1520-99-6

Basic information

• Product Name: 2,5-bis(butylamino)cyclohexa-2,5-diene-1,4-dione
• CAS NO: 1520-99-6
• Molecular Formula: C₁₄H₂₂N₂O₂
• Molecular Weight: 250.3367
• Mol File: 1520-99-6.mol

Chemical Properties

• Boiling Point: 389.1°C at 760 mmHg
• Flash Point: 138.1°C
• Density: 1.05g/cm³
• Vapor Pressure: 2.92E-06mmHg at 25°C
• Refractive Index: 1.517
• CAS DataBase Reference: 2,5-bis(butylamino)cyclohexa-2,5-diene-1,4-dione(CAS DataBase Reference)
• NIST Chemistry Reference: 2,5-bis(butylamino)cyclohexa-2,5-diene-1,4-dione(1520-99-6)
• EPA Substance Registry System: 2,5-bis(butylamino)cyclohexa-2,5-diene-1,4-dione(1520-99-6)

Safety Data

• Hazardous Substances Data: 1520-99-6(Hazardous Substances Data)

Usage

Uses

Used in Coordination Chemistry:
2,5-bis(butylamino)cyclohexa-2,5-diene-1,4-dione is used as a ligand for forming coordination complexes with metal ions. Its ability to chelate metals provides opportunities for the development of new materials with specific properties, such as catalysts or sensors, due to its unique binding capabilities.
Used in Organic Synthesis:
As a precursor in organic synthesis, 2,5-bis(butylamino)cyclohexa-2,5-diene-1,4-dione is utilized to synthesize a variety of complex organic molecules. Its presence in the synthesis process can lead to the creation of pharmaceuticals, agrochemicals, or other specialty chemicals that require its specific structural features.
Used in Pharmaceutical Development:
2,5-bis(butylamino)cyclohexa-2,5-diene-1,4-dione is used as a starting material for the development of new pharmaceutical compounds. Given its barbituric acid heritage, it may have potential applications as a sedative or hypnotic agent, subject to further research and development to explore its therapeutic effects and safety profile.
Used in Research and Development:
In the field of research and development, 2,5-bis(butylamino)cyclohexa-2,4-diene-1,4-dione serves as a model compound for studying the effects of structural modifications on chemical behavior and reactivity. This can lead to a better understanding of molecular interactions and the design of new chemical processes or compounds with tailored properties.

Upstream product

• 3117-03-1 2,5-dimethoxyquinone 
• 109-73-9 N-butylamine 
• 106-51-4 p-benzoquinone 
• 16523-31-2 4,6-diaminoresorcin dihydrochloride 
• 110-82-7 cyclohexane 
• 1131-29-9 N-t-butyl-p-benzoquinone imine N-oxide 
• 1127-42-0 N-tert-butyl-N-phenylhydroxylamine 
• 83933-58-8 N-phenyl-N-(1,1,3,3-tetramethylbutyl)hydroxylamine 
• 83933-63-5 N-(1,1,3,3-tetramethylbutyl)-p-benzoquinone imine N-oxide 
• 123-31-9 hydroquinone 
• 24171-03-7 2,5-Diamino-1,4-benzenediol bis hydrochloride 

Relevant articles and documents

Tunable N-substitution in zwitterionic benzoquinonemonoimine derivatives: Metal coordination, tandemlike synthesis of zwitterionic metal complexes, and supramolecular structures

Full details on a very efficient transamination reaction for the synthesis of zwitterionic N,N′-dialkyl-2-amino-5-alcoholate-1,4- benzoquinonemonoiminium derivatives [C6H2(=NHR) 2(=O)2] 5-16 are reported. The mo

A Catalytic Oxidative Quinone Heterofunctionalization Method: Synthesis of Strongylophorine-26

The preparation of heteroatom-substituted p-quinones is ideally performed by direct addition of a nucleophile followed by in situ reoxidation. Albeit an appealing strategy, the reactivity of the p-quinone moiety is not easily tamed and no broadly applicable method for heteroatom functionalization exists. Shown herein is that Co(OAc)2 and Mn(OAc)3?2 H2O act as powerful catalysts for oxidative p-quinone functionalization with a collection of O, N, and S nucleophiles, using oxygen as the terminal oxidant. Preliminary mechanistic observations and the first synthesis of the cytotoxic natural product strongylophorine-26 is presented.

