96872-40-1

Basic information

• Product Name: Stannane, 1,4-phenylenebis[triphenyl-
• CAS NO: 96872-40-1
• Molecular Formula: C42H34Sn2
• Molecular Weight: 776.152
• Mol File: 96872-40-1.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: Stannane, 1,4-phenylenebis[triphenyl-(CAS DataBase Reference)
• NIST Chemistry Reference: Stannane, 1,4-phenylenebis[triphenyl-(96872-40-1)
• EPA Substance Registry System: Stannane, 1,4-phenylenebis[triphenyl-(96872-40-1)

Safety Data

• Hazardous Substances Data: 96872-40-1(Hazardous Substances Data)

Upstream product

• 57246-14-7 Tetraethyl 1,4-phenylene bis(phosphate) 
• 16498-01-4 O,O-diethyl O-4-bromophenyl phosphate 
• 107839-20-3 BrYbC₆H₄YbBr 
• 639-58-7 triphenyltin chloride 
• 106-46-7 para-dichlorobenzene 
• 892-20-6 triphenylstannane 
• 7270-42-0 1,4-dilithiobenzene 
• 112106-68-0 ClSmC₆H₄SmCl 
• 112135-85-0 ClYbC₆H₄YbCl 
• 112106-67-9 BrSmC₆H₄SmCl 
• 112106-66-8 BrYbC₆H₄YbCl 
• 107839-21-4 C₆H₄Sm₂Br₂ 

Relevant articles and documents

Phenols as starting materials for the synthesis of arylstannanes via SRN11

Phenols are converted into aryl diethyl phosphate esters (ArDEP), which on reaction with sodium trimethylstannide (1) or sodium triphenylstannide (2) in liquid ammonia afford arylstannanes by the SRN1 mechanism. Thus, the photostimulated reaction of phenylDEP (3), (4-methoxyphenyl)DEP (4), (4-biphenyl)DEP (5), (1-naphthyl)DEP (6), (2-naphthyl)DEP (7), and 2- (34), 3- (32), and (4-pyridyl)DEP (35) with 1 leads to monostannylated product in fair to excellent yields (20-98%). Also, substrates containing two or three leaving groups react with 1 under irradiation, affording the corresponding di- or tristannylated aryl compounds. With tetraethyl m-phenylene bisphosphate (15), tetraethyl p-phenylene bisphosphate (21), (4-chlorophenyl)DEP (22), and 1,3,5-tris(diethylphospho)benzene (30), the di- or trisubstitution products 1,3-bis(trimethylstannyl)benzene (19) (79%), 1,4-bis(trimethylstannyl)benzene (23) (95 and 97%), and 1,3,5-tris(trimethylstannyl)benzene (31) (57%) are obtained, respectively. Also, the reaction of 6 and 7 with 2 leads to substitution products in quantitative yields, and the reaction of 21, 22, and (4-bromophenyl)DEP (24) with 2 affords 1,4-bis(triphenylstannyl)benzene (38) in high yields (70-100%). On the other hand, the results obtained in the photostimulated reaction of 24 and (4-iodophenyl)DEP (25) with 1, as well as in the reaction of 25 with 2, clearly indicate a fast HME reaction.

Reactions of haloarenes, haloheteroarenes and dihalobenzenes with triphenylstannyl anions in DMSO and acetonitrile

We studied different haloarenes, haloheteroarenes and dihalobenzenes with Ph3Sn- ions in DMSO or acetonitrile (CH3CN) as solvents, in the dark or under irradiation to determine whether the halogen metal exchange (HME) reaction or the SRN1 process prevails. With p-chloroanisole the photostimulated reaction is sluggish in DMSO. There is an HME reaction with 2- and 3-chlorothiophene. Bromoarenes (p-bromoanisole, p-dibromobenzene and 1-bromonaphthalene) and p-iodoanisole react with Ph3Sn- ions faster by an HME mechanism than by the SRN1 process. In the photostimulated reaction of 1-chloronaphthalene, 2-chloro and 3-chloropyridines with Ph3Sn- ions in DMSO, the substitution products are obtained in 72, 82 and 93% yields, respectively. With p-dichlorobenzene the di-substitution product is obtained in 90% yield. All these reactions occur by the SRN1 mechanism. Yields improve when the reactions are carried out in DMSO rather than in CH3CN.