198644-01-8

Basic information

• Product Name: [(C₆H₃(CHO)-2-(CO₂H)-5)Pd(PPh₃)(2,2'-bipyridine)](CF₃SO₃)
• CAS NO: 198644-01-8
• Molecular Weight: 823.094
• Mol File: 198644-01-8.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: [(C₆H₃(CHO)-2-(CO₂H)-5)Pd(PPh₃)(2,2'-bipyridine)](CF₃SO₃)(CAS DataBase Reference)
• NIST Chemistry Reference: [(C₆H₃(CHO)-2-(CO₂H)-5)Pd(PPh₃)(2,2'-bipyridine)](CF₃SO₃)(198644-01-8)
• EPA Substance Registry System: [(C₆H₃(CHO)-2-(CO₂H)-5)Pd(PPh₃)(2,2'-bipyridine)](CF₃SO₃)(198644-01-8)

Safety Data

• Hazardous Substances Data: 198644-01-8(Hazardous Substances Data)

Upstream product

• 198644-37-0 (C₆H₃(CHO)-2-(CO₂H)-5)PdCl(2,2'-bipyridine) 
• 2926-27-4 potassium trifluoromethansulfonate 
• 603-35-0 triphenylphosphine 

Relevant articles and documents

Synthesis of mercury(II) and palladium(II) organometallic derivatives of terephthaldehyde by metalation, transmetalation, oxidation, and condensation reactions.

The organomercurials [HgCl{C6H3(CHO)2-2,5}] (1) and [Hg{C6H3(CHO)2-2,5}2] (2) have been prepared by mercuriation of terephthaldehyde. Palladium complexes [PdCl{C6H3-(CHO)2-2,5}(N-N)] (N-N = N,N,N′,N′-tetramethylethylenediamine (tmeda) (3) or 2,2′-bipyridine (bpy) (3′)) or trans-[PdCl{C6H3(CHO)2-2,5}(PPh 3)2]·H2O (4) have been obtained by reacting (Me4N)2[Pd2Cl6] or trans-[PdCl2(PPh3)2], respectively, with 1 or 2. The reaction of potassium permanganate with complexes 3 and 3′ or mercurial 1 results in the selective oxidation of the 5-formyl substituent affording [PdCl{C6H3(CHO)-2-(CO2H)-5}(N-N)] (N-N = tmeda (5), bpy (5′)) or, respectively, a mixture whose major component is the fully oxidized [HgCl{C6H3(CO2H)2-2,5}] (7) or a mixture of isomers [HgCl{C6H3(CHO)-2-(CO2H)-5}]/[HgCl-{C 6H3(CO2H)-2-(CHO)}] (8a/8b) depending on the molar ratio of the reagents. The reaction of mixtures containing 7 or 8 with trans-[PdCl2(PPh3)2] give pure trans-[PdCl{C6H3(CO2H) 2-2,5}(PPh3)2] (9) or trans-[PdCl{C6H3(CHO)-2-(CO2H)-5}(PPh 3)2] (10), respectively. Complexes 3 and 3′ react with amines and NaClO4·H2O or Tl(CF3SO3) to give, depending of the reaction conditions, cyclopalladated derivatives [Pd{C6H3(CH=NR)-2-(CH=NR)-5}(N-N)]+ or [Pd-{C6H3(CH=NR)-2-(CHO)-5}(tmeda)]+. The mercurial 1 reacts with hydroxylamine to give the mercuriated oxime [HgCl{C6H3(CH=NOH)2-2,5}] (14), which reacts with (Me4N)2[Pd2-Cl6] to give the cyclopalladated complex [Pd{C6H3(CH=NOH)-2-(CH=NOH)-5}(μ-Cl]2 (15). From 15 some derivatives have been prepared. Complex 3 reacts with NH2OMe to give [Pd{C6H3(CH=NOMe)-2-(CH=NOMe)-5}(tmeda)]ClO 4(19). Theimine C6H4(CH=NTo)2-1,4(To = C6H4Me-4) reacts with palladium(II) acetate to give the dipalladated imine [Pd{C6H 2-(CH=NTo)-2-{Pd(μ-OAc)}-4-(CH=NTo)-5}(μ-OAc)]n (20). Hydrolysis of 20 in the presence of potassium bromide and bpy results in the formation of [C6H2{PdBr(bpy)}2-1,4-(CHO)2-2,5] (21), from which [C6H2{Pd(PPh3)(bpy)}2-1,4-(CHO) 2-2,5](CF3SO3)2 (22) can be prepared. The structures of 9·Me2CO·1.5MeOH, 10·2CH2Cl2 and [Pd{C6H3(CH=NR)-2-(CHO)-5}(tmeda)]CF3SO 3 (R = C6H4NH2-4) (12c′) have been determined by X-ray crystallography.