185509-30-2

Basic information

• Product Name: Phenol, 2,4-bis(1,1-dimethylethyl)-6-[(1-methylethyl)phenylphosphino]-
• CAS NO: 185509-30-2
• Molecular Formula: C23H33OP
• Molecular Weight: 356.488
• Mol File: 185509-30-2.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: Phenol, 2,4-bis(1,1-dimethylethyl)-6-[(1-methylethyl)phenylphosphino]-(CAS DataBase Reference)
• NIST Chemistry Reference: Phenol, 2,4-bis(1,1-dimethylethyl)-6-[(1-methylethyl)phenylphosphino]-(185509-30-2)
• EPA Substance Registry System: Phenol, 2,4-bis(1,1-dimethylethyl)-6-[(1-methylethyl)phenylphosphino]-(185509-30-2)

Safety Data

• Hazardous Substances Data: 185509-30-2(Hazardous Substances Data)

Upstream product

• 54006-34-7 chloro(isopropyl)phenylphosphane 
• 20834-61-1 2-bromo-4,6-di-tert-butylphenol 

Downstream Products

• 252334-17-1 rac-cis-bis(4,6-di-tert-butyl-2-(isopropyl(phenyl)phosphino)phenolato-O,P)nickel(II) 
• 252334-17-1 bis[4,6-di-tert-butyl-2-(isopropylphenylphosphanyl)phenolato[P,O]] nickel(II) complex 
• 264258-94-8 trans-[4,6-di-tert-butyl-2-(isopropylphenylphosphanyl)phenolato[P,O]]methyl(trimethylphosphane)nickel(II) complex 

Relevant articles and documents

Formation of η1-P-(2-phosphinophenol)Ni(0)(PMe3)3 and oxidation to cis/trans-bis(2-phosphinophenolato)nickel(II) complexes

o-Phosphinophenols 1 (P∩OH) react with equimolar amounts of Ni(PMe3)4 at low temperatures to give yellow Ni(0) complexes such as [(HO～P)Ni(PMe3)3] 2a with only P coordination of the P∩OH ligand. Oxidation of solutions of 1 and Ni(PMe3)4 by dioxygen leads to brown bis(o-phosphinophenolato-P∩O)nickel chelate complexes 3a-d. Structure elucidation by NMR is consistent with a cis-square planar geometry for 3a-c and a trans-square planar solution structure of the tert-butylphenylphosphino derivative 3d. The geometric isomers were distinguished by different ranges of phosphorus coordination shifts and 31P-13C-2 and 31P-13C-1 coupling constants. In the solid state, 3d adopts also a cis-square planar geometry. The steric stress of the substituents causes anti-orientation of the tert-butyl groups at phosphorus (R,R and S,S diastereoisomers) and a significant distorsion (22°) of the planes of the two five-membered rings. With less bulky substituents the R,S and S,R diastereoisomers are preferred as in the cis-square planar complex 3c with syn-orientation of the two isopropyl and phenyl groups, respectively.