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343536

Sigma-Aldrich

1-Boc-piperazine

97%

Synonym(s):

tert-Butyl piperazine-1-carboxylate

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1 G
$35.40
5 G
$118.00
25 G
$313.00

About This Item

Empirical Formula (Hill Notation):
C9H18N2O2
CAS Number:
57260-71-6
Molecular Weight:
186.25
Beilstein/REAXYS Number:
879985
MDL number:
MFCD00075265
UNSPSC Code:
12352100
PubChem Substance ID:
24861171
NACRES:
NA.22
form:
solid
assay:
97%

$35.40

In StockDetails

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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] 1-Boc-piperazine undergoes Buchwald-Hartwig coupling reactions with aryl halides.[2] 1-Boc-piperazine can be prepared in 80% yield via solvent-free N-Boc protection catalyzed by iodine.[3]

Application

1-Boc-piperazine may be used in:
  • preparation of series of (m-phenoxy)phenyl substituted piperazine derivatives[4]
  • termination step during synthesis of α,β-poly(2-oxazoline) lipopolymers via living cationic ring opening polymerization[5]
  • preparation of monosubstituted piperazines, e.g. in the synthesis of indazole DNA gyrase inhibitors[6]

pictograms

Exclamation mark
GHS07

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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

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Certificates of Analysis (COA)

Lot/Batch Number
BCCJ2948
BCCJ4544
BCBW3835
BCBL4205V
MKBJ3407V

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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
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
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
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
Nisar Ullah
Journal of enzyme inhibition and medicinal chemistry, 29(2), 281-291 (2013-03-16)
A series of new 5-piperidinyl and 5-piperazinyl-1H-benzo[d]imidazol-2(3H)-ones have been synthesized and evaluated for dual D2 and 5-HT1A receptor binding affinities. The synthesized ligands are structurally related to bifeprunox, a potential atypical antipsychotic, having potent D2 receptor antagonist and 5-HT1A receptor
View All Related Papers

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  1. How can I determine the shelf life / expiration / retest date of this product?

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    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/449/386/product-dating-information-mk.pdf

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  2. How is shipping temperature determined? And how is it related to the product storage temperature?

    1 answer

    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

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