27913-98-0

Basic information

• Product Name: 4-PIPERAZIN-1-YL-BENZALDEHYDE
• Synonyms: 4-PIPERAZIN-1-YL-BENZALDEHYDE;4-PIPERAZIN-1-YL-BENZALDEHYDE, 95+%;4-piperazine-1-H-benzaldehyde;Zinc02563689
• CAS NO: 27913-98-0
• Molecular Formula: C₁₁H₁₄N₂O
• Molecular Weight: 190.24
• EINECS: 604-604-1
• Mol File: 27913-98-0.mol
• Article Data: 8

Chemical Properties

• Boiling Point: 373.6 °C at 760 mmHg
• Flash Point: 179.7 °C
• Appearance: /
• Density: 1.123 g/cm³
• PKA: 8.82±0.10(Predicted)
• CAS DataBase Reference: 4-PIPERAZIN-1-YL-BENZALDEHYDE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-PIPERAZIN-1-YL-BENZALDEHYDE(27913-98-0)
• EPA Substance Registry System: 4-PIPERAZIN-1-YL-BENZALDEHYDE(27913-98-0)

Safety Data

• Hazard Codes: Xi
• Hazardous Substances Data: 27913-98-0(Hazardous Substances Data)

Usage

General Description

4-PIPERAZIN-1-YL-BENZALDEHYDE is a chemical compound with the molecular formula C14H16N2O. It is an organic compound containing a piperazine ring and a benzaldehyde moiety. 4-PIPERAZIN-1-YL-BENZALDEHYDE has been studied for its potential therapeutic applications, particularly in the field of medicinal chemistry. It possesses diverse activities such as antitumor, antimalarial, and antiviral properties, making it a subject of interest for drug discovery and development. Its unique structure and biological activities make it a promising candidate for further research and potential pharmaceutical use.

Synthetic route

piperazine (110-85-0) + 4-fluorobenzaldehyde (459-57-4) → 4-(piperazin-1-yl) benzaldehyde (27913-98-0)

Conditions	Yield
In 2-methoxy-ethanol; water for 3h; Heating;	68%
In 2-methoxy-ethanol; water for 3h; Reflux;	65.9%
In 2-methoxy-ethanol for 3h; Reflux;	65%

4-(4-(1,1-dimethylethoxycarbonyl)piperazinyl)benzaldehyde (197638-83-8) → 4-(piperazin-1-yl) benzaldehyde (27913-98-0)

Conditions	Yield
With trifluoroacetic acid In dichloromethane at 20℃; for 1.5h;

4-(piperazin-1-yl) benzaldehyde (27913-98-0) + 9-amino-3,4-dihydro-1H-pyrido[4,3-e][1,4]diazepin-5(2H)-one → 1-(4-(piperazin-1-yl)phenyl)-8,9-dihydro-2,4,7,9a-tetraazabenzo[cd]azulen-6(7H)-one

Conditions	Yield
With palladium 10% on activated carbon In methanol at 120℃; for 24h; Sealed tube;	92.6%

4-(piperazin-1-yl) benzaldehyde (27913-98-0) + di-tert-butyl dicarbonate (24424-99-5) → 4-(4-(1,1-dimethylethoxycarbonyl)piperazinyl)benzaldehyde (197638-83-8)

Conditions	Yield
In tetrahydrofuran; dichloromethane at 20℃; for 16h; Inert atmosphere;	92%

4-(piperazin-1-yl) benzaldehyde (27913-98-0) + 3-dicyanomethylidene-1,5,5-trimethylcyclohexene (23051-44-7) → (E)-2-(5,5-dimethyl-3-(4-(piperazin-1-yl)styryl)cyclohex-2-en-1-ylidene)malononitrile

Conditions	Yield
In ethanol Concentration; Reflux;	87%

4-(piperazin-1-yl) benzaldehyde (27913-98-0) + p-toluenesulfonyl chloride (98-59-9) → C18H20N2O3S

Conditions	Yield
With triethylamine In dichloromethane at 20 - 30℃; Inert atmosphere;	83.1%

4-(piperazin-1-yl) benzaldehyde (27913-98-0) + 4-(3-Hydroxy-4-oxo-4H-chromen-2-yl)benzoic acid → 4-(4-(4-(3-hydroxy-4-oxo-4H-chromen-2-yl)benzoyl)piperazin-1-yl)benzaldehyde

