61478-28-2

Basic information

• Product Name: (2S,4S)-(-)-N-BOC-4-Diphenylphosphino-2-diphenylphosphinomethyl-pyrrolidine
• Synonyms: (-)-BPPM;BPPM;(2S,4S)-1-TERT-BUTOXYCARBONYL-4-DIPHENYLPHOSPHINO-2-(DIPHENYLPHOSPHINOMETHYL)PYRROLIDINE;(2S,4S)-(-)-1-BOC-4-DIPHENYLPHOSPHINO-2-(DIPHENYLPHOSPHINOMETHYL)PYRROLIDINE;(2S,4S)-1-BOC-4-DIPHENYLPHOSPHINO-2-(DIPHENYLPHOSPHINOMETHYL)PYRROLIDINE;(2S,4S)-1-T-BUTOXYCARBONYL 4-DIPHENYLPHOSPHINO 2-DIPHENYLPHOSPHINOMETHYL-PYRROLIDINE;(2S,4S)-(-)-1-TBOC-4-DIPHENYLPHOSPHINO-2-(DIPHENYLPHOSPHINOMETHYL)PYRROLIDINE;(2s,4s)-(-)-n-boc-4-diphenylphosphino-2-diphenylphosphinomethyl-pyrrolidine
• CAS NO: 61478-28-2
• Molecular Formula: C₃₄H₃₇NO₂P₂
• Molecular Weight: 553.61
• Product Categories: API intermediates;Chiral Phosphine
• Mol File: 61478-28-2.mol
• Article Data: 3

Chemical Properties

• Melting Point: 96-100 °C
• Boiling Point: 638.8 °C at 760 mmHg
• Flash Point: 340.2 °C
• Appearance: white/Powder
• Vapor Pressure: 0mmHg at 25°C
• Storage Temp.: 2-8°C
• PKA: -2.47±0.60(Predicted)
• Sensitive: air sensitive
• CAS DataBase Reference: (2S,4S)-(-)-N-BOC-4-Diphenylphosphino-2-diphenylphosphinomethyl-pyrrolidine(CAS DataBase Reference)
• NIST Chemistry Reference: (2S,4S)-(-)-N-BOC-4-Diphenylphosphino-2-diphenylphosphinomethyl-pyrrolidine(61478-28-2)
• EPA Substance Registry System: (2S,4S)-(-)-N-BOC-4-Diphenylphosphino-2-diphenylphosphinomethyl-pyrrolidine(61478-28-2)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• F: 10-23
• Hazardous Substances Data: 61478-28-2(Hazardous Substances Data)

Usage

General Description

"(2S,4S)-(-)-N-BOC-4-Diphenylphosphino-2-diphenylphosphinomethyl-pyrrolidine" is a complex chemical compound. It is known as a pyrrolidine derivative, which describes its basic organic structure, and features specific functional groups like N-BOC (tert-butoxycarbonyl) and two diphenylphosphino groups. These functional groups suggest that this compound may exhibit properties such as stereo-specific reactions and phosphorus-related activity. It possibly could be used as a chiral ligand in asymmetric catalysis, or as a complexing agent, based on its structure. Overall, specific information about its synthesis, applications, and safety considerations is not widely available, possibly due to its complex structure and niche use within specific areas of organic chemistry.

InChI:InChI=1/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

Upstream product

• 1079-66-9 chloro-diphenylphosphine 
• 98-59-9 p-toluenesulfonyl chloride 
• 61478-27-1 (2S,4S)-N-(tert-butoxycarbonyl)-4-(p-toluenesulfonyloxy)-2-<(p-toluenesulfonyloxy)methyl>pyrrolidine 
• 829-85-6 diphenylphosphane 
• 15475-27-1 potassium diphenylphosphine 
• 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 
• 1070-19-5 N-(tert-butyloxycarbonyl) azide 
• 51-35-4 4R-4-hydroxyproline 
• 37813-30-2 (2S,4R)-4-hydroxyproline-1,2-dicarboxylic acid 1-tert-butyl 2-ethyl ester 

