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Phosphorus pentachloride is the chemical compound with the formula PCl 5. It is one of the most important phosphorus chlorides/oxychlorides, others being PCl 3 and POCl 3. PCl 5 finds use as a chlorinating reagent. It is a colourless, water-sensitive solid, although commercial samples can be yellowish and contaminated with hydrogen chloride.
The von Braun amide degradation is the chemical reaction of a monosubstituted amide with phosphorus pentachloride or thionyl chloride to give a nitrile and an organohalide. [1] It is named after Julius Jacob von Braun, who first reported the reaction. [2] [3] The von Braun amide degradation
The Vilsmeier–Haack reaction (also called the Vilsmeier reaction) is the chemical reaction of a substituted formamide (1) with phosphorus oxychloride and an electron-rich arene (3) to produce an aryl aldehyde or ketone (5): RC(=O)NR ′ R″ + HArZ + POCl 3 + H 2 O → RC(=O)ArZ + NR ′ R″H + HCl + H 3 PO 4
Phosphorus pentachloride, phosphorus pentabromide, and phosphorus heptabromide are ionic in the solid and liquid states; PCl 5 is formulated as PCl 4 + PCl 6 –, but in contrast, PBr 5 is formulated as PBr 4 + Br −, and PBr 7 is formulated as PBr 4 + Br 3 −. They are widely used as chlorinating and brominating agents in organic chemistry.
The Michaelis–Arbuzov reaction is the chemical reaction of a trivalent phosphorus ester with an alkyl halide to form a pentavalent phosphorus species and another alkyl halide. Commonly, the phosphorus substrate is a phosphite ester (P(OR) 3) and the alkylating agent is an alkyl iodide. [11] The mechanism of the Michaelis–Arbuzov reaction
Alkyl chlorides are most easily prepared by treating alcohols with thionyl chloride (SOCl 2) or phosphorus pentachloride (PCl 5), but also commonly with sulfuryl chloride (SO 2 Cl 2) and phosphorus trichloride (PCl 3): ROH + SOCl 2 → RCl + SO 2 + HCl 3 ROH + PCl 3 → 3 RCl + H 3 PO 3 ROH + PCl 5 → RCl + POCl 3 + HCl
Phosphoryl chloride (commonly called phosphorus oxychloride) is a colourless liquid with the formula P O Cl 3. It hydrolyses in moist air releasing phosphoric acid and fumes of hydrogen chloride. It is manufactured industrially on a large scale from phosphorus trichloride and oxygen or phosphorus pentoxide. [4] It is mainly used to make ...
Phosphoric chloride difluoride can be made by the reaction of liquid phosphorus pentachloride with phosphorodifluoridic acid HPO 2 F 2 or diphosphoridic tetrafluoride P 2 O 3 F 4. This reaction takes place at room temperature up to 60 °C. The POF 2 Cl bubbles off as a gas, and can be condensed by cooling with dry ice-acetone mixture. [3]