tert-butyl (2S,4S)-4-(diphenylphosphanyl)-2-[(diphenylphosphanyl)methyl]pyrrolidine-1-carboxylate

• ChemBase ID: 152762
• Molecular Formular: C34H37NO2P2
• Molecular Mass: 553.610602
• Monoisotopic Mass: 553.22995269
• SMILES: CC(C)(C)OC(=O)N1C[C@H](C[C@H]1CP(c1ccccc1)c1ccccc1)P(c1ccccc1)c1ccccc1
• Canonical SMILES: O=C(N1C[C@H](C[C@H]1CP(c1ccccc1)c1ccccc1)P(c1ccccc1)c1ccccc1)OC(C)(C)C
• InChI: InChI=1S/C34H37NO2P2/c1-34(2,3)37-33(36)35-25-32(39(30-20-12-6-13-21-30)31-22-14-7-15-23-31)24-27(35)26-38(28-16-8-4-9-17-28)29-18-10-5-11-19-29/h4-23,27,32H,24-26H2,1-3H3/t27-,32-/m0/s1
• InChIKey: BFMKBYZEJOQYIM-UCGGBYDDSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: tert-butyl (2S,4S)-4-(diphenylphosphanyl)-2-[(diphenylphosphanyl)methyl]pyrrolidine-1-carboxylate
• IUPAC Traditional name: tert-butyl (2S,4S)-4-(diphenylphosphanyl)-2-[(diphenylphosphanyl)methyl]pyrrolidine-1-carboxylate
• Synonyms: (2S,4S)-BPPM; (2S,4S)-1-Boc-4-diphenylphosphino-2-(diphenylphosphinomethyl)pyrrolidine; BPPM; (2S,4S)-1-tert-Butoxycarbonyl-4-diphenylphosphino-2-(diphenylphosphinomethyl)pyrrolidine; (2S,4S)-1-Boc-4-diphenylphosphino-2-(diphenylphosphinomethyl)pyrrolidine; (2S,4S)-(-)-N-Boc-4-Diphenylphosphino-2-diphenylphosphinomethyl-pyrrolidine; (2S,4S)-1-Boc-4-二苯基膦-2-(二苯基膦甲基)吡咯烷; (2S,4S)-1-叔丁氧基羰基-4-二苯基膦-2-(二苯基膦基甲基)吡咯烷

Database IDs

• CAS Number: 61478-28-2
• MDL Number: MFCD01631275
• Beilstein Number: 466510
• PubChem SID: 24852242; 162246905
• PubChem CID: 10209545

CALCULATED PROPERTIES

• H Acceptors: 1
• H Donor: 0
• LogD (pH = 5.5): 7.5347
• LogD (pH = 7.4): 7.5347
• Log P: 7.5347
• Molar Refractivity: 161.7613 cm^3
• Polarizability: 64.18278 Å^3
• Polar Surface Area: 29.54 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Melting Point: 100-103°C; 96-100 °C
• Optical Rotation: [α]20/D -39±2°, c = 1% in benzene

Safety Information

• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-36; 26-37
• TSCA Listed: 否
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338; P261-P305+P351+P338-P302+P352-P321-P405-P501A
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥96.0% (sum of enantiomers, HPLC); 95+%
• Empirical Formula (Hill Notation): C34H37NO2P2

DETAILS

Sigma Aldrich - 20424

Other Notes
Chiral phosphine ligand for the rhodium catalyzed asymmetric hydrogenation of olefins and ketones. α-Amino acids are obtained in very high optical purity 1; Hydrogenation of ketones to alcohols2; Hydroformylation3
Packaging
1 g in glass bottle