Basic information
- Standard SMILES
C1CCC(P(C2CCCCC2)C2CCCCC2)CC1- InChIKey
WLPUWLXVBWGYMZ-UHFFFAOYSA-N- Molecular formula
- C18H33P
- Average molar mass
- 280.4 g/mol
- Monoisotopic mass
- 280.23198769
Names & identifiers
- Preferred name
- Tricyclohexylphosphine
- IUPAC
- tricyclohexylphosphane
- English name
- Tricyclohexyl phosphine
- Molecular formula
- C18H33P
- Molecular weight
- 280.43
Names & synonyms
Show more names
Database identifiers
- CAS
2622-14-2- PubChem CID
- 75806
- DTXSID
DTXSID9062562- UNII
- 34HJS55VCG
- EC Number
- 220-069-2
- Nikkaji
- J87.295D
Properties
Computed structural properties
- XLogP
- 5.4
- Topological polar surface area
- 0 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 0
- Rotatable bonds
- 3
- Heavy atoms
- 19
- Formal charge
- 0
- Complexity
- 202
Experimental & physicochemical properties
Physicochemical properties
- Melting point
- 81 · 81-83 °C (lit.)
- Boiling point
- 383.4 · 383.4±9.0 °C | Condition: Press: 760 Torr
- Density
- 0.909 g/mL · 0.909 g/mL at 25 °C
- Flash point
- 48 °F · 48 °F
- storage temp.
- 2 · Inert atmosphere,2-8°C
- solubility
- Chloroform (Slightly), DMSO (Slightly, Heated, Sonicaetd), Ethyl Acetate (Slightly)
- form
- Solution
- Specific Gravity
- 0.9 · 0.9
- color
- White to off-white
- Water Solubility
- Soluble in most organic solvents. Insoluble in water.
- Sensitive
- Air Sensitive
- Hydrolytic Sensitivity
- 8 · 8: reacts rapidly with moisture, water, protic solvents
- BRN
- 957171 · 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 · 2622-14-2(CAS DataBase Reference)
- FDA UNII
- 34 HJS55VCG · 34HJS55VCG
- NIST Chemistry Reference
- Phosphine, tricyclohexyl-(2622-14-2)
- EPA Substance Registry System
- Phosphine, tricyclohexyl- (2622-14-2)
- UNSPSC Code
- 12350000 · 12350000
- NACRES
- 22 · NA.22
- Symbol(GHS)
- 2 · GHS02,GHS07,GHS08
- Signal word
- Danger
- Hazard statements
- 225 · H225-H304-H315-H319-H335-H336-H361d-H373-H412
- Precautionary statements
- 210 · P210-P273-P301+P310-P303+P361+P353-P305+P351+P338-P331
- target organs
- Central nervous system, Respiratory system
- PPE
- Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter
- Hazard Codes
- Xi,Xn,F
- Risk Statements
- 36 · 36/37/38-22-37/38-36-19-11-67-65-63-48/20-40
- Safety Statements
- 26 · 26-36/37-62-37/39-36-33-29-16
- RIDADR
- 2056 · UN 2056 3/PG 2
- WGK Germany
- 3 · 3
- TSCA
- TSCA listed
- HazardClass
- 3 · 3
- PackingGroup
- III
- HS Code
- 29319090 · 29319090
- Storage Class
- 3 · 3 - Flammable liquids
- Hazard Classifications
- 3 Asp · Aquatic Chronic 3Asp. Tox. 1Eye Irrit. 2Flam. Liq. 2Repr. 2Skin Irrit. 2STOT RE 2STOT SE 3
Safety & regulation
GHS classification
GHS Classification
Danger
H251 (18.7%): Self-heating; may catch fire [Danger Self-heating substances and mixtures]
P235, P261, P264, P264+P265, P270, P271, P273, P280, P301+P316, P301+P317, P302+P352, P304+P340, P305+P351+P338, P319, P321, P330, P332+P317, P337+P317, P362+P364, P391, P403+P233, P405, P407, P410, P413, P420, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 91 reports by companies from 14 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Safety data
- PPE
- Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter
- wgk
- 3
- tsca
- TSCA listed
- ridadr
- UN 2056 3/PG 2
- hs_code
- 29319090
- risk_code
- 36/37/38-22-37/38-36-19-11-67-65-63-48/20-40
- Signal word
- Danger
- Symbol(GHS)
- GHS02,GHS07,GHS08
- hazard_code
- Xi,Xn,F
- safety_code
- 26-36/37-62-37/39-36-33-29-16
- hazard_class
- 3
- Storage Class
- 3 - Flammable liquids
- packing_group
- III
- target organs
- Central nervous system, Respiratory system
- Hazard statements
- H225-H304-H315-H319-H335-H336-H361d-H373-H412
- Hazard Classifications
- Aquatic Chronic 3Asp. Tox. 1Eye Irrit. 2Flam. Liq. 2Repr. 2Skin Irrit. 2STOT RE 2STOT SE 3
- Precautionary statements
- P210-P273-P301+P310-P303+P361+P353-P305+P351+P338-P331
Chemistry & industry
Uses & manufacturing
Applications
DescriptionTricyclohexyl 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.
UsesTricyclohexyl 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.
UsesTricyclohexylphosphine 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. Grubbscatalysts consists of transition metal ruthenium and tricylohexyl phosphine utilized in olefin metathesis in synthetic organic chemistry.
Upstream & downstream products
Upstream raw materials
Downstream products
Suppliers50 total
Related reactions
Linked notes
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