Tricyclohexylphosphine

Base Information

• Chemical Name: Tricyclohexylphosphine
• CAS No.: 2622-14-2
• Molecular Formula: C18H33P
• Molecular Weight: 280.434
• Hs Code.: HOSPHINE PRODUCT IDENTIFICATION
• European Community (EC) Number: 220-069-2
• NSC Number: 158657
• UNII: 34HJS55VCG
• DSSTox Substance ID: DTXSID9062562
• Nikkaji Number: J87.295D
• Wikipedia: Tricyclohexylphosphine
• Wikidata: Q10860579
• Mol file: 2622-14-2.mol

Synonyms:Tricyclohexylphosphine;2622-14-2;TRICYCLOHEXYL PHOSPHINE;Tricyclohexylphosphane;Phosphine, tricyclohexyl-;PCy3;Tricyclohexyl-phosphane;tris(cyclohexyl)phosphine;MFCD00003853;34HJS55VCG;C18H33P;EINECS 220-069-2;Tricyclohexyl Phosphine (90per cent);NSC 158657;NSC-158657;P(Cy)3;tricyclohexylphophine;tricyclohexylphoshine;tricyclohexylphospine;tricylcohexylphosphine;triscyclohexylphospine;NSC158657;TCHP;tricyclohexyl phospine;tricyclohexyl-phospine;tricydohexyl phosphine;tricyclo-hexylphosphine;tricyclohexyl-phosphine;Cy3P;P(cHex)3;tri(cyclohexyl)phosphine;tri-cyclohexyl phosphine;tri-cyclohexyl-phosphine;P(c-Hex)3;tri cyclo hexyl phosphine;tri-(cyclohexyl)phosphine;Tri(cyclohexyl)-phosphine;UNII-34HJS55VCG;(Cy)3P;SCHEMBL26953;DTXSID9062562;AMY11744;BCP22580;C18-H33-P;AKOS015840835;GC10101;AS-58394;BP-10825;CS-0020124;FT-0634408;T1165;EN300-67378;A25286;10.14272/WLPUWLXVBWGYMZ-UHFFFAOYSA-N.1;doi:10.14272/WLPUWLXVBWGYMZ-UHFFFAOYSA-N.1;J-016328;J-525065;Q10860579;F0001-2552;PCY3;PHOSPHORUS TRICYCLOHEXYL;TRICYCLOHEXYL-PHOSPHANE;TRICYCLOHEXYLPHOSPHINE;Tricyclohexyl phosphine;Piperazine-1-carboxylic acid TERT-Butyl ester;PIBOC;N-(T-BOC)Piperazine;N-T-Butoxycarbonylpiperazine

Chemical Property of Tricyclohexylphosphine

Chemical Property:

• Appearance/Colour: white to yellow crystalline powder
• Vapor Pressure: 9.7E-06mmHg at 25°C
• Melting Point: 81-83 °C(lit.)
• Boiling Point: 383.434 °C at 760 mmHg
• Flash Point: 195.609 °C
• PSA: 13.59000
• Density: 0.909 g/mL at 25 °C
• LogP: 6.46640
• Storage Temp.: −20°C
• Sensitive.: Air Sensitive
• Water Solubility.: Soluble in most organic solvents. Insoluble in water.
• XLogP3: 5.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 3
• Exact Mass: 280.231988050
• Heavy Atom Count: 19
• Complexity: 202

Purity/Quality:

99% ^*data from raw suppliers

TricyclohexylPhosphine(90%) ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn,Xi,F
• Hazard Codes: Xi,Xn,F
• Statements: 36/37/38-22-37/38-36-19-11-67-65-63-48/20-40
• Safety Statements: 26-36/37-62-37/39-36-33-29-16

