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1-Boc-piperazine

Name: 1-Boc-piperazine
Brand: ALDRICH

97%

Synonym(s):

tert-Butyl piperazine-1-carboxylate

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About This Item

Empirical Formula (Hill Notation):

C₉H₁₈N₂O₂

CAS Number:

57260-71-6

Molecular Weight:

186.25

Beilstein:

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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Related Categories

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

WGK

WGK 3

Flash Point(F)

closed cup

Flash Point(C)

closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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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

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

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

Efficient copper-catalyzed cross-coupling of 1-Boc-piperazine with aryl iodides and its application in the synthesis of trazodone.

Yong FF, et al.

Tetrahedron Letters, 54(39), 5332-5334 (2013)

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