Triphenylphosphine oxide

Names
Preferred IUPAC name

Triphenyl-λ5-phosphanone

Other names

Triphenylphosphine oxide

Identifiers

CAS Number

* 791-28-6 Y

3D model (JSmol)

* Interactive image

Beilstein Reference

| 745854
ChEBI |

* CHEBI:36601 Y

ChEMBL |

* ChEMBL482091 Y

ChemSpider |

* 12549 Y

EC Number |

* 212-338-8

Gmelin Reference

| 6758

PubChem CID

* 13097

RTECS number |

* SZ1676000

UNII |

* Z69161FKI3 Y

InChI

* InChI=1S/C18H15OP/c19-20(16-10-4-1-5-11-16,17-12-6-2-7-13-17)18-14-8-3-9-15-18/h1-15H Y

Key: FIQMHBFVRAXMOP-UHFFFAOYSA-N Y

* InChI=1/C18H15OP/c19-20(16-10-4-1-5-11-16,17-12-6-2-7-13-17)18-14-8-3-9-15-18/h1-15H

Key: FIQMHBFVRAXMOP-UHFFFAOYAB

SMILES

* O=P(c1ccccc1)(c2ccccc2)c3ccccc3

Properties

Chemical formula

| OP(C

Molar mass | 278.291 g·mol−1
Appearance  | white crystals
Density | 1.212 g/cm3
Melting point |  154 to 158 °C (309 to 316 °F; 427 to 431 K)
Boiling point |  360 °C (680 °F; 633 K)

Solubility in water

| low
Solubility in other solvents  | polar organic solvents
Structure

Molecular shape

| tetrahedral
Hazards
Main hazards | Harmful if swallowed. Harmful to aquatic life with long lasting effects.
GHS pictograms |
GHS Signal word | Warning

GHS hazard statements

| H302, H412

GHS precautionary statements

| P261, P264, P270, P271, P273, P280, P301+312, P302+352, P304+340, P305+351+338, P312, P330, P332+313, P337+313, P362, P403+233, P405
Related compounds

Related compounds

* Triphenylphosphine sulfide
* Triphenylphosphine
* Phosphoryl chloride
* Phosphorus pentachloride

Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Y verify (what is YN ?)
Infobox references

Tracking categories (test):

* SizeSet

Triphenylphosphine oxide (often abbreviated TPPO) is the organophosphorus compound with the formula O=P(C

3, also written as Ph
3PO or PPh
3O (Ph = C

5). It is one of the more common phosphine oxides. This colourless crystalline compound is a common but potentially useful waste product in reactions involving triphenylphosphine. It is a popular reagent to induce the crystallizing of chemical compounds.

## Contents

* 1 Structure and properties
* 2 As a byproduct of organic synthesis
* 3 Coordination chemistry
* 4 References

## Structure and properties

3PO is structurally related to POCl
3.[2] As established by X-ray crystallography, the geometry around P is tetrahedral, and the P-O distance is 1.48 Å.[3] Other modifications of Ph
3PO have been found: For example, a monoclinic form crystallizes in the space group P21/c with Z = 4 and a = 15.066(1) Å, b = 9.037(2) Å, c = 11.296(3) Å, and β = 98.47(1)°.The orthorhombic modification crystallizes in the space group Pbca with Z = 4 and 29.089(3) Å, b = 9.1347(9), c = 11.261(1) Å.[4]

The oxygen center is relatively basic. The rigidity of the backbone and the basicity of the oxygen center make this species a popular agent to crystallize otherwise difficult to crystallize molecules. This trick is applicable to molecules that have acidic hydrogen atoms, e.g. phenols.[5]

## As a byproduct of organic synthesis

3PO is a byproduct of many useful reactions in organic synthesis including the Wittig, Staudinger, and Mitsunobu reactions. It is also formed when PPh
3Cl
2 is employed to convert alcohols into alkyl chlorides:

3PCl
2 \+ ROH → Ph
3PO + HCl + RCl

Triphenylphosphine can be regenerated from its oxide by treatment with a variety of deoxygenation agents, such as phosgene or trichlorosilane/triethylamine:[6]

