2-((4-Bromophenyl)(hydroxy)methylene)malononitrile
[CAS# 1502821-65-9]

Identification

• Classification: Organic raw materials >> Nitrile compound
• Name: 2-((4-Bromophenyl)(hydroxy)methylene)malononitrile
• Molecular Formula: C₁₀H₅BrN₂O
• Molecular Weight: 249.06
• CAS Registry Number: 1502821-65-9
• SMILES: C1=CC(=CC=C1C(=C(C#N)C#N)O)Br

Properties

• Density: 1.7$+/-$0.1 g/cm³ Calc.^*
• Boiling point: 353.5$+/-$42.0 $degree$C 760 mmHg (Calc.)^*
• Flash point: 167.6$+/-$27.9 $degree$C (Calc.)^*
• Index of refraction: 1.641 (Calc.)^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Discovery and Applications

2-((4-Bromophenyl)(hydroxy)methylene)malononitrile is an organic compound belonging to the family of highly activated olefinic malononitrile derivatives. Compounds of this type attracted considerable attention in organic and medicinal chemistry during the twentieth century because the presence of the malononitrile group strongly activates adjacent double bonds and enables a wide range of condensation and cyclization reactions. The development and study of substituted benzylidene malononitriles, including compounds bearing halogenated phenyl groups, formed part of broader research aimed at producing useful intermediates for synthetic chemistry and biologically active molecules. The discovery of compounds structurally related to 2-((4-Bromophenyl)(hydroxy)methylene)malononitrile occurred through investigations of the Knoevenagel condensation reaction. In this reaction, aromatic aldehydes react with malononitrile under basic conditions to produce highly conjugated arylidene malononitrile derivatives. Chemists studying the reactivity of aromatic aldehydes containing substituents such as halogens found that the condensation with malononitrile yielded products with strong electron-withdrawing character and distinctive physical properties. The introduction of a bromine atom into the phenyl ring was of particular interest because halogen substitution can influence both electronic properties and reactivity in subsequent chemical transformations. The compound has been investigated primarily as a synthetic intermediate. The activated double bond between the aromatic ring and the malononitrile moiety allows the molecule to participate in a variety of organic reactions. Chemists have used similar benzylidene malononitrile derivatives in Michael addition reactions, cyclization reactions, and heterocycle synthesis. The presence of two cyano groups strongly stabilizes negative charge during these transformations, which makes such compounds valuable building blocks in the preparation of more complex molecular structures. Another area of application for compounds of this structural class is in the synthesis of heterocyclic compounds. The electrophilic double bond of benzylidene malononitriles can react with nucleophiles containing nitrogen, sulfur, or oxygen atoms to form rings such as pyridines, pyrimidines, and other heterocycles. These reactions have been used extensively in research laboratories to generate libraries of heterocyclic compounds for pharmacological screening. Because heterocycles are common structural motifs in pharmaceuticals and agrochemicals, intermediates like this compound have played a role in the development of new molecules for biological evaluation. Substituted benzylidene malononitriles have also been examined in materials-related research. The conjugated structure produced by the aromatic ring, the central carbon-carbon double bond, and the electron-withdrawing cyano groups gives these molecules strong electronic polarization. This property has led chemists to explore related compounds for potential applications in organic electronic materials and nonlinear optical systems. Although not all derivatives have practical technological applications, the structural features present in this compound have contributed to studies of molecular electronic effects and conjugated systems. In synthetic organic chemistry, compounds of this type have often served as versatile intermediates in multicomponent reactions. Multicomponent condensation processes involving aromatic aldehydes, malononitrile, and other reagents can generate complex molecular frameworks in a single synthetic step. These methods have been widely studied because they provide efficient routes to functionalized molecules with potential biological activity. The ability of benzylidene malononitrile derivatives to participate in such reactions has made them useful starting materials in the design of new synthetic methodologies. The brominated aromatic ring in 2-((4-Bromophenyl)(hydroxy)methylene)malononitrile also offers additional opportunities for chemical modification. Bromine atoms attached to aromatic rings can participate in substitution reactions or metal-catalyzed coupling reactions, allowing chemists to introduce other functional groups or extend the conjugated system. Such transformations have been important in the preparation of more complex aromatic compounds and advanced intermediates used in chemical research. Through its structural features and reactivity, 2-((4-Bromophenyl)(hydroxy)methylene)malononitrile represents a member of a broader group of activated malononitrile derivatives that have been widely used in organic synthesis. Studies of these compounds have contributed to the development of numerous synthetic strategies for constructing heterocycles, functionalized aromatic molecules, and other chemically important structures. Their role as reactive intermediates has ensured their continued use in laboratory research focused on developing new reactions and preparing compounds of potential practical significance.

References

2022. Aromatic amide compound, pharmaceutical composition and use thereof (granted). CN Patent.
URL: CN-115894376-B

2022. Aromatic amide compound, pharmaceutical composition and application thereof. CN Patent.
URL: CN-115894376-A