4164-39-0

Basic information

• Product Name: 1,4-DIFORMYLPIPERAZINE
• Synonyms: 1,4-PIPERAZINE DIALDEHYDE;1,4-PIPERAZINEDICARBALDEHYDE;1,4-PIPERAZINEDICARBOXALDEHYDE;1,4-DIFORMYLPIPERAZINE;piperazine-1,4-dicarbaldehyde;1,4-Diformylpiperazine, 98+%;1,4-Piperazinedicarboxaldehyde,98%;1,4-Piperazinedicarboxaldehyde 98%
• CAS NO: 4164-39-0
• Molecular Formula: C₆H₁₀N₂O₂
• Molecular Weight: 142.16
• EINECS: 224-011-7
• Product Categories: Building Blocks;C4 to C8;Chemical Synthesis;Heterocyclic Building Blocks;Piperazines
• Mol File: 4164-39-0.mol

Chemical Properties

• Melting Point: 126-129 °C(lit.)
• Boiling Point: 154°C 0,25mm
• Flash Point: 154°C/0.25mm
• Appearance: white to yellow crystalline powder
• Density: 1.2298 (rough estimate)
• Vapor Pressure: 9.17E-06mmHg at 25°C
• Refractive Index: 1.5010 (estimate)
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• PKA: 1.26±0.70(Predicted)
• Sensitive: Air Sensitive
• BRN: 121175
• CAS DataBase Reference: 1,4-DIFORMYLPIPERAZINE(CAS DataBase Reference)
• NIST Chemistry Reference: 1,4-DIFORMYLPIPERAZINE(4164-39-0)
• EPA Substance Registry System: 1,4-DIFORMYLPIPERAZINE(4164-39-0)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 24/25-36/37-26
• WGK Germany: 3
• TSCA: Yes
• Hazardous Substances Data: 4164-39-0(Hazardous Substances Data)

Usage

Uses

Used in Chemical Synthesis Studies:
1,4-DIFORMYLPIPERAZINE is used as a key intermediate for the synthesis of various chemical compounds, particularly in the pharmaceutical and chemical industries. Its formyl groups can be utilized for the formation of new carbon-carbon or carbon-heteroatom bonds, leading to the creation of a wide range of molecules with diverse properties and applications.
Used in Pharmaceutical Industry:
1,4-DIFORMYLPIPERAZINE is used as a building block for the development of new pharmaceutical compounds, such as drugs targeting specific receptors or enzymes in the human body. Its unique structure and reactivity make it a valuable asset in the design and synthesis of novel therapeutic agents.
Used in Chemical Research:
1,4-DIFORMYLPIPERAZINE is used as a research tool in the field of organic chemistry, allowing scientists to explore new reaction pathways and mechanisms involving heterocyclic compounds. Its formyl groups can be employed in various reactions, such as reductive amination, Wittig reactions, and cross-coupling reactions, to generate a diverse array of chemical products.

InChI:InChI=1/C6H10N2O2/c9-5-7-1-2-8(6-10)4-3-7/h5-6H,1-4H2

Upstream product

• 110-85-0 piperazine 
• 64-18-6 formic acid 
• 77287-34-4 formamide 
• 109-94-4 formic acid ethyl ester 
• 201230-82-2 carbon monoxide 
• 51855-89-1 piperazinium bis(hydrogen oxalate) 
• 67-66-3 chloroform 
• 142-63-2 piperazine hexahydrate 
• 68-12-2 N,N-dimethyl-formamide 
• 124-38-9 carbon dioxide 
• 7755-92-2 piperazine-1-carbaldehyde 
• 50-00-0 formaldehyd 
• 56-81-5 glycerol 
• 96-26-4 dihydroxyacetone 

Downstream Products

• 7755-92-2 piperazine-1-carbaldehyde 
• 4164-37-8 1,4-dinitropiperazine 
• 1335040-82-8 1,4-diformylpiperazine bis(4-imino-2,3-dimethyl-1-phenyl-3-pyrazolin-5-one) 
• 1628470-77-8 1,4-bis(1,5-diphenylpenta-1,4-diyn-3-yl)piperazine 
• 57238-77-4 4-benzoyl-1-piperazinecarboxaldehyde 
• 6091-41-4 1,4-dibenzoylpiperazine 
• 110-85-0 piperazine 
• 67-56-1 methanol 

Relevant articles and documents

Nickel-Catalyzed Amination of Aryl Chlorides with Amides

A nickel-catalyzed amination of aryl chlorides with diverse amides via C-N bond cleavage has been realized under mild conditions. A broad substrate scope with excellent functional group tolerance at a low catalyst loading makes the protocol powerful for synthesizing various aromatic amines. The aryl chlorides could selectively couple to the amino fragments rather than the carbonyl moieties of amides. Our protocol complements the conventional amination of aryl chlorides and expands the usage of inactive amides.

