137037-20-8

Basic information

• Product Name: (R,R)-2,2′-Bipyrrolidinyl
• Synonyms: (R,R)-2,2′-Bipyrrolidinyl;(2R,2'R)-2,2'-Bipyrrolidine >=99.0% (GC)
• CAS NO: 137037-20-8
• Molecular Formula: C₈H₁₆N₂
• Molecular Weight: 140.22604
• Mol File: 137037-20-8.mol

Chemical Properties

• Melting Point: 212-216 °C(Solv: water (7732-18-5))
• Boiling Point: 150 °C(Press: 15 Torr)
• Appearance: colorless/liquid
• Density: 0.979±0.06 g/cm3(Predicted)
• Storage Temp.: 2-8°C
• PKA: 10.72±0.10(Predicted)
• Sensitive: air sensitive
• BRN: 5376257
• CAS DataBase Reference: (R,R)-2,2′-Bipyrrolidinyl(CAS DataBase Reference)
• NIST Chemistry Reference: (R,R)-2,2′-Bipyrrolidinyl(137037-20-8)
• EPA Substance Registry System: (R,R)-2,2′-Bipyrrolidinyl(137037-20-8)

Safety Data

• Hazard Codes: C
• Statements: 22-34
• Safety Statements: 26-36/37/39-45
• RIDADR: UN 3259PSN1 8 / PGII
• WGK Germany: 3
• Hazardous Substances Data: 137037-20-8(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
(R,R)-2,2′-Bipyrrolidinyl is used as a chiral ligand in the synthesis of pharmaceuticals for its ability to provide high enantioselectivity in the formation of carbon-carbon and carbon-heteroatom bonds. This ensures the production of enantiomerically pure compounds, which is crucial for the development of effective and safe drugs.
Used in Agrochemical Industry:
(R,R)-2,2′-Bipyrrolidinyl is used as a chiral ligand in the synthesis of agrochemicals to achieve high enantioselectivity in the formation of key bonds. This ensures the production of enantiomerically pure active ingredients, which is essential for the development of effective and environmentally friendly agrochemicals.
Used in Advanced Materials Production:
(R,R)-2,2′-Bipyrrolidinyl is used as a chiral ligand in the production of advanced materials, such as chiral catalysts, chiral sensors, and chiral polymers. Its ability to facilitate the formation of enantiomerically pure compounds contributes to the development of innovative materials with unique properties and applications.
Used in Asymmetric Catalysis:
(R,R)-2,2′-Bipyrrolidinyl is used as a ligand in asymmetric catalysis to achieve high enantioselectivity in various organic reactions. This is crucial for the synthesis of enantiomerically pure compounds, which are important in various fields, including pharmaceuticals, agrochemicals, and materials science. The use of (R,R)-2,2′-Bipyrrolidinyl in asymmetric catalysis has led to significant advancements in the chemical industry and the development of novel synthetic methods.

Upstream product

• 136937-01-4 dl-1,1'-dibenzoyl-2,2'-bipyrrolidine 
• 10087-65-7 2-(3,4-dihydro-2H-pyrrol-5-yl)pyrrole 
• 74295-58-2 2,2’-bipyrrolidine 
• 5724-81-2 1-pyrroline 
• 51097-60-0 (Z)-oct-4-enedial 
• 1415264-07-1 (2R,2'R)-N,N'-di((R)-1-(1-naphthyl)ethyl)-2,2'-bipyrrolidine 
• 1415263-76-1 (Z)-N,N'-di((R)-1-(1-naphthyl)ethyl)oct-4-ene-1,8-diamine 
• 325686-39-3 N,N'-Bis[(S)-1-phenylethyl]-(R,R)-2,2'-bipyrrolidine 

Downstream Products

• 1617519-30-8 C₂₈H₃₈Br₂N₂O₂ 
• 1617519-29-5 C₃₀H₄₂Br₂N₂O₂ 
• 1617519-28-4 C₂₂H₂₄Br₄N₂O₂ 
• 1182734-44-6 C₃₆H₄₀N₂O₂ 
• 1420291-79-7 (2R,2′R)-1,1′-bis({[2-(diphenylphosphanyl)phenyl]methyl})-2,2′-bipyrrolidine 
• 1420291-78-6 C₄₆H₄₂N₂O₂P₂ 

Relevant articles and documents

Enantioselective Reductive Coupling of Imines Templated by Chiral Diboron

We herein report a general, practical, and highly efficient method for asymmetric synthesis of a wide range of chiral vicinal diamines via reductive coupling of imines templated by chiral diboron. The protocol features high enantioselectivity and stereospecificity, mild reaction conditions, simple operating procedures, use of readily available starting materials, and a broad substrate scope. The method signifies the generality of diboron-enabled [3,3]-sigmatropic rearrangement.

A New, Short, and Stereocontrolled Synthesis of C2-Symmetric 1,2-Diamines

The previously unknown 5-spirocyclohexylisoimidazole has been made efficiently and simply by reaction of ammonia, glyoxal hydrate, and cyclohexanone. It is a very useful precursor for the diastereocontrolled synthesis of many C2-symmetric 1,2-diamines, a class which is important for the generation of a variety of C2-symmetric reagents and catalysts for enantioselective synthesis.

Efficient synthesis of chiral 2,2′-bipyrrolidines by an anti -selective alkene diamination

The rapid and efficient construction of complex chiral bicyclic amines is possible using a novel alkene diamination reaction. Electrophilic iodinating agents promote the intramolecular anti-selective diamination of alkenes and allow the efficient synthesi

Chiral phosphoramide-catalyzed enantioselective addition of allylic trichlorosilanes to aldehydes. Preparative studies with bidentate phosphorus-based amides

On the basis of the mechanistic insight that more than one Lewis basic moiety (phosphoramide) is involved in the rate- and stereochemistry-determining step of enantioselective allylation, bidentate chiral phosphoramides were developed. Different chiral phosphoramide moieties were connected by tethers of methylene chains of varying length. The rate and enantioselectivity of allylation with allyltrichlorosilane promoted by the bidentate phosphoramides was found to be highly dependent on the tether length. A new phosphoramide based on a 2,2′-bispyrrolidine skeleton has been designed and afforded good yield, efficient turnover, and high enantioselectivity in allylation reactions. The synthesis of enantiopure 2,2′-bispyrrolidine was easily accomplished on large scale by photodimerization of pyrrolidine followed by resolution with L(or D)-tartaric acid. The scope of the allylation reaction was examined with variously substituted allylic trichlorosilanes and unsaturated aldehydes. This method has been applied to the construction of stereogenic, quaternary centers by the addition of unsymmetrically γ-disubstituted allylic trichlorosilanes.

Synthesis of chiral 2,2'-bipyrrolidine derivatives

Optically pure 2,2'-bipyrrolidine (1) and its 1,1'-disubstituted derivatives have been synthesized from pyrrole and 2-pyrrolidone.