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1-Boc-piperazine

Name: 1-Boc-piperazine
Brand: ALDRICH

97%

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Synonym(s):

tert-Butyl piperazine-1-carboxylate

Empirical Formula (Hill Notation):

C₉H₁₈N₂O₂

CAS Number:

57260-71-6

Molecular Weight:

186.25

Beilstein:

879985

MDL number:

MFCD00075265

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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Heterocyclic Building Blocks

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

GHS07

Signal Word

Warning

Hazard Statements

H315 - H319 - H335

Precautionary Statements

P261 - P264 - P271 - P280 - P302 + P352 - P305 + P351 + P338

Hazard Classifications

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

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

235.4 °F - closed cup

Flash Point(C)

113 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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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)

Molecular iodine-catalyzed facile procedure for N-Boc protection of amines.

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

Inhibition of noroviruses by piperazine derivatives.

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

1-alkyl-4-acylpiperazines as a new class of imidazole-free histamine H(3) receptor antagonists.

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

Design, synthesis and structure-activity relationship studies of novel indazole analogues as DNA gyrase inhibitors with Gram-positive antibacterial activity.

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

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