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473006

Sigma-Aldrich

(1S,4S)-(+)-2,5-Diazabicyclo[2.2.1]heptane dihydrobromide

97%

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Synonym(s):
(1S,4S)-2,5-Diazabicyclo[2.2.1]heptane dihydrobromide
Empirical Formula (Hill Notation):
C5H10N2 · 2HBr
CAS Number:
132747-20-7
Molecular Weight:
259.97
MDL number:
MFCD08272741
UNSPSC Code:
12352005
PubChem Substance ID:
24870860
NACRES:
NA.22

Assay

97%

optical activity

[α]23/D +22°, c = 1 in H2O

mp

300 °C (dec.) (lit.)

SMILES string

Br.Br.C1N[C@@H]2CN[C@H]1C2

InChI

1S/C5H10N2.2BrH/c1-4-2-6-5(1)3-7-4;;/h4-7H,1-3H2;2*1H/t4-,5-;;/m0../s1

InChI key

ISYQWKOXKGJREA-RSLHMRQOSA-N

Application

(1S,4S)-(+)-2,5-Diazabicyclo[2.2.1]heptane dihydrobromide can be used as:
  • A starting material for the synthesis of chiral diazabicyclic ligands, applicable in the preparation of dicopper(II) complexes.
  • A precursor in the preparation of diazabicyclo[2.2.1]heptane derivatives as catalysts, which are applicable in the asymmetric catalysis reactions.
  • An organocatalyst in Biginelli reaction of aromatic aldehydes with ethyl acetoacetate and urea.

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Regulatory Information

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Dicopper (II) complexes of chiral C2-symmetric diamino-bis (2-methylpyridyl) and diamino-bis (2-methylbenzimidazolyl) ligands
Melgar-Fernandez R, et al.
European Journal of Organic Chemistry, 2008(4), 655-672 (2008)
Application of (1S, 4S)-2, 5-diazabicyclo [2.2. 1] heptane derivatives in asymmetric organocatalysis: the Biginelli reaction
Gonzalez-Olvera R, et al.
ARKIVOC (Gainesville, FL, United States), 6(4) (2008)
Dicopper (II) complexes of chiral C2-symmetric diamino-bis (2-methylpyridyl) and diamino-bis (2-methylbenzimidazolyl) ligands
Perez V, et al.
Inorganic Chemistry Communications, 14(2), 389-391 (2011)

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