Lot numbers can be found on the outside label of a product:
N,N-Bis[(1R)-1-phenylethyl]dibenzo[d,f][1,3,2]dioxaphosphepin-6-amine
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CAS No. 500103-26-4
- Cat. No. CS-0035270
- Purity≥97%
- MDL No.None
*For research and further manufacturing use only, not for direct human use.
![N,N-Bis[(1R)-1-phenylethyl]dibenzo[d,f][1,3,2]dioxaphosphepin-6-amine|CS-0035270](https://file.chemscene.com/productPIC/CS-0035270.gif)
Structure of 500103-26-4
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General Information
- CAS No. 500103-26-4
- Cat. No. CS-0035270
- Purity ≥97%
- MDL No. None
- Storage 4°C, protect from light, stored under nitrogen
- Shipping Room temperature in continental US; may vary elsewhere.
- Molecular Formula C₂₈H₂₆NO₂P
- Molecular Weight 439.49
- Synonym(s) N,N-bis[(1S)-1-phenylethyl]-Dibenzo[d,f][1,3,2]dioxaphosphepin-6-aMine
- SMILES C[C@H](C1=CC=CC=C1)N([C@H](C)C2=CC=CC=C2)P3OC4=C(C5=CC=CC=C5O3)C=CC=C4
Description
N,N-Bis[(1R)-1-phenylethyl]dibenzo[d,f][1,3,2]dioxaphosphepin-6-amine is a chiral phosphine ligand featuring a rigid, electron-rich dioxaphosphepin scaffold. This structure imparts exceptional stability and defined stereochemistry, enabling high enantioselectivity in transition metal-catalyzed asymmetric reactions. The bulky phenylethyl substituents provide steric shielding around the phosphorus center, enhancing catalyst performance and resistance to oxidation under standard conditions.
Application
N,N-Bis[(1R)-1-phenylethyl]dibenzo[d,f][1,3,2]dioxaphosphepin-6-amine serves as a sterically hindered, chiral phosphine ligand that enables efficient transition-metal-catalyzed cross-coupling reactions. Its rigid dibenzo-dioxaphosphepin core provides enhanced thermal stability and resistance to oxidation, while the bulky (1R)-1-phenylethyl groups promote high enantioselectivity in asymmetric transformations. The amine functionality facilitates coordination to palladium and nickel centers, supporting catalytic cycles in Suzuki-Miyaura and Negishi couplings with excellent functional group tolerance and ease of purification.
Synthesis
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Route1
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In-stock
1806-29-7 -
10024-74-5 - ~%
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In-stock
500103-26-4
References
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Duran, Juan; Gulias, Moises; Castedo, Luis; Mascarenas, Jose L. Organic Letters, 2005 , vol. 7, # 25 p. 5693 - 5696
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Route2
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In-stock
1806-29-7
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777067-26-2 - ~%
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In-stock
500103-26-4
References
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Monti, Chiara; Gennari, Cesare; Piarulli, Umberto; De Vries, Johannes G.; De Vries, Andre H. M.; Lefort, Laurent Chemistry - A European Journal, 2005 , vol. 11, # 22 p. 6701 - 6717
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Route3
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10024-74-5
- ~%
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In-stock
500103-26-4
References
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Monti, Chiara; Gennari, Cesare; Piarulli, Umberto Chemistry - A European Journal, 2007 , vol. 13, # 5 p. 1547 - 1558
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Safety Information
Download SDS|
GHS Pictogram :
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GHS No : GHS07
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Signal Word : Warning
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UN#: N/A
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Class : N/A
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Packing Group : N/A
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Hazard Statements : H302-H315-H319-H335
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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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Quality Control
Computational Chemistry Data
- TPSA 29.52
- LogP 8.7504
- H_Acceptors 3
- H_Donors 0
- Rotatable_Bonds 5
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Key Words
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