139332-66-4

Basic information

• Product Name: 4-Nitro-7-(1-piperazinyl)-2,1,3-benzoxadiazole
• Synonyms: 4-NITRO-7-(1-PIPERAZINYL)-2,1,3-BENZOXADIAZOLE;4-NITRO-7-PIPERAZINO-2,1,3-BENZOXADIAZOLE;4-NITRO-7-PIPERAZINOBENZOFURAZAN;NBD-PZ;NBD-PZ(=4-NITRO-7-PIPERAZINO-2,1,3-BENZOXADIAZOLE)[FOR HPLC LABELING];nbd-pzforHPLClabeling;4-NITRO-7-PIPERAZINO-2,1,3-BENZOXADIAZOLE, NBD-PZ, FOR HPLC LABELING;NBD-PZ (=4-Nitro-7-piperazino-2,1,3-benzoxadiazole)
• CAS NO: 139332-66-4
• Molecular Formula: C₁₀H₁₁N₅O₃
• Molecular Weight: 249.23
• Product Categories: HPLC Labeling Reagents;Analytical Chemistry;Carboxyl Group Labeling Reagents for Fluorescence HPLC;Fluorescence Detection (HPLC Labeling Reagents)
• Mol File: 139332-66-4.mol

Chemical Properties

• Melting Point: 208-212 °C
• Boiling Point: 475.679 °C at 760 mmHg
• Flash Point: 241.482 °C
• Appearance: /
• Density: 1.441 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.645
• Storage Temp.: 2-8°C(protect from light)
• BRN: 7936339
• CAS DataBase Reference: 4-Nitro-7-(1-piperazinyl)-2,1,3-benzoxadiazole(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Nitro-7-(1-piperazinyl)-2,1,3-benzoxadiazole(139332-66-4)
• EPA Substance Registry System: 4-Nitro-7-(1-piperazinyl)-2,1,3-benzoxadiazole(139332-66-4)

Safety Data

• Hazard Codes: Xn
• Statements: 22-36/37/38
• Safety Statements: 26
• WGK Germany: 3
• Hazardous Substances Data: 139332-66-4(Hazardous Substances Data)

Usage

Uses

Used in Analytical Chemistry:
4-Nitro-7-(1-piperazinyl)-2,1,3-benzoxadiazole is used as a derivatizing agent for the determination of monoand diisocyanates by liquid chromatography (LC) and mass spectrometry (MS). Its application in this field is due to its ability to form stable derivatives with isocyanates, which can be detected using ultraviolet (UV) or fluorescent detection methods. This allows for the accurate identification and quantification of these compounds in various samples, such as environmental, industrial, and biological matrices.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 4-Nitro-7-(1-piperazinyl)-2,1,3-benzoxadiazole may be used as a building block or intermediate for the synthesis of various drug candidates. Its unique chemical structure and functional groups can be exploited to design and develop new molecules with potential therapeutic applications, such as those targeting specific receptors or enzymes in the treatment of diseases.
Used in Material Science:
4-Nitro-7-(1-piperazinyl)-2,1,3-benzoxadiazole may also find applications in the field of material science, particularly in the development of new materials with specific properties. For example, its incorporation into polymers or other materials could lead to the creation of materials with enhanced optical, electronic, or mechanical properties, depending on the desired application.

InChI:InChI=1/C10H11N5O3/c16-15(17)8-2-1-7(9-10(8)13-18-12-9)14-5-3-11-4-6-14/h1-2,11H,3-6H2

Upstream product

• 110-85-0 piperazine 
• 10199-89-0 NBD chloride 
• 142-64-3 piperazine dihydrochloride 
• 871508-91-7 4-(7-nitrobenzo[1,2,5]oxadiazol-4-yl)piperazine-1-carboxylic acid tert butyl ester 

Downstream Products

• 1269638-06-3 4-[4-(7-nitrobenzo[1,2,5]oxadiazol-4-yl)piperazin-1-yl]-4-oxobutyric acid pentafluorophenyl ester 

Relevant articles and documents

A novel two-photon fluorescent probe for hydrogen sulfide in living cells using an acedan-NBD amine dyad based on FRET process with high selectivity and sensitivity

Two-photon imaging, due to its unique advantage to utilize near-infrared light as the excitation source, has emerged as an important tool for biomedical research. Herein, the first NBD amine based two-photon fluorescence probe L using a FRET strategy was developed for detecting H2S in vitro and in vivo. The probe L not only afforded high selectivity and sensitivity for the detection of H2S, but also displayed a linear response to H2S with a low detection limit of 24 nM. Furthermore, the living cell experiments indicated that L can be effective for the both exogenous and endogenous detection of H2S inside living cells by two-photon fluorescence imaging.

