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688622 Sigma-Aldrich

(R,R)-2,2′-Bipyrrolidine L-tartrate trihydrate

99%

Synonym: (2R,2′R)-2,2′-Bipyrrolidine (2R,3R)-2,3-dihydroxybutanedioate

  • CAS Number 137037-21-9 (anhydrous)

  • Empirical Formula (Hill Notation) C8H16N2 · C4H6O6 · 3H2O

  • Molecular Weight 344.36

  •  Beilstein/REAXYS Number 5387053

  •  MDL number MFCD11656040

  •  PubChem Substance ID 329761180

  •  NACRES NA.22

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Properties

Related Categories Asymmetric Synthesis, Chemical Synthesis, Chiral Building Blocks, Heterocyclic Building Blocks, Pyrrolidines More...
assay   ≥98.5% (sum of enantiomers, GC)
  99%
optical purity   ee: ≥99.5% (GC)
mp   117-118 °C (dec.) (lit.)
  117-118 °C (lit.)
SMILES string   O.O.O.O[C@H]([C@@H](O)C(O)=O)C(O)=O.C1CNC(C1)C2CCCN2
InChI   1S/C8H16N2.C4H6O6.3H2O/c1-3-7(9-5-1)8-4-2-6-10-8;5-1(3(7)8)2(6)4(9)10;;;/h7-10H,1-6H2;1-2,5-6H,(H,7,8)(H,9,10);3*1H2/t7-,8-;1-,2-;;;/m11.../s1
InChI key   XWLGYXKNZXAYBR-WIGUQUGVSA-N

Description

Application

(R,R)-2,2′-Bipyrrolidine L-tartrate trihydrate can be used to prepare the ligand (+)-(2R,2′R)- 1,1′-bis(2-pyridylmethyl)-2,2′-bipyrrolidine, which in turn can be used to synthesize its iron complexes applicable in C-N bond formation reaction.

Packaging

1, 5 g in glass bottle

Safety & Documentation

Safety Information

Symbol 
GHS07  GHS07
Signal word 
Warning
Hazard statements 
Precautionary statements 
Personal Protective Equipment 
RIDADR 
NONH for all modes of transport
WGK Germany 
WGK 3
Flash Point(F) 
Not applicable
Flash Point(C) 
Not applicable

Documents

Certificate of Analysis (COA)

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Protocols & Articles

Articles

Chiral 2,2’-Bipyrrolidines

C2-symmetrical, chiral 2,2’-bipyrrolidines have recently emerged as interesting structural chiral motifs in a number of ligands for asymmetric transformations (Figure 1). When the two nitrogen atoms ...
Daniel Weibel
ChemFiles Volume 10 Article 4
Keywords: Asymmetric synthesis, Catalysis, Dihydroxylations, Ligands, Oxidations, Preferential Oxidation, Type

Peer-Reviewed Papers
15

References

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