CAS 98327-87-8

BINAP

Description:

BINAP, or 2,2'-bis(diphenylphosphino)-1,1'-binaphthyl, is a chiral bidentate ligand widely used in asymmetric synthesis and catalysis. It features a binaphthyl backbone, which provides a rigid structure that facilitates the coordination of metal centers, particularly transition metals. The presence of two diphenylphosphino groups allows BINAP to effectively chelate metals, enhancing their catalytic properties in various reactions, such as hydrogenation and cross-coupling processes. BINAP is known for its ability to induce chirality in reactions, making it valuable in the production of enantiomerically pure compounds. The compound is typically characterized by its high stability and solubility in organic solvents, which makes it suitable for a range of catalytic applications. Additionally, BINAP's stereochemical properties can be finely tuned by modifying the substituents on the phosphine groups, allowing for the optimization of catalytic performance in specific reactions. Overall, BINAP is a crucial ligand in modern synthetic chemistry, particularly in the field of asymmetric catalysis.

Formula: C₄₄H₃₂P₂

InChI: InChI=1S/C44H32P2/c1-5-19-35(20-6-1)45(36-21-7-2-8-22-36)41-31-29-33-17-13-15-27-39(33)43(41)44-40-28-16-14-18-34(40)30-32-42(44)46(37-23-9-3-10-24-37)38-25-11-4-12-26-38/h1-32H

InChI key: InChIKey=MUALRAIOVNYAIW-UHFFFAOYSA-N

SMILES: P(C1=C(C2=C(C=C1)C=CC=C2)C3=C(P(C4=CC=CC=C4)C5=CC=CC=C5)C=CC6=C3C=CC=C6)(C7=CC=CC=C7)C8=CC=CC=C8

Synonyms:

• (+/-)-(1,1'-Binaphthalene-2,2'-Diyl)Bis(Diphenylphosphine)
• (?-2,2-Bis(Diphenylphosphino)-1,1-Binaphthyl
• 1,1′-Binaphthalene-2,2′-diylbis(diphenylphosphane)
• 1,1′-[1,1′-Binaphthalene]-2,2′-diylbis[1,1-diphenylphosphine]
• 1.1'-Binaphthyl-2.2'-Diphemyl Phosphine
• 2,2'-Bis(diphenylphosphino)-1,1'-binaphthalene
• 2,2′-Bis(diphenylphosphanyl)-1,1′-binaphthyl
• Binap
• Phosphine, 1,1′-[1,1′-binaphthalene]-2,2′-diylbis[1,1-diphenyl-
• Phosphine, [1,1′-binaphthalene]-2,2′-diylbis[diphenyl-
• Rac-2,2-Bis(Diphenylphosphino)-1,1-Binaphthyl
• S(-)-(1,1'-Binaphthalene-2,2'-Diyl)Bis(Diphenylphosphine)
• [1,1′-Binaphthalene]-2,2′-diylbis[diphenylphosphine]

(±)-BINAP

CAS: 98327-87-8

Formula: C₄₄H₃₂P₂

Purity: >97.0%(GC)

Color and Shape: White to Almost white powder to crystal

Molecular weight: 622.69

Ref: 3B-B2383

(+/-)-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl, 97+%

CAS: 98327-87-8

()-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 demethylthiocholchin

Formula: C₄₄H₃₂P₂

Purity: 97+%

Color and Shape: White to pale cream, Powder

Molecular weight: 622.69

Ref: 02-H26226

racemic-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl, 98% rac-BINAP

CAS: 98327-87-8

racemic-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl, 98% rac-BINAP

Formula: C₄₄H₃₂P₂

Purity: 98%

Color and Shape: white to light-yellow xtl.

Molecular weight: 622.70

Ref: 08-15-0433

2,2’-Bis(diphenylphosphino)-1,1’-binaphthalene

CAS: 98327-87-8

Formula: C₄₄H₃₂P₂

Purity: 98%

Color and Shape: Solid

Molecular weight: 622.6724

Ref: IN-DA0032WO

Rac-2,2''-bis(diphenylphosphino)-1,1''-binaphthyl

CAS: 98327-87-8

Formula: C₄₄H₃₂P₂

Purity: ≥ 97.0%

Color and Shape: White to off-white powder or crystals

Molecular weight: 622.69

Ref: 7W-GK4790

(+/-)-2,2′-Bis(diphenylphosphino)-1,1′-dinaphthalene

CAS: 98327-87-8

Formula: C₄₄H₃₂P₂

Purity: 97.0%

Color and Shape: Solid, Crystalline Powder or Powder

Molecular weight: 622.688

Ref: 10-F069132

2,2'-Bis(diphenylphosphino)-[1,1']-binaphthyl

CAS: 98327-87-8

2,2'-Bis(diphenylphosphino)-[1,1']-binaphthyl

Formula: C₄₄H₃₂P₂

Purity: 98%

Color and Shape: white to off white solid

Molecular weight: 622.67g/mol

Ref: 54-OR18264

2,2'-Bis(diphenylphosphino)-1,1'-dinaphthalene

Controlled Product

CAS: 98327-87-8

Applications 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.
References DiBari, L., et al.: J. Am. Chem. Soc., 121, 7998 (1999); Hatano, M., et al.: J. Am. Chem. Soc., 130, 16858 (2008); Kitamura, M., et al.: Tetrahedron Lett., 32, 4163 (1991); Shimada, T., et al.: J. Org. Chem., 66, 8854 (2001)

Formula: C₄₄H₃₂P₂

Color and Shape: Neat

Molecular weight: 622.67

Ref: TR-B430370

(±)-BINAP

CAS: 98327-87-8

The compound (±)-BINAP is a chelate ligand that binds to metal ions. It has been shown to inhibit the reaction between amines and trifluoroacetic acid, as well as between amines and tiglic acid. The reaction mechanism of this compound is not fully understood. However, it has been shown to be a potent antagonist in reactions involving nitrogen atoms with the ligand binap. (±)-BINAP is a white solid that can act as a catalyst for asymmetric synthesis.

Formula: C₄₄H₃₂P₂

Purity: Min. 98 Area-%

Color and Shape: White Powder

Molecular weight: 622.67 g/mol

Ref: 3D-FB46149