3PO + SiHCl
3 → PPh
3 \+ 1/n (OSiCl

n \+ HCl

Triphenylphosphine oxide can be difficult to remove from reaction mixtures by means of chromatography. It is poorly soluble in hexane and cold diethyl ether. Trituration or chromatography of crude products with these solvents often leads to a good separation of triphenylphosphine oxide. Its removal is facilitated by conversion to its Mg(II) complex, which is poorly soluble in toluene or dichloromethane and can be filtered off.[7] An alternative filtration method where ZnCl
2(TPPO)
2 is formed upon addition of ZnCl
2 may be used with more polar solvents such as ethanol, ethyl acetate and tetrahydrofuran.[8]

## Coordination chemistry

NiCl
2(OPPh

3PO forms a variety of complexes. A representative complex is the tetrahedral species NiCl
2(OPPh

2.[9]

3PO is a common impurity in PPh
3. The oxidation of PPh
3 by oxygen, including air, is catalysed by many metal ions:

2 PPh
3 \+ O
2 → 2 Ph
3PO

## References

1. ↑ "Triphenylphosphine oxide" (in en). https://pubchem.ncbi.nlm.nih.gov/compound/13097#section=Safety-and-Hazards.
2. ↑ D. E. C. Corbridge "Phosphorus: An Outline of its Chemistry, Biochemistry, and Technology" 5th Edition Elsevier: Amsterdam. ISBN 0-444-89307-5.
3. ↑ Spek, Anthony L. (1987). "Structure of a Second Monoclinic Polymorph of Triphenylphosphine Oxide". Acta Crystallographica C43 (6): 1233–1235. doi:10.1107/S0108270187092345. Bibcode: 1987AcCrC..43.1233S.
4. ↑ Al-Farhan, Khalid A. (1992). "Crystal structure of triphenylphosphine oxide". Journal of Crystallographic and Spectroscopic Research 22 (6): 687–689. doi:10.1007/BF01160986.
5. ↑ M. C. Etter and P. W. Baures (1988). "Triphenylphosphine oxide as a crystallization aid". J. Am. Chem. Soc. 110 (2): 639–640. doi:10.1021/ja00210a076.
6. ↑ van Kalkeren, H. A.; van Delft, F. L.; Rutjes, F. P. J. T. (2013). "Organophosphorus Catalysis to Bypass Phosphine Oxide Waste". ChemSusChem 6 (9): 1615–24. doi:10.1002/cssc.201300368. PMID 24039197. Bibcode: 2013ChSCh...6.1615V.
7. ↑ Patent WO 1998007724. "Process for the preparation of 7-alkoxyalkyl-1,2,4-triazolo[1,5-a] pyrimidine derivatives"
8. ↑ Batesky, Donald C.; Goldfogel, Matthew J.; Weix, Daniel J. (2017). "Removal of Triphenylphosphine Oxide by Precipitation with Zinc Chloride in Polar Solvents" (in en). The Journal of Organic Chemistry 82 (19): 9931–9936. doi:10.1021/acs.joc.7b00459. PMID 28956444.
9. ↑ D. M. L. Goodgame and M. Goodgame (1965). "Near-Infrared Spectra of Some Pseudotetrahedral Complexes of Cobalt (II) and Nickel(II)". Inorg. Chem. 4 (2): 139–143. doi:10.1021/ic50024a002.

