Хлордифенилфосфин

Description

Chlorodiphenylphosphine (diphenylchlorophosphine) is a chlorophosphine, a key precursor in the synthesis of tertiary phosphines and phosphine ligands for metal complex catalysis. The phosphorus atom in the molecule carries two phenyl substituents and a chlorine atom, which is reactive with nucleophiles: reaction with Grignard reagents, organolithium compounds or other nucleophilic reagents replaces the chlorine and introduces a third substituent on the phosphorus, giving a wide range of unsymmetrical tertiary phosphines.

Basic Attributes

• CAS No.: 1079-66-9
• Chemical formula: C12H10ClP
• English name: Chlorodiphenylphosphine
• Molecular Weight: 220.63
• Exact weight: 220.63
• BRN: 512032
• EU number: 214-093-2
• UNII: WO975PJK1Y
• NSC Number: 60407
• DSSTox ID: DTXSID7038789
• HS code: 29310095
• PSA Features: 0
• XLogP3: 3.8

Physico-chemical characteristics

• Appearance: colorless to yellow liquid
• Density: 1.19 g/cm3
• Melting point: 15–16 °C
• Boiling point: 100–102 °C at 1 Torr pressure
• Flash point: >230°F
• Refractive index: n 20/D 1.636 (lit.)
• Solubility in water: reacts violently; mixes with alcohol; slightly miscible with ammonia
• Storage Conditions: Store at room temperature (R.T.)
• Steam pressure: 1.3 hPa (20 °C)

Scope of application

• precursor for the synthesis of tertiary and chelating phosphine ligands used in catalysis on transition metal complexes
• a reagent for introducing a diphenylphosphine group into organic molecules through reaction with organometallic nucleophiles
• raw materials for the production of phosphine oxides, phosphonium salts and other organophosphorus derivatives

Storage and transportation

The substance is stored at room temperature, in a sealed container, under an inert atmosphere of nitrogen or argon, since the compound reacts violently with water and is sensitive to atmospheric oxygen. The container is kept separate from water, alcohols and oxidizing agents. A vapor pressure of 1.3 hPa at 20 °C indicates moderate volatility, so work should be carried out in a well-ventilated fume hood.

Practical features of work

The nucleophile substitution reaction for chlorine is usually carried out at reduced temperature in an anhydrous ether solvent by adding a Grignard reagent or organolithium compound dropwise to the chlorophosphine solution to control the exothermicity of the process and minimize the by-oxidation of the resulting tertiary phosphine. The resulting phosphines are often additionally protected from oxidation by atmospheric oxygen by conversion into borane complexes or sulfides at intermediate stages of isolation and purification, removing the protection at the last stage of synthesis of the target ligand.

Related compounds

Chlorodiphenylphosphine is one of the representatives of a series of arylchlorophosphines, which also includes dichlorophenylphosphine (with two chlorine atoms) and chlorodialkylphosphines. The number of chlorine atoms on phosphorus determines how many new organic substituents can be introduced by successive substitution reactions: diphenylchlorophosphine with one chlorine gives unsymmetrical tertiary phosphines in one step, while dichlorophosphines allow the construction of more complex, including chelating, ligand structures in two successive reactions.