846-20-8

Basic information

• Product Name: 2-bromo-1,4,5,8-naphthalenetetracarboxylic acid dianhydride
• Synonyms: 2-bromo-1,4,5,8-naphthalenetetracarboxylic acid dianhydride
• CAS NO: 846-20-8
• Molecular Weight: 347.078
• Mol File: 846-20-8.mol
• Article Data: 13

Chemical Properties

• Melting Point: 360 °C
• Boiling Point: 666.0±50.0 °C(Predicted)
• Density: 2.090±0.06 g/cm3(Predicted)
• CAS DataBase Reference: 2-bromo-1,4,5,8-naphthalenetetracarboxylic acid dianhydride(CAS DataBase Reference)
• NIST Chemistry Reference: 2-bromo-1,4,5,8-naphthalenetetracarboxylic acid dianhydride(846-20-8)
• EPA Substance Registry System: 2-bromo-1,4,5,8-naphthalenetetracarboxylic acid dianhydride(846-20-8)

Safety Data

• Hazardous Substances Data: 846-20-8(Hazardous Substances Data)

Usage

Description

2-bromo-1,4,5,8-naphthalenetetracarboxylic acid dianhydride is a chemical compound with the molecular formula C12H2Br2O6. It is a derivative of naphthalene tetracarboxylic acid and is characterized by the presence of a bromine atom in its chemical structure.

Uses

Used in Polyimide Films and Coatings Production:
2-bromo-1,4,5,8-naphthalenetetracarboxylic acid dianhydride is used as a key component in the production of polyimide films and coatings due to its high thermal stability, excellent mechanical properties, and resistance to chemicals and solvents.
Used in Organic Compounds Synthesis:
2-bromo-1,4,5,8-naphthalenetetracarboxylic acid dianhydride is used as a building block in the synthesis of various organic compounds, contributing to the development of new materials and products.
Used in Drug Development:
2-bromo-1,4,5,8-naphthalenetetracarboxylic acid dianhydride is used as a starting material in drug development, owing to its potential applications in the creation of pharmaceutical compounds.
Used in Pharmaceutical Applications:
2-bromo-1,4,5,8-naphthalenetetracarboxylic acid dianhydride is used as a subject of research for its potential antibacterial and antifungal properties, indicating its possible use in the development of new pharmaceuticals for treating infections.

Upstream product

• 81-30-1 1,4,5,8-naphthalenetetracarboxylic dianhydride 

Downstream Products

• 926643-78-9 N,N′-bis(n-octyl)-2,6-dibromo-1,4,5,8-naphthalenetetracarboxylic diimide 
• 942130-54-3 N,N’-bis(n-octyl)-2-bromonaphthalene-1,4,5,8-bis(dicarboximide) 
• 1315605-26-5 N,N'-di(n-hexyl)-2-bromonaphthalene-1,4,5,8-bis(dicarboximide) 
• 1224622-74-5 2-bromo-1,4,5,8-tetra(n-butoxycarbonyl)naphthalene 
• 1224622-75-6 2,6-dibromo-1,4,5,8-tetra(n-butoxycarbonyl)naphthalene 

Relevant articles and documents

Organic room-temperature phosphorescence from halogen-bonded organic frameworks: hidden electronic effects in rigidified chromophores

Development of purely organic materials displaying room-temperature phosphorescence (RTP) will expand the toolbox of inorganic phosphors for imaging, sensing or display applications. While molecular solids were found to suppress non-radiative energy dissipation and make the RTP process kinetically favourable, such an effect should be enhanced by the presence of multivalent directional non-covalent interactions. Here we report phosphorescence of a series of fast triplet-forming tetraethyl naphthalene-1,4,5,8-tetracarboxylates. Various numbers of bromo substituents were introduced to modulate intermolecular halogen-bonding interactions. Bright RTP with quantum yields up to 20% was observed when the molecule is surrounded by a Br?O halogen-bonded network. Spectroscopic and computational analyses revealed that judicious heavy-atom positioning suppresses non-radiative relaxation and enhances intersystem crossing at the same time. The latter effect was found to be facilitated by the orbital angular momentum change, in addition to the conventional heavy-atom effect. Our results suggest the potential of multivalent non-covalent interactions for excited-state conformation and electronic control. This journal is

Controlling intermolecular redox-doping of naphthalene diimides

Naphthalene diimide (NDI) with tertiary amine side chains is used to n-dope a series of NDI derivatives of varying energy levels. We demonstrate a photoinduced, intermolecular redox-doping process in which a dimethylpropyl amine side chain attached to one NDI reduces another NDI derivative to form radical anions. The influence of the aromatic core substituents on energy levels, doping efficacy and radical anion stability is studied by cyclic voltammetry, UV-Vis and electron paramagnetic resonance (EPR) spectroscopy. In general, the HOMO energy level of the NDI is responsible for the doping process and the LUMO for air stability of the resulting radical anion. The most electron deficient NDI derivative having two cyano substituents displays the highest doping yield and yields air stable radical anions for both light- and thermally-induced doping. Thermal doping is further accompanied by morphologic changes that stabilize radical anions in air.

Targeting Multiple Effector Pathways in Pancreatic Ductal Adenocarcinoma with a G-Quadruplex-Binding Small Molecule

Human pancreatic ductal adenocarcinoma (PDAC) involves the dysregulation of multiple signaling pathways. A novel approach to the treatment of PDAC is described, involving the targeting of cancer genes in PDAC pathways having over-representation of G-quadruplexes, using the trisubstituted naphthalene diimide quadruplex-binding compound 2,7-bis(3-morpholinopropyl)-4-((2-(pyrrolidin-1-yl)ethyl)amino)benzo[lmn][3,8]phenanthroline-1,3,6,8(2H,7H)-tetraone (CM03). This compound has been designed by computer modeling, is a potent inhibitor of cell growth in PDAC cell lines, and has anticancer activity in PDAC models, with a superior profile compared to gemcitabine, a commonly used therapy. Whole-transcriptome RNA-seq methodology has been used to analyze the effects of this quadruplex-binding small molecule on global gene expression. This has revealed the down-regulation of a large number of genes, rich in putative quadruplex elements and involved in essential pathways of PDAC survival, metastasis, and drug resistance. The changes produced by CM03 represent a global response to the complexity of human PDAC and may be applicable to other currently hard-to-treat cancers.