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

InChIKey

WLPUWLXVBWGYMZ-UHFFFAOYSA-N

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 

Yes

HazardClass 

3

PackingGroup 

III

HS Code 

29319090

MSDS

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

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