7755-92-2

Basic information

• Product Name: 1-Piperazinecarbaldehyde
• Synonyms: Formylpiperazine;LABOTEST-BB LT00233197;1-FORMYLPIPERAZINE;1-PIPERAZINECARBALDEHYDE;1-PIPERAZINECARBOXALDEHYDE;N-FORMYLPIPERAZINE;PIPERAZINE-1-CARBOXALDEHYDE;1-Piperazinecarboxaldehyde~Piperazine-1-carboxaldehyde
• CAS NO: 7755-92-2
• Molecular Formula: C₅H₁₀N₂O
• Molecular Weight: 114.15
• EINECS: 231-813-0
• Product Categories: Piperidines, Piperidones, Piperazines;API intermediates;Piperazines;Building Blocks;C4 to C8;Chemical Synthesis;Heterocyclic Building Blocks
• Mol File: 7755-92-2.mol

Chemical Properties

• Melting Point: 88-91
• Boiling Point: 264-266 °C
• Flash Point: 215 °F
• Appearance: Clear colorless to yellow/Liquid
• Density: 1.107 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.00192mmHg at 25°C
• Refractive Index: n20/D 1.512
• Storage Temp.: 2-8°C
• PKA: 8.58±0.10(Predicted)
• Sensitive: Air Sensitive
• BRN: 110295
• CAS DataBase Reference: 1-Piperazinecarbaldehyde(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Piperazinecarbaldehyde(7755-92-2)
• EPA Substance Registry System: 1-Piperazinecarbaldehyde(7755-92-2)

Safety Data

• Hazard Codes: Xn,Xi
• Statements: 22-37/38-41-36/37/38
• Safety Statements: 26-36
• WGK Germany: 2
• TSCA: Yes
• Hazardous Substances Data: 7755-92-2(Hazardous Substances Data)

Usage

Uses

Used in Kinetic Studies:
1-Piperazinecarbaldehyde is used as a test compound in the kinetic study of the reaction between 4-nitrophenyl 2-thiophenecarboxylate and secondary alicyclic amines. This application is valuable for understanding the reaction mechanisms and kinetics of such amide bond formations, which are crucial in the synthesis of various pharmaceuticals and bioactive molecules.

InChI:InChI=1/C5H10N2O/c8-5-7-3-1-6-2-4-7/h5-6H,1-4H2

Upstream product

• 110-85-0 piperazine 
• 4164-39-0 N,N'-diformylpiperazine 
• 107-31-3 Methyl formate 
• 77287-34-4 formamide 
• 109-94-4 formic acid ethyl ester 
• 201230-82-2 carbon monoxide 
• 73486-77-8 piperazine-oxalate 
• 51855-89-1 piperazinium bis(hydrogen oxalate) 
• 68-12-2 N,N-dimethyl-formamide 
• 124-38-9 carbon dioxide 
• 110-74-7 propyl methanoate 
• 96-26-4 dihydroxyacetone 
• 50-00-0 formaldehyd 
• 110-70-3 N,N`-dimethylethylenediamine 

Downstream Products

• 303-26-4 N-(4-chlorobenzhydryl)piperazine 
• 6935-82-6 4-benzylpiperazine-1-carbaldehyde 
• 21863-67-2 4-(n-Butyl)-1-formylpiperazine 
• 859298-18-3 4-formyl-piperazine-1-carboxylic acid amide 
• 88268-16-0 2-(4-formyl-1-piperazinyl)primidine 
• 155791-74-5 1,1'-[1,4-phenylenebis(methylene)]bis(4-piperazinecarbaldehyde) 
• 145276-51-3 4-(6-chloropyridazin-3-yl)piperazine-1-carbaldehyde 
• 145389-95-3 1-(4-chloro-3-sulfamoylbenzoyl)-4-formylpiperazine 
• 108-98-5 thiophenol 
• 67199-20-6 1-Diphenylacetyl-4-formylpiperazine 
• 1849-36-1 para-nitrobenzenethiol 
• 143210-47-3 4-(3,3-Diphenyl-propionyl)-piperazine-1-carbaldehyde 
• 100940-08-7 4-(2,5-Dimethoxy-benzoyl)-piperazine-1-carbaldehyde 
• 106-45-6 para-thiocresol 

Relevant articles and documents

Tetracoordinate borates as catalysts for reductive formylation of amines with carbon dioxide

We report sodium trihydroxyaryl borates as the first robust tetracoordinate organoboron catalysts for reductive functionalization of CO2. These catalysts, easily synthesized from condensing boronic acids with metal hydroxides, activate main group element-hydrogen (E-H) bonds efficiently. In contrast to BX3 type boranes, boronic acids and metal-BAr4 salts, under transition metal-free conditions, sodium trihydroxyaryl borates exhibit high reactivity of reductive N-formylation toward a variety of amines (106 examples), including those with functional groups such as ester, olefin, hydroxyl, cyano, nitro, halogen, MeS-, ether groups, etc. The over-performance to catalyze formylation of challenging pyridyl amines affords a promising alternative method to the use of traditional formylation reagents. Mechanistic investigation supports electrostatic interactions as the key for Si/B-H activation, enabling alkali metal borates as versatile catalysts for hydroborylation, hydrosilylation, and reductive formylation/methylation of CO2.

