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Tricyclohexylphosphine oxide

Catalog Number
ACM13689195
Product Name
Tricyclohexylphosphine oxide
CAS
13689-19-5
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Synonyms
Dicyclohexylphosphorylcyclohexane
IUPAC Name
dicyclohexylphosphorylcyclohexane
Molecular Weight
296.42
Molecular Formula
C18H33OP
Canonical SMILES
C1CCC(CC1)P(=O)(C2CCCCC2)C3CCCCC3;
InChI
LEFPWWWXFFNJAA-UHFFFAOYSA-N
InChI Key
InChI=1S/C18H33OP/c19-20(16-10-4-1-5-11-16,17-12-6-2-7-13-17)18-14-8-3-9-15-18/h16-18H,1-15H2
Boiling Point
466.6±12.0 °C(Predicted)
Melting Point
155-157 °C
Purity
98%
Density
1 g/cm3
Appearance
Solid
Complexity
281
Covalently-Bonded Unit Count
1
Exact Mass
296.227g/mol
H-Bond Acceptor
1
Heavy Atom Count
20
Isomeric SMILES
C1CCC(CC1)P(=O)(C2CCCCC2)C3CCCCC3
Monoisotopic Mass
296.227g/mol
NSC Number
222417
Rotatable Bond Count
3
Topological Polar Surface Area
17.1A^2
Application
Tricyclohexylphosphine oxide serves as a versatile ligand in various metal-catalyzed organic reactions. It is fundamental in the palladium-catalyzed coupling of malononitrile with aryl halides and plays a crucial role as a bulky phosphine ligand when used with a palladium(0)-triolefinic macrocycle catalyst in the Suzuki coupling of aryl bromides and chlorides. Additionally, it is employed with nickel as an essential intermediate in the synthesis of cyclopentane compounds.
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