33397-21-6

Basic information

• Product Name: tris(4-methoxyphenyl)bismuth
• Synonyms: tris(4-methoxyphenyl)bismuth
• CAS NO: 33397-21-6
• Molecular Weight: 530.376
• Mol File: 33397-21-6.mol

Chemical Properties

• CAS DataBase Reference: tris(4-methoxyphenyl)bismuth(CAS DataBase Reference)
• NIST Chemistry Reference: tris(4-methoxyphenyl)bismuth(33397-21-6)
• EPA Substance Registry System: tris(4-methoxyphenyl)bismuth(33397-21-6)

Safety Data

• Hazardous Substances Data: 33397-21-6(Hazardous Substances Data)

Upstream product

• 104-92-7 1-bromo-4-methoxy-benzene 
• 7440-69-9 bismuth 
• 7787-60-2 bismuth(III) chloride 
• 50619-99-3 4,4'-dimethoxy-diphenyliodonium chloride 
• 95825-92-6 iododiphenylbismuth(III) 
• 5153-28-6 diphenylbismuth(III) chloride 
• 108858-14-6 diphenylbismuth 4-methylbenzenesulfonate 
• 104202-65-5 di(p-anisyl)methylbismuthane 
• 51752-30-8 chlorobis(4-methoxyphenyl)bismuthane 
• 13139-86-1 4-methoxyphenyl magnesium bromide 
• 64-17-5 ethanol 

Downstream Products

• 2132-80-1 4,4'-Dimethoxybiphenyl 
• 2314-80-9 2-(4-methoxyphenyl)succinimide 
• 121-97-1 4-Methoxypropiophenone 
• 345-89-1 4-fluoro-4'-methoxybenzophenone 
• 611-94-9 4-Methoxybenzophenone 
• 39070-97-8 (4-methoxyphenyl)(2-naphthyl)methanone 
• 13021-18-6 1-(4'-methoxy-biphenyl-4-yl)-ethanone 
• 15970-74-8 furan-2-yl(4-methoxyphenyl)methanone 
• 4160-63-8 2-(4-methoxybenzoyl)thiophene 
• 7477-29-4 1,3-phenylenebis[(4-methoxyphenyl)methanone] 
• 4160-51-4 1-(4-methoxyphenyl)-1-butanone 
• 40877-19-8 4-chloro-1-(4-methoxyphenyl)butan-1-one 
• 92-52-4 biphenyl 
• 613-37-6 4-methoxylbiphenyl 

Relevant articles and documents

METHOD FOR PREPARING HETEROLEPTIC TRIARYLBISMUTHANES AND COMPOUNDS PRODUCED BY THE SAME

A method for controlling dismutation in the synthesis of a heteroleptic triarylbismuthane is provided as are compounds produced by such a method and use of the same to inhibit the replication of microorganisms.

Synthesis, structures, and some reactions of [(Thioacyl)thio]- and (Acylseleno)antimony and -bismuth derivatives ((RCSS)xMR 3-x1 and (RCOSe)xMR3-x1 with M=Sb, Bi and x=1-3)

