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Merck
CN

473006

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

97%

Synonym(s):

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

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About This Item

Empirical Formula (Hill Notation):
C5H10N2 · 2HBr
CAS Number:
132747-20-7
Molecular Weight:
259.97
NACRES:
NA.22
PubChem Substance ID:
24870860
UNSPSC Code:
12352005
MDL number:
MFCD08272741
Assay:
97%

Key Documents

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InChI

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

SMILES string

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

InChI key

ISYQWKOXKGJREA-RSLHMRQOSA-N

assay

97%

optical activity

[α]23/D +22°, c = 1 in H2O

mp

300 °C (dec.) (lit.)

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.

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
S40106
18116CO
13519HR
12307BI
33065

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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)
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)
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)

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