53597-69-6

Basic information

• Product Name: 1,3,5-Triaza-7-phosphaadamantane,min.97%
• Synonyms: 1,3,5-Triaza-7-phosphaadamantane,min.97%;1,3,5-TRIAZA-7-PHOSPHAADAMANTANE, MIN. 97%;1,3,5-Triaza-7-phosphaadamantane;1,3,5-Triaza-7-phosphatricyclo[3.3.1.13.7]decane, NSC 266642, PTA;1,3,5-Triaza-7-phosphatricyclo[3.3.1.13,7]decane;1,3,5-Triaza-9-phospha-adamantane;Nsc266642;1,3,5-Triaza-7-phosphaadaMantane, Min. 97% PTA
• CAS NO: 53597-69-6
• Molecular Formula: C₆H₁₂N₃P
• Molecular Weight: 157.15
• Product Categories: organophosphine ligand
• Mol File: 53597-69-6.mol
• Article Data: 2

Chemical Properties

• Melting Point: 244-250 °C
• Boiling Point: 232.5°Cat760mmHg
• Flash Point: 94.4°C
• Appearance: White/Solid
• Density: g/cm³
• Vapor Pressure: 0.0588mmHg at 25°C
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• PKA: 5.78±0.20(Predicted)
• Sensitive: Hygroscopic
• CAS DataBase Reference: 1,3,5-Triaza-7-phosphaadamantane,min.97%(CAS DataBase Reference)
• NIST Chemistry Reference: 1,3,5-Triaza-7-phosphaadamantane,min.97%(53597-69-6)
• EPA Substance Registry System: 1,3,5-Triaza-7-phosphaadamantane,min.97%(53597-69-6)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 53597-69-6(Hazardous Substances Data)

Usage

Reaction

Air-stable, water-soluble version of trimethylphosphine. Reagent used in the β-olefination of 2-alkynoates leading to trisubstituted 1,3-dienes. Ligand/rhodium catalyst used in the branch selective allylation of acetylacetone. Ligand/oxorhenium complex used as a catalyst for the Baeyer-Villiger oxidation of ketones.

General Description

Air stable organocatalyst for Baylis-Hillman transformation

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

Upstream product

• 916730-63-7 1-boranyl-1,3,5-triaza-7-phosphaadamantane 
• 7732-18-5 water 
• 50-00-0 formaldehyd 
• 2372-88-5 diaminomethane 
• 2767-80-8 tris(hydroxymethyl)phosphine 

Downstream Products

• 226400-60-8 triscarbonyl(1,3,5-triaza-7-phosphaadamantane)nickel⁽⁰⁾ 
• 630416-10-3 Pd(CH₃)PN₃(CH₂)6C₆H₃(CH(CH₃)2)2NCHC₆H₃ONO₂ 
• 630416-14-7 Pd(CH₃)PN₃(CH₂)6C₆H₃(CH(CH₃)2)2NCHC₆H₃OC₆H₅ 
• 630416-11-4 Pd(CH₃)PN₃(CH₂)6C₆H₃(CH(CH₃)2)2NCHC₆H₃OOCH₃ 
• 630416-12-5 Pd(CH₃)PN₃(CH₂)6C₆H₃(CH(CH₃)2)2NCHC₆H₂O(CH)4 
• 630416-03-4 Ni(C₆H₅)PN₃(CH₂)6C₆H₃(CH(CH₃)2)2NCHC₆H₃NO₂O 
• 148131-92-4 W(CO)4(1,3,5-triaza-7-phosphaadamantane)2 
• 909292-05-3 cis-[W(CO)4(1,3,5-triaza-7-phosphaadamantane)(triphenylphosphine)] 
• 923285-88-5 (η⁵-C₈H₉)Ru(1,3,5-triaza-7-phosphaadamantane)(PPh₃)Cl 
• 537035-75-9 [chlorobis(1,3,5-triaza-7-phosphaadamantane-P)(cyclopentadienyl)ruthenium(II)] 
• 877864-62-5 [(η⁵-cyclopentadienyl)Ru(1,3,5-triaza-7-phosphaadamantane)(PPh₃)Cl] 
• 876069-43-1 [Au(C₆F₅)(1,3,5-triaza-7-phosphaadamantane)] 
• 923285-90-9 [(η⁵-indenyl)Ru(1,3,5-triaza-7-phosphaadamantane)(PPh₃)Cl] 
• 876069-46-4 [Au(C₆F₅)3(1,3,5-triaza-7-phosphaadamantane)] 

Relevant articles and documents

Borane adducts of the water soluble phosphine PTA (PTA = 1,3,5-triaza-7-phosphaadamantane)

Boronation of the water soluble phosphine PTA (PTA = l,3,5-triaza-7- phosphaadamantane) in dry THF easily affords the N-boronated adduct N-B-PTABH3 which represents the first N-coordinated adduct of this popular water soluble phosphine (N-B-PTABH3 = 1-boranyl-1,3,5-triaza- 7-phosphaadamantane). In situ 31P NMR spectroscopy suggests the occurrence of a stepwise boronation resulting in the addition of as many as four equivalents of BH3 to PTA to give the polyboranyl species N x, Py-B-PTA(BH3)(x+y) (x = 1-3, y = 0, 1). Hydrolysis of the monoboranyl adduct occurs slowly in the presence of water yielding back PTA and boric acid, H3BO3.