20048-27-5

Basic information

• Product Name: BANDROWSKI'S BASE
• Synonyms: 4-diamine,3,6-bis((p-aminophenyl)imino)-4-cyclohexadiene-1;n,n’’-(2,5-diamino-2,5-cyclohexadiene-1,4-diylidene)bis-4-benzenediamine;BANDROWSKI'S BASE;N,N''-(2,5-Diamino-2,5-cyclohexadiene-1,4-diylidene)bis(1,4-benzenediamine)
• CAS NO: 20048-27-5
• Molecular Formula: C18H18N6
• Molecular Weight: 318.38
• Product Categories: marker
• Mol File: 20048-27-5.mol

Chemical Properties

• Boiling Point: 523.5°Cat760mmHg
• Flash Point: 270.4°C
• Appearance: /
• Density: 1.36g/cm³
• PKA: 5.81±0.10(Predicted)
• CAS DataBase Reference: BANDROWSKI'S BASE(CAS DataBase Reference)
• NIST Chemistry Reference: BANDROWSKI'S BASE(20048-27-5)
• EPA Substance Registry System: BANDROWSKI'S BASE(20048-27-5)

Safety Data

• Hazardous Substances Data: 20048-27-5(Hazardous Substances Data)

Usage

Uses

Used in Chemical Synthesis:
BANDROWSKI'S BASE is used as an intermediate in the synthesis of various organic compounds, particularly those involving the formation of complex molecular structures. Its unique chemical properties allow it to act as a building block for the creation of new molecules with specific functionalities.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, BANDROWSKI'S BASE is used as a starting material for the development of novel drugs. Its ability to form trimer structures from 1,4-phenylenediamine makes it a valuable component in the design and synthesis of new therapeutic agents.
Used in Dye Manufacturing:
BANDROWSKI'S BASE is also utilized in the manufacturing of dyes, where its unique chemical structure contributes to the development of dyes with specific color properties and stability.
Used in Research and Development:
Due to its unique chemical properties, BANDROWSKI'S BASE is employed in research and development for the exploration of new chemical reactions and the discovery of new compounds with potential applications in various industries, including pharmaceuticals, materials science, and environmental science.

Upstream product

• 98-95-3 nitrobenzene 
• 106-50-3 1,4-phenylenediamine 
• 24295-03-2 2-Acetylthiazole 
• 149-73-5 trimethyl orthoformate 
• 1934-75-4 sodium dicyanamide 
• 111-30-8 Glutaraldehyde 
• 2237-30-1 m-cyanoaniline 
• 121-47-1 3-aminobenzenesulfonic acid 
• 99-05-8 meta-aminobenzoic acid 
• 64-17-5 ethanol 
• 858242-20-3 N-(4-bromo-2,5-dinitro-phenyl)-p-phenylenediamine 

Downstream Products

• 74-90-8 hydrogen cyanide 
• 15719-64-9 methylammonium carbonate 
• 106-50-3 1,4-phenylenediamine 
• 106-51-4 p-benzoquinone 
• 1422271-42-8 C₄₂H₅₆N₆Si₂ 
• 1422271-40-6 C₃₈H₃₂N₆O₂ 
• 1422271-39-3 C₃₈H₃₂N₆O₂ 
• 1217433-85-6 1,5-diphenylamine 2,6-bis(2-[4-[2-(5-chloro-2-methyl-3-thienyl)cyclopent-1-en-1-yl]-5-methyl]thienyl)benzo[1,2-d:4,5-d']diimidazole 
• 1217433-84-5 1,5-diphenylamine 2,6-bis(2-thienyl)benzo[1,2-d:4,5-d']diimidazole 

Relevant articles and documents

Liquid chromatography–mass spectrometry analysis of dyes formed by in situ oxidative methods then purified by absorption and extraction from hair wefts

The dye mixtures formed from three commercial hair colour formers were purified by absorption onto human hair wefts, washed and dried, extracted with dichloromethane:trifluoroacetic acid (75:25) and then analysed by liquid chromatography–mass spectrometry. Only 1–2 dyes were identified from each complex mixture of commercial aromatic amines along with a broad UV absorption mainly consisting of mixtures of quaternary ammonium salts from shampoos and some surfactants. Mecetronium ethyl sulfate and didecyldimethylammonium chloride were the main ammonium salts.

