| Identification | More | [Name]
Tricyclohexyl phosphine | [CAS]
2622-14-2 | [Synonyms]
PHOSPHORUS TRICYCLOHEXYL
TCHP
TRICYCLOHEXYL-PHOSPHANE
TRICYCLOHEXYLPHOSPHINE
tricyclohexyl-phosphin
TRICYCLOHEXYLPHOSPHINE, 20 WT. % SOLUTI&
TRICYCLOHEXYLPHOSPHINE, 1M IN TOLUENE
TRICYCLOHEXYLPHOSPHINE, 1M IN TETRAHYDR&
Tricyclohexylphosphine, 20% Toluene Solution
Tricyclohexylphosphine,97%
Tricyclohexylphosphine(20%intoluene),min.88%
tricyclohexylphosphine solution
PCY3
tricyclohexylphospine
TRICYCLOHEXYLPHOSPHINE: (20% IN TOLUENE)
TRICYCLOHEXYLPHOSPHINE, DISSOLVED IN TOLUENE (20% CONCENTRATION)
TRICYCLOHEXYL PHOSPHINE (TCHP)
Tricyclohexylphosphine, technical grade
Tricyclohexylphosphine (contains Tricyclohexylphosphine Oxide) (ca. 18% in Toluene, ca. 0.60mol/L)
Phosphine, tricyclohexyl- | [EINECS(EC#)]
220-069-2 | [Molecular Formula]
C18H33P | [MDL Number]
MFCD00003853 | [Molecular Weight]
280.43 | [MOL File]
2622-14-2.mol |
| Chemical Properties | Back Directory | [Appearance]
White or pale yellow crystalline powder | [Melting point ]
81-83 °C (lit.) | [Boiling point ]
110°C | [density ]
0.909 g/mL at 25 °C
| [Fp ]
48 °F
| [storage temp. ]
−20°C
| [solubility ]
Chloroform (Slightly), DMSO (Slightly, Heated, Sonicaetd), Ethyl Acetate (Slightly) | [form ]
Solution | [color ]
White to off-white | [Specific Gravity]
0.9 | [Water Solubility ]
Soluble in most organic solvents. Insoluble in water. | [Hydrolytic Sensitivity]
8: reacts rapidly with moisture, water, protic solvents | [Sensitive ]
Air Sensitive | [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) | [Storage Precautions]
Air sensitive;Store under nitrogen | [EPA Substance Registry System]
2622-14-2(EPA Substance) |
| Questions And Answer | Back Directory | [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. |
| Safety Data | Back Directory | [Hazard Codes ]
Xi,Xn,F | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin .
R22:Harmful if swallowed.
R37/38:Irritating to respiratory system and skin .
R36:Irritating to the eyes.
R19:May form explosive peroxides.
R11:Highly Flammable.
R67:Vapors may cause drowsiness and dizziness.
R65:Harmful: May cause lung damage if swallowed.
R63:Possible risk of harm to the unborn child.
R48/20:Harmful: danger of serious damage to health by prolonged exposure through inhalation . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36/37:Wear suitable protective clothing and gloves .
S62:If swallowed, do not induce vomiting: seek medical advice immediately and show this container or label .
S37/39:Wear suitable gloves and eye/face protection .
S36:Wear suitable protective clothing .
S33:Take precautionary measures against static discharges .
S29:Do not empty into drains .
S16:Keep away from sources of ignition-No smoking . | [RIDADR ]
UN 2056 3/PG 2 | [WGK Germany ]
3 | [TSCA ]
Yes | [HazardClass ]
3 | [PackingGroup ]
III | [HS Code ]
29319090 |
| Hazard Information | Back Directory | [Chemical Properties]
clear colorless to pale yellow solution | [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 c | [Purification Methods]
It recrystallises from EtOH [Boert et al. J Am Chem Soc 109 7781 1987]. [Beilstein 16 IV 947.] |
| Questions and Answers (Q&A) | Back Directory | [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.
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