Tricyclohexyl phosphine Chemical Properties

Melting point:

81-83 °C (lit.)

Boiling point:

383.4±9.0 °C | Condition: Press: 760 Torr

Density 

0.909 g/mL at 25 °C

Flash point:

48 °F

storage temp. 

Inert atmosphere,2-8°C

solubility 

Chloroform (Slightly), DMSO (Slightly, Heated, Sonicaetd), Ethyl Acetate (Slightly)

form 

Solution

Specific Gravity

0.9

color 

White to off-white

Water Solubility 

Soluble in most organic solvents. Insoluble in water.

Sensitive 

Air Sensitive

Hydrolytic Sensitivity

8: reacts rapidly with moisture, water, protic solvents

BRN 

957171

Stability:

Air Sensitive, Moisture Sensitive

InChI

1S/C18H33P/c1-4-10-16(11-5-1)19(17-12-6-2-7-13-17)18-14-8-3-9-15-18/h16-18H,1-15H2

InChIKey

WLPUWLXVBWGYMZ-UHFFFAOYSA-N

SMILES

C1CCC(CC1)P(C2CCCCC2)C3CCCCC3

CAS DataBase Reference

2622-14-2(CAS DataBase Reference)

NIST Chemistry Reference

Phosphine, tricyclohexyl-(2622-14-2)

EPA Substance Registry System

Phosphine, tricyclohexyl- (2622-14-2)

Safety Information

Hazard Codes 

Xi,Xn,F

Risk 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

RIDADR 

UN 2056 3/PG 2

WGK Germany 

3

TSCA 

TSCA listed

HazardClass 

3

PackingGroup 

III

HS Code 

29319090

Storage Class

3 - Flammable liquids

Hazard Classifications

Aquatic Chronic 3
Asp. Tox. 1
Eye Irrit. 2
Flam. Liq. 2
Repr. 2
Skin Irrit. 2
STOT RE 2
STOT SE 3

MSDS

• Language:English Provider:Tricyclohexyl phosphine
• Language:English Provider:ACROS
• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

Tricyclohexyl phosphine Usage And Synthesis

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.

Chemical Properties

clear colorless to pale yellow solution

Uses

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.

Uses

1. Tricyclohexyl Phosphine is a ligand catalyst used primarily in organometallic chemistry.
2. Ligand used in the Pd-catalyzed coupling of malononitrile with aryl halides.
3. suzuki reaction: Bulky phosphine ligand used with a Pd(0)-triolefinic macrocycle catalyst for Suzuki coupling of aryl bromides and chlorides.
4. This ligand is applied with Ni as a key intermediate in the formation of cylcopentane compounds.
5. As a reagent, Tricyclohexylphosphine is used for a range of metal-catalyzed organic transformations.
6. 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.
7. Grubbs' catalysts consists of transition metal ruthenium and tricylohexyl phosphine utilized in olefin metathesis in synthetic organic chemistry.

reaction suitability

reaction type: Cross Couplings
reagent type: ligand
reaction type: Heck Reaction
reagent type: ligand
reaction type: Hiyama Coupling
reagent type: ligand
reaction type: Sonogashira Coupling
reagent type: ligand
reaction type: Suzuki-Miyaura Coupling

Synthesis

Triphenylphosphine oxide (1 mmol), dry n-hexane (1 mL) and complexed aluminum hydroxide reagent (1 mmol) were added to the Schlenk tube under nitrogen atmosphere and then the reaction was carried out with stirring at room temperature for 10 minutes. The completion of the reaction mixture was monitored by TLC spot plate and at the end of the reaction, the reaction mixture was filtered through silica gel and the reaction mixture was washed several times with ethyl acetate, the residue obtained from the evaporation of ethyl acetate was separated and purified by silica gel column chromatography using pure cyclohexane to obtain the tricyclohexylphosphine product.

Purification Methods

It recrystallises from EtOH [Boert et al. J Am Chem Soc 109 7781 1987]. [Beilstein 16 IV 947.]

Tricyclohexyl phosphine(2622-14-2)Related Product Information

• DICYCLOHEXYLPHOSPHINE
• TRICYCLOHEXYLPHOSPHINE OXIDE
• TRICYCLOHEXYLPHOSPHONIUM TETRAFLUOROBORATE
• TRICYCLOPENTYLPHOSPHINE
• TRIHEXYLPHOSPHINE
• O-(2,2,2-Trifluoroethyl)hydroxylamine hydrochloride
• Trimethylsilyl 2-(fluorosulfonyl)difluoroacetate
• BIS(TRICYCLOHEXYLPHOSPHINE)[(PHENYLTHIO)METHYLENE]RUTHENIUM (IV) DICHLORIDE
• Benzylidene-bis(tricyclohexylphosphine)dichlororuthenium
• (3-Phenyl-1H-inden-1-ylidene)bis(tricyclohexylphosphine)rutheniuM(IV) Dichloride
• Phosphine
• Bis(tricyclohexylphosphine)palladium(0)
• Bis(tricyclohexylphosphine)palladium(II) Dichloride
• TRICYCLOHEXYL-D33-PHOSPHINE CARBON DISULFIDE COMPLEX
• GRUBBS CATALYST 2ND GENERATION
• Dichlorobis(tricyclohexylphosphine) palladium
• CYCLOHEXYLPHOSPHINE
• (1,5-CYCLOOCTADIENE)(PYRIDINE)(TRICYCLOHEXYLPHOSPHINE)IRIDIUM(I) HEXAFLUOROPHOSPHATE