(1S,2S)-N1,N2-Bis[2-(diphenylphosphino)benzyl]cyclohexane-1,2-diamine

Name: (1S,2S)-N1,N2-Bis[2-(diphenylphosphino)benzyl]cyclohexane-1,2-diamine
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CAS No. 174677-83-9
Cat. No. CS-0085215
Purity≥95%
MDL No.MFCD17014022

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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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(1S,2S)-N1,N2-Bis[2-(diphenylphosphino)benzyl]cyclohexane-1,2-diamine|CS-0085215

Structure of 174677-83-9

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General Information

CAS No. 174677-83-9
Cat. No. CS-0085215
Purity ≥95%
MDL No. MFCD17014022
Storage 4°C, protect from light, stored under nitrogen
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₄₄H₄₄N₂P₂
Molecular Weight 662.78
Synonym(s) (1S,2S)-N1,N1-Bis(2-(diphenylphosphino)benzyl)cyclohexane-1,2-diamine
SMILES [C@@H]1(NCC2=CC=CC=C2P(C3=CC=CC=C3)C4=CC=CC=C4)[C@@H](NCC5=C(P(C6=CC=CC=C6)C7=CC=CC=C7)C=CC=C5)CCCC1

Description

This chiral diphosphine-diamine ligand features a rigid cyclohexane backbone that enforces precise spatial orientation of its two diphenylphosphino groups. The (1S,2S) stereochemistry ensures high enantioselectivity in transition metal catalysis, particularly in palladium- and nickel-catalyzed cross-coupling reactions. Its electron-rich phosphine centers facilitate oxidative addition and stabilize low-valent metal intermediates. The ligand exhibits excellent thermal stability and compatibility with air-sensitive processes under standard conditions.

Application

(1S,2S)-N,N-Bis[2-(diphenylphosphino)benzyl]cyclohexane-1,2-diamine serves as a highly effective chiral ligand in transition metal-catalyzed asymmetric synthesis, particularly in palladium- and rhodium-mediated reactions. Its rigid bicyclic scaffold and strategically positioned bidentate phosphine donors enable precise stereocontrol, while the robust diphenylphosphino groups offer excellent functional group tolerance and stability under standard reaction conditions. This ligand facilitates efficient enantioselective C–C and C–heteroatom bond formations, making it a valuable tool for synthesizing complex chiral intermediates in medicinal chemistry and natural product synthesis.

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-P280-P302+P352

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Computational Chemistry Data

TPSA 24.06
LogP 7.3936
H_Acceptors 2
H_Donors 2
Rotatable_Bonds 12

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(1S,2S)-N1,N2-Bis[2-(diphenylphosphino)benzyl]cyclohexane-1,2-diamine

CAS No. 174677-83-9

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