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67176

Sigma-Aldrich

(R)-2-Piperazinecarboxylic acid dihydrochloride

≥98.0%

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About This Item

Empirical Formula (Hill Notation):
C5H10N2O2 · 2HCl
CAS Number:
Molecular Weight:
203.07
MDL number:
UNSPSC Code:
12352005
PubChem Substance ID:
NACRES:
NA.22

Quality Level

assay

≥98.0% (T)
≥98.0%

form

solid

optical activity

[α]20/D +5±1°, c = 1% in H2O

SMILES string

Cl.Cl.OC(=O)[C@H]1CNCCN1

InChI

1S/C5H10N2O2.2ClH/c8-5(9)4-3-6-1-2-7-4;;/h4,6-7H,1-3H2,(H,8,9);2*1H/t4-;;/m1../s1

InChI key

WNSDZBQLMGKPQS-RZFWHQLPSA-N

Application

(R)-2-Piperazinecarboxylic acid dihydrochloride can be used as a starting material for the synthesis of (R)-enantiomers of anthramycin analogs, which are potential antiproliferative agents.[1] It can also be employed in the preparation of piperazinemethanol chiral ligands, which can be utilized in the enantioselective borane reduction of aromatic ketones, ketimine, and oxime ether.[2]

pictograms

Exclamation mark

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Warning

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Storage Class

13 - Non Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves


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Enantiomerically pure 2-piperazinemethanols as novel chiral ligands of oxazaborolidine catalysts in enantioselective borane reductions
Inoue T, et al.
Tetrahedron Letters, 40(29), 5379- 5382 (1999)
Novel (S)-1, 3, 4, 12a-tetrahydropyrazino [2, 1-c][1, 4] benzodiazepine-6, 12 (2H, 11H)-dione derivatives: Selective inhibition of MV-4-11 biphenotypic b myelomonocytic leukemia cells? growth is accompanied by reactive oxygen species overproduction and apoptosis
Mieczkowski A, et al.
Bioorganic & medicinal chemistry letters, 28(4), 618- 625 (2018)

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