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 8h;	82%
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 0.8h;	128 mg

4-(piperazin-1-yl) benzaldehyde (27913-98-0) + 6-bromo-2-(2-morpholinoethyl)-1H-benzo[de]isoquinoline1,3 (2 H)-dione (182344-68-9) → C29H30N4O4

Conditions	Yield
In 2-methoxy-ethanol at 80℃; for 8h;	72%

4-(piperazin-1-yl) benzaldehyde (27913-98-0) + 4,6-dichloro-2-methylquinoline (53342-53-3) → C21H19Cl2N3

Conditions	Yield
With toluene-4-sulfonamide In toluene at 120℃; for 12h;	72%

4-(piperazin-1-yl) benzaldehyde (27913-98-0) + 4-chloro-2-methylquinoline (4295-06-1) → C21H20ClN3

Conditions	Yield
With toluene-4-sulfonamide In toluene at 120℃; for 12h;	71%

4-(piperazin-1-yl) benzaldehyde (27913-98-0) + benzyl chloroformate (501-53-1) → benzyl 4-(4-formylphenyl)piperazine-1-carboxylate (104055-50-7)

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; Inert atmosphere;	70%

4-(piperazin-1-yl) benzaldehyde (27913-98-0) + 4-(dicyanomethylene)-2-isopropyl-6-methyl-4H-pyran (263902-75-6) → 2-{2-[4-(piperazin-1-yl)styryl]-6-isopropyl-4H-pyran-4-ylidene}malonodinitrile (950583-83-2)

Conditions	Yield
With piperidine; acetic acid In acetonitrile for 8h; Heating;	65%

4-(piperazin-1-yl) benzaldehyde (27913-98-0) + 2,3-diamino-6-fluorobenzamide → C23H26FN5O3

Conditions	Yield
With sodium hydrogen sulfite In methanol for 12h; Reflux;	64%

4-(piperazin-1-yl) benzaldehyde (27913-98-0) + 4-bromo-N-butylnaphthalimide (92874-17-4) → C27H27N3O3

Conditions	Yield
In N,N-dimethyl-formamide for 6h; Reflux; Inert atmosphere;	62%

4-(piperazin-1-yl) benzaldehyde (27913-98-0) + C27H29ClN4O2 (923950-47-4) → C38H42N6O3

Conditions	Yield
In acetonitrile for 6h; Reflux;	61%

4-(piperazin-1-yl) benzaldehyde (27913-98-0) + 3-dicyanomethylidene-1,5,5-trimethylcyclohexene (23051-44-7) → -2-(5,5-dimethyl-3-(4-(piperazin-1-yl)styryl)cyclohex-2-en-1-ylidene) malononitrile

Conditions	Yield
With piperidine In ethanol for 5h; Inert atmosphere; Reflux;	61%
With piperidine In ethanol for 5h; Inert atmosphere; Reflux;	61%
With piperidine; acetic acid In toluene for 8h; Reflux;	42%

4-(piperazin-1-yl) benzaldehyde (27913-98-0) + N2,N6-bis(1-hydrazinyl-2-methyl-1-oxopropan-2-yl)pyridine-2,6-dicarboxamide (1233515-62-2) → N2,N6-bis(N-(1-{(2E)-2-[4-(piperazin-1-yl)benzylidene]hydrazinyl}-2-methyl-1-oxo-propan-2-yl))pyridine-2,6-dicarboxamide

Conditions	Yield
With acetic acid Reflux;	57%

4-(piperazin-1-yl) benzaldehyde (27913-98-0) + 1,3,5-trichloro-2,4,6-triazine (108-77-0) → C25H26ClN7O2

Conditions	Yield
With caesium carbonate In chloroform at 20℃; for 16h;	56%

4-(piperazin-1-yl) benzaldehyde (27913-98-0) + C11H12NO4(1-)*K(1+) → C21H25N3O3

Conditions	Yield
With manganese(IV) oxide; copper(l) iodide; zinc diacetate In N,N-dimethyl-formamide at 30℃; for 45h; Inert atmosphere; Sealed tube; chemoselective reaction;	53%

4-(piperazin-1-yl) benzaldehyde (27913-98-0) + 4-methoxy-6-methyl-2H-pyran-2-one (672-89-9) → (E)-4-methoxy-6-(4-(piperazin-1-yl)styryl)-2H-pyran-2-one

