(S)-(-)-2,2′-Bis(diphenylphosphino)-1,1′-binaphthyl Cas 76189-56-5

Chemical Name: (S)-(-)-2,2′-Bis(diphenylphosphino)-1,1′-binaphthyl
Other Name: S-BINAP
CAS No.: 76189-56-5
Molecular Weight: 622.67
MolecularStructure: C44H32P2
Appearance: Almost white crystalline powder

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Professional Guide for (S)-(-)-2,2′-Bis(diphenylphosphino)-1,1′-binaphthyl (CAS 76189-56-5)

1. Product Overview & Key Specifications
2. Applications in Asymmetric Catalysis
3. Case Studies & Industrial Applications
4. Safety & Handling Guidelines
5. Supplier Information & Quotation

1. Product Overview & Key Specifications

Parameter	Value
CAS Number	76189-56-5
Molecular Formula	C₄₄H₃₂P₂
Molecular Weight	622.67 g/mol
Appearance	White to off-white crystalline powder
Melting Point	238–242°C
Specific Rotation ([α]¹⁹_D)	−233° (c = 0.3 in toluene)
Storage Conditions	Sealed, dry, and protected from light

2. Applications in Asymmetric Catalysis

(S)-(-)-BINAP is a C₂-symmetric chiral bisphosphine ligand widely used in asymmetric catalysis. Key applications include:

Asymmetric Hydrogenation: Enantioselective reduction of α,β-unsaturated acids, β-ketoesters, and aryl ketones using Ru or Rh complexes.
Heck Reactions: Palladium-catalyzed asymmetric coupling for synthesizing chiral biaryl compounds.
Isomerization: Allylic amine isomerization for chiral amine production.
Hydroxyanation: Formation of chiral alcohols via hydroxylation of olefins.

Its rigid binaphthyl backbone ensures high enantioselectivity (>90% ee) in diverse reactions.

3. Case Studies & Industrial Applications

Case Study 1: Synthesis of Chiral Pharmaceuticals

A leading pharmaceutical company utilized (S)-(-)-BINAP in the asymmetric hydrogenation of β-ketoesters to produce intermediates for antihypertensive drugs, achieving 95% ee and reducing waste by 40%.

Case Study 2: Agrochemical Production

In the synthesis of a chiral herbicide, Pd/(S)-(-)-BINAP catalyzed an asymmetric Heck reaction, yielding 92% ee and scaling to 500 kg batches with >99% purity.

Case Study 3: Fragrance Industry

Ru/(S)-(-)-BINAP complexes enabled enantioselective isomerization of allylic alcohols for luxury fragrances, achieving 98% ee and 85% yield.

4. Safety & Handling Guidelines

Hazard Code	Risk Statements	Safety Precautions
Xi	Irritant (skin/eyes/respiratory)	Use PPE: gloves, goggles, and lab coat. Ensure ventilation.

First Aid: Rinse with water for 15 min if exposed. Seek medical attention if irritation persists.

5. Supplier Information & Quotation

Certified Suppliers

Supplier A: Purity ≥98%, bulk quantities available.
Supplier B: Custom synthesis and Ru/Pd complexes (CAS 132071-87-5, 127593-28-6).

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(S)-(-)-2,2′-Bis(diphenylphosphino)-1,1′-binaphthyl Cas 76189-56-5

Professional Guide for (S)-(-)-2,2′-Bis(diphenylphosphino)-1,1′-binaphthyl (CAS 76189-56-5)

Table of Contents

1. Product Overview & Key Specifications

2. Applications in Asymmetric Catalysis

3. Case Studies & Industrial Applications