page_title: Organophosphorus compound
section_title: Primary and secondary phosphines
hierarchical_section_title: Organophosphorus compound / Organophosphorus(III) compounds, main categories / Phosphines / Primary and secondary phosphines
caption_attribution_description: English: Phosphane Stability
context_page_description: Organophosphorus compounds are organic compounds containing phosphorus. They are used primarily in pest control as an alternative to chlorinated hydrocarbons that persist in the environment. Some organophosphorus compounds are highly effective insecticides, although some are extremely toxic to humans, including sarin and VX nerve agents.
  Organophosphorus chemistry is the corresponding science of the properties and reactivity of organophosphorus compounds. Phosphorus, like nitrogen, is in group 15 of the periodic table, and thus phosphorus compounds and nitrogen compounds have many similar properties. The definition of organophosphorus compounds is variable, which can lead to confusion. In industrial and environmental chemistry, an organophosphorus compound need contain only an organic substituent, but need not have a direct phosphorus-carbon bond. Thus a large proportion of pesticides, are often included in this class of compounds.
  Phosphorus can adopt a variety of oxidation states, and it is general to classify organophosphorus compounds based on their being derivatives of phosphorus(V) vs phosphorus(III), which are the predominant classes of compounds.
context_section_description: In addition to the other reactions associated with phosphines, those bearing P-H groups exhibit additional reactivity associated with the P-H bonds. They are readily deprotonated using strong bases to give phosphide anions.  Primary and secondary phosphines are generally prepared by reduction of related phosphorus halides or esters.  For example, phosphonates are reduced to primary phosphines:
  The stability is attributed to conjugation between the aromatic ring and the phosphorus lone pair.
caption: Example of reduction of phosphonate ester to a primary phosphine.
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