Rapid and facile solvent-free mechanosynthesis in a cell lysis mill: Preparation and mechanochemical complexation of aminobenzoquinones

A cell lysis mill, typically used for the breakdown of biological structures in microbiological and biochemical studies, was used as a tool for rapid, solvent-free and general synthesis of short- and long-chain substituted zwitterionic meta- and para-amin

Development of quinone analogues as dynamin GTPase inhibitors

Virtual screening of the ChemDiversity and ChemBridge compound databases against dynamin I (dynI) GTPase activity identified 2,5-bis-(benzylamino)-1,4- benzoquinone 1 as a 273 ± 106 μM inhibitor. In silico lead optimization and focused library-led synthesis resulted in the development of four discrete benzoquinone/naphthoquinone based compound libraries comprising 54 compounds in total. Sixteen analogues were more potent than lead 1, with 2,5-bis-(4-hydroxyanilino)-1,4-benzoquinone (45) and 2,5-bis(4-carboxyanilino)- 1,4-benzoquinone (49) the most active with IC50 values of 11.1 ± 3.6 and 10.6 ± 1.6 μM respectively. Molecular modelling suggested a number of hydrogen bonding and hydrophobic interactions were involved in stabilization of 49 within the dynI GTP binding site. Six of the most active inhibitors were evaluated for potential inhibition of clathrin-mediated endocytosis (CME). Quinone 45 was the most effective CME inhibitor with an IC50(CME) of 36 ± 16 μM.

THYMOQUINONE ANALOGS FOR THE TREATMENT OF PANCREATIC CANCER

Analogs of thymoquinone, an active compound extracted from Nigellasativa (black seed oil) are 2,5-bis (alkyl/aryl amino) 1, 4-benzoquinones, are more potent than the naturally-occurring compound (e.g, have a lower IC50) in terms of inhibition o

Synthesis and biological evaluation of 2,5-bis(alkylamino)-1,4- benzoquinones

A series of twelve 2,5-bis(alkylamino)-1,4-benzoquinones were prepared in yields ranging from 9-58% via the reaction between p-benzoquinone and various amines. The structures of the synthesized compounds were confirmed by IR, 1H- and 13/s

Structure-activity studies on therapeutic potential of thymoquinone analogs in pancreatic cancer

Purpose: Pancreatic cancer (PC) is one of the deadliest of all tumors. Previously, we were the first to show that Thymoquinone (TQ) derived from black seed (Nigella sativa) oil has anti-tumor activity against PC. However, the concentration of TQ required

Straightforward synthesis of substituted p-Quinones: Isolation of a key intermediate and use as a bridging ligand in a diruthenium complex

(Figure Presented) Keep it simple: A new transamination method is reported for the synthesis of diamino-substituted p-quinones (see scheme). Asymmetrically substituted p-quinones are shown to be key intermediates in this reaction. The redox properties of these ligands are discussed and their utility in coordination and redox chemistry is shown with a representative example.

Synthesis of 2,5-Diaminoquinones by one-pot copper-catalyzed aerobic oxidation of hydroquinones and addition reaction of amines

The aerobic oxidation of various hydroquinones was achieved by using copper nanoparticles entrapped in aluminum oxyhydroxide [Cu/ AlO(OH)] at room temperature. Furthermore, 2,5diamino-1,4-benzoquinones were synthesized directly from hydroquinone and amines by a one-pot procedure consisting of the copper-catalyzed aerobic oxidation of hydroquinones and the double addition of amines to the resulting quinones.

Alkyl Nitrenes from N-Alkylbenzoquinone Imine N-Oxides

Alkyl nitrenes have been generated by photolysis of two N-t-alkylbenzoquinone imine N-oxides.These mainly abstract hydrogen to give the corresponding amines which are trapped by reaction with benzoquinone.Intramolecular hydrogen abstraction followed by cyclisation to give a pyrrolidine is a minor process in one case.Attempts to generate α-substituted benzyl nitrenes in this way led mainly to the production of substituted benzyl radicals by C-N bond cleavage of the N-benzylbenzoquinone imine N-oxides.