158076-64-3Relevant academic research and scientific papers
Synthesis and characterization of hydroxylated polychlorinated biphenyls (PCBs) identified in human serum
Safe,Safe, Stephen,Washburn,Washburn, Kent,Zacharewski,Zacharewski, Timothy,Phillips,Phillips, Timothy
, p. 3017 - 3023 (2007/10/03)
Hydroxylated polychlorinated biphenyls (PCBs) have been identified in wildlife and human samples. Most of these compounds are highly chlorinated (penta-hepatachloro) and contain a single meta- or para-hydroxyl group. Using the Cadogan coupling procedure, the following hydroxy-PCBs congeners were synthesized: 2,3,3',4',5-pentachloro-4-biphenylol, 2,3',4,4',5-pentachloro-3-biphenylol, 2',3,3',4',5-pentachloro-4-biphenylol, 2,2',3',4,4'-pentachloro-3-biphenylol, 2,2',3,3',4',5-pentachloro-4-biphenylol, 2,2',3',4,4',5-hexachloro-3-biphenylol, 2,2',3,4',5,5'-hexachloro-4-biphenylol, 2,2',3,3',4',5,5'-heptachloro-4-biphenyl 2,2',3',4,4',5,5'-heptachloro-3-biphenylol, 2,2',3,4',5,5',6-heptachloro-4-biphenylol. Many of these compounds have been detected as residues in human serum and current studies are investigating their activities as agonists and antagonists for several endocrine-mediated responses.
Hydroxylated PCB Derivatives. Synthesis and Structure Elucidation by NMR Spectroscopy and X-Ray Diffraction
Mannila, Erkki,Kolehmainen, Erkki,Rissanen, Kari
, p. 684 - 688 (2007/10/02)
Structures of eight PCB derivatives: 2',3,4',5',6-pentachloro-2-biphenylol (1). 2,2',4',5,5'-pentachloro-3-biphenylol (2), 2,2',4',5,5'-pentachloro-4-biphenylol (3), 2',4,4',5,5',6-hexachloro-2-biphenylol (4), 2', 3', 4,4', 5,6,6'-heptachloro-2-biphenylol (5), 2,2',3',4,4',5,5'-heptachloro-3-biphenylol (6), 2,2', 3,3',4',5,5'-heptachloro-4-biphenylol (7) and 2',3',4,4',5,5',6,6'-octachloro-2-biphenylol (8) have been elucidated by use of 1H-NMR chemical shift assignment of 1-8, a heteronuclear 13C-1H chemical shift correlation spectroscopy (C,H-COSY) experiment on 1, mass spectra and high resolution mass spectra of 1-8 and X-ray crystallographic analysis of 4 and 8.All compounds were synthesized by a modification of the aromatic arylation method of Cadogan by coupling the corresponding chloroaniline and chloroanisole in the presence of isoamyl nitrite, followed by demethylation with boron tribomide in CH2Cl.Compound 4 crystallizes in the monoclinic space group P21n (No. 14) with cell dimensions: a = 8.988(2), b = 19.490(3) and c = 10.722(2) Angstroem and V = 1813.8(5) Angstroem-3 with Z = 4.Full-matrix least-squares refinement of 208 parameters gave R = 0.048 for 2195 reflections .Compound 8 crystallizes in the triclinic space group PI (No. 2) with cell dimensions: a = 8.440(2), b = 7.726(2) and c = 13.328(3) Angstroem and V = 780(1) Angstroem-3 with Z = 2.Full-matrix least-squares refinement of 190 parameters gave R = 0.057 for 1551 reflections .
