343536
1-Boc-piperazine
97%
Synonym(s):
tert-Butyl piperazine-1-carboxylate
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About This Item
Empirical Formula (Hill Notation):
C9H18N2O2
CAS Number:
Molecular Weight:
186.25
UNSPSC Code:
12352100
NACRES:
NA.22
PubChem Substance ID:
MDL number:
Beilstein/REAXYS Number:
879985
Assay:
97%
Form:
solid
Quality Level
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
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
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signalword
Warning
hcodes
Hazard Classifications
Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3
target_organs
Respiratory system
Storage Class
11 - Combustible Solids
wgk
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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Articles
Explore gamma-valerolactone (GVL) as a greener solvent replacing DMF, NMP, and DMAc in organic synthesis with efficiency and low toxicity.
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
Global Trade Item Number
| SKU | GTIN |
|---|---|
| 343536-1G | 04061826758212 |
| 343536-25G | 04061826758229 |
| 343536-5G | 04061826758236 |