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Sigma-Aldrich

1,3,5-Triaza-7-phosphaadamantane

97%

Synonym(s):

1,3,5-Triaza-7-phosphatricyclo[3.3.1.13.7]decane, NSC 266642, PTA

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About This Item

Empirical Formula (Hill Notation):
C6H12N3P
CAS Number:
53597-69-6
Molecular Weight:
157.15
MDL number:
MFCD00154905
UNSPSC Code:
12352005
PubChem Substance ID:
329761745
NACRES:
NA.22

Assay

97%

form

solid

reaction suitability

reagent type: ligand
reaction type: Hydroformylations
reagent type: ligand
reaction type: Hydrogenations
reagent type: ligand
reaction type: Morita-Baylis-Hillman Reactions
reagent type: ligand
reaction type: Sonogashira Coupling
reagent type: ligand
reaction type: Suzuki-Miyaura Coupling

mp

244-250 °C

functional group

phosphine

SMILES string

C1N2CN3CN1CP(C2)C3

InChI

1S/C6H12N3P/c1-7-2-9-3-8(1)5-10(4-7)6-9/h1-6H2

InChI key

FXXRPTKTLVHPAR-UHFFFAOYSA-N

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General description

Air stable organocatalyst for Baylis-Hillman transformation

Application

  • The molecular mechanisms of antimetastatic ruthenium compounds explored through DIGE proteomics.: This study examines the antimetastatic properties of ruthenium compounds using DIGE proteomics. The involvement of 1,3,5-Triaza-7-phosphaadamantane in the complexation with ruthenium and its biological effects were analyzed, highlighting its potential in anticancer therapies (Guidi et al., 2013).
  • Synthesis, antimicrobial and antiproliferative activity of novel silver(I) tris(pyrazolyl)methanesulfonate and 1,3,5-triaza-7-phosphadamantane complexes.: This research details the synthesis of novel silver complexes containing 1,3,5-Triaza-7-phosphaadamantane, evaluating their antimicrobial and antiproliferative activities, which demonstrates the compound′s utility in biomedical applications (Pettinari et al., 2011).

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

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Phillips, A. D.; Gonsalvi, L. et al.
Coordination Chemistry Reviews, 248, 955-955 (2004)
William D J Tremlett et al.
Journal of inorganic biochemistry, 199, 110768-110768 (2019-07-30)
Organometallic compounds based on bioactive ligand systems have shown promising antiproliferative properties. The use of 8-hydroxyquinoline and its derivatives as bioactive ligands resulted in organometallic complexes with potent anticancer activity, but they lack aqueous solubility for further development. We report
He, Z. et al
Advanced Synthesis & Catalysis, 368, 413-413 (2006)
Leila Tabrizi et al.
Dalton transactions (Cambridge, England : 2003), 48(2), 728-740 (2018-12-19)
The new cyclometalated ruthenium(ii) complex, [Ru(CCC-Nap)(Ibu)(PTA)] was designed and synthesized using ibuprofen (Ibu), 1,3,5-triaza-7-phosphaadamantane (PTA) and CCC-pincer containing naproxen moiety (CCC-Nap) as ligands. The compounds were fully characterized by elemental analysis, FT-IR, multinuclear (1H, 13C, and 31P) NMR spectroscopy, and
Sabina W Jaros et al.
Molecules (Basel, Switzerland), 25(9) (2020-05-07)
The present study reports the synthesis, characterization, and crystal structure of a novel bioactive metal-organic framework, [Ag4(µ-PTA)2(µ3-PTA)2(µ4-pma)(H2O)2]n·6nH2O (bioMOF 1), which was assembled from silver(I) oxide, 1,3,5-triaza-7-phosphaadamantane (PTA), and pyromellitic acid (H4pma). This product was isolated as a stable microcrystalline solid
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Trialkylphosphine for MBH Reactions

Amines and phosphines in nucleophilic catalysis are discussed, addressing the air sensitivity of phosphines.

Related Content

Frost Group – Professor Product Portal

The Frost group has a longstanding interest in aqueous phase organometallic chemistry with an emphasis on water-soluble phosphine ligands. One focus of this research group has been centered on the chemistry of the neutral, air stable, and water-soluble heterocyclic phosphine 1,3,5-Triaza-7-phosphaadamantane (PTA). PTA is a small phosphine ligands with a cone angle of ~103°. PTA binds metal centers quite strongly and is electronically more donating than PPh3. Ruthenium complexes of PTA have exhibited impressive anticancer activity. A wide variety of transition metal complexes of PTA have been utilized as catalysts for reactions such as hydrogenation, C-C bond forming reactions, atom transfer radical addition, and nitrile hydration.

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