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Wittig Reagent

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Identification
Molecular formula
C21H17OP
CAS number
2136-75-6
IUPAC name
1-(triphenyl-lambda5-phosphanylidene)propan-2-one
State
State

At room temperature, the Wittig Reagent is typically in a solid state. When pure, it is a fine crystalline solid that needs to be handled under inert atmosphere to prevent decomposition.

Melting point (Celsius)
78.00
Melting point (Kelvin)
351.15
Boiling point (Celsius)
280.00
Boiling point (Kelvin)
553.15
General information
Molecular weight
336.26g/mol
Molar mass
336.2640g/mol
Density
1.2000g/cm3
Appearence

The Wittig Reagent typically appears as a yellow to orange crystalline solid. It can also be observed as a pale yellow powder. It is sensitive to air and moisture, which can affect its appearance if not stored properly.

Comment on solubility

Solubility of 1-(triphenyl-lambda5-phosphanylidene)propan-2-one

The solubility of 1-(triphenyl-lambda5-phosphanylidene)propan-2-one can be influenced by several factors due to its unique structure. It contains a phosphanylidene group attached to a ketone, which can impact its interactions with solvents. When considering the solubility of this compound, a few key points emerge:

  • Polarity: The presence of both the triphenylphosphine unit and the ketone can lead to a moderately polar character, which suggests that it might be more soluble in polar solvents.
  • Solvent Compatibility: Common polar aprotic solvents such as dimethyl sulfoxide (DMSO) or acetonitrile could facilitate dissolution due to favorable solute-solvent interactions.
  • Limited Solubility in Non-polar Solvents: Conversely, in non-polar solvents such as hexane or toluene, this compound may exhibit limited or extremely low solubility as a result of its polar functionality.

In summary, while the solubility of 1-(triphenyl-lambda5-phosphanylidene)propan-2-one can be significant in polar solvents, its behavior in non-polar environments may be quite different. Therefore, careful selection of solvents is crucial when working with this compound in practical applications.

Interesting facts

Overview of 1-(Triphenyl-lambda5-phosphanylidene)propan-2-one

1-(Triphenyl-lambda5-phosphanylidene)propan-2-one is a fascinating chemical compound that showcases the interactions between phosphorus and carbonyl functionalities.

Key Features

  • Versatile Usage: This compound has significant applications in the field of organic synthesis and catalysis, particularly in the activation of carbonyl compounds.
  • Phosphorus Role: The phosphorus atom in the compound plays a crucial role in stabilizing the carbonyl group, affecting its reactivity and properties.
  • Synthetic Applications: It is often utilized as a reagent for the construction of complex organic molecules, displaying a broad scope of reactions.

Scientific Insights

The unique structure of this compound allows scientists to explore various properties, such as:

  • Electron-Withdrawing Properties: The triphenylphosphine moiety acts as an electron-withdrawing group, which can influence the behavior of attached functional groups.
  • Stability in Different Conditions: The compound exhibits intriguing stability under various environmental conditions, making it a subject of study in thermochemical analyses.
  • Potential in Material Science: There’s ongoing research into the potential of such phosphorus-containing compounds in the development of new materials and pharmaceuticals.

Anecdote

One of the interesting aspects observed in research is how compounds like 1-(triphenyl-lambda5-phosphanylidene)propan-2-one can behave differently when interacting with biological systems compared to traditional organic compounds, leading to unexpected reactions that can foster new developments in drug design.

In summary, 1-(triphenyl-lambda5-phosphanylidene)propan-2-one not only enhances our understanding of phosphorus chemistry but also demonstrates the beauty and complexity of molecular interactions in organic synthesis.

Synonyms
1-(Triphenylphosphoranylidene)acetone
2-Propanone, 1-(triphenylphosphoranylidene)-
Acetylmethylenetriphenylphosphorane
215-878-2
1439-36-7
(Acetylmethylene)triphenylphosphorane
1-(Triphenylphosphoranylidene)propan-2-one
1-(Triphenylphosphoranylidene)-2-propanone
(Acetonylidenetriphenyl)phosphorane
(Acetylmethylene)triphenylphosphine
(Triphenylacetylmethylene)phosphorane
2-Propanone, (triphenylphosphoranylidene)-
MFCD00008774
Triphenylphosphoranylidene-2-propanone
NSC 407394
1-(triphenyl-lambda5-phosphanylidene)propan-2-one
Acetylmethylene-triphenylphosphorane
2-PROPANONE, TRIPHENYLPHOSPHORANYLIDENE-
(Triphenylphosphoranylidene)-2-propanone
1-TRIPHENYLPHOSPHORANYLIDENE-2-PROPANONE
AI3-63066
EINECS 215-878-2
BRN 0750077
Phosphonium, acetonyltriphenyl-
1-(triphenyl-$l^{5}-phosphanylidene)propan-2-one
(2-Oxopropylidene)triphenylphosphorane
SCHEMBL1508
Acetonyltriphenylphosphonium-
WLN: 1V1UPR&R&R
acetonylidenetriphenylphosphorane
triphenylphosphoranylideneacetone
1-(Triphenylphosphoranyl)acetone
acetonylidene-triphenylphosphorane
DTXSID60162572
acetylmethylene triphenylphosphorane
2-oxopropylidenetriphenylphosphorane
acetylmethylidene triphenylphosphoran
STR03989
triphenylphosphoranyliden-2-propanone
NSC407394
Phosphonium, (2-oxopropyl)triphenyl-
2-oxo-1-propylidenetriphenylphosphoran
AKOS002528407
NSC-407394
1-(Triphenylphosphanylidene)propan-2-one
methylcarbonylmethylenetriphenylphosphorane
1-triphenylphosphoran-ylidene-2-propanone
BP-12292
SY007889
methylcarbonylmethylenetriphenyl phosphorane
DB-018031
A1439
CS-0041020
NS00044656
1-(Triphenyl-5-phosphanylidene)-propan-2-one
EN300-102571
Methyl (triphenylphosphoranylidene)methyl ketone
1-(Triphenylphosphoranylidene)-2-propanone, 99%
1-(TRIPHENYL-??-PHOSPHANYLIDENE)PROPAN-2-ONE
InChI=1/C21H19OP/c1-18(22)17-23(19-11-5-2-6-12-19,20-13-7-3-8-14-20)21-15-9-4-10-16-21/h2-17H,1H