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General chemical structure of the organophosphate functional group. In organic chemistry, organophosphates (also known as phosphate esters, or OPEs) are a class of organophosphorus compounds with the general structure O=P(OR) 3, a central phosphate molecule with alkyl or aromatic substituents. [1]
Phosphate esters have the general structure P(=O)(OR) 3 feature P(V). Such species are of technological importance as flame retardant agents, and plasticizers. Lacking a P−C bond, these compounds are in the technical sense not organophosphorus compounds but esters of phosphoric acid. Many derivatives are found in nature, such as ...
Tris(2,4-di-tert-butylphenyl)phosphite is an organophosphorus compound with the formula [(C 4 H 9) 2 C 6 H 3 O] 3 P. This white solid is a widely used stabilizer in polymers where it functions as a secondary antioxidant.
See the general structure image of an ortho- (or mono-) phosphate ester below on the left, where any of the R groups can be a hydrogen or an organic radical. Di- and tripoly- (or tri-) phosphate esters, etc. are also possible.
As a reagent in organic synthesis, it is used to convert alcohols to the corresponding diethylphosphate esters. It is a colorless liquid with a fruity odor. It is a corrosive, and as a cholinesterase inhibitor, highly toxic through dermal absorption. [1] The molecule is tetrahedral.
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Phosphite esters may be used as reducing agents in more specialised cases. For example, triethylphosphite is known to reduce certain hydroperoxides to alcohols formed by autoxidation [7] (scheme). In this process the phosphite is converted to a phosphate ester. This reaction type is also utilized in the Wender Taxol total synthesis.
Purple acid phosphatases (PAPs) (EC 3.1.3.2) are metalloenzymes that hydrolyse phosphate esters and anhydrides under acidic condition. [1] [2] In their oxidised form, PAPs in solution are purple in colour. This is due to the presence of a dinuclear iron centre, [3] to which a tyrosine residue is connected via a charge transfer. [4]