* v
* t
* e

TRP channel modulators

TRPA|

| Activators|

* 4-Hydroxynonenal
* 4-Oxo-2-nonenal
* 4,5-EET
* 12S-HpETE
* 15-Deoxy-Δ12,14-prostaglandin J2
* α-Sanshool (ginger, Sichuan and melegueta peppers)
* Acrolein
* Allicin (garlic)
* Allyl isothiocyanate (mustard, radish, horseradish, wasabi)
* AM404
* Bradykinin
* Cannabichromene (cannabis)
* Cannabidiol (cannabis)
* Cannabigerol (cannabis)
* Cinnamaldehyde (cinnamon)
* CR gas (dibenzoxazepine; DBO)
* CS gas (2-chlorobenzal malononitrile)
* Curcumin (turmeric)
* Dehydroligustilide (celery)
* Diallyl disulfide
* Dicentrine (Lindera spp.)
* Farnesyl thiosalicylic acid
* Formalin
* Gingerols (ginger)
* Hepoxilin A3
* Hepoxilin B3
* Hydrogen peroxide
* Icilin
* Isothiocyanate
* Ligustilide (celery, Angelica acutiloba)
* Linalool (Sichuan pepper, thyme)
* Methylglyoxal
* Methyl salicylate (wintergreen)
* N-Methylmaleimide
* Nicotine (tobacco)
* Oleocanthal (olive oil)
* Paclitaxel (Pacific yew)
* Paracetamol (acetaminophen)
* PF-4840154
* Phenacyl chloride
* Polygodial (Dorrigo pepper)
* Shogaols (ginger, Sichuan and melegueta peppers)
* Tear gases
* Tetrahydrocannabinol (cannabis)
* Thiopropanal S-oxide (onion)
* Umbellulone (Umbellularia californica)
* WIN 55,212-2

|

Blockers|

* Dehydroligustilide (celery)
* Nicotine (tobacco)
* Ruthenium red

TRPC|

| Activators|

* Adhyperforin (St John's wort)
* Diacyl glycerol
* GSK1702934A
* Hyperforin (St John's wort)
* Substance P

|

Blockers|

* DCDPC
* DHEA-S
* Flufenamic acid
* GSK417651A
* GSK2293017A
* Meclofenamic acid
* N-(p-Amylcinnamoyl)anthranilic acid
* Niflumic acid
* Pregnenolone sulfate
* Progesterone
* Pyr3
* Tolfenamic acid

TRPM|

| Activators|

* ADP-ribose
* BCTC
* Calcium (intracellular)
* Cold
* Coolact P
* Cooling Agent 10
* CPS-369
* Eucalyptol (eucalyptus)
* Frescolat MGA
* Frescolat ML
* Geraniol
* Hydroxycitronellal
* Icilin
* Linalool
* Menthol (mint)
* PMD 38
* Pregnenolone sulfate
* Rutamarin (Ruta graveolens)
* Steviol glycosides (e.g., stevioside) (Stevia rebaudiana)
* Sweet tastants (e.g., glucose, fructose, sucrose; indirectly)
* Thio-BCTC
* WS-3
* WS-12
* WS-23

|

Blockers|

* Capsazepine
* Clotrimazole
* DCDPC
* Elismetrep
* Flufenamic acid
* Meclofenamic acid
* Mefenamic acid
* N-(p-Amylcinnamoyl)anthranilic acid
* Nicotine (tobacco)
* Niflumic acid
* Ruthenium red
* Rutamarin (Ruta graveolens)
* Tolfenamic acid
* TPPO

TRPML|

| Activators|

* MK6-83
* PI(3,5)P2
* SF-22

|

TRPP|

| Activators|

* Triptolide (Tripterygium wilfordii)

