61478-29-3

Basic information

• Product Name: (2S,4S)-4-Diphenylphosphino 2-diphenylphosphinomethyl pyrrolidine
• Synonyms: (2S,4S)-(-)-4-DIPHENYLPHOSPHINO-2-(DIPHENYLPHOSPHINOMETHYL)PYRROLIDINE;(2S,4S)-4-(DIPHENYLPHOSPHINO)-2-(DIPHENYLPHOSPHINOMETHYL)PYRROLIDINE;(2S,4S)-(-)-DIPHENYLPHOSPHINO 2-DIPHENYLPHOSPHINOMETHYL PYRROLIDINE;(2S,4S)-PPM;(-)-PPM;PPM;(S)-4-Diphenylphosphino-2-(Diphenylphosphino)pyrrolidine;(2S 4S)-(-)-4-(DIPHENYLPHOSPHINO)-2-(DI&
• CAS NO: 61478-29-3
• Molecular Formula: C₂₉H₂₉NP₂
• Molecular Weight: 453.49
• Product Categories: API intermediates;Chiral Phosphine;PM Series
• Mol File: 61478-29-3.mol
• Article Data: 4

Chemical Properties

• Melting Point: 102-104 °C(lit.)
• Boiling Point: 575.753°C at 760 mmHg
• Flash Point: 302.005°C
• Appearance: white/Powder
• Vapor Pressure: 0mmHg at 25°C
• Storage Temp.: 0-6°C
• PKA: 9.87±0.10(Predicted)
• Sensitive: air sensitive
• CAS DataBase Reference: (2S,4S)-4-Diphenylphosphino 2-diphenylphosphinomethyl pyrrolidine(CAS DataBase Reference)
• NIST Chemistry Reference: (2S,4S)-4-Diphenylphosphino 2-diphenylphosphinomethyl pyrrolidine(61478-29-3)
• EPA Substance Registry System: (2S,4S)-4-Diphenylphosphino 2-diphenylphosphinomethyl pyrrolidine(61478-29-3)

Safety Data

• Hazard Codes: Xn
• Statements: 20/21/22
• Safety Statements: 36/37
• WGK Germany: 3
• F: 10-23
• Hazardous Substances Data: 61478-29-3(Hazardous Substances Data)

Usage

General Description

(2S,4S)-4-Diphenylphosphino 2-diphenylphosphinomethyl pyrrolidine is a chiral compound with two phosphine groups and a pyrrolidine backbone. It is commonly used as a ligand in metal catalysis and asymmetric synthesis due to its ability to stabilize metal complexes and induce chirality in reactions. The compound's phosphine groups enable it to coordinate to transition metals, allowing for the formation of stable complexes that can facilitate various organic transformations. Additionally, the chiral nature of the compound allows for the induction of asymmetry in reactions, making it an important tool in the synthesis of complex organic molecules with high levels of stereochemical control.

InChI:InChI=1/C29H29NP2/c1-5-13-25(14-6-1)31(26-15-7-2-8-16-26)23-24-21-29(22-30-24)32(27-17-9-3-10-18-27)28-19-11-4-12-20-28/h1-20,24,29-30H,21-23H2/t24-,29-/m0/s1

Upstream product

• 98-59-9 p-toluenesulfonyl chloride 
• 1079-66-9 chloro-diphenylphosphine 
• 51-35-4 4R-4-hydroxyproline 
• 37813-30-2 (2S,4R)-4-hydroxyproline-1,2-dicarboxylic acid 1-tert-butyl 2-ethyl ester 
• 61478-26-0 tert-butyl (2S,4R)-4-hydroxy-2-hydroxymethyl-pyrrolidine-1-carboxylate 
• 33996-30-4 trans-4-hydroxy-L-proline ethyl ester hydrochloride 
• 61478-27-1 (2S,4S)-N-(tert-butoxycarbonyl)-4-(p-toluenesulfonyloxy)-2-<(p-toluenesulfonyloxy)methyl>pyrrolidine 
• 61478-28-2 (2S,4S)-N-butoxycarbonyl-4-diphenylphosphino-2-diphenylphosphinomethylpyrrolidine 