Conditions	Yield
With magnesium methanolate In methanol for 20h; Reflux; Inert atmosphere;	20%

4-(piperazin-1-yl) benzaldehyde (27913-98-0) + C33H37N4O3(1+) → C44H49N6O3(1+)

Conditions	Yield
With potassium iodide In ethanol for 12h; Inert atmosphere; Reflux;	15%

piperidine (110-89-4) + 4-(piperazin-1-yl) benzaldehyde (27913-98-0) + 2-oxoindole (59-48-3) → 3-[4-(4-Formylpiperazin-1-yl)benzylidenyl]-2-indolinone

Conditions	Yield
In ethanol	199.5 mg (65%)

4-(piperazin-1-yl) benzaldehyde (27913-98-0) + 2,4-dichloro-5-bromopyrimidine (36082-50-5) → C15H16Cl2N4O (1259179-50-4)

Conditions	Yield
Stage #1: 2,4-dichloro-5-bromopyrimidine With isopropylmagnesium chloride In tetrahydrofuran at -78 - -40℃; Inert atmosphere; Stage #2: 4-(piperazin-1-yl) benzaldehyde In tetrahydrofuran at -40 - 0℃; Inert atmosphere; Stage #3: With water; ammonium chloride In tetrahydrofuran Inert atmosphere;

4-(piperazin-1-yl) benzaldehyde (27913-98-0) → 1-(4-(4-(6-bromo-7-(4-((5-methylisoxazol-3-yl)methyl)piperazin-1-yl)-3H-imidazo[4,5-b]pyridin-2-yl)phenyl)piperazin-1-yl)ethanone (1402709-63-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: N-ethyl-N,N-diisopropylamine / dichloromethane / 4 h / 20 °C / Inert atmosphere 2: sodium dithionite / ethanol; water / 20 h / 80 °C View Scheme

4-(piperazin-1-yl) benzaldehyde (27913-98-0) + acetyl chloride (75-36-5) → 4-(4-acetylpiperazin-1-yl)benzaldehyde (890092-19-0)

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 4h; Inert atmosphere;	0.052 g

4-(piperazin-1-yl) benzaldehyde (27913-98-0) + 4-Chloro-2-(pyridin-2-yl)-quinazoline (91748-47-9) → 1-(4-{4-[2-(pyridin-2-yl)quinazolin-4-yl]piperazin-1-yl}phenyl)methanone (1431939-93-3)

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In 1,4-dioxane at 110℃;

4-(piperazin-1-yl) benzaldehyde (27913-98-0) + C16H11N3OS → C27H23N5OS

Conditions	Yield
With piperidine In ethanol at 80℃; for 16h;	25 mg

4-(piperazin-1-yl) benzaldehyde (27913-98-0) + C17H12N2OS (924200-99-7) → C28H24N4OS

Conditions	Yield
With piperidine In ethanol at 80℃; for 16h;	26 mg

4-(piperazin-1-yl) benzaldehyde (27913-98-0) + 7-azaoxindole (5654-97-7) → C18H18N4O

Conditions	Yield
With sodium ethanolate In ethanol at 20℃;

4-(piperazin-1-yl) benzaldehyde (27913-98-0) → C20H19N3O2

Conditions	Yield
Multi-step reaction with 2 steps 1: sodium ethanolate / ethanol / 20 °C 2: 50 °C View Scheme

Upstream product

• 197638-83-8 4-(4-(1,1-dimethylethoxycarbonyl)piperazinyl)benzaldehyde 
• 110-85-0 piperazine 
• 459-57-4 4-fluorobenzaldehyde 

Downstream Products

• 950583-83-2 2-{2-[4-(piperazin-1-yl)styryl]-6-isopropyl-4H-pyran-4-ylidene}malonodinitrile 
• 1259179-50-4 C₁₅H₁₆Cl₂N₄O 
• 1402709-63-0 1-(4-(4-(6-bromo-7-(4-((5-methylisoxazol-3-yl)methyl)piperazin-1-yl)-3H-imidazo[4,5-b]pyridin-2-yl)phenyl)piperazin-1-yl)ethanone 
• 890092-19-0 4-(4-acetylpiperazin-1-yl)benzaldehyde 
• 104055-50-7 benzyl 4-(4-formylphenyl)piperazine-1-carboxylate 

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