| 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 | [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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