A preparation method of Ranolazine

The present invention relates to the technical field of ranolazine, in particular to a ranolazine preparation method, the method comprises the following steps: piperazine through the hydroformylation reaction to obtain the 1 - formyl piperazine, then with 2 - chloro - N - (2, 6 - dimethyl-phenyl) acetamide for carrying out the alkylation reaction to obtain N - (2, 6 - dimethyl-phenyl) - 2 - (4 - formyl piperazine) acetamide, then through hydrolytic reaction to obtain N - (2, 6 - dimethyl-phenyl) - 2 - (1 - piperazinyl) acetamide, finally with 2 - (2 - methyl-phenoxymethyl) oxirane ring opening reaction to obtain the ranolazine. The invention preparation of the ranolazine purity is good, high yield.

Sustainable Co-Synthesis of Glycolic Acid, Formamides and Formates from 1,3-Dihydroxyacetone by a Cu/Al2O3 Catalyst with a Single Active Sites

Glycolic acid (GA), as important building block of biodegradable polymers, has been synthesized for the first time in excellent yields at room temperature by selective oxidation of 1,3-dihyroxyacetone (DHA) using a cheap supported Cu/Al2O3 catalyst with single active CuII species. By combining EPR spin-trapping and operando ATR-IR experiments, different mechanisms for the co-synthesis of GA, formates, and formamides have been derived, in which .OH radicals formed from H2O2 by a Fenton-like reaction play a key role.

Ru/ceria-catalyzed direct formylation of amines and CO to produce formamides

We herein report a new strategy of directly converting amines and CO to formamides with 100% atom utilization efficiency. It is suitable for up to 25 amine substrates with no additives. Ru/ceria is found to be an excellent catalyst for this reaction due the efficient co-activation of CO and amine on Ru species.

Supported nano-gold-catalyzed N-formylation of amines with paraformaldehyde in water under ambient conditions

A simple and efficient Au/Al2O3 catalyst was prepared by the co-precipitation method for the oxidative N-formylation of amines with paraformaldehyde. Under the optimized reaction conditions, excellent amine conversion and N-formamide selectivity can be obtained with up to 97% yield with water as the solvent under ambient conditions. This catalyst tolerated a wide range of primary amines and second amines, and it can be reused for at least five runs without obvious deactivation.

C-N and N-H Bond Metathesis Reactions Mediated by Carbon Dioxide

Herein, we report CO2-mediated metathesis reactions between amines and DMF to synthesize formamides. More than 20 amines, including primary, secondary, aromatic, and heterocyclic amines, diamines, and amino acids, are converted to the corresponding formamides with good-to-excellent conversions and selectivities under mild conditions. This strategy employs CO2 as a mediator to activate the amine under metal-free conditions. The experimental data and in situ NMR and attenuated total reflectance IR spectroscopy measurements support the formation of the N-carbamic acid as an intermediate through the weak acid-base interaction between CO2 and the amine. The metathesis reaction is driven by the formation of a stable carbamate, and a reaction mechanism is proposed.

K3PO4-catalyzed carbonylation of amines to formamides

Synthesis of formamides from the catalytic carbonylation of amines with CO is of great interest due to their wide applications of formamides as synthetic intermediates and aprotic polar solvents. Up to now, the most commonly used catalysts are either expensive noble metal compounds or difficult-to-handle alkali metal alkoxides. We have found that a solid base, K3PO4 is a highly active and selective catalyst for the carbonylation of primary and cyclic secondary amines, producing corresponding formaldehydes in yields up to 99% at relatively mild conditions. Spectroscopic and quantum mechanical calculation results indicate that such high activity of K3PO4 is closely related to the strong hydrogen bonding ability of PO43- with the amino group of an amine, thereby enhancing the nucleophilicity of the amino group enough to interact with a neutral molecule, CO and mediating proton transfer from the amino group to the carbonyl group. Characterization of spent catalyst by FT-IR and XRD implies that small portion of K3PO4 is converted into less active K2HPO4 during the carbonylation reaction.

Copper-diphosphine complex catalysts for N-formylation of amines under 1 atm of carbon dioxide with polymethylhydrosiloxane

N-formylation of a wide range of amines proceeded using copper-diphosphine complexes as homogeneous catalysts with polymethylhydrosiloxane (PMHS) under 1 atm of CO2. In the reaction of piperidine, for example, the turnover number (TON) reached 11700 in 23 h with 90% yield of the formylated product. This TON value is much higher than those of the reported catalysts for the formylation of amines under 1 atm of CO2 with hydrosilanes. The Cu complexes with phosphines having ortho-phenylene structures acted as good ligands for the formylation, as compared to a bidentate ligand connected with a propyl chain and a monodentate ligand. Among these diphosphines, ligands with alkyl functionalities, such as isopropyl and cyclohexyl groups, produced better results than the phenyl group. Not only cyclic secondary amines, but also linear secondary amines and aromatic and aliphatic primary amines were found to be reactive substrates. In the case of 2,2,6,6-tetramethylpiperidin-4-amine, the formylation proceeded regioselectively. A catalytic reaction pathway was proposed from a separate experiment using [Me2NCO2] [Me2NH2]. The Royal Society of Chemistry 2013.

Aralkyl-ketone piperazine derivatives and their uses as new antalgic or ataractic agent

Arylalkyl ketone piperazine derivatives of the formula: and pharmaceutical compositions comprising the same. Also dislcosed are methods for using the compounds as analgesic and sedative agents. The compounds of the present invention have good analgesic and sedative activities but few side effects.