Triphenylphosphine: Difference between revisions

Chemical Compound
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UNII
ChEBI
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	Properties
Chemical Formula
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Revision as of 23:46, 9 February 2025

An organophosphorus compound used in organic synthesis

Triphenylphosphine (often abbreviated as TPP or PPh_) is an organophosphorus compound with the formula P(C_H_)_. It is a common reagent in organic synthesis and is used as a ligand in coordination chemistry.

Structure and properties

Triphenylphosphine is a white crystalline solid at room temperature. It is soluble in organic solvents such as benzene, diethyl ether, and chloroform. The compound is characterized by a trigonal pyramidal geometry around the phosphorus atom, with three phenyl groups attached.

Synthesis

Triphenylphosphine is typically synthesized by the reaction of phosphorus trichloride with phenylmagnesium bromide or phenyl lithium. The reaction proceeds as follows:

${PCl}_{3} + 3 C_{6} H_{5} MgBr \to P (C_{6} H_{5})_{3} + 3 MgBrCl$

Applications

In organic synthesis

Triphenylphosphine is widely used in organic synthesis. It is a key component in the Wittig reaction, which is used to convert carbonyl compounds into alkenes. The reaction involves the formation of a phosphonium ylide intermediate.

Deoxygenation reactions

Triphenylphosphine is also used in deoxygenation reactions, such as the conversion of amine oxides to amines. This reaction is depicted in the following image:

As a ligand

In coordination chemistry, triphenylphosphine acts as a ligand that can stabilize transition metal complexes. It is often used in homogeneous catalysis, such as in the hydroformylation of olefins.

Derivatives

Triphenylphosphine can be modified to form various derivatives, such as TPPTS (triphenylphosphine-3,3',3-trisulfonate), which is used in aqueous catalysis.

Safety

Triphenylphosphine is generally considered to be of low toxicity, but it can cause irritation to the skin and eyes. Proper handling and storage are recommended to avoid exposure.