Photoinduced Electron Transfer in the p-Phenylenediamine-Paraquat Molecular Complex

Flash photolysis of the charge-transfer band of the p-phenylenediamine-paraquat complex yields the paraquat radical cation (λmax=610 nm) and the p-phenylenediamine radical cation (λmax=475 nm).Since the photoreaction is energetically uphill, back-electron transfer from the paraquat radical to the p-phenylenediamine radical occurs spontaneously, with a rate constant (25 deg C) of 1.0E9 M-1s-1.The excited state from which electron transfer occurs is shown not to be S1 of paraquat (ES0-S1=92 kcal/mol), T1 of paraquat (ES0-S1=71.5 kcal/mol), S1 of p-phenylenediamine (ES0-S1=87 kcal/mol), or T1 of p-phenylenediamine (ES0-T1>44 kcal/mol).Failure of a cyanine dye (ES0-T1=39.2 kcal/mol) and oxygen (E3Σg-1Δ=22.5 kcal/mol) to decrease the radical yield implies that, if the reaction involves a triplet state, it lies lower than 22,5 kcal/mol; otherwise electron transfer originates from a charge-transfer singlet state.

Kinetic Studies of the Promoting Effect of Glutaraldehyde on the Oxidation of p-Phenylenediamine by Hydrogen Peroxide

Glutaraldehyde accelerates the oxidation of p-phenylenediamine by hydrogen peroxide, and this effect has been used for the "catalytic" detection of aldehyde groups and for the determination of these groups on the surface of modified (by glutaraldehyde) aminosilane glass to be used for protein immobilization.A reexamination of the effect of glutaraldehyde (25 deg C, 1.00 M ionic strength, and pH 5.00) has demonstrated that the unprotonated form of p-phenylenediamine is the reactive species, that glutaraldehyde acts as a promoter and not as a true catalyst, and that once formed the product of the reaction (Bandarowski's base) is destroyed by further reaction with hydrogen peroxide.An empirical reaction model of the oxidation was analysed by computer, and satisfactory reproduction of experimental data suggests three regions in the overall reaction profile: (1) early periods of reaction in which the predominant process is the conversion of p-phenylenediamine to Bandarowski's base by a complex formed between glutaraldehyde and hydrogen peroxide, (2) an intermediate region in which the uncatalyzed oxidation also becomes a significant contributor to the overall rate, and (3) late reaction times when the destruction of Bandarowski's base by hydrogen peroxide dominates.

Bandrowski's base

Molecules of N,N″-(2,5-diamino-2,5-cyclohexadiene-1,4-diylidene)bis(1,4-benzenediamine) , C18H18N6, lie across crystallographic inversion centres. The angle between the central ring and each of the terminal rings is 60.2 (5)°. Hydrogen bonding links molecules into chains along b.

NLRP3 INHIBITORS

The present application relates to compounds with NLRP3inhibitory activity and to associated salts, solvates, prodrugs and pharmaceutical compositions. The present application further relates to the use of such compounds in the treatment and prevention of medical disorders and diseases, most especially by NLRP3inhibition.

