(2S,4S)-Pentane-2,4-diylbis(bis(3,5-dimethylphenyl)phosphine)

Name: (2S,4S)-Pentane-2,4-diylbis(bis(3,5-dimethylphenyl)phosphine)
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CAS No. 551950-92-6
Cat. No. CS-0526808
Purity≥97%
MDL No.None

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Type	HazMat Fee
Excepted Quantity	$0.00
FedEx Limited Quantities Ground	$0.00
Hazmat Ground shipping	$50.00+
Inaccessible (Haz class 6.1 or 9), Domestic	$68.00+
Accessible (Haz class 3, 4, 5 or 8), Domestic	$158.00+
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(2S,4S)-Pentane-2,4-diylbis(bis(3,5-dimethylphenyl)phosphine)|CS-0526808

Structure of 551950-92-6

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General Information

CAS No. 551950-92-6
Cat. No. CS-0526808
Purity ≥97%
MDL No. None
Storage 4°C, stored under nitrogen
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₃₇H₄₆P₂
Molecular Weight 552.71
Synonym(s) Phosphine, 1,1'-[(1S,3S)-1,3-dimethyl-1,3-propanediyl]bis[1,1-bis(3,5-dimethylphenyl)-
SMILES CC1=CC(C)=CC(P(C2=CC(C)=CC(C)=C2)[C@@H](C)C[C@H](C)P(C3=CC(C)=CC(C)=C3)C4=CC(C)=CC(C)=C4)=C1

Description

This chiral bisphosphine features two sterically shielded phosphine groups flanked by 3,5-dimethylphenyl rings, enabling robust coordination to transition metals. The (2S,4S)-configured diol backbone provides high stereochemical integrity, facilitating asymmetric catalysis in cross-coupling and hydrogenation reactions under standard conditions.

Application

(2S,4S)-Pentane-2,4-diylbis(bis(3,5-dimethylphenyl)phosphine) serves as a sterically encumbered, chiral bidentate phosphine ligand that enables selective transition-metal-catalyzed cross-coupling reactions. Its rigid backbone and electron-rich arylphosphine moieties enhance catalyst stability and facilitate reductive elimination in palladium-catalyzed processes. The ligand demonstrates robust performance in Suzuki-Miyaura and Negishi couplings, offering improved yields and turnover numbers under standard reaction conditions.

Safety Information

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GHS Pictogram :	GHS No : GHS07
Signal Word : Warning	UN#: N/A
Class : N/A	Packing Group : N/A
Hazard Statements : H302-H315-H319-H335
Precautionary Statements : P261-P264-P270-P271-P280-P302+P352-P304+P340-P305+P351+P338-P330-P362+P364-P403+P233-P405-P501

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Computational Chemistry Data

TPSA 0
LogP 8.88666
H_Acceptors 0
H_Donors 0
Rotatable_Bonds 8

Other Classifications

Building Blocks Skeleton Aromatic ring compounds Benzene compounds

Catalysis Phosphorous Compounds Polydentate Phosphine Ligands

Catalysis Asymmetric Synthesis Chiral Catalysts, Chiral Ligands, Chiral Reagents Hydrogenation

Catalysis Asymmetric Synthesis Chiral Catalysts, Chiral Ligands, Chiral Reagents Chiral Ligands (Other)

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(2S,4S)-Pentane-2,4-diylbis(bis(3,5-dimethylphenyl)phosphine)

CAS No. 551950-92-6

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