6746-22-1

Basic information

• Product Name: TETRA-P-TOLYLTIN
• Synonyms: Tetra-p-tolytin;TETRAKIS(P-TOLYL)TIN;TETRA-4-TOLYLTIN;TETRA-P-TOLYLTIN
• CAS NO: 6746-22-1
• Molecular Formula: C₂₈H₂₈Sn
• Molecular Weight: 483.23
• Mol File: 6746-22-1.mol
• Article Data: 6

Chemical Properties

• Melting Point: 236-237°C
• Boiling Point: 517.9°C at 760 mmHg
• Flash Point: 265.3°C
• Appearance: /
• Vapor Pressure: 2.58E-10mmHg at 25°C
• CAS DataBase Reference: TETRA-P-TOLYLTIN(CAS DataBase Reference)
• NIST Chemistry Reference: TETRA-P-TOLYLTIN(6746-22-1)
• EPA Substance Registry System: TETRA-P-TOLYLTIN(6746-22-1)

Safety Data

• TSCA: No
• Hazardous Substances Data: 6746-22-1(Hazardous Substances Data)

Usage

General Description

Tetra-p-tolyltin, a chemical compound, is a derivative of tin and is composed of four p-tolyl groups attached to a central tin atom. It is commonly utilized as a catalyst in organic synthesis, particularly in the production of polyurethane foam and other polymers. Tetra-p-tolyltin is also employed as a stabilizer in the manufacturing of PVC and as a biocide in wood preservatives and antifouling paints. However, it is important to note that tetra-p-tolyltin has been associated with environmental and health concerns, including its toxicity to aquatic life and potential hazards to human health. As a result, there are increasing regulatory restrictions on the use of tetra-p-tolyltin in various industries.

InChI:InChI=1/4C7H7.Sn/c4*1-7-5-3-2-4-6-7;/h4*3-6H,1H3;/rC28H28Sn/c1-21-5-13-25(14-6-21)29(26-15-7-22(2)8-16-26,27-17-9-23(3)10-18-27)28-19-11-24(4)12-20-28/h5-20H,1-4H3

Upstream product

• 2417-95-0 p-tolyllithium 
• 4294-57-9 para-methylphenylmagnesium bromide 
• 624-31-7 4-tolyl iodide 
• 106-38-7 para-bromotoluene 
• 7646-78-8 tin(IV) chloride 
• 106-43-4 para-chlorotoluene 
• 539-43-5 4-methylphenylmercuric chloride 

Downstream Products

• 135-58-0 Mesulfen 
• 106-43-4 para-chlorotoluene 
• 99-99-0 1-methyl-4-nitrobenzene 
• 613-33-2 (4,4'-dimethyl-1,1'-biphenyl) 
• 80331-24-4 4-(4-methylphenyl)-4-phenylbutan-2-one 
• 32538-28-6 tris(4-methylphenyl)tin(IV) chloride 
• 5720-05-8 4-methylphenylboronic acid 
• 106-38-7 para-bromotoluene 
• 58436-46-7 tris(4-methylphenyl)tin(IV) bromide 
• 32538-29-7 di(p-tolyl)tin dichloride 
• 41269-16-3 tris(4-methylphenyl)tin(IV) iodide 
• 624-31-7 4-tolyl iodide 
• 4250-45-7 dichloro-p-tolyl-borane 
• 7646-78-8 tin(IV) chloride 

Relevant articles and documents

Room-Temperature Palladium(II)-Catalyzed Direct 2-Arylation of Indoles with Tetraarylstannanes

A palladium(II)-catalyzed direct 2-arylation of indoles by tetraarylstannanes with oxygen (balloon) as the oxidant at room temperature has been developed. Various tetraarylstannanes can be employed as aryl sources for 2-arylation of indoles in up to 89% yield, providing a practical and efficient catalytic protocol for accessing 2-arylindoles.

Palladium(II)- and rhodium(III)-catalyzed carbonylation reaction of aryltin compounds

The Pd(II)- and Rh(III)-catalyzed carbonylation reaction of several aryltin compounds, i.e., tetraphenyltin (Ph4Sn), in acetonitrile (MeCN) and acetic acid was studied. The reaction of Ph4Sn with 1 atm of CO in the presence of a stoichiometric amount of Pd(II) salt was performed to confirm whether more than one of the four phenyl groups could be transferred to the products. To accelerate the carbonylation, LiCl was added, thus, producing benzophenone, benzoic acid, and a small amount of biphenyl as organic products, but only one of the four phenyl groups was transferred to the products. For the Rh(II)-mediated and -catalyzed carbonylation of aryltin compounds in MeCN, benzophenone was mainly produced together with benzoic acid and biphenyl. Seventy-five percent of the four phenyl groups were transferred to the products. The product yield was > 100% based on the amount of Rh(III) chloride used, showing that the Rh(III) salt itself worked as a catalyst without reoxidant addition. Thus, More than one of two, three, or four aryl groups of aryltin compounds, and almost all of them in some cases, could be transferred to the products in this catalytic carbonylation.

Ueber Tetraaryl-Methan-Analoga in der Gruppe 14.III. Ar4Sn/Pb (Ar=Ph, p-, m-, o-Tol, 2,4-Xyl und 2,5-Xyl): Gegenueberstellung von Bindungslaengen und Winkeln, von NMR chemischen Verschiebungen und Kopplungskonstanten und von Schwingungsdaten

The title compounds have been synthesized Grignard reactions or pyrolysis of diplumbanes respectively.The crystal structures of m-Tol4Pb and Ph4Pb (redetermination) have been determined.All eight compounds (Ph/Tol)4(Sn/Pb) are S4 symmetric and contracted along this unique axis.The 13C-NMR chemical shifts and the couplings 1J(119Sn/207Pb-13C) as well depend additively upon the methyl substituents.The ratios 1K(207Pb-13C):1K(119Sn-13C) of the reduced coupling constants are all near to 1.61; a comparison with values from the literature for alkyl, alkenyl and alkinyl substituents is given.The ratio δ(207Pb):δ(119Sn) results in 2.28.IR (700 down to 200 cm-1) and Raman (700 down to 50 cm-1) data are given.Key words: Tin; Lead; Group 14; Vibrational data; Nuclear magnetic resonance; Crystal structure