rel-di-tert-butyl((2R,3R)-3-(tert-butyl)-4-(dimethylamino)-2,3-dihydrobenzo[d][1,3]oxaphosphol-2-yl)phosphine oxide

Name: rel-di-tert-butyl((2R,3R)-3-(tert-butyl)-4-(dimethylamino)-2,3-dihydrobenzo[d][1,3]oxaphosphol-2-yl)phosphine oxide
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CAS No. 1788085-47-1
Cat. No. CS-0091058
Purity≥97%
MDL No.MFCD31707612

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rel-di-tert-butyl((2R,3R)-3-(tert-butyl)-4-(dimethylamino)-2,3-dihydrobenzo[d][1,3]oxaphosphol-2-yl)phosphine oxide|CS-0091058

Structure of 1788085-47-1

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General Information

CAS No. 1788085-47-1
Cat. No. CS-0091058
Purity ≥97%
MDL No. MFCD31707612
Storage 4°C, protect from light, stored under nitrogen
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₂₁H₃₇NO₂P₂
Molecular Weight 397.47
Synonym(s) di-tert-butyl((2R,3R)-3-(tert-butyl)-4-(dimethylamino)-2,3-dihydrobenzo[d][1,3]oxaphosphol-2-yl)phosphine oxide
SMILES CN(C)C1=C([P@](C(C)(C)C)[C@@H](P(C(C)(C)C)(C(C)(C)C)=O)O2)C2=CC=C1

Description

This rel-di-tert-butyl((2R,3R)-3-(tert-butyl)-4-(dimethylamino)-2,3-dihydrobenzo[d][1,3]oxaphosphol-2-yl)phosphine oxide features a sterically shielded phosphorus center with a chiral oxaphospholane scaffold, delivering enhanced stability and selective coordination in asymmetric catalysis. The dimethylamino group contributes electron density to the phosphorus atom, facilitating efficient ligand-metal interactions. This structure enables reliable performance in transition metal-catalyzed transformations under standard conditions.

Application

rel-di-tert-butyl((2R,3R)-3-(tert-butyl)-4-(dimethylamino)-2,3-dihydrobenzo[d][1,3]oxaphosphol-2-yl)phosphine oxide serves as a sterically encumbered, bench-stable phosphine oxide building block for asymmetric synthesis. Its rigid chiral framework enables controlled stereochemical transfer in catalytic transformations, while the dimethylamino group enhances nucleophilicity and modulates electronic properties. The molecule exhibits high functional group tolerance and facilitates efficient P–C bond formation under standard coupling conditions, making it valuable for constructing complex organophosphorus scaffolds in medicinal chemistry and catalyst development.

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 29.54
LogP 6.2944
H_Acceptors 3
H_Donors 0
Rotatable_Bonds 2

Key Words

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rel-di-tert-butyl((2R,3R)-3-(tert-butyl)-4-(dimethylamino)-2,3-dihydrobenzo[d][1,3]oxaphosphol-2-yl)phosphine oxide

CAS No. 1788085-47-1

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