Downstream Products

• 73300-49-9 N-Acryloyl-(2S,4S)-4-(diphenylphosphino)-2-<(diphenylphosphino)methyl>pyrrolidine 
• 138945-92-3 (2S,4S)-4-(Diphenylphosphino)-2-<(diphenylphosphino)-methyl>-N-phenoxycarbonylpyrrolidine 
• 138965-38-5 (2S,4S)-N-tert-Butylcarbamoyl-4-(diphenylphosphino)-2-<(diphenylphosphino)-methyl>pyrrolidine 
• 66505-77-9 (2S,4S)-N-Benzoyl-4-(diphenylphosphino)-2-<(diphenylphosphino)-methyl>pyrrolidine 
• 138945-91-2 (2S,4S)-4-(Diphenylphosphino)-2-<(diphenylphosphino)-methyl>-N-methoxycarbonylpyrrolidine 
• 66505-76-8 (2S,4S)-4-(Diphenylphosphino)-2-<(diphenylphosphino)-methyl>-N-formylpyrrolidine 
• 64145-67-1 (2S,4S)-4-(Diphenylphosphino)-2-<(diphenylphosphino)-methyl>-N-pivaloylpyrrolidine 
• 74571-27-0 (2S,4S)-4-(Diphenylphosphino)-2-<(diphenylphosphino)-methyl>-N-phenylcarbamoylpyrrolidine 
• 64145-66-0 (2S,4S)-N-Acetyl-4-(diphenylphosphino)-2-<(diphenylphosphino)-methyl>pyrrolidine 
• 74571-32-7 (2S,4S)-4-(Diphenylphosphino)-2-<(diphenylphosphino)-methyl>-N-methylcarbamoylpyrrolidine 
• 113714-64-0 (2S,4S)-N-staroyl-4-diphenylphosphino-2-diphenylphosphinomethylpyrrolidine 

Relevant articles and documents

Chiral rhodium complexes covalently anchored on carbon nanotubes for enantioselective hydrogenation

Chiral rhodium hybrid nanocatalysts have been prepared by covalent anchorage of pyrrolidine-based diphosphine ligands onto functionalized CNTs. This work constitutes the first attempt at covalent anchoring of homogeneous chiral catalysts on CNTs. The catalysts, prepared with two different chiral phosphines, were characterized by ICP, XPS, N2 adsorption and TEM, and have been tested in the asymmetric hydrogenation of two different substrates: methyl 2-acetamidoacrylate and α-acetamidocinnamic acid. The hybrid nanocatalysts have shown to be active and enantioselective in the hydrogenation of α-acetamidocinnamic acid. A good recyclability of the catalysts with low leaching and without loss of activity and enantioselectivity was observed. This journal is the Partner Organisations 2014.

Asymmetric Hydrogenation of Prochiral Olefins Catalyzed by Rhodium Complexes with Chiral Pyrrolidinodiphosphines. Crucial Factors for the Effective Asymmetric Induction

Remarkable effects of hydrogen pressure on the stereoselectivity were observed in the asymmetric hydrogenations of itaconic acid, α-(acylamino)acrylic acid, and their derivatives catalyzed by rhodium complexes of chiral pyrrolidinodiphosphines.Effects of added triethylamine on the pressure dependency of stereoselectivity were also studied.Marked differences in the direction of asymmetric induction were found in the asymmetric hydrogenations of the methylsuccinic acid precursors itaconic acid, citraconic acid, and mesaconic acid.This result clearly indicates that the chiral recognition by the rhodium catalyst is extremely sensitive to the stereochemistry of the prochiral olefins.Possible mechanisms are discussed on the basis of these results. 31PNMR studies on the key intermediates in asymmetric hydrogenations have revealed that the mode of the bidentate complexation of the prochiral substrates is extremely regioselective.The "induced-fit" phenomena of the chiral rhodium complex were observed.A possible mechanism for the chiral recognition of enantiofaces in the chiral coordination sphere is proposed.