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CS-W001157 4
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Tricyclohexylphosphine oxide

  • CAS No. 13689-19-5

  • Cat. No. CS-0155317
  • Purity≥98%
  • MDL No.MFCD00014298

*For research and further manufacturing use only, not for direct human use.

Tricyclohexylphosphine oxide|CS-0155317

Structure of 13689-19-5

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General Information

  • CAS No. 13689-19-5
  • Cat. No. CS-0155317
  • Purity ≥98%
  • MDL No. MFCD00014298
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₈H₃₃OP
  • Molecular Weight 296.43
  • Synonym(s) tricyclohexylphosphane oxide
  • SMILES C1CCC(CC1)P(=O)(C2CCCCC2)C3CCCCC3

Description

Tricyclohexylphosphine oxide features a bulky, electron-rich phosphine oxide structure that enhances stability and solubility in organic media. This robust ligand resists oxidation while maintaining strong coordination to transition metals, making it ideal for catalytic systems requiring prolonged performance under demanding reaction conditions.

Application

Tricyclohexylphosphine oxide serves as a stable, bench-ready phosphine ligand that facilitates palladium-catalyzed cross-coupling reactions. Its steric bulk and moderate electron-donating character enhance catalyst longevity and reactivity in Suzuki-Miyaura and Stille couplings. The oxide functionality improves handling and storage stability compared to free phosphines, enabling reliable performance in complex molecule synthesis.

Synthesis

  • Route1

    References

    • Basf SE Patent: US2010/137643 A1, 2010 ; Location in patent: Page/Page column 14 ;
  • Route2

    References

    • Verbitskiy, Egor V.; Cheprakova, Ekaterina M.; Zhilina, Ekaterina F.; Kodess, Mikhail I.; Ezhikova, Marina A.; Pervova, Marina G.; Slepukhin, Pavel A.; Subbotina, Julia O.; Schepochkin, Aleksandr V.; Rusinov, Gennady L.; Chupakhin, Oleg N.; Charushin, Valery N. Tetrahedron, 2013 , vol. 69, # 25 p. 5164 - 5172
  • Route3

    References

    • Verbitskiy, Egor V.; Cheprakova, Ekaterina M.; Zhilina, Ekaterina F.; Kodess, Mikhail I.; Ezhikova, Marina A.; Pervova, Marina G.; Slepukhin, Pavel A.; Subbotina, Julia O.; Schepochkin, Aleksandr V.; Rusinov, Gennady L.; Chupakhin, Oleg N.; Charushin, Valery N. Tetrahedron, 2013 , vol. 69, # 25 p. 5164 - 5172

Safety Information

Download SDS
GHS Pictogram :
GHS No : GHS06
Signal Word : Danger
UN#: 2811
Class : 6.1
Packing Group : Ⅲ
Hazard Statements : H301-H315-H319-H335
Precautionary Statements : P261-P264-P270-P271-P280-P302+P352-P304+P340-P330-P362+P364-P405-P501

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Computational Chemistry Data

  • TPSA   17.07
  • LogP   6.3476
  • H_Acceptors   1
  • H_Donors   0
  • Rotatable_Bonds   3

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