124779-66-4

Basic information

• Product Name: (2S,2'S)-2,2'-Bipyrrolidine
• Synonyms: (2S,2'S)-2,2'-Bipyrrolidine;(2S,2'S)-Octahydro-2,2'-bi[1H-pyrrole];[2S,2'S,(+)]-Octahydro-2,2'-bi[1H-pyrrole];2,2'-Bi[(2S)-pyrrolidine];(2S,2'S)-(+)-2,2'-Bipyrrolidine,99%;(S,S)-2,2′-Bipyrrolidinyl;(2S,2'S)-2,2'-Bipyrrolidine >=99.0% (GC)
• CAS NO: 124779-66-4
• Molecular Formula: C₈H₁₆N₂
• Molecular Weight: 140
• Mol File: 124779-66-4.mol

Chemical Properties

• Melting Point: 214-218 °C(Solv: water (7732-18-5))
• Boiling Point: 97-98 °C(Press: 8.0 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: 5376256
• CAS DataBase Reference: (2S,2'S)-2,2'-Bipyrrolidine(CAS DataBase Reference)
• NIST Chemistry Reference: (2S,2'S)-2,2'-Bipyrrolidine(124779-66-4)
• EPA Substance Registry System: (2S,2'S)-2,2'-Bipyrrolidine(124779-66-4)

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: 124779-66-4(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Synthesis:
(2S,2'S)-2,2'-Bipyrrolidine is utilized as a key building block in the synthesis of various pharmaceuticals and natural products. Its unique structure and chiral properties contribute to the development of new and effective medications, enhancing the therapeutic potential of these compounds.
Used in Organic Chemistry:
In the field of organic chemistry, (2S,2'S)-2,2'-Bipyrrolidine serves as a valuable tool for researchers. Its cyclic amine structure and chiral center make it an ideal candidate for the study of asymmetric synthesis and the development of novel chiral catalysts, which can improve the efficiency and selectivity of chemical reactions.
Used in Drug Discovery:
(2S,2'S)-2,2'-Bipyrrolidine plays a crucial role in drug discovery, where its potential biological activities are being explored. Its unique structure allows for the investigation of its interactions with biological targets, potentially leading to the discovery of new therapeutic agents with improved efficacy and selectivity.
Used in Chiral Catalyst Development:
As a potential chiral catalyst, (2S,2'S)-2,2'-Bipyrrolidine is employed in the development of new catalysts for asymmetric synthesis. Its chiral properties enable the design of catalysts that can selectively promote specific reactions, leading to the production of enantiomerically pure compounds, which are essential in various applications, including pharmaceuticals and agrochemicals.

Upstream product

• 136937-01-4 dl-1,1'-dibenzoyl-2,2'-bipyrrolidine 
• 172511-89-6 (S,S)-1,1'-bis(tert-butoxycarbonyl)-2,2'-bipyrrolidine 
• 172511-88-5 (4S,5S)-4,5-di(tert-butoxycarbonylamino)-1,8-octanediol 
• 172511-87-4 (4S,5S)-4,5-di(tert-butoxycarbonylamino)-1,8-octanediol dibenzyl ether 
• 10087-65-7 2-(3,4-dihydro-2H-pyrrol-5-yl)pyrrole 
• 1224300-81-5 tert-butyl (2S,2'S)-1'-((S)-tert-butylsulfinyl)-2,2'-bipyrrolidine-1-carboxylate 
• 136937-03-6 (S,S′)-2,2′-bipyrrolidine tartrate 
• 74295-58-2 2,2’-bipyrrolidine 

Downstream Products

• 1172999-19-7 C₂₂H₂₄Cl₄N₂O₂ 
• 1172999-18-6 (2S,2′S)-[N,N′-bis(1-(2-hydroxy-3,5-di-tert-butylphenylmethyl))]-2,2′-bipyrrolidine 
• 959395-07-4 (?)?2?(((S)?2?((S)?1?(pyridin?2?ylmethyl)pyrrolidin?2?yl)pyrrolidin?1?yl)methyl)pyridine 

Relevant articles and documents

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.

Short asymmetric synthesis of (S,S)-PDP using l-prolinol derivative as economic starting material

(S,S)-PDP (5d) and its backbone (2S,2′S)-bipyrrolidine (1) have been extensively applied as the scaffold of various chiral ligands in catalytic asymmetric syntheses. In this study, new short asymmetric syntheses of these two important C2-symmetrical nitrogen heterocycles have been accomplished employing economically available l-prolinol derivative 10 as the starting material. Excellent diastereoselectivity was achieved of the key Grignard addition to imine intermediate utilizing (S)-N-tert-butanesulfinamide as the chiral auxiliary.

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.

New Convenient, Enantiospecific Synthesis of (S,S)- and (R,R)-2,2'-Bipyrrolidine Derivatives

An enantiomer pair of (S,S)- and (R,R)-bipyrrolidine derivatives has been prepared from D- and L-tartaric acids or D-mannitol as optically active starting materials.Taking advantage of the C2-symmetric nature of these chiral sources, the synthe

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.