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Tris(triphenylphosphine)rhodiu

CAS：14694-95-2
MW:925.2
MF：C54H45ClP3Rh-

Tris(triphenylphosphine)rhodium(I) chloride, with the chemical formula C54H45ClP3Rh and CAS registry number 14694-95-2, is a compound known for its applications in catalysis and coordination chemistry. This complex, also referred to as Wilkinson's catalyst, consists of a rhodium atom coordinated to three triphenylphosphine ligands and a chloride ion. It is commonly used as a homogeneous catalyst for various organic transformations, including hydrogenation, hydroformylation, and carbonylation reactions. Tris(triphenylphosphine)rhodium(I) chloride exhibits high stability and reactivity, making it a valuable tool in synthetic chemistry. Its versatile nature and wide range of applications have contributed to its popularity in the field of organometallic chemistry.

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Names and ldentifier
Properties
Use and Manufacturing
Msds
NMR Spectrum
Other Information
Computational chemical data
Related Questions
Realated Product Infomation

1. Names and Identifiers

1.1 Name: Tris(triphenylphosphine)rhodiu

1.2 Synonyms: (SP-4-2)-Chlorotris(triphenylphosphine)rhodium; CHLOROTRIS(TRIPHENYLPHOSPHINE)RHODATE (I); Chlorotris(triphenylphosphine)rhodium; Chlorotris(triphenylphosphine)rhodium(I); DECARBON; MFCD00010016; NSC 124140; Phosphine, triphenyl-, rhodium salt, hydrochloride (1:1:1); Rhodium - triphenylphosphine hydrochloride (1:1:1); Rhodium tris(triphenylphosphine) chloride; Rhodium, chlorotris(triphenylphosphine)-; Rhodium, chlorotris(triphenylphosphine)-, (SP-4-2)-; TRIS(TRIPHENYLPHOSPHINE)CHLORORHODIUM; Tris(triphenylphosphine)chlororhodium(I); Tris(triphenylphosphine)rhodium chloride; Tris(triphenylphosphine)rhodium monochloride; TRIS(TRIPHENYLPHOSPHINE)RHODIUM(1) CHLORIDE; TRIS(TRIPHENYLPHOSPHINE)RHODIUM(I) CHLORIDE; TRIS(TRIPHENYLPHOSPHINE)RHODIUM(I) CHLORIDE POLYMER BOUND; WILKINSON CATALYST; Wilkinson's catalyst; Wilkinson's complex;

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1.3 CAS No.: 14694-95-2

1.4 CID: 84599

1.5 EINECS: 238-744-5

1.6 Molecular Formula: C54H45ClP3Rh-

1.7 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;/p-1

1.8 InChkey: QBERHIJABFXGRZ-UHFFFAOYSA-M

1.9 Canonical Smiles: C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.[Cl-].[Rh]

1.10 Isomers Smiles: C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.[Cl-].[Rh]

2. Properties

2.1 Solubility: Soluble in most solvents (e.g. benzene, ethanol, chloroform, dichloromethane) but with phosphine dissociation. Reacts with O{2} in solution

2.2 Appearance: Red-brown to maroonCrystalline Powder

2.3 Storage: Keep Cold.

2.4 Chemical Properties: magenta crystals

2.5 Color/Form: Red-brown to maroon

2.6 Water Solubility: insoluble

2.7 StorageTemp: 2-8°C

3. Use and Manufacturing

3.1 Description

Tris(triphenylphosphine)rhodium(I) chloride, with the chemical formula RhCl(PPh3)3, has the CAS number 14694-95-2. It is a coordination compound consisting of a rhodium(I) ion coordinated with three triphenylphosphine ligands and one chloride ion. It appears as a yellow crystalline solid with no distinct odor. The molecular formula of tris(triphenylphosphine)rhodium(I) chloride is RhCl(C18H15P)3. This compound is insoluble in water, but soluble in organic solvents such as chloroform and benzene. Tris(triphenylphosphine)rhodium(I) chloride is considered to be stable under normal conditions. However, it should be handled with care as it may be harmful if swallowed, inhaled, or in contact with skin. It is also important to avoid exposure to high temperatures or open flames, as it may emit toxic fumes. Proper protective measures should be taken when working with this compound to ensure safety.

