• 1. Kinetics of the decomposition of a chemiluminescent reagent bis(2,4-dinitrophenyl) oxalate in aqueous acetonitrile
  Helmi Neuvonen J. Chem. Soc. Perkin Trans. 2 1994 89
• 2. Characteristics of key intermediates generated in uncatalyzed bis(2,4-dinitrophenyl) oxalate (DNPO) chemiluminescence reactions
  Ji Hoon Lee,James C. Rock,Mark A. Schlautman,Elizabeth R. Carraway J. Chem. Soc. Perkin Trans. 2 2002 1653
• 3. Novel aryl oxalate esters for peroxyoxalate chemiluminescence reactions
  Kazuhiro Imai,Hiroyoshi Nawa,Motoaki Tanaka,Hiroshi Ogata Analyst 1986 111 209
• 4. Synthesis and evaluation of aryl oxalates as peroxyoxalate chemiluminescence reagents
  Kenichiro Nakashima,Kouichi Maki,Shuzo Akiyama,Wei Hong Wang,Yukie Tsukamoto,Kazuhiro Imai Analyst 1989 114 1413
• 5. Self-reporting of damage in underwater hierarchical ionic skins via cascade reaction-regulated chemiluminescence
  Liangying Jia,Jing Xiao,Jiwei Cui,Jingcheng Hao,Xu Wang Mater. Horiz. 2022 9 2128

• Solvents and Organic Chemicals Organic Compounds Benzenoids Benzene and substituted derivatives Phenoxyacetic acid derivatives
• Other Chemical Reagents

Bis(2,4-dinitrophenyl) oxalate (CAS No. 16536-30-4): Properties, Applications, and Research Insights

Bis(2,4-dinitrophenyl) oxalate, with the CAS No. 16536-30-4, is a specialized organic compound that has garnered significant attention in both academic and industrial research. This compound, often abbreviated as DNPO, belongs to the class of aryl oxalates and is characterized by its unique molecular structure, which includes two 2,4-dinitrophenyl groups attached to an oxalate core. Its distinct properties make it a subject of interest in fields such as chemiluminescence, analytical chemistry, and material science.

The chemical formula of Bis(2,4-dinitrophenyl) oxalate is C₁₄H₆N₄O₁₀, and its molecular weight is 414.22 g/mol. The presence of nitro groups in its structure contributes to its high reactivity and potential applications in energy transfer processes. Researchers have explored its role in chemiluminescent reactions, where it acts as a key component in light-emitting systems. This property has led to its use in forensic science for detecting trace amounts of substances, as well as in environmental monitoring for analyzing pollutants.

One of the most intriguing aspects of Bis(2,4-dinitrophenyl) oxalate is its ability to generate chemiluminescence when combined with hydrogen peroxide and a fluorescent dye. This reaction, known as the peroxyoxalate chemiluminescence, is widely studied for its efficiency and sensitivity. The mechanism involves the formation of a high-energy intermediate, which transfers energy to the dye, resulting in light emission. This phenomenon has practical applications in bioimaging, medical diagnostics, and even security inks for anti-counterfeiting measures.

In recent years, the demand for sustainable and eco-friendly materials has driven research into Bis(2,4-dinitrophenyl) oxalate as a potential candidate for green chemistry applications. Its ability to participate in energy-efficient reactions aligns with the global push for reducing carbon footprints. Additionally, its photophysical properties have been investigated for use in organic electronics, such as light-emitting diodes (LEDs) and sensors, where its stability and performance are critical.

The synthesis of Bis(2,4-dinitrophenyl) oxalate typically involves the reaction of oxalyl chloride with 2,4-dinitrophenol under controlled conditions. This process requires precise temperature and pH control to ensure high yield and purity. Analytical techniques such as nuclear magnetic resonance (NMR) and mass spectrometry (MS) are commonly employed to characterize the compound and verify its structure. Researchers are also exploring alternative synthetic routes to improve efficiency and reduce waste, in line with green chemistry principles.

From a safety and handling perspective, Bis(2,4-dinitrophenyl) oxalate should be stored in a cool, dry environment away from direct sunlight and incompatible materials. While it is not classified as a hazardous substance under standard regulations, proper laboratory practices should always be followed to minimize risks. This includes the use of personal protective equipment (PPE) such as gloves and goggles when handling the compound.

The versatility of Bis(2,4-dinitrophenyl) oxalate extends to its potential use in nanotechnology and advanced materials. For instance, its incorporation into nanoparticle-based systems could enhance the efficiency of chemiluminescent probes for biomedical applications. Furthermore, its electron-accepting properties make it a candidate for organic photovoltaic cells, contributing to the development of renewable energy technologies.

In conclusion, Bis(2,4-dinitrophenyl) oxalate (CAS No. 16536-30-4) is a multifaceted compound with wide-ranging applications in science and technology. Its unique chemiluminescent properties, combined with its potential for sustainable chemistry, position it as a valuable tool for researchers and industries alike. As advancements in material science and green chemistry continue, the role of DNPO is expected to expand, offering new opportunities for innovation and discovery.

• 134145-66-7(Acetic acid, (2,4,6-trinitrophenoxy)-)
• 7614-96-2(Phenol, 2,4,6-trinitro-, acetate (ester))
• 1523-09-7(Phenol, 2,6-dinitro-,1-acetate)
• 25141-25-7(Acetic acid,2-(2,4-dinitrophenoxy)-)
• 139004-51-6(Acetic acid, (2,6-dinitrophenoxy)-)
• 131761-75-6(Acetic acid, (5-methoxy-2-nitrophenoxy)-, methyl ester)
• 17318-84-2(Ethanedioic acid, ethyl 2-nitrophenyl ester)
• 1878-87-1(2-(2-nitrophenoxy)acetic acid)
• 19125-93-0(Ethanedioic acid, bis(2-nitrophenyl) ester)
• 7506-93-6(methyl (2-nitrophenoxy)acetate)