Tricyclohexylphosphine

HCID 75806CAS 2622-14-2

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

TricyclohexylphosphinePhosphine, tricyclohexyl-EINECS 220-069-2NSC 158657DTXSID9062562Phosphine, tricyclohexylRefChem:191427DTXCID8037469220-069-2WLPUWLXVBWGYMZ-UHFFFAOYSA-N2622-14-2TRICYCLOHEXYL PHOSPHINE
Show more names
TCHPP(4-MeOC6H4)3TricycLProtein TCHPtricyclohexylphospine
TricyclohexylphosphanePCy3Tricyclohexyl-phosphaneMFCD00003853tris(cyclohexyl)phosphineP(Cy)3Cy3PP(cHex)3

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

Experimental & physicochemical properties

Chemical ClassesOther Classes -> Phosphorus Compounds
Physical DescriptionCrystalline powder or chunks; [Sigma-Aldrich MSDS]

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)

Safety & regulation

GHS classification

GHS Classification · 4 items

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

Hazards SummaryA skin and strong eye irritant; [Sigma-Aldrich MSDS] See Triphenylphosphine.
Hazard Classes and CategoriesSelf-heat. 1 (18.7%)

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

Chemistry & industry

Uses & manufacturing

General Manufacturing InformationPhosphine, tricyclohexyl-: ACTIVE
Applications · 3 items

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.

Suppliers50 total

国药集团化学试剂有限公司86-21-63210123 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
INTATRADE GmbH+49 3493/605464 · [email protected]
T&W GROUP021-61551611 13296011611 · [email protected]
科瑞迪化学400-821-5857 021-64326257 · [email protected]

Related reactions

2,387 records

Linked notes

Loading…