Applicable Fields

Catalysis: Tris(triphenylphosphine)rhodium(I) chloride is widely used as a catalyst in various chemical reactions. Its purpose in catalysis involves its ability to activate certain substrates and facilitate the formation of new chemical bonds. The mechanism of action in catalysis is based on the coordination of the rhodium(I) ion with the triphenylphosphine ligands, which allows for the stabilization of reactive intermediates and the promotion of desired reactions.

Organometallic Chemistry: This compound is also utilized in organometallic chemistry research and synthesis. Its purpose in this field involves its ability to serve as a precursor for the preparation of other rhodium complexes and organometallic compounds. Tris(triphenylphosphine)rhodium(I) chloride can undergo various reactions to form different coordination complexes, which can be further utilized in the development of new catalysts and functional materials.

Storage

Conditions: Store in a cool and dry place.

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3.2 Purification Methods: It forms dark burgundy crystals from hot EtOH after refluxing for 30minutes. When the solution is heated for only 5minutes, orange crystals are formed. Heating the orange crystals in EtOH yields red crystals. Crystallisation from Me2CO gives the orange crystals. The two forms have similar IR spectra, but the X-ray diffraction patterns are slighly different. [Osborne et al. J Chem Soc (A) 1711 1966, Osborne & Wilkinson Inorg Synth X 67 1967, Bennett & Donaldson Inorg Chem 16 655 1977.] The solubilities are as follows: in CH2Cl2 ~2% (25o), in toluene 0.2% (25o), and less soluble in Me2CO, MeOH, BuOH and AcOH, but insoluble in pet ethers and cyclohexane. It reacts with donor solvents such as pyridine, DMSO and MeCN. Tris(triphenylphosphine)rhodiuSupplier

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3.3 Usage: suzuki reaction

4. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

Acute toxicity - Oral, Category 4

Skin sensitization, Category 1A

Hazardous to the aquatic environment, long-term (Chronic) - Category Chronic 4

2.2 GHS label elements, including precautionary statements

Pictogram(s)
Signal word	Warning
Hazard statement(s)	H302 Harmful if swallowed H317 May cause an allergic skin reaction H413 May cause long lasting harmful effects to aquatic life
Precautionary statement(s)
Prevention	P264 Wash ... thoroughly after handling. P270 Do not eat, drink or smoke when using this product. P261 Avoid breathing dust/fume/gas/mist/vapours/spray. P272 Contaminated work clothing should not be allowed out of the workplace. P280 Wear protective gloves/protective clothing/eye protection/face protection. P273 Avoid release to the environment.
Response	P301+P312 IF SWALLOWED: Call a POISON CENTER/doctor/\u2026if you feel unwell. P330 Rinse mouth. P302+P352 IF ON SKIN: Wash with plenty of water/... P333+P313 If skin irritation or rash occurs: Get medical advice/attention. P321 Specific treatment (see ... on this label). P362+P364 Take off contaminated clothing and wash it before reuse.
Storage	none
Disposal	P501 Dispose of contents/container to ...

