYL-2,2'-DIPHENYL PHOSPHINE
  • RACEMIC-BINAP
  • RACEMIC-2,2'-BIS(DIPHENYLPHOSPHINO)-1,1'-BINAPHTHYL
  • RAC-2,2'-BIS(DIPHENYLPHOSPHINO)-1,1'-BINAPHTHYL
  • RAC-2,2-BIS(DIPHENYLPHOSPHINO)-1,1-BINAPHTHYL
  • RAC-BINAP
  • R(+)-2,2'-BIS(DIPHENYLPHOSPHINO)-1,1'-BINAPHTHALENE
  • PHOSPHINE, 1,1''-[1,1''-BINAPHTHALENE]-2,2''-DIYLBIS[1,1-DIPHENYL-
  • (±)-BINAP, (±)-(1,1μ-Binaphthalene-2,2μ-diyl)bis(diphenylphosphine)
  • (±)-BINAP, (±)-(1,1μ-Binaphthalene-2,2μ-diyl)bis(diphenylphosphine), (±)-2,2μ-Bis(diphenylphosphino)-1,1μ-binaphthalene
  • (+/-)-2,2-bis(Diphenylphosphino)-1,1-dinaphthyl
  • (+/-)-2,2-Bis(diphenylphosphino)-1,1-binapthyl
  • (±)-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl, BINAP
  • (±)-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl,98%
  • (R)-(+)-2,2’-BIS(DIPHENYLPHOSPHINO)-1,1’-BIS(DIPHENYLPHOSPHI
  • (+/-)-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl,98% rac-BINAP
  • 1.1’-Binaphthyl-2.2’-diphemyl phosphine
  • (±)-2,2'-bis(diphenylphosphino)-1,1'-binaphtyl
  • (±)-2,2′-Bis(diphenylphosphino)-1,1′-binaphthalene,(±)-(1,1′-Binaphthalene-2,2′-diyl)bis(diphenylphosphine), (±)-BINAP
  • 2,2′-Bis(diphenylphosphino)-1,1′-binaphthalene,(±)-(1,1′-Binaphthalene-2,2′-diyl)bis(diphenylphosphine), (±)-2,2′-Bis(diphenylphosphino)-1,1′-binaphthalene, (±)-BINAP
  • (±)-2,2'-BIS(DIPHENYLPHOSPHINO (MFCD00010805)
  • racemic-2,-Bis(diphenylphosphino)-1,-binaphthyl
  • (§1)-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl, 98%
  • 1'-binaphthyl
  • 2'-Bis(diphenylphosphino)-1
  • rac-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl, 98% rac-BINAP
  • (+/-)-2,2'-Bis(diphenylphosphino)-[1,1']-binaphthyl 98%
  • {1-[2-(diphenylphosphanyl)naphthalen-1-yl]naphthalen-2-yl}diphenylphosphane
  • RACEMIC-2,2-BIS (BIPHENYL PHOSPHINO)-1,1-BINAPHTHALENE (BINAP)
  • 2,2'-Bis(diphenylphosphino)-1,1'-binaphthalene (BINAP)
  • 98% Rac-BINAP
  • 2,2'-Bis(diphenylphosphanyl)-1,1'-binaphthyl
  • Phosphine, [1,1'-binaphthalene]-2,2'-diylbis[diphenyl- (9CI)
  • DL-2,2'-Bis(diphenylphosphino)-1,1'-dinaphthalene
  • BINAP, (+/-)-2,2'-bis(diphenylphosphino)-1,1'-binaphthyl
  • [1-(2-diphenylphosphanyl-1-naphthyl)-2-naphthyl]-diphenyl-phosphane
  • (+/-)-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl In stock Factory
  • 2,2'-Bis(diphenylphosphanyl)-1,1'-binaphthalene
  • rac-BINAP / racemic-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl