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343536

Sigma-Aldrich

1-Boc-piperazine

97%

Synonyme(s) :

tert-Butyl piperazine-1-carboxylate

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About This Item

Formule empirique (notation de Hill):
C9H18N2O2
Numéro CAS:
57260-71-6
Poids moléculaire :
186.25
Numéro Beilstein :
879985
Numéro MDL:
MFCD00075265
Code UNSPSC :
12352100
ID de substance PubChem :
24861171
Nomenclature NACRES :
NA.22

Pureté

97%

Forme

solid

Pf

43-47 °C (lit.)

Chaîne SMILES 

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

Clé InChI

CWXPZXBSDSIRCS-UHFFFAOYSA-N

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Description générale

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

Pictogrammes

Exclamation mark
GHS07

Mention d'avertissement

Warning

Mentions de danger

H315,H319,H335

Classification des risques

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

Organes cibles

Respiratory system

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

235.4 °F - closed cup

Point d'éclair (°C)

113 °C - closed cup

Équipement de protection individuelle

dust mask type N95 (US), Eyeshields, Gloves

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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
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
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
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)
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
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