126257-22-5

Basic information

• Product Name: 1-(9-anthracenylmethyl)piperazine
• Synonyms: 1-(9-anthracenylmethyl)piperazine;1-(Anthracen-9-ylmethyl)piperazine
• CAS NO: 126257-22-5
• Molecular Formula: C₁₉H₂₀N₂
• Molecular Weight: 276.3755
• Mol File: 126257-22-5.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 464.0±25.0 °C(Predicted)
• Appearance: /
• Density: 1.151±0.06 g/cm3(Predicted)
• PKA: 9.14±0.10(Predicted)
• CAS DataBase Reference: 1-(9-anthracenylmethyl)piperazine(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(9-anthracenylmethyl)piperazine(126257-22-5)
• EPA Substance Registry System: 1-(9-anthracenylmethyl)piperazine(126257-22-5)

Safety Data

• Hazardous Substances Data: 126257-22-5(Hazardous Substances Data)

Usage

Uses

1-(9-Anthracenylmethyl)piperazine was an analytical derivatization reagent for sampling and HPLC analysis of total isocyanate group in air.

Synthetic route

4-anthracen-9-ylmethylpiperazine-1-carboxylic acid tert-butyl ester (1419212-75-1) → 9-(1',4'-diazacyclohexyl)methylanthracene (126257-22-5)

Conditions	Yield
With trifluoroacetic acid In dichloromethane at 20℃; for 2h;	93%
With hydrogenchloride In methanol; water at 20℃; for 1h; Inert atmosphere;	70%

piperazine (110-85-0) + anthracenylmethyl chloride (24463-19-2) → 9-(1',4'-diazacyclohexyl)methylanthracene (126257-22-5)

Conditions	Yield
In toluene for 6h; Heating;

anthracenylmethyl chloride (24463-19-2) → 4-(4'-(9''-anthrylmethyl)-1'-piperazino)phenylsulfonium hexafluorophosphate + 9-(1',4'-diazacyclohexyl)methylanthracene (126257-22-5)

Conditions	Yield
In piperazine

anthracenylmethyl chloride (24463-19-2) → 9-(1',4'-diazacyclohexyl)methylanthracene (126257-22-5)

Conditions	Yield
Multi-step reaction with 2 steps 1: potassium carbonate / acetonitrile / 18 h / Reflux; Inert atmosphere 2: hydrogenchloride / water; methanol / 1 h / 20 °C / Inert atmosphere View Scheme
Multi-step reaction with 2 steps 1: potassium carbonate / acetonitrile / 60 °C 2: trifluoroacetic acid / dichloromethane / 2 h / 20 °C View Scheme

Upstream product

• 1419212-75-1 4-anthracen-9-ylmethylpiperazine-1-carboxylic acid tert-butyl ester 
• 24463-19-2 anthracenylmethyl chloride 
• 110-85-0 piperazine 

Relevant articles and documents

Localized intracellular pH measurement using a ratiometric photoinduced electron-transfer-based nanosensor

Intracellular analysis: Changes in the concentration of hydrogen ions can lead to cellular dysfunction. Thus, quantification of the intracellular pH in localized compartments (see A and B) is important. A pH nanosensor based on photoinduced electron transfer is described that targets acidic organelles. A combination of confocal fluorescence microscopy and spectroscopy is used for localized pH measurements within living cells. Copyright

PROCASPASE-ACTIVATING COMPOUNDS AND COMPOSITIONS

The invention provides compounds and compositions useful for the modulation of certain enzymes. The compounds and compositions can induce of cell death, particularly cancer cell death. The invention also provides methods for the synthesis and use of the compounds and compositions, including the use of compounds and compositions in therapy for the treatment of cancer and selective induction of apoptosis in cells.

Chelation-enhanced fluorescence of anthrylazamacrocycle conjugate probes in aqueous solution

In this paper, we report the synthesis of several anthrylazamacrocycles designed to provide chelation-enhanced fluorescence on complexation of nonquenching metal ions [e.g., Zn(II) and Cd(II)] in totally aqueous solution. The N3, N4, N5, and N6 derivatives are water-soluble compounds whose fluorescence is enhanced by addition of Zn(II) and Cd(II) and quenched by addition of Cu(II) and Hg(II). While the background fluorescence of anthrylazamacrocycles is higher in water than in aprotic solvents, large (20-190-fold) overall fluorescence changes are still obtained on complexation. The titration of these metal ions is unaffected at pH 12 by even very high (1 M) concentrations of nonbinding metals such as Na+. pH-fluorescence profiles for the anthrylazamacrocycles support intramolecular amine fluorescence quenching at basic pH. These results suggest that the large body of literature on the synthesis of selective azamacrocycle binders can be used in a direct way for the design of conjugate fluorescent probes for those metals.