chlororhodium; tris(triphenylphosphane)

• ChemBase ID: 112767
• Molecular Formular: C54H45ClP3Rh
• Molecular Mass: 925.214883
• Monoisotopic Mass: 924.14776801
• SMILES: Cl[Rh].c1ccc(cc1)P(c1ccccc1)c1ccccc1.c1ccc(cc1)P(c1ccccc1)c1ccccc1.c1ccc(cc1)P(c1ccccc1)c1ccccc1
• Canonical SMILES: c1ccc(cc1)P(c1ccccc1)c1ccccc1.c1ccc(cc1)P(c1ccccc1)c1ccccc1.c1ccc(cc1)P(c1ccccc1)c1ccccc1.[Rh]Cl
• InChI: InChI=1S/3C18H15P.ClH.Rh/c3*1-4-10-16(11-5-1)19(17-12-6-2-7-13-17)18-14-8-3-9-15-18;;/h3*1-15H;1H;/q;;;;+1/p-1
• InChIKey: IXAYKDDZKIZSPV-UHFFFAOYSA-M

NAMES AND DATABASE IDS

Names

• IUPAC name: chlororhodium; tris(triphenylphosphane)
• IUPAC Traditional name: chlororhodium; tris(triphenylphosphine)
• Synonyms: RHODIUM TRIS(TRIPHENYLPHOSPHINE)CHLORIDE; NSC 124140; RhCl(PPh3)3; Rhodium(I) tris(triphenylphosphine) chloride; Wilkinson’s catalyst; Tris(triphenylphosphine)rhodium(I) chloride; Wilkinson's catalyst; Tris(triphenylphosphine)rhodium(I) chloride; Chlorotris(triphenylphosphine)rhodium(I); Wilkinson 催化剂; 三(三苯膦基)氯化铑(I); 三(三苯基膦)氯化铑(I)

Database IDs

• CAS Number: 14694-95-2
• EC Number: 238-744-5
• MDL Number: MFCD00010016
• Beilstein Number: 4581440
• Merck Index: 1410047
• PubChem SID: 24889752; 162097567; 24852305; 24851950
• PubChem CID: 0

CALCULATED PROPERTIES

• H Acceptors: 0
• H Donor: 0
• LogD (pH = 5.5): 5.1066
• LogD (pH = 7.4): 5.1066
• Log P: 5.1066
• Molar Refractivity: 81.6229 cm^3
• Polarizability: 32.34495 Å^3
• Polar Surface Area: 0.0 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Soluble in most solvents (e.g. benzene, ethanol, chloroform, dichloromethane) but with phosphine dissociation. Reacts with O2 in solution
• Apperance: Micro Crystals
• Melting Point: 245-250 °C (dec.); ca 250°C dec.

Safety Information

• European Hazard Symbols: Corrosive (C)
• German water hazard class: 3
• Risk Statements: 53; R:34
• Safety Statements: 60-61; S:26-27/28-36/37/39-46-64
• TSCA Listed: 是
• GHS Hazard statements: H413
• GHS Precautionary statements: P273-P501A
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥97.0% (CH); 97%; 99.9% trace metals basis
• Grade: purum
• Linear Formula: [(C6H5)3P]3RhCl

DETAILS

MP Biomedicals - 05225710

MP Biomedicals Rare Chemical collection

Sigma Aldrich - 205036

Application
Useful catalyst for the efficient cross-coupling of activated alkenyl tosylates with arylboronic acids.6 Also used to catalyze the cleavage of allyl phenolic ethers to phenols with DABCO.7
Hydrosilylation CatalystsCatalyst used for many organic reactions including:
• Chemoselective allylic alkylations1
• Stoichiometric activation of Si-H bonds2 and hydrosilylations3
• Inter- and intramolecular hydroacylation of alkenes along with a cocatalyst4
• Polymerization of diorganostannanes5
Packaging
1 g in glass bottle
250 mg in glass bottle
5 g in poly bottle

Sigma Aldrich - 199982

Packaging
1, 5 g in glass bottle
Application
Hydrosilylation CatalystsCatalyst used for many organic reactions including:
• Chemoselective allylic alkylations1
• Stoichiometric activation of Si-H bonds2 and hydrosilylations3
• Inter- and intramolecular hydroacylation of alkenes along with a cocatalyst4
• Polymerization of diorganostannanes5

Sigma Aldrich - 93403

Application
Hydrosilylation CatalystsCatalyst used for many organic reactions including:
• Chemoselective allylic alkylations1
• Stoichiometric activation of Si-H bonds2 and hydrosilylations3
• Inter- and intramolecular hydroacylation of alkenes along with a cocatalyst4
• Polymerization of diorganostannanes5

REFERENCES

• Homogeneous hydrogenation catalyst: J. Chem. Soc.(A), 1711 (1966), useful e.g. for the selective reduction of an unhindered alkene, of an unconjugated in the presence of a conjugated alkene: Org. Synth. Coll., 6, 459 (1988), or an alkene in the presence of a nitro group: J. Org. Chem., 67, 3163 (2002). Hydroxyl groups protected as their allyl ethers may be deprotected by isomerization with Wilkinson's Catalyst to the more readily-hydrolyzed 1-propenyl ether: J. Org. Chem., 38, 3224 (1973).
• Aldehydes undergo decarbonylation with the complex: Tetrahedron Lett., 3969 (1965); J. Am. Chem. Soc., 93, 5465 (1971). The need for stoichiometric amounts of the complex, due to formation of an inactive Rh carbonyl complex, is a serious disadvantage. However, in the presence of Diphenylphosphonic azide, A12124, which regenerates the catalyst from the carbonyl complex, decarbonylations can be carried out catalytically at room temperature, providing a much more cost-effective and attractive method for this type of transformation: J. Org. Chem., 57, 5075 (1992).
• Catalyst for hydrosilylation reactions, e.g. with Triethylsilane, A10320, including ɑ?-unsaturated ketones to silyl enol ethers, which can be hydrolyzed to saturated ketones: Organometallics, 1, 1390 (1982), and ɑ?-unsaturated esters to silyl ketene acetals with high (Z)-selectivity: Synth. Commun., 17, 1 (1989).
• Co-catalyst giving improved results in intramolecular Heck coupling reactions catalyzed by Pd(OAc)₂: J. Org. Chem., 64, 3461 (1999).
• Used by Grigg for the catalytic [2+2+2] cyclotrimerization of alkynes, providing an efficient route to benzene-fused ring systems. See, e.g.: J. Chem. Soc., Perkin 1, 1357 (1988). For an intermolecular example with reaction scheme, see 1,6-Heptadiyne, A11318. Intramolecular assembly of suitably constructed triynes can also be accomplished to form benzene rings: Tetrahedron, 45, 6239 (1989). Also catalyzes the [5+2] cycloaddition of vinylcyclopropanes and alkynes: J. Am. Chem. Soc., 117, 4720 (1995); 120, 1940 (1998).
• Electron-deficient olefins undergo Rh-catalyzed 1,4-addition with Bis(pinacolato)diboron, L16088, e.g. 2-cyclohexen-1-one to the ?-borylcyclohexanone: Tetrahedron Lett., 43, 2323 (2002):