Copper catalyzed: N-formylation of α-silyl-substituted tertiary N-alkylamines by air

A site-selective method to prepare N-formyl amines efficiently that relies on the copper(i)-catalyzed oxidation of α-silyl-substituted tertiary N-alkylamines by air at room temperature is described. The oxidative protocol was shown to exhibit excellent functional group tolerance as it was applicable to a wide variety of amine substrates and a number of bioactive molecules and natural products. Moreover, it delinates a ligand-and additive-free amine oxidation process mediated by a low-cost metal salt with oxygen from air taking on the role of both the terminal oxidant and as part of the formylation reagent, which is unprecedented in copper catalysis. It also offers the first synthetic method that can selectively generate α-amino radical species as reactive intermediates from α-silylamines under non-photochemical reaction conditions.

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.

UiO-66 as an efficient catalyst for N-formylation of amines with CO2 and dimethylamine borane as a reducing agent

The most effective way to make the best use of CO2, is the reductive formylation of amines, as formamides have many applications in industry. A new protocol has been developed for reductive N-formylation of amines with CO2 as a C1 carbon source and DMAB (Dimethylamine borane) as a reducing agent in the presence of Zr-containing metal–organic framework (MOF) as an efficient, heterogeneous recyclable catalyst. We used UiO-66 and UiO-66-NH2 as catalysts for N-formylation of amines and observed that both the catalyst performs equally. Therefore, we continued our studies with UiO-66 as a catalyst. The UiO-66 MOF shows good catalytic activity and affording the desired formamides in good to excellent yield. This catalytic system is very efficient for several amines including primary and secondary aliphatic cyclic and aromatic amines. Moreover, the prepared catalyst was recycled up to four recycled without a considerable decrease in catalytic activity.

Novel clamp metal complex and application thereof

The invention discloses a method for preparing a novel clamp-shaped complex and application of the novel clamp-shaped complex in the reaction of catalytic hydrogenation of carboxylic acid ester compounds to produce corresponding alcohols and reaction of carbon dioxide catalytic hydrogenation to form formamide compounds. Carboxylic acid esters and hydrogen as raw materials or carbon dioxide, hydrogen and amine compounds as raw materials are reacted in an organic solvent condition or a solvent-free condition in the presence of a transition metal complex as a catalyst to respectively form the corresponding alcohol compounds and/or corresponding formamide compounds. The method has the advantages of being high in reaction efficiency, good in selectivity, mild in conditions, economical, environmentally-friendly, and simple in operation, and has good promotion and application prospects.

Mn-Catalyzed Selective Double and Mono-N-Formylation and N-Methylation of Amines by using CO2

Functionalization of amines by using CO2 is of fundamental importance considering the abundance of amines and CO2. In this context, the catalytic formylation and methylation of amines represent convenient and successful protocols for selective CO2 utilization as a C1 building block. This study represents the first example of selective catalytic double N-formylation of aryl amines by using a dinuclear Mn complex in the presence of phenylsilane. This robust system also allows for selective formylation and methylation of amines under a range of conditions.

Method for preparing N-formylated amine compounds

The invention discloses a method for preparation N-formylated amine compounds. In the method, the amine compounds and 1,3-dihydroxy acetone are taken as reaction raw materials reacting in a reactor for 2-48 hours at the reaction temperature of 0-100DEG C in a reaction medium in the presence of composite catalysts and oxidants, and the N-formylated amine compounds are obtained. The method is simpleand moderate in reaction conditions, cost can be reduced, target products can be obtained with high yield, and the catalysts used have high catalytic activity and are easy to be separated from a reaction system and reuses; the method is environment friendly during the whole process, the reaction raw materials are easy to be converted from biodiesel by-product propylene glycol, and use of glycerolis facilitated.

METHOD FOR PREPARING FORMAMIDE COMPOUND

Disclosed is a method for preparing a formamide compound, the method uses carbon dioxide, hydrogen and an amine compound as raw materials and a transition metal complex as a catalyst, and the reaction is carried out in an organic solvent or in the absence of a solvent to form a formamide compound. The method of the present invention is an effective method of chemical utilization of carbon dioxide, which has the advantages of high reaction efficiency, a good selectivity, mild conditions, economic and environmental protection, being simple and convenient to operate and the like, and has a good popularization and application prospect.

N-Formylation of Amines with CO2 and H2 by Using NHC–Iridium Coordination Assemblies as Solid Molecular Catalysts

One of the NHC–iridium coordination assemblies containing 1,5-cyclooctadiene (COD) and iodide ion has been demonstrated as robust, efficient, recyclable solid molecular catalyst for N-formylation of diverse primary and secondary amines with CO2 and H2 under mild reaction conditions. Remarkably, in the case of N,N-dimethylformamide production, even at 0.1 mol % catalyst loading under solvent-free conditions, the solid catalyst can be readily recovered by simply filtration and reused more than 10 runs without noticeable loss of activity.

An Efficient Ruthenium Catalyst Bearing Tetradentate Ligand for Hydrogenations of Carbon Dioxide

A ruthenium complex with a tetradentate bipyridine ligand was proved to be a highly efficient catalyst for the conversions of CO2. Turnover numbers up to 300 000, 9800, and 2100 were achieved for the hydrogenations of CO2 to formamides, formamides to methanol and amines, and the direct hydrogenation of CO2 to methanol, respectively.