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Merck
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Documentos

343536

Sigma-Aldrich

1-Boc-piperazine

97%

Sinónimos:

tert-Butyl piperazine-1-carboxylate

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About This Item

Fórmula empírica (notación de Hill):
C9H18N2O2
Número de CAS:
57260-71-6
Peso molecular:
186.25
Beilstein/REAXYS Number:
879985
MDL number:
MFCD00075265
UNSPSC Code:
12352100
PubChem Substance ID:
24861171
NACRES:
NA.22

Quality Level

200

assay

97%

form

solid

mp

43-47 °C (lit.)

SMILES string

CC(C)(C)OC(=O)N1CCNCC1

InChI

1S/C9H18N2O2/c1-9(2,3)13-8(12)11-6-4-10-5-7-11/h10H,4-7H2,1-3H3

InChI key

CWXPZXBSDSIRCS-UHFFFAOYSA-N

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General description

1-Boc-piperazine is an N-Boc protected piperazine. Crosscoupling of 1-Boc-piperazine with aryl iodides using CuBr/1,1′-bi-2-naphthol (catalyst) and K3PO4 (base) has been reported. 1-Boc-piperazine undergoes Buchwald-Hartwig coupling reactions with aryl halides. 1-Boc-piperazine can be prepared in 80% yield via solvent-free N-Boc protection catalyzed by iodine.

Application

1-Boc-piperazine may be used in:
  • preparation of series of (m-phenoxy)phenyl substituted piperazine derivatives
  • termination step during synthesis of α,β-poly(2-oxazoline) lipopolymers via living cationic ring opening polymerization
  • preparation of monosubstituted piperazines, e.g. in the synthesis of indazole DNA gyrase inhibitors

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

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

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

235.4 °F - closed cup

flash_point_c

113 °C - closed cup

ppe

dust mask type N95 (US), Eyeshields, Gloves

Certificados de análisis (COA)

Busque Certificados de análisis (COA) introduciendo el número de lote del producto. Los números de lote se encuentran en la etiqueta del producto después de las palabras «Lot» o «Batch»

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Sigma-Aldrich

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Sigma-Aldrich

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Dengfeng Dou et al.
Bioorganic & medicinal chemistry letters, 22(1), 377-379 (2011-11-29)
There is currently an unmet need for the development of small-molecule therapeutics for norovirus infection. The piperazine scaffold, a privileged structure embodied in many pharmacological agents, was used to synthesize an array of structurally-diverse derivatives which were screened for anti-norovius
Florencio Zaragoza et al.
Journal of medicinal chemistry, 47(11), 2833-2838 (2004-05-14)
With the aim of identifying structurally novel, centrally acting histamine H(3) antagonists, arrays of monoacyldiamines were screened. This led to the discovery of a series of 1-alkyl-4-acylpiperazines which were potent antagonists at the human histamine H(3) receptor. The most potent
Akihiko Tanitame et al.
Bioorganic & medicinal chemistry letters, 14(11), 2857-2862 (2004-05-06)
In this study, we report the design, synthesis and structure-activity relationships of novel indazole derivatives as DNA gyrase inhibitors with Gram-positive antibacterial activity. Our results show that selected compounds from this series exhibit potent antibacterial activity against Gram-positive bacteria including
Ravi Varala et al.
The Journal of organic chemistry, 71(21), 8283-8286 (2006-10-10)
An efficient and practical protocol for the protection of various structurally and electronically divergent aryl and aliphatic amines using (Boc)2O in the presence of a catalytic amount of molecular iodine (10 mol %) under solvent-free conditions at ambient temperature is
α,ω-Functionalized Poly (2-Oxazoline) s Bearing Hydroxyl and Amino Functions.
Reif M and Jordan R.
Macromolecular Chemistry and Physics, 212(16), 1815-1824 (2011)
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