Related pages

References

@@ Line 1: / Line 1: @@
-'''Triphenylphosphine''' ('''PPh<sub>3</sub>''') is a [[phosphine]] ligand often used in [[organometallic chemistry]] and [[coordination chemistry]]. It is a common and versatile reagent characterized by its bulky size and its ability to stabilize metal complexes. The compound consists of a phosphorus atom bonded to three phenyl groups.
+{{Short description|An organophosphorus compound used in organic synthesis}}
+{{Chembox
+| verifiedrevid = 477239679
+| ImageFile = Triphenylphosphine-2D-skeletal_Smokefoot-style.svg
+| ImageSize = 200px
+| ImageAlt = Skeletal formula of triphenylphosphine
+| IUPACName = Triphenylphosphane
+| OtherNames = TPP, PPh_
+| Section1 = {{Chembox Identifiers
+  | CASNo = 603-35-0
+  | PubChem = 1038
+  | ChemSpiderID = 1010
+  | UNII = 0F8P2QJZ0T
+  | ChEBI = 30089
+  | ChEMBL = 1405
+  | SMILES = c1ccc(cc1)P(c2ccccc2)c3ccccc3
+  | InChI = 1S/C18H15P/c1-4-10-16(11-5-1)19(17-12-6-2-7-13-17)18-14-8-3-9-15-18/h1-15H
+  | InChIKey = RIOQSEWOXXDEQQ-UHFFFAOYSA-N
+}}
+}}
-==Properties==
+'''Triphenylphosphine''' (often abbreviated as '''TPP''' or '''PPh_''') is an [[organophosphorus compound]] with the formula '''P(C_H_)_'''. It is a common [[reagent]] in [[organic synthesis]] and is used as a [[ligand]] in [[coordination chemistry]].
-Triphenylphosphine is a white, crystalline solid at room temperature. It is soluble in many organic solvents, such as [[diethyl ether]], [[benzene]], and [[acetone]]. The molecule is relatively stable in air, although it can slowly oxidize, turning yellow upon prolonged exposure to air due to the formation of phosphine oxide.
+==Structure and properties==
+Triphenylphosphine is a [[white]] [[crystalline]] solid at room temperature. It is soluble in [[organic solvents]] such as [[benzene]], [[diethyl ether]], and [[chloroform]]. The compound is characterized by a [[trigonal pyramidal]] geometry around the phosphorus atom, with three phenyl groups attached.
 ==Synthesis==
-The synthesis of triphenylphosphine involves the reaction of [[chlorobenzene]] with [[phosphorus trichloride]] in the presence of a base such as sodium. This process is known as the Schwenk synthesis:
+Triphenylphosphine is typically synthesized by the reaction of [[phosphorus trichloride]] with [[phenylmagnesium bromide]] or [[phenyl lithium]]. The reaction proceeds as follows:
-C<sub>6</sub>H<sub>5</sub>Cl + PCl<sub>3</sub> → P(C<sub>6</sub>H<sub>5</sub>)<sub>3</sub> + 3 HCl
+<math>\text{PCl}_3 + 3 \text{C}_6\text{H}_5\text{MgBr} \rightarrow \text{P}(\text{C}_6\text{H}_5)_3 + 3 \text{MgBrCl}</math>
 ==Applications==
-Triphenylphosphine finds extensive use in the field of [[organic synthesis]] and [[catalysis]]. It acts as a ligand for various metal catalysts involved in processes such as the [[Suzuki coupling]] and the [[Mizoroki-Heck reaction]]. Additionally, it is used in the synthesis of [[phosphonium salts]], which are intermediates in the [[Wittig reaction]] for the formation of alkenes.
+===In organic synthesis===
+Triphenylphosphine is widely used in organic synthesis. It is a key component in the [[Wittig reaction]], which is used to convert [[carbonyl compounds]] into [[alkenes]]. The reaction involves the formation of a [[phosphonium ylide]] intermediate.
+===Deoxygenation reactions===
+Triphenylphosphine is also used in deoxygenation reactions, such as the conversion of [[amine oxides]] to [[amines]]. This reaction is depicted in the following image:
+[[File:Deoxygenation_of_an_aromatic_amine_oxide_using_triphenylphosphine.png|thumb|center|400px|Deoxygenation of an aromatic amine oxide using triphenylphosphine]]
+===As a ligand===
+In coordination chemistry, triphenylphosphine acts as a [[ligand]] that can stabilize [[transition metal]] complexes. It is often used in [[homogeneous catalysis]], such as in the [[hydroformylation]] of [[olefins]].
+==Derivatives==
+Triphenylphosphine can be modified to form various derivatives, such as [[TPPTS]] (triphenylphosphine-3,3',3''-trisulfonate), which is used in [[aqueous]] [[catalysis]].
+[[File:TPPTS.png|thumb|right|200px|Structure of TPPTS]]
 ==Safety==
-Triphenylphosphine is generally considered to be of low toxicity, but it should be handled with care. It can cause irritation to the skin, eyes, and respiratory system. Proper personal protective equipment should be worn when handling this chemical.
+Triphenylphosphine is generally considered to be of low toxicity, but it can cause irritation to the skin and eyes. Proper handling and storage are recommended to avoid exposure.
-==See Also==
+==Related pages==
 * [[Phosphine]]
-* [[Organometallic chemistry]]
+* [[Wittig reaction]]
 * [[Coordination chemistry]]
-* [[Catalysis]]
-[[Category:Chemical compounds]]
+==References==
-[[Category:Phosphines]]
+{{Reflist}}
 [[Category:Organophosphorus compounds]]
-[[Category:Ligands]]
+[[Category:Reagents for organic chemistry]]
-{{Chem-stub}}

Chemical Compound


Identifiers
CAS Number
PubChem CID
ChemSpider ID
UNII
ChEBI
ChEMBL
Properties
Chemical Formula
Molar Mass
Appearance
Density
Melting Point
Boiling Point
Hazards
GHS Pictograms	[[File:\|50px]]
GHS Signal Word
GHS Hazard Statements
NFPA 704	[[File:\|50px]]
References