Vanadyl acetylacetonate

Names
IUPAC name

oxobis(2,4-pentanedionato)vanadium(IV)

Other names

VO(acac)2, VO(pd)2

Identifiers

CAS Number

* 3153-26-2 Y

3D model (JSmol)

* Interactive image

ChemSpider |

* 17344686

EC Number |

* 221-590-8

PubChem CID

* 16217092

InChI

* InChI=1S/2C5H8O2.O.V/c2*1-4(6)3-5(2)7;;/h2*3,6H,1-2H3;;/b2*4-3+;;

Key: FSJSYDFBTIVUFD-XHTSQIMGSA-N

SMILES

* CC(=[O+]1)C=C(C)O[V-3]12(#[O+])OC(C)=CC(C)=[O+]2

Properties

Chemical formula

| C10H14O5V
Molar mass | 265.157 g/mol
Appearance  | blue-green
Density | 1.50 g/cm3
Melting point |  258 °C (496 °F; 531 K)
Boiling point |  174 °C (345 °F; 447 K) at 0.2 torrs (27 Pa)

Solubility in water

| CHCl3, CH2Cl2, Benzene, CH3OH, CH3CH2OH

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

Vanadyl acetylacetonate is the chemical compound with the formula VO(acac)2, where acac– is the conjugate base of acetylacetone. It is a blue-green solid that dissolves in polar organic solvents. The coordination complex consists of the vanadyl group, VO2+, bound to two acac– ligands via the two oxygen atoms on each. Like other charge-neutral acetylacetonate complexes, it is not soluble in water.

## Contents

* 1 Synthesis
* 2 Structure and properties
* 3 Applications
* 4 Biomedical aspects
* 5 External links
* 6 References

## Synthesis

The complex is generally prepared from vanadium(IV), e.g. vanadyl sulfate:[1]

VOSO4 \+ 2 Hacac → VO(acac)2 \+ H2SO4

It can also be prepared by a redox reaction starting with vanadium pentoxide. In this reaction, some acetylacetone is oxidized to 2,3,4-Pentanetrione.[1]

## Structure and properties

The complex has a square pyramidal structure with a short V=O bond. This d1 compound is paramagnetic. Its optical spectrum exhibits two transitions. It is a weak Lewis acid, forming adducts with pyridine and methylamine.[1]

## Applications

It is used in organic chemistry as a catalyst for the epoxidation of allylic alcohols by tert-butyl hydroperoxide (TBHP). The VO(acac)2–TBHP system exclusively epoxidizes geraniol at the allylic alcohol position, leaving the other alkene of geraniol untouched. By comparison, m-CPBA, another epoxidizing agent, reacts with both alkenes, creating the products in a two to one ratio favoring reaction at the alkene away from the hydroxyl group. TBHP oxidizes VO(acac)2 to a vanadium(V) species which coordinates the alcohol of the substrate and the hydroperoxide, directing the epoxidation to occur at the alkene close to this coordination site.[2][3]

## Biomedical aspects

Vanadyl acetylacetonate exhibits insulin mimetic properties, in that it can stimulate the phosphorylation of protein kinase B (PKB/Akt) and glycogen synthase kinase 3 (GSK-3).[4] It has also been shown inhibit tyrosine phosphatase (PTPase), PTPases[clarification needed] such as PTP1B, which dephosphorylates insulin receptor beta subunit, thus increasing its[clarification needed] phosphorylation, allowing for a prolonged activation of IRS-1, PKB, and GSK-3, allowing them to exert their anti-diabetic properties.[4]

## External links

* Oxidations tutorial

## References

1. ↑ 1.0 1.1 1.2 Rowe, Richard A.; Jones, Mark M. (1957). "Vanadium(IV) Oxy(acetylacetonate)". Inorganic Syntheses. Inorganic Syntheses. 5. pp. 113–116. doi:10.1002/9780470132364.ch30. ISBN 978-0-470-13236-4.
2. ↑ Itoh, Takashi; Jitsukawa, Koichiro; Kaneda, Kiyotomi; Teranishi, Shiichiro (1979). "Vanadium-catalyzed epoxidation of cyclic allylic alcohols. Stereoselectivity and stereocontrol mechanism". Journal of the American Chemical Society 101 (1): 159–169. doi:10.1021/ja00495a027. Bibcode: 1979JAChS.101..159I.
3. ↑ Rossiter, Bryant E.; Wu, Hsyueh-Liang; Hirao, Toshikazu (2007-03-15). "Vanadyl Bis(acetylacetonate)". Encyclopedia of Reagents for Organic Synthesis. John Wiley & Sons. doi:10.1002/047084289X.rv003m.pub2. ISBN 978-0-471-93623-7.
4. ↑ 4.0 4.1 Mehdi, Mohamad Z.; Srivastava, Ashok K. (2005). "Organo-vanadium compounds are potent activators of the protein kinase B signaling pathway and protein tyrosine phosphorylation: Mechanism of insulinomimesis". Archives of Biochemistry and Biophysics 440 (2): 158–164. doi:10.1016/j.abb.2005.06.008. PMID 16055077.

* v
* t
* e

Vanadium compounds

Vanadium(0)|

* V(CO)6

Vanadium(II)|

* VBr2
* VCl2
* VO
* VS

Vanadium(III)|

* VBr3
* VCl3
* VF3
* VI3
* VN
* V2O3
* V2(SO4)3
* V2S3

Vanadium(IV)|

* VC
* VO2
* VS2
* VCl4
* VF4

| Organovanadium(IV) compounds|

* VO(C5H7O2)2

|

Vanadyl(IV) compounds|

* VOSO4

Vanadium(V)|

* V2O5
* VOCl3
* VOF3
* VF5
* V2S5

| Vanadyl(V) compounds|

* VO(ClO4)3

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