A series of [(thioacyl)thio]- and (acylseleno)antimony and [(thioacyl)thio]- and (acylseleno)bismuth, i.e., (RCSS)xMR 3-x1 and (RCOSe)xMR3-x1 (M = Sb, Bi, R1 = aryl, x = 1 - 3), were synthesized in moderate to good yields by treating piperidinium or sodium carbodithioates and -selenoates with antimony and bismuth halides. Crystal structures of (4-MeC 6H4CSS)2Sb(4-MeC6H4) (9b′), (4-MeOC6H4COSe)2Sb(4-MeC 6H4) (12c′), (4-MeOC6H 4COS)2Bi(4-MeC6H4) (15c′), and (4-MeOC6H4CSS)2BiPh (18c) along with (4-MeC6H4COS)2SbPh (6b) and (4-MeC 6H4COS)3Sb (7b) were determined (Figs. 1 and 2). These compounds have a distorted square pyramidal structure, where the aryl or carbothioato (=acylthio) ligand at the central Sb- or Bi-atom is perpendicular to the plane that includes the two carbodithioato (=(thioacyl)thio), carboselenato (=acylseleno), or carbothioato ligand and exist as an enantiomorph pair. Despite the large atomic radii, the C=S...Sb distances in (RCSS)2MR1 (M = As, Sb, Bi; R1 = aryl) and the C=O...Sb distances in (RCOS)xMR3-x 1 (M = As, Sb, Bi; x = 2, 3) are comparable to or shorter than those of the corresponding arsenic derivatives (Tables 2 and 3). A molecular-orbital calculation performed on the model compounds (MeC(E)E1) 3-xMMex (M = As, Sb, Bi; E = O, S; E1 = S, Se; x = 1, 2) at the RHF/LANL2DZ level supported this shortening of C=E...Sb distances (Table 4). Natural-bond-orbital (NBO) analyses of the model compounds also revealed that two types of orbital interactions nS → σ*MC and nS → σ* MS(1) play a role in the (thioacyl)thio derivatives (MeCSS) 3-xMMex (x = 1, 2) (Table 5). In the acylthio- MeCOSMMe2 (M = As, Sb, Bi), nO → σ* MC contributes predominantly to the orbital interactions, but in MeCOSeSbMe2, none of nO → σ*MC and nO → σ*MSe contributes to the orbital interactions. The nS → σ*MC and nS → σ*MS(1) orbital interactions in the (thioacyl)thio derivatives are greater than those of nO → σ*MC and nO → σ*ME in the acylthio and acylseleno derivatives (MeCOE)3-xMMex (E = S, Se; M = As, Sb, Bi; x = 1, 2). The reactions of RCOSeSbPh2 (R = 4-MeC6H4) with piperidine led to the formation of piperidinium diphenylselenoxoantimonate(1-) (=piperidinium diphenylstibinoselenoite) (H2NC5H10) +Ph2SbSe-, along with the corresponding N-acylpiperidine (Table 6). Similar reactions of the bis-derivatives (RCOSe)2SbR1 (R, R1 = 4-MeC6H 4) with piperidine gave the novel di(piperidinium) phenyldiselenoxoantimonate(2-) (=di(piperidinium) phenylstibonodiselenoite), [(H2NC5H10)+] 2(PhSbSe2)2-, in which the negative charges are delocalized on the SbSe2 moiety (Table 6). Treatment of RCOSeSbR21 (R, R1=4-MeC6H 4) with N-halosuccinimides indicated the formation of Se-(halocyclohexyl) arenecarboselenoates (Table 8). Pyrolysis of bis(acylseleno)arylbismuth at 150° gave Se-aryl carboselenoates in moderate to good yields (Table 9).

Synthesis of Mixed Substituted Triorganobismuthanes

Sodium dimethylbismuthide, generated from dimethylbismuth bromide and sodium in liquid ammonia, was treated with alkyl halides to produce dimethylalkylbismuthanes, Me2Bi(alk) (alk = C2H5, n-C3H7, n-C4H9, C3H5, i-C3H7) as thermolabile liquids in yields ranging from 70 to 90percent.With methylene chloride bis(dimethylbismutho)methane, (Me2Bi)2CH2, was obtained.Aryldimethylbismuthanes, (aryl)BiMe2, were prepared by treating dimethylbismuth bromide in THF with elemental lithium (-78 deg C) and subsequent reaction with aryl halides (aryl = 4-C6H4CH3, 4-C6H4OCH3, 2,4,6-C6H2(CH3)3).At 90 deg C in an N2-stream, the thermolabile compounds react quantitatively to form diarylmethylbismuthanes, (aryl)2BiMe and Me3Bi. - Keywords: Dimethylalkylbismuthanes, Bis(dimethylbismutho)methane, Aryldimethylbismuthanes, Diarylmethylbismuthanes