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
• Article Data: 16

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

Description

BANDROWSKI'S BASE, also known as a quinone imine, is a chemical compound characterized by amino substituents in the 2and 5-positions and 4-aminophenyl substituents on both of the imine nitrogens. It is a trimer formed from 1,4-phenylenediamine, which gives it unique properties and potential applications in various fields.

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 
• 111-30-8 Glutaraldehyde 
• 24295-03-2 2-Acetylthiazole 
• 149-73-5 trimethyl orthoformate 
• 1934-75-4 sodium dicyanamide 
• 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

• 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 
• 74-90-8 hydrogen cyanide 
• 15719-64-9 methylammonium carbonate 
• 106-50-3 1,4-phenylenediamine 
• 106-51-4 p-benzoquinone 

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.

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.

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.

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.