Facile synthesis of oligo anilines as permanent hair dyes: How chemical modifications impart colour and avoid toxicity

Many dyes for long-lasting hair coloring contain aromatic amines that undergo oxidative polymerizations, resulting in allergic contact dermatitis, with the potential to develop serious toxic effects. Among these amines, para-phenylenediamine (PPD) is a small molecule form of aniline commonly used in beauty products despite being a known allergen to humans. Hence, in this study we designed and synthesized safer PPD analogues through the synthesis of oligomeric PPD and the introduction of bulky side chains on PPD to overcome the PPD dye's toxicity. We hypothesized that (a) an increase in the molecular size of PPD by addition of the PPD monomer unit on free amines and (b) strategic functionalizations at the ortho position of PPD with strong electron-donating bulky groups are able to maintain the hair coloring properties, and increase the resistance to binding to skin proteins and therefore decrease the chance of skin sensitization. 13 oligomers were synthesized, with the aim to produce safer hair dyes while minimising eventual toxicity to humans. In particular, oligomers with bulky sidechains, PPD 6 (13), PPD 7 (14) and PPD 8 (15), displayed weak-to-moderate (27.1%, 24.1% and 34.0%) sensitization potential. The results confirmed the importance of having bulky and strong electron donating O-alkyl substituents in order to decrease the reactivity of PPD analogues towards skin proteins, thus preventing the interaction with immune cells and providing safer hair dyes.

Synthesis and biological evaluation of thiazole derivatives as novel USP7 inhibitors

Herpesvirus-associated Ubiquitin-Specific Protease (HAUSP, also called USP7) interacts with and stabilizes Mdm2, and represents one of the first examples that deubiquitinases oncogenic proteins. USP7 has been regarded as a potential drug target for cancer therapy. Inhibitors of USP7 have been recently shown to suppress tumor cell growth in vitro and in vivo. Based on leading USP7 inhibitors P5091 and P22077, we designed and synthesized a series of thiazole derivatives. The results of in vitro assays showed that the thiazole compounds exhibited low micromolar inhibition activity against both USP7 enzyme and cancer cell lines. The compounds induced cell death in a p53-dependent and p53-independent manner. Taken together, this study may provide thiazole compounds as a new class of USP7 inhibitors.

Eco-friendly synthesis of indo dyes mediated by a bacterial laccase

Several aminoindamine and indoaniline dyes were obtained in good to excellent yields (64-98%) by oxidative cross-coupling between 1,4-phenylenediamine (1), 4-aminophenol (2) or 2,5-diaminotoluene (3) and several meta- and meta,para-substituted couplers (4a-j) using a green biocatalyst, the bacterial enzyme CotA-laccase from Bacillus subtilis, in water and under mild conditions of pH and temperature. Our results show that the enzymatic route described represents an efficient and sustainable alternative to the chemical synthesis of indo dyes, with a potentially high impact in the cosmetic and hair dye industries.

FUSED TRICYCLIC SILYL COMPOUNDS AND METHODS OF USE THEREOF FOR THE TREATMENT OF VIRAL DISEASES

no abstract published

Laccase-catalysed homocoupling of primary aromatic amines towards the biosynthesis of dyes

Coloured disubstituted benzoquinonimine trimeric structures are obtained as main reaction products of the oxidation of p-electron donor pri-mary aromatic amines using two different laccases, CotA-laccase from Baccilus subtilus and TvL from Trametes versicolor. These orange-red to purple products, presenting high molar extinction coeffi-cients, presumably result from oxidative homocou-pling reactions, through the formation of N-C bonds at positions 2 and 5, of the laccase oxidised inter-mediate as showed in the proposed oxidative path-way. The product of 1,4-phenylenediamine is shown to be the trimer known as Bandrowski's base which has an established role in hair and fur dyeing. Our results also show that the occurrence and/or rates of oxidation of aromatic amines are strongly dependent on the presence of p-electron releasing substituents in the aromatic ring and are independent on the properties of the enzyme used. Overall our data con-tribute for (i) understanding key features of laccase reactivity with p-substituted aromatic amines and (ii) establishing enzymatic processes that lead to the syn-thesis of coloured bio-products under mild condi-tions with potential impact in the cosmetic and dye industries.