|

Blockers|

* Ruthenium red

TRPV|

| Activators|

* 2-APB
* 5',6'-EET
* 9-HODE
* 9-oxoODE
* 12S-HETE
* 12S-HpETE
* 13-HODE
* 13-oxoODE
* 20-HETE
* α-Sanshool (ginger, Sichuan and melegueta peppers)
* Allicin (garlic)
* AM404
* Anandamide
* Bisandrographolide (Andrographis paniculata)
* Camphor (camphor laurel, rosemary, camphorweed, African blue basil, camphor basil)<!--TRPV1 and TRPV3-->
* Cannabidiol (cannabis)
* Cannabidivarin (cannabis)
* Capsaicin (chili pepper)
* Carvacrol (oregano, thyme, pepperwort, wild bergamot, others)
* DHEA
* Diacyl glycerol
* Dihydrocapsaicin (chili pepper)
* Estradiol
* Eugenol (basil, clove)
* Evodiamine (Euodia ruticarpa)
* Gingerols (ginger)
* GSK1016790A
* Heat
* Hepoxilin A3
* Hepoxilin B3
* Homocapsaicin (chili pepper)
* Homodihydrocapsaicin (chili pepper)
* Incensole (incense)
* Lysophosphatidic acid
* Low pH (acidic conditions)
* Menthol (mint)
* N-Arachidonoyl dopamine
* N-Oleoyldopamine
* N-Oleoylethanolamide
* Nonivamide (PAVA) (PAVA spray)
* Nordihydrocapsaicin (chili pepper)
* Paclitaxel (Pacific yew)
* Paracetamol (acetaminophen)
* Phorbol esters (e.g., 4α-PDD)
* Piperine (black pepper, long pepper)
* Polygodial (Dorrigo pepper)
* Probenecid
* Protons
* RhTx
* Rutamarin (Ruta graveolens)
* Resiniferatoxin (RTX) (Euphorbia resinifera/pooissonii)
* Shogaols (ginger, Sichuan and melegueta peppers)
* Tetrahydrocannabivarin (cannabis)
* Thymol (thyme, oregano)
* Tinyatoxin (Euphorbia resinifera/pooissonii)
* Tramadol
* Vanillin (vanilla)
* Zucapsaicin

|

Blockers|

* α-Spinasterol (Vernonia tweediana)
* AMG-517
* Asivatrep
* BCTC
* Cannabigerol (cannabis)
* Cannabigerolic acid (cannabis)
* Cannabigerovarin (cannabis)
* Cannabinol (cannabis)
* Capsazepine
* DCDPC
* DHEA
* DHEA-S
* Flufenamic acid
* GRC-6211
* HC-067047
* Lanthanum
* Mavatrep
* Meclofenamic acid
* N-(p-Amylcinnamoyl)anthranilic acid
* NGD-8243
* Niflumic acid
* Pregnenolone sulfate
* RN-1734
* RN-9893
* Ruthenium red
* SB-705498
* Tivanisiran
* Tolfenamic acid

See also: Receptor/signaling modulators • Ion channel modulators

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Retrieved from "https://handwiki.org/wiki/index.php?title=Chemistry:Triphenylphosphine_oxide&oldid=4177814"
*[CID]: Compound ID
*[H302]: Harmful if swallowed
*[H412]: Harmful to aquatic life with long lasting effects
*[P261]: Avoid breathing dust/fume/gas/mist/vapours/spray
*[P264]: Wash … thoroughly after handling
*[P270]: Do not eat, drink or smoke when using this product
*[P271]: Use only outdoors or in a well-ventilated area
*[P273]: Avoid release to the environment
*[P280]: Wear protective gloves/protective clothing/eye protection/face protection
*[P301+312]: IF SWALLOWED: Call a POISON CENTER or doctor/physician if you feel unwell
*[P302+352]: IF ON SKIN: Wash with soap and water
*[P304+340]: IF INHALED: Remove victim to fresh air and keep at rest in a position comfortable for breathing
*[P305+351+338]: IF IN EYES: Rinse continuously with water for several minutes. Remove contact lenses if present and easy to do – continue rinsing
*[P312]: Call a POISON CENTER or doctor/physician if you feel unwell
*[P330]: Rinse mouth
*[P332+313]: If skin irritation occurs: Get medical advice/attention
*[P337+313]: Get medical advice/attention
*[P362]: Take off contaminated clothing and wash before reuse
*[P403+233]: Store in a well ventilated place. Keep container tightly closed
*[P405]: Store locked up
*[v]: View this template
*[t]: Discuss this template
*[e]: Edit this template
*[TRP]: Transient receptor potential
*[TRPA]: Transient receptor potential ankyrin channel
*[TRPC]: Transient receptor potential canonical channel
*[TRPM]: Transient receptor potential melastatin channel
*[TRPML]: Transient receptor potential mucolipin channel
*[TRPP]: Transient receptor potential polycystin channel
*[TRPV]: Transient receptor potential vanilloid channel