Platinum(II) as bifunctional linker in antibody-drug conjugate formation: Coupling of a 4-nitrobenzo-2-oxa-1,3-diazole fluorophore to trastuzumab as a model

The potential of platinum(II) as a bifunctional linker in the coordination of small molecules, such as imaging agents or (cytotoxic) drugs, to monoclonal antibodies (mAbs) was investigated with a 4-nitrobenzo-2-oxa-1,3-diazole (NBD) fluorophore and trastu

A GLUT1 inhibitor-based probe significantly ameliorates the sensitivity of tumor detection and diagnostic imaging

We report a non-antibody GLUT1 inhibitor probe NBDQ that is 30 times more sensitive than the traditional GLUT1 transportable tracer for cancer cell imaging and Warburg effect-based tumor detection. NBDQ reveals significant advantages in terms of tumor sel

4-Nitro-7-piperazino-2,1,3-benzoxadiazole as a reagent for monitoring of airborne isocyanates by liquid chromatography

4-Nitro-7-piperazino-2,1,3-benzoxadiazole (NBDPZ) is presented as a new reagent for the determination of mono- and diisocyanates in air samples. NBDPZ readily reacts with the airborne analytes, thus yielding the corresponding urea derivatives, which are s

Investigation of thiolysis of NBD amines for the development of H2S probes and evaluating the stability of NBD dyes

In order to evaluate the thiolysis of NBD (7-nitro-1,2,3-benzoxadiazole) amines for development of H2S probes, herein we investigated the reactivity and selectivity of a series of NBD amines for the first time. The piperazinyl- and piperidyl-ba

Synthesis and characterizations of a highly sensitive and selective fluorescent probe for hydrogen sulfide

Hydrogen sulfide (H2S) is an important endogenous signaling molecule with a variety of biological functions. To detect H2S in living biological systems, herein we developed a new fluorescent probe for highly sensitive and selective s

Triphenylamine derivative, preparation method thereof and application of triphenylamine derivative in double-channel fluorescence detection of hydrogen sulfide

The invention belongs to the technical field of fluorescent probes for H2S detection, and provides a triphenylamine derivative, a preparation method thereof, and application of the triphenylamine derivative in double-channel fluorescence detection of hydr

7-nitro-1,2,3-benzooxadiazole derivative and synthesis method and application thereof

The invention provides a 7-nitro-1,2,3-benzoxadiazole (NBD) derivative and a synthesis method and application thereof, and belongs to the field of detection of NBD derivatives and mercury ions. The synthesis method of the NBD derivatives comprises the following steps of: first, dissolving 4-chlorine-7-nitrobenzo-1,2,3-benzoxadiazole and anhydrous piperazine in 2-methoxyethanol, heating and refluxing, and separating by column chromatography to obtain a compound 1; then, heating and refluxing 2,6-bis (chloromethyl) pyridine and 8-hydroxyquinoline in an acetone solution, and separating by the column chromatography to obtain a compound 2; finally, dissolving the compound 1 and the compound 2 in acetonitrile, refluxing for 12 hours, and separating by the column chromatography to obtain the product NBD derivative. The invention also provides a method for detecting the mercury ions, which comprises the step of quantitatively detecting the content of Hg in a solution of all water (pH = 7.4) by using the NBD derivative as a probe. The detection method can detect the mercury ions in an aqueous solution with high selectivity and sensitivity, and is simple, convenient and rapid to operate.Meanwhile, test paper for detecting the mercury ions is provided, so that the Hg detection is more convenient.

Benzooxaoxadiazole derivative as well as preparation method and application thereof

The invention discloses a benzooxaoxadiazole derivative as well as a preparation method and application thereof. The benzooxaoxadiazole derivative is prepared as follows: firstly, NBD-PZ is obtained by reaction between NBD-Cl and piperazine; then 4-nitro-7-(N-1'-acryloylpiperazine)-2,1,3-benzoxoxaoxadiazole is obtained by reaction between NBD-PZ and acryloyl chloride. The benzooxaoxadiazole derivative BGAS disclosed by the invention as a fluorescent probe has high selectivity for cysteine, can specifically detect the cysteine, particularly has a rapid detection effect on the cysteine in waterand simultaneously has relatively high sensitivity, thereby being applied to the detection of the cysteine in living cells.

A highly selective and sensitive fluorescent probe for simultaneously distinguishing and sequentially detecting H2S and various thiol species in solution and in live cells

A novel dual-channel fluorescent probe (NCR) based on differences in reactivity among H2S, Cys/Hcy, and GSH was rationally designed for simultaneously distinguishing and sequentially sensing H2S, Cys/Hcy, and GSH using two emission channels, which also demonstrated that NCR can be used for targeting mitochondria in mammalian cells.