(2R)-1-tert-butyl-2-[(2R)-1-tert-butylphospholan-2-yl]phospholane

• ChemBase ID: 142110
• Molecular Formular: C16H32P2
• Molecular Mass: 286.372802
• Monoisotopic Mass: 286.19792428
• SMILES: CC(C)(C)P1CCC[C@@H]1[C@H]1CCCP1C(C)(C)C
• Canonical SMILES: CC(P1CCC[C@@H]1[C@H]1CCCP1C(C)(C)C)(C)C
• InChI: InChI=1S/C16H32P2/c1-15(2,3)17-11-7-9-13(17)14-10-8-12-18(14)16(4,5)6/h13-14H,7-12H2,1-6H3/t13-,14-,17?,18?/m1/s1
• InChIKey: SJNUZTRUIDRSJK-JDPPGYRCSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R)-1-tert-butyl-2-[(2R)-1-tert-butylphospholan-2-yl]phospholane
• IUPAC Traditional name: (2R)-1-tert-butyl-2-[(2R)-1-tert-butylphospholan-2-yl]phospholane
• Synonyms: (1S,1S′,2R,2R′)-1,1′-Di-tert-butyl-(2,2′)-diphospholane; (S,S′,R,R′)-TangPhos; (1S,1S′,2R,2R′)-1,1′-二叔丁基-(2,2′)-二磷烷

Database IDs

• CAS Number: 470480-32-1
• PubChem SID: 162236341; 24883788
• PubChem CID: 16717654

CALCULATED PROPERTIES

• H Acceptors: 0
• H Donor: 0
• LogD (pH = 5.5): 1.7824057
• LogD (pH = 7.4): 1.9463521
• Log P: 2.9672
• Molar Refractivity: 94.1238 cm^3
• Polarizability: 34.19518 Å^3
• Polar Surface Area: 0.0 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 60-65 °C

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Product Information

• Empirical Formula (Hill Notation): C16H32P2

DETAILS

Sigma Aldrich - 650889

Application
Highly efficient in rhodium-catalyzed hydrogenation of α-dehyroamino acids and α-arylenamides,6 β-(acylamino)acrylates,7 itaconic acids, and enol acetates.8 Also gives outstanding enantioselectivities in asymmetric hydroformylation reactions.9
Chiral Quest Phosphine Ligands for Asymmetric HydrogenationCatalytic ligand used in:
• Preparation of α-borono-substituted alkylarenes by asymmetric hydroboration of styrenes catalyzed by copper(I)1
• Enantioselective synthesis of spiroindane di-Me acetic acid via hydrogenation of spiroindane di-Me acetic acid catalyzed by Ru(II)2
• Asymmetric γ-addition of thiols to allenoates3
• Rhodium-catalyzed intermolecular enantioselective hydroacylation of alkynes to give alpha- and beta-substituted unsaturated ketones by kinetic resolution4
• Stereoselective preparation of β-amino nitriles via rhodium-catalyzed asymmetric hydrogenation of amino acrylonitriles5
Packaging
100, 500 mg in glass bottle