2.3 Other hazards which do not result in classification

none

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5. NMR Spectrum

13C NMR : in CDCl3

1H NMR : 400 MHz in DMSO-d6

IR : KBr disc

IR : nujol mull

6. Synthesis Route

14694-95-2Total: 19 Synthesis Route

603-35-0 288 Suppliers

14694-95-2 176 Suppliers

89178-76-7

14694-95-2 176 Suppliers

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7. Precursor and Product

precursor:

869117-74-8

93860-48-1

15320-81-7

603-35-0

15318-33-9

36564-80-4

12092-47-6

product:

4144-94-9

7739-21-1

98-00-0

501-65-5

17185-29-4

603-35-0

19377-75-4

15318-33-9

2049-55-0

5557-98-2

87-99-0

8. Computed Properties

Molecular Weight：925.2g/mol
Molecular Formula：C₅₄H₄₅ClP₃Rh-
Compound Is Canonicalized：True
XLogP3-AA：924.14776
Monoisotopic Mass：924.14776
Complexity：202
Rotatable Bond Count：9
Hydrogen Bond Donor Count：0
Hydrogen Bond Acceptor Count：1
Topological Polar Surface Area：0
Heavy Atom Count：：59
Defined Atom Stereocenter Count：0
Undefined Atom Stereocenter Count：0
Defined Bond Stereocenter Count：0
Undefined Bond Stereocenter Count：0
Isotope Atom Count：0
Covalently-Bonded Unit Count：5
CACTVS Substructure Key Fingerprint：AAADcfB8AAMEAAAAABAAAAAAAAAAAAAAAAAwYMGDAAAAAAABVAAAGAgAAAAACACAEAAwAIAAACCAACBCAAACAAAgAAAIiAAAAIgIICKAERCAIAAggAAIiAcAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAA==

9.Other Information

Merck: 14,9758

BRN: 4581440

Chemical Properties: magenta crystals

Uses: suzuki reaction

Uses: Homogeneous hydrogenation catalyst.

Purification Methods: It forms dark burgundy crystals from hot EtOH after refluxing for 30minutes. When the solution is heated for only 5minutes, orange crystals are formed. Heating the orange crystals in EtOH yields red crystals. Crystallisation from Me2CO gives the orange crystals. The two forms have similar IR spectra, but the X-ray diffraction patterns are slighly different. [Osborne et al. J Chem Soc (A) 1711 1966, Osborne & Wilkinson Inorg Synth X 67 1967, Bennett & Donaldson Inorg Chem 16 655 1977.] The solubilities are as follows: in CH2Cl2 ~2% (25o), in toluene 0.2% (25o), and less soluble in Me2CO, MeOH, BuOH and AcOH, but insoluble in pet ethers and cyclohexane. It reacts with donor solvents such as pyridine, DMSO and MeCN.

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Usage: Chlorotris(triphenylphosphine)rhodium(I) is used as a homogeneous hydrogenation catalyst. It is used in the selective hydrogenation of alkenes and alkynes.

10. Toltal 166 Suppliers View more

Chlorotris(triphenylphosphine)rhodium(I)

Hebei Yanxi Chemical Co.,Ltd

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Baoji Guokang Healthchem co.,ltd

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Factory Supply Rhodium,chlorotris(triphenylphosphine)-, (SP-4-2)-

Amitychem Corporation

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Wuhan Circle Star Chem-medical Technology Co.,Ltd

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Tris(triphenylphosphine)rhodium(I) chloride

Dayang Chem (Hangzhou) Co., Ltd.

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Tel: Update Time:2024/06/17

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11. Related Questions

: What are the characteristics, synthesis methods, and applications of Tris(triphenylphosphine)rhodium?Introduction Tris(triphenylphosphine)rhodium is a red-purple crystalline solid, with a purity requirement of rhodium (Rh) content not less than 11.1%. This compound slowly decomposes in air and is sol..; What is the description of Tris(triphenylphosphine)rhodium? Brief description of Tris(triphenylphosphine)rhodiu The molecular formula of Tris(triphenylphosphine)rhodiu is [(C6H5) 3P]3RhCl is an aromatic compound with a special structure. It is a red-purple cr..; What is the oxidation state of Wilkinson's catalyst?Wilkinson's catalyst oxidation state refers to the electronic configuration of the metal atom in the catalyst. It is a scientific term used to describe the oxidation condition of a metal in a molecule..

12. Realated Product Infomation