Downstream Products

• 100277-66-5 5-{(2S,4S)-4-Diphenylphosphanyl-2-[(diphenylphosphanyl)-methyl]-pyrrolidine-1-carbonyl}-isobenzofuran-1,3-dione 
• 1619940-58-7 N-[(2S,4S)-(-)-4-diphenylphosphino-2-(diphenylphosphinomethyl)pyrrolidyne]-N'-(2,3,6,2',3',4',6'-hexa-O-acetyl-β-D-cellobiose)urea 
• 1619940-68-9 N-[(2S,4S)-(-)-4-diphenylphosphino-2-(diphenylphosphinomethyl)pyrrolidyne]-N'-(2,3,6,2',3',4',6'-hexa-O-acetyl-β-D-lactose)urea 
• 1399975-47-3 C₄₃H₅₂N₂O₅P₂ 
• 1237783-96-8 C₄₃H₅₂N₂O₅P₂ 
• 1399975-57-5 C₃₄H₃₆N₂O₃P₂*C₂HF₃O₂ 
• 1399975-42-8 C₄₂H₅₀N₂O₅P₂ 
• 1399975-40-6 C₄₂H₅₀N₂O₅P₂ 
• 1237783-98-0 C₄₂H₅₀N₂O₅P₂ 
• 1399975-55-3 C₃₃H₃₄N₂O₃P₂*C₂HF₃O₂ 
• 1399975-52-0 C₃₃H₃₄N₂O₃P₂*C₂HF₃O₂ 
• 1399975-49-5 C₃₃H₃₄N₂O₃P₂*C₂HF₃O₂ 
• 1186423-45-9 (2S,4S)-N-3-({tris[3-(dimethylisopropoxysilyl)propyl]silyl}propyl)-aminocarbonyl-4-(diphenylphosphino)-2-[(diphenylphosphino)methyl]pyrrolidine 
• 1186423-36-8 C₅₇H₈₆N₂OP₂Si₄ 

Relevant articles and documents

Efficient preparation of optically active (S)-(-)-3-methyl-γ-butyrolactone by catalytic asymmetric hydrogenation using chiral N-substituted pyrrolidinebisphosphine rhodium complexes

(S)-(-)-2-Methyl succinamic acid, which is a good precursor of (S)-(-)-3-methyl-γ-butyrolactone, can be prepared by homogeneous asymmetric hydrogenation of 2-methylene succinamic acid catalyzed by (2S,4S)-N-substituted-4-(diphenylphosphino)-2-[(diphenylphosphino)-meth yl]pyrrolidine-rhodium complexes. Various N-substituted pyrrolidine-bisphosphines were synthesized to find the optimum ligand for this purpose and to compare the effects of the N-substituents.

Transition-Metal-Catalyzed Asymmetric Organic Synthesis via Polymer-Attached Optically Active Phosphine Ligands. 5. Preparation of Amino Acids in High Optical Yield via Catalytic Hydrogenation

Two new optically active phosphinopyrrolidine monomers were prepared by the reaction of (2S,4S)-4-(diphenylphosphino)-2-pyrrolidine and (2R,4R)-4-(diphenylphosphino)-2-pyrrolidine with acryloyl chloride to give N-acryloyl-(2S,4S)-4-(diphenylphosphino)-2-pyrrolidine (1) and N-acryloyl-(2R,4R)-4-(diphenylphosphino)-2-pyrrolidine (2).Copolymerization of 1 and 2 with hydrophilic comonomers and a divinyl monomer provided cross-linked insoluble polymers containing 3-5percentof 1 or 2 that would swell in polar solvents.Exchange of rhodium (I) onto the polymer gave catalysts which were active for the asymmetric hydrogenation of N-acyl α-amino acids in high optical yields, the phosphine derived from the enantiomer of the naturally occurring 4-hydroxyproline giving (S)-amino acids.The catalysts could be reused with no loss in selectivity by simple filtration.