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Other Classes -> Phosphorus Compounds
• Canonical SMILES: C1CCC(CC1)P(C2CCCCC2)C3CCCCC3
• Recent ClinicalTrials: RAGE Inhibition to Decrease Therapy Cardiotoxicity in Women With Early Breast Cancer
• Description: Tricyclohexyl phosphine is the tertiary phosphine with the formula P( C 6H11) 3. Commonly used as a ligand in organometallic chemistry, it is often abbreviated to PCy 3, where Cy stands for cyclohexyl. It is characterized by both high basicity (pK a = 9.7) and a large ligand cone angle (170°). Tricyclohexyl-phosphine is more basic (and so a better c-donor) than tribu tyiphosphine, which in turn is more basic than triphenyl phosphIne.
• Uses: Tricyclohexyl Phosphine is a ligand catalyst used primarily in organometallic chemistry. Ligand used in the Pd-catalyzed coupling of malononitrile with aryl halides. suzuki reaction: Bulky phosphine ligand used with a Pd(0)-triolefinic macrocycle catalyst for Suzuki coupling of aryl bromides and chlorides. This ligand is applied with Ni as a key intermediate in the formation of cylcopentane compounds. As a reagent, Tricyclohexylphosphine is used for a range of metal-catalyzed organic transformations. Crabtree's catalyst is an organoiridium compound containing tricyclohexyl phosphine used for hydrogenation of mono-, di-, tri-, and tetra- substituted substrates and hydrogen transfer reactions. Grubbs' catalysts consists of transition metal ruthenium and tricylohexyl phosphine utilized in olefin metathesis in synthetic organic chemistry. Tricyclohexylphosphine is used as a ligand in organometallic chemistry. As a reagent, it is used for a range of metal-catalyzed organic transformations. Crabtree's catalyst is an organoiridium compound containing tricyclohexyl phosphine used for hydrogenation of mono-, di-, tri-, and tetra- substituted substrates and hydrogen transfer reactions. Grubbs?catalysts consists of transition metal ruthenium and tricylohexyl phosphine utilized in olefin metathesis in synthetic organic chemistry.

Technology Process of Tricyclohexylphosphine

There total 53 articles about Tricyclohexylphosphine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 95.0%

pyridine (110-86-1) + RuCl2(PCy3)2(=13CH2) → RuCl2(13CH2PCy3)(py)3 + tricyclohexylphosphine (2622-14-2)

Guidance literature:

In benzene-d6; at 20 ℃; for 0.166667h; Inert atmosphere; Glovebox;

DOI:10.1021/jacs.6b08372

Reference yield: 92.0%

PCy3*BH3 → tricyclohexylphosphine (2622-14-2)

Guidance literature:

With methanol; 4 A molecular sieve; In 1,4-dioxane; at 115 ℃; for 42h;

DOI:10.1246/bcsj.77.1931

Reference yield: 90.0%

tricyclohexylphosphonium chloride → tricyclohexylphosphine (2622-14-2)

Guidance literature:

With sodium hydroxide; In water; Product distribution / selectivity;

upstream raw materials:

cyclohexylmagnesiumchloride

cyclohexylmagnesium bromide

tricyclohexyl(dithiocarboxylato)phosphonium

triphenylphosphine

Downstream raw materials:

butyl-tricyclohexyl-phosphonium; iodide

tricyclohexylmethylphosphonium iodide

tricyclohexylphosphine oxide

tricyclohexylphosphine sulfide

Refernces

Hydride and borohydride derivatives of (pentamethylcyclopentadienyl)(tertiary phosphine)ruthenium

10.1021/om00150a032

The research focused on the synthesis and characterization of hydride and borohydride derivatives of (pentamethylcyclopentadienyl)(tertiary phosphine)ruthenium complexes. The purpose of this study was to explore the chemistry of middle- and late-transition-metal polyhydride complexes, which are of interest due to their potential as catalysts for H/D exchange reactions and C-H bond activation. The researchers successfully synthesized a series of trihydride complexes, (q5-C5Me5)RuH3(PR3), and tetrahydroborate complexes, (q5-C5Me5)Ru(PR3)(BH4), using various phosphine ligands (PR3) such as PMe3, PEt3, P(i-Pr)3, PCy3, PPh2Me, and PPh3. The synthesis involved the reaction of NaBH4 with (q5-C5Me5)RuCl2(PR3) in ethanol, and the resulting trihydrides were characterized by IR and 'H NMR spectroscopy. The study also included a single-crystal X-ray diffraction study of (q5-C5Me5)RuH3(PPh3), revealing its pseudo C3 symmetry. Additionally, the research investigated the photoinduced H/D exchange reaction under UV irradiation, which led to the exchange among the hydrides, coordinated phosphine, and solvent. The conclusions of the study provided insights into the structure and reactivity of these ruthenium complexes, contributing to the understanding of their potential applications in catalysis.