685569

(11bS)-N,N-dimethyl-8,9,10,11,12,13,14,15-octahydrodinaphtho[2,1-d:1′,2′-f][1,3,2]dioxaphosphepin-4-amine

• Synonym(s): MonoPhos Ligand
• Empirical Formula (Hill Notation): C₂₂H₂₆NO₂P
• CAS Number: 389130-06-7
• Molecular Weight: 367.42
• MDL number: MFCD04117692
• UNSPSC Code: 12352005
• PubChem Substance ID: 329760980
• NACRES: NA.22

Properties

• form: solid
• Quality Level: 100
• optical activity: [α]22/D 282.0°, c = 1 in chloroform
• mp: 86-94 °C
• functional group: amine
• SMILES string: CN(C)P1Oc2ccc3CCCCc3c2-c4c(O1)ccc5CCCCc45
• InChI: 1S/C22H26NO2P/c1-23(2)26-24-19-13-11-15-7-3-5-9-17(15)21(19)22-18-10-6-4-8-16(18)12-14-20(22)25-26/h11-14H,3-10H2,1-2H3
• InChI key: OIZQADYWBXZQKE-UHFFFAOYSA-N

Description

Application

DSM MonoPhos Family of Highly Efficient Privileged Ligands

(11bS)-N,N-dimethyl-8,9,10,11,12,13,14,15-octahydrodinaphtho[2,1-d:1′,2′-f][1,3,2]dioxaphosphepin-4-amine is a monodentate phosphoramidite (MonoPhos) chiral ligand that can be used:

• In the Cu-catalyzed synthesis of chiral 3-(arylbut-1-yn-1-yl)silane derivatives by reacting N-tosylhydrazones with silyl-substituted alkynes via asymmetric insertion.
• In the Rh-catalyzed asymmetric hydrogenation of R-isopropylcinnamic acid derivative, a key intermediate of renin inhibitor aliskiren.
• In the Rh-catalyzed conjugate addition of arylboronic acids to lactones, enones, and nitroalkenes.

Legal Information

Sold under license from DSM for research purposes only.

Safety Information

• Storage Class Code: 11 - Combustible Solids
• WGK: WGK 3
• Flash Point(F): Not applicable
• Flash Point(C): Not applicable
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves