119008-53-6

Basic information

• Product Name: (2R,5R)-N-Benzyl-2,5-dimethylpyrrolidine
• Synonyms: (2R,5R)-N-Benzyl-2,5-dimethylpyrrolidine
• CAS NO: 119008-53-6
• Molecular Formula: C₁₃H₁₉N
• Molecular Weight: 189.29666
• Product Categories: Aromatics;Chiral Reagents;Heterocycles;Aromatics, Chiral Reagents, Heterocycles
• Mol File: 119008-53-6.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 83-84°C/2mm
• Flash Point: 95.6°C
• Appearance: /
• Density: 0.955g/cm³
• Vapor Pressure: 0.0229mmHg at 25°C
• Refractive Index: 1.523
• Storage Temp.: Refrigerator
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• CAS DataBase Reference: (2R,5R)-N-Benzyl-2,5-dimethylpyrrolidine(CAS DataBase Reference)
• NIST Chemistry Reference: (2R,5R)-N-Benzyl-2,5-dimethylpyrrolidine(119008-53-6)
• EPA Substance Registry System: (2R,5R)-N-Benzyl-2,5-dimethylpyrrolidine(119008-53-6)

Safety Data

• Hazardous Substances Data: 119008-53-6(Hazardous Substances Data)

Usage

Chemical Properties

Colourless Oil

Uses

(2R,5R)-N-Benzyl-2,5-dimethylpyrrolidine is a reagent used for asymmetric syntheses.

InChI:InChI=1/C13H19N/c1-11-8-9-12(2)14(11)10-13-6-4-3-5-7-13/h3-7,11-12H,8-10H2,1-2H3/t11-,12-/m1/s1

Upstream product

• 34338-96-0 (2S,5S)-2,5-hexanediol 
• 97100-85-1 (2S,5S)-hexane-2,5-diyl diacetate 
• 750635-93-9 (4S,7S)-4,7-Dimethyl-[1,3,2]dioxathiepane 2-oxide 
• 100-46-9 benzylamine 
• 220224-82-8 (4S,7S)-4,7-dimethyl-1,3,2-dioxathiepane 2,2-dioxide 
• 119008-52-5 (S,S)-2,5-bis(methylsulfonyloxy)hexane 

Downstream Products

• 749897-99-2 2-[(2R,5R)-2,5-dimethylpyrrolidin-1-yl]ethanol 
• 70144-18-2 (2R,5R)-2,5-dimethyltetrahydro-1H-1-pyrrolylidium chloride 

Relevant articles and documents

Alternate Self-Regeneration of Stereocenters: Enantioselective Generation of a C2-Symmetric Chiral Nitroxide and Its Reduction to the Corresponding, Highly Sterically Hindered Amine

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An evaluation of some hindered diamines as chiral modifiers of metal-promoted reactions

Diamino analogues of the C2-symmetric chiral diphosphine ligands DuPHOS and BPE have been prepared and evaluated as chiral modifiers of the osmium tetraoxide dihydroxylation of stilbene. NMR experiments showed that these ligands were too bulky to coordinate to osmium. Less hindered analogues of these ligands were prepared and some were shown to act as ligands in dihydroxylation reactions but with poor enantioselectivity (e.e. 10%). The diamines have also been briefly evaluated as ligands in rhodium-catalyzed hydroformylation and copper-catalyzed phenolic coupling reactions. Once again, only low enantioselectivity was obtained.