21450-51-1

Basic information

• Product Name: Antimony, dichlorotris(2-methoxyphenyl)-
• CAS NO: 21450-51-1
• Molecular Formula: C21H21Cl2O3Sb
• Molecular Weight: 514.052
• Mol File: 21450-51-1.mol

Chemical Properties

• CAS DataBase Reference: Antimony, dichlorotris(2-methoxyphenyl)-(CAS DataBase Reference)
• NIST Chemistry Reference: Antimony, dichlorotris(2-methoxyphenyl)-(21450-51-1)
• EPA Substance Registry System: Antimony, dichlorotris(2-methoxyphenyl)-(21450-51-1)

Safety Data

• Hazardous Substances Data: 21450-51-1(Hazardous Substances Data)

Upstream product

• 78665-37-9 tris(2-methoxyphenyl)antimony 
• 683238-77-9 {2-CH₃OC₆H₄N₂}SbCl₄ 
• 193361-71-6 tris(2-methoxyphenyl)stibane oxide 
• 16750-63-3 2-methoxyphenylmagnesium bromide 
• 7647-01-0 hydrogenchloride 
• 382148-91-6 [(trichloroacetyl)imino]tris(2-methoxyphenyl)-λ5-stibane 

Relevant articles and documents

Synthesis, structure, and reactions of (acylimino)triaryl-λ5-bismuthanes: First comparative study of the (acylimino)pnictorane series

The synthesis, structure, and reactions of (acylimino)triaryl-λ5-bismuthanes and a comparative study of the structure and reactivity of a series of (acylimino)pnictoranes are reported. Treatment of ortho-substituted triarylbismuth dichlorides 1 (Ar3BiCl2; Ar = 2-MeC6H4, 2-MeOC6H4, 2,4,6-Me3C6H2) with amides 2 (H2-NCOR; R = CF3, CCl3, 3,5-(CF3)2C6H3) in the presence of 2.2 equiv of KO-t-Bu in dichloromethane afforded (acylimino)triaryl-λ5-bismuthanes 3 (Ar3Bi=NCOR) in yields of 77-96%. The ortho-substituted aryl ligands and the electron-withdrawing N-substituents afford kinetic and thermodynamic stabilization, respectively, to the reactive Bi=N bond. The structures and properties of a series of (acylimino)pnictoranes (Ar3M=NCOR and H3M=NCOCF3; M = P, As, Sb, Bi) are compared by IR and 13C and 15N NMR, X-ray crystallography, and ab initio molecular orbital calculations. It was found that the contribution of the M+-N=C-O- canonical form becomes more prominent and the single-bond character of the M=N bond increases progressively as the pnictogen atom becomes heavier. The Bi=N bond of (acylimino)-λ5-bismuthanes 3 possesses a highly polarized single-bond character, probably due to the differences in orbital size and electronegativity between the bismuth and nitrogen atoms. Thermal decomposition of (aroylimino)triaryl-λ5-bismuthane 3f (o-Tol3Bi=NCOAr; Ar = 3,5-(CF3)2C6H3) produces a gel in dry conditions or aniline 12 (ArNH2) in slightly wet conditions with a good recovery of tris(2-methylphenyl)bismuthane (4a). It is likely that the aryl isocyanate 13 (ArNCO) is produced during the thermolysis via a concerted C → N migration of the Ar group with an elimination of the triarylbismuthonio group as bismuthane 4a. (Acylimino)triaryl-λ5-bismuthanes 3 oxidize 1,1,2,2-tetraphenylethanediol, benzenethiol, methanol, and ethanol to benzophenone, diphenyl disulfide, methyl formate, and acetaldehyde, respectively, in two different reaction pathways depending on the structure of the substrates. Compound 3d (o-Tol3Bi=NCOCCl3) transfers the nitrenoid moiety to triphenylphosphane, triphenylarsane, and tris(2-methylphenyl)stibane to give the corresponding (acylimino)pnictoranes (Ar3M=NCOCl3; M = P, As, Sb) and 4a, suggesting that 3d is thermodynamically much less stable than their lighter pnictogen counterparts. The copper-catalyzed decomposition of 3 (o-Tol3Bi=NCOR) afforded N-acyl-o-toluidines 18 (o-TolNHCOR) via a Bi → N migration of the tolyl group. The observed reactivities of (acylimino)triaryl-λ5-bismuthanes 3 demonstrate a good leaving ability of the bismuthonio group.