Chloro(cyclopentadienyl)bis(triphenylphosphine)ruthenium

CpRuCl(PPh3)2

Identifiers

CAS Number

* 32993-05-8 Y

3D model (JSmol)

* Interactive image

ChemSpider |

* 34560989 N

PubChem CID

* 78076231

InChI

* InChI=1S/2C18H15P.C5H5.ClH.Ru/c2*1-4-10-16(11-5-1)19(17-12-6-2-7-13-17)18-14-8-3-9-15-18;1-2-4-5-3-1;;/h2*1-15H;1-3H,4H2;1H;/q;;-1;;+2/p-1 N

Key: WGQMSPWAXIDKEY-UHFFFAOYSA-M N

* InChI=1/2C18H15P.C5H5.ClH.Ru/c2*1-4-10-16(11-5-1)19(17-12-6-2-7-13-17)18-14-8-3-9-15-18;1-2-4-5-3-1;;/h2*1-15H;1-3H,4H2;1H;/q;;-1;;+2/p-1

Key: WGQMSPWAXIDKEY-REWHXWOFAY

SMILES

* c1ccc(cc1)P(c2ccccc2)c3ccccc3.c1ccc(cc1)P(c2ccccc2)c3ccccc3.c1ccc[cH-1]1.[Cl-].[Ru+2]

Properties

Chemical formula

| C41H35ClP2Ru
Molar mass | 726.19 g/mol
Appearance  | Orange solid
Melting point |  135 °C (275 °F; 408 K)

Solubility in water

| Insoluble
Hazards
GHS pictograms |
GHS Signal word | Warning

GHS hazard statements

| H302, H312, H315, H319, H332, H335

GHS precautionary statements

| P261, P264, P270, P271, P280, P301+312, P302+352, P304+312, P304+340, P305+351+338, P312, P321, P322, P330, P332+313, P337+313, P362, P363, P403+233, P405, P501

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

N verify (what is YN ?)
Infobox references

Tracking categories (test):

* SizeSet

Chloro(cyclopentadienyl)bis(triphenylphosphine)ruthenium is the organoruthenium half-sandwich compound with formula RuCl(PPh3)2(C5H5). It as an air-stable orange crystalline solid that is used in a variety of organometallic synthetic and catalytic transformations. The compound has idealized Cs symmetry. It is soluble in chloroform, dichloromethane, and acetone.

## Contents

* 1 Preparation
* 2 Reactions
* 3 Applications
* 4 References

## Preparation

Chloro(cyclopentadienyl)bis(triphenylphosphine)ruthenium was first reported in 1969 when it was prepared by reacting dichlorotris(triphenylphosphine)ruthenium(II) with cyclopentadiene.[1]

RuCl2(PPh3)3 \+ C5H6 → RuCl(PPh3)3(C5H5) + HCl

It is prepared by heating a mixture of ruthenium(III) chloride, triphenylphosphine, and cyclopentadiene in ethanol.[2]

## Reactions

Chloro(cyclopentadienyl)bis(triphenylphosphine)ruthenium(II) undergoes a variety of reactions often by involving substitution of the chloride. With phenylacetylene it gives the phenyl vinylidene complex:

(C5H5)(PPh3)2RuCl + HC2Ph + NH4[PF6] → [Ru(C:CHPh)(PPh3)2(C5H5)][PF6] + NH4Cl

Displacement of one PPh3 by carbon monoxide affords a chiral compound.[3]

(C5H5)(PPh3)2RuCl + CO → (C5H5)(PPh3)(CO)RuCl + PPh3

The compound can also be converted into the hydride:[4]

(C5H5)(PPh3)2RuCl + NaOMe → (C5H5)(PPh3)2RuH + NaCl + CH2O

A related complex is tris(acetonitrile)cyclopentadienylruthenium hexafluorophosphate, which has three labile MeCN ligands.

## Applications

Chloro(cyclopentadienyl)bis(triphenylphosphine)ruthenium(II) serves as a catalyst for a variety of specialized reactions. For example, in the presence of NH4PF6 it catalyzes the isomerisation of allylic alcohols to the corresponding saturated carbonyls.[5]

## References

1. ↑ "New Complexes of Ruthenium(II) with Triphenylphosphine and other Ligands". J. Chem. Soc.: 1749. 1969. doi:10.1039/J19690001749.
2. ↑ Bruce, M. I.; Hamiester, C., Swincer, A. G., Wallis, R. C. "Some η5-Cyclopentadienylruthenium(II) Complexes Containing Triphenylphosphine" Inorganic Syntheses 1982, volume 21, pp 78-82. doi:10.1002/9780470132524
3. ↑ "Some New η-Cyclopentadienyltuthenium Complexes". J. Chem. Soc. A: 2376–2382. 1971. doi:10.1039/J19710002376.
4. ↑ Wilczewski, T.; Bochenska, M.; Biernat, J. (1981). "Cyclobentadienyl-Ruthenium Complexes". J. Organomet. Chem. 215: 87–96. doi:10.1016/S0022-328X(00)84619-7.
5. ↑ Murahashi, Shun-Ichi. "Ruthenium in Organic Synthesis" (2006) Wiley-VCH: Weinheim. ISBN 978-3-527-30692-3

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Ruthenium compounds

Ru(0)|

* Ru3(CO)12
* Ru(P(C6H5)3)3(CO)2

Ru(I)|

* (C5(C6H5)4O)2H(Ru(CO)2)2H

Ru(II)|

* RuB2
* Na4Ru(N2C12H6(C6H4SO3)2)3
* (Ru((NC5H4)2)3)Cl2
* Ru(P(C6H5)3)3Cl2
* Ru(SO(CH3)2)4Cl2
* (RuCl2C6H4CH3CH(CH3)2)2
* RuClC5H5(P(C6H5)3)2
* C43H72Cl2P2Ru
* (C5H5)2Ru

Ru(III)|

* RuCl3

Ru(IV)|

* RuO2
* Sr2RuO4

Ru(V)|

* RuF5

Ru(VI)|

* RuF6

Ru(VII)|

* N(C3H7)4RuO4

Ru(VIII)|

* RuO4

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*[CID]: Compound ID
*[H302]: Harmful if swallowed
*[H312]: Harmful in contact with skin
*[H315]: Causes skin irritation
*[H319]: Causes serious eye irritation
*[H332]: Harmful if inhaled
*[H335]: May cause respiratory irritation
*[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
*[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+312]: IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell
*[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
*[P321]: Specific treatment (see … on this label)
*[P322]: Specific measures (see … on this label)
*[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
*[P363]: Wash contaminated clothing before reuse
*[P403+233]: Store in a well ventilated place. Keep container tightly closed
*[P405]: Store locked up
*[P501]: Dispose of contents/container to …
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