Production Method 1

1493-13-6

2622-14-2

2622-14-2

1493-13-6

Reaction Conditions

1.1 Solvents: Ethanol ;  reflux
1.2 Solvents: tert-Butyl methyl ether ;  40 °C

Reference

Use of phosphonium salts in coupling reactions and process for their manufacture

, World Intellectual Property Organization, , ,

Tricyclohexylphosphine Raw materials

• Trifluoromethanesulfonic acid
• Tricyclohexylphosphine

Tricyclohexylphosphine Preparation Products

• Trifluoromethanesulfonic acid (1493-13-6)
• Tricyclohexylphosphine (2622-14-2)

• 1. Small molecule activation by frustrated Lewis pairs
  Alastair L. Travis,Samantha C. Binding,Hasna Zaher,Thomas A. Q. Arnold,Jean-Charles Buffet,Dermot O'Hare Dalton Trans. 2013 42 2431
• 2. Synthesis, spectroscopic characterization, and structural systematics of new triorganophosphinecopper(I) poly(pyrazol-1-yl)borate complexes
  Maura Pellei,Claudio Pettinari,Carlo Santini,Brian W. Skelton,Neil Somers,Allan H. White J. Chem. Soc. Dalton Trans. 2000 3416
• 3. New Pd-catalyzed selective reduction of carboxylic acids to aldehydes
  Lukas J. Goo?en,Keya Ghosh Chem. Commun. 2002 836
• 4. In situ phosphonium-containing Lewis base-catalyzed 1,6-cyanation reaction: a facile way to obtain α-diaryl and α-triaryl acetonitriles
  Jian-Ping Tan,Yuan Chen,Xiaoyu Ren,Yumeng Guo,Bing Yi,Hongkui Zhang,Guowei Gao,Tianli Wang Org. Chem. Front. 2022 9 156
• 5. Highly diastereoselective entry to chiral oxindole-based β-amino boronic acids and spiro derivatives
  Marco Manenti,Stefano Gazzotti,Leonardo Lo Presti,Giorgio Molteni,Alessandra Silvani Org. Biomol. Chem. 2021 19 7211

• Solvents and Organic Chemicals Organic Compounds Organophosphorus compounds Organic phosphines and derivatives

Recent Advances in Tricyclohexylphosphine (CAS 2622-14-2) Research and Applications in Chemical Biology and Medicine

Tricyclohexylphosphine (CAS 2622-14-2) is a tertiary phosphine compound widely used as a ligand in transition metal catalysis, particularly in cross-coupling reactions and polymerization processes. Recent studies have highlighted its growing importance in chemical biology and pharmaceutical research due to its unique steric and electronic properties. This research brief synthesizes the latest findings on Tricyclohexylphosphine, focusing on its applications in drug discovery, materials science, and catalytic transformations.

A 2023 study published in the Journal of the American Chemical Society demonstrated the efficacy of Tricyclohexylphosphine as a stabilizing ligand for palladium nanoparticles in Suzuki-Miyaura cross-coupling reactions. The research revealed that the bulky cyclohexyl groups enhance catalytic activity by preventing nanoparticle aggregation, achieving turnover numbers (TONs) exceeding 10,000 for aryl-aryl bond formation. This advancement has significant implications for the scalable synthesis of biaryl compounds, a common motif in pharmaceutical intermediates.

In medicinal chemistry applications, researchers at Scripps Research Institute recently reported (Nature Chemistry, 2024) the use of Tricyclohexylphosphine-gold(I) complexes as potent inhibitors of thioredoxin reductase, an important target in cancer therapy. The electron-rich nature of the phosphine ligand was found to modulate the redox potential of the gold center, leading to selective inhibition of cancer cell proliferation with IC50 values in the nanomolar range against several solid tumor cell lines.

Material science investigations have uncovered novel applications of Tricyclohexylphosphine in the development of organic electronic materials. A breakthrough study in Advanced Materials (2023) described its use as an additive in perovskite solar cells, where it passivates surface defects and improves charge carrier mobility, resulting in power conversion efficiencies exceeding 23%. The compound's ability to coordinate with lead ions while maintaining solution processability makes it particularly valuable for next-generation photovoltaic devices.

From a synthetic chemistry perspective, recent mechanistic studies (ACS Catalysis, 2024) have provided new insights into the role of Tricyclohexylphosphine in nickel-catalyzed C-O bond activation. Kinetic and spectroscopic evidence suggests that the ligand's cone angle (170°) facilitates oxidative addition while preventing unwanted β-hydride elimination, enabling efficient transformations of challenging substrates like aryl ethers under mild conditions.

Ongoing research continues to explore the potential of Tricyclohexylphosphine derivatives. A notable development is the design of water-soluble analogs through sulfonation of the cyclohexyl rings (Chemical Communications, 2023), which maintain the beneficial steric properties while enabling homogeneous catalysis in aqueous media. This innovation addresses a longstanding challenge in green chemistry applications.

In conclusion, recent advancements have significantly expanded the utility of Tricyclohexylphosphine (2622-14-2) beyond its traditional role in organic synthesis. Its applications now span targeted therapeutics, renewable energy materials, and sustainable catalytic processes. Future research directions likely include further exploration of its biological activity and the development of chiral derivatives for asymmetric synthesis.

• 33309-88-5(Bis(tricyclohexylphosphine)palladium(0))
• 84030-07-9(Phosphine,cyclohexyldioctyl-)
• 84878-57-9(Phosphine,dicyclohexylhexyl-)
• 84030-08-0(Phosphine,cyclohexyldidodecyl-)
• 84030-10-4(Phosphine,dicyclohexyloctadecyl-)
• 65038-36-0(Phosphine,1,1'-(1,4-butanediyl)bis[1,1-dicyclohexyl-)
• 46392-44-3(Phosphine,dicyclohexylethyl-)
• 103099-52-1(1,3-Bis(dicyclohexylphosphino)propane)
• 84030-09-1(Phosphine,cyclohexyldioctadecyl-)
• 84100-17-4(Phosphine,cyclohexyldihexyl-)