Description:
O-Phthaloyl chloride, also known by synonyms such as phthaloyl dichloride and 1,2-benzenedicarbonyl dichloride, and identified by CAS number 88-95-9, is a significant organic chemical compound. It is the diacyl chloride derivative of phthalic acid. Typically, it presents as a colorless to pale yellow fuming liquid or a low-melting point solid, characterized by a sharp, pungent odor. Its notable reactivity is due to the two acyl chloride groups, which readily participate in nucleophilic acyl substitution reactions. This chemical behavior makes O-phthaloyl chloride an essential reagent in a wide array of chemical syntheses. Due to its high reactivity, particularly with water and atmospheric moisture which leads to hydrolysis, it requires careful handling under anhydrous conditions and appropriate storage to maintain its integrity and prevent decomposition.
Properties:
Property Value CAS Number 88-95-9 Chemical Formula Molar Mass 203.02 g/mol Appearance Colorless to pale yellow fuming liquid or low-melting solid Melting Point Approximately 11-14 Boiling Point Approximately 275-281 (slight decomposition) Density Approximately 1.40-1.42 g/cm³ Solubility Reacts with water and alcohols; soluble in many aprotic organic solvents (e.g., benzene, chloroform, diethyl ether) Synonyms Phthaloyl dichloride, 1,2-Benzenedicarbonyl dichloride, Phthalic acid dichloride IUPAC Name Benzene-1,2-dicarbonyl dichloride Usage:
O-Phthaloyl chloride is a highly versatile and crucial intermediate in organic synthesis, widely utilized for its capacity to introduce the phthaloyl moiety or to facilitate the formation of cyclic compounds. Its principal application lies as a potent acylating agent in various chemical transformations.
Examples of its applications include:
- Polymer Chemistry: It is a key monomer in the synthesis of high-performance polymers such as polyimides, polyesters (e.g., polyarylates), and polyphthalamides through reactions with diamines or diols.
- Dye Manufacturing: Employed as a precursor in the production of various dyestuffs, notably phthalein dyes (like phenolphthalein through Friedel-Crafts reaction with phenols) and anthraquinone-based dyes.
- Pharmaceutical Intermediates: Acts as a building block in the synthesis of certain active pharmaceutical ingredients (APIs) and other pharmaceutical compounds.
- Agrochemical Synthesis: Used in the creation of specific pesticides and herbicides.
- Organic Synthesis Reagent: Commonly used to introduce the phthaloyl protecting group for primary amines, forming phthalimides, which are stable and can be subsequently deprotected. It is also used to prepare esters, amides, and in Friedel-Crafts acylation reactions.
- Chemiluminescent Reagents: It is a critical reagent in the synthesis of luminol, a substance known for its chemiluminescence and widely used in forensic science for blood detection.
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