3590-84-9

Usage

Uses

Used in Chemical Synthesis:
Tetraoctyltin is used as a catalyst in chemical synthesis for promoting the coupling of C-H bonds with 2-aryl and 2-benzyl-substituted 4,4-dimethyl-2-oxazolines and pyridines. This application is significant because it allows for the efficient formation of benzene ring-alkylated products, which are important intermediates in the synthesis of various organic compounds.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, Tetraoctyltin is used as a catalyst for the synthesis of complex organic molecules that serve as potential drug candidates. The ability of Tetraoctyltin to facilitate C-H bond coupling reactions can lead to the development of new drugs with improved efficacy and reduced side effects.
Used in Material Science:
Tetraoctyltin can also be employed in the field of material science, where it can be used as a catalyst for the synthesis of novel materials with specific properties. The benzene ring-alkylated products formed using Tetraoctyltin as a catalyst can be used to create advanced materials with applications in various industries, such as electronics, aerospace, and automotive.

Synthetic route

1-Chlorooctane (111-85-3) + tin(IV) chloride (7646-78-8) → tetraoctyltin (3590-84-9)

Conditions	Yield
With magnesium In diethyl ether; toluene at 50 - 65℃; Solvent; Inert atmosphere; Flow reactor;	98.5%
With sodium In Petroleum ether 13 h;	65-80
With Na In petroleum ether 13 h;	65-80

1-Chlorooctane (111-85-3) + di-n-octyltin dichloride (3542-36-7) → tetraoctyltin (3590-84-9)

Conditions	Yield
With Na	98%
With sodium	98%

tin(IV) chloride (7646-78-8) + trioctylaluminum (1070-00-4) → tetraoctyltin (3590-84-9)

Conditions	Yield
In dibutyl ether 70°C;	98%
In dibutyl ether 70°C;	98%
In dibutyl ether 70°C;	98%

tin(IV) chloride (7646-78-8) + di-n-octylmagnesium (24219-37-2) → tetraoctyltin (3590-84-9)

Conditions

Yield

In tetrahydrofuran; n-heptane a soln. of SnCl4 (18 mmol) in heptane was added dropwise within 10 min to a soln. of (C8H17)2Mg (44 mmol) in THF with stirring (pptn.); the mixt. was refluxed for 3 1/3 h, then treated with H2O and 10% HCl;; the org. layer was separated and dried with CaCl2, the solvents were distilled off in vac., the residue was istilled in high vac.; 99.1% purity (asdetermined by gas chromy.); identified by mass spectrometry; elem. anal.;;

95%

octylmagnesium bromide (17049-49-9) + tin(IV) chloride (7646-78-8) → tetraoctyltin (3590-84-9)

Conditions	Yield
In toluene	90%
In n-heptane	87.93%
In n-heptane	87.93%
In diethyl ether 130-140°C, 10 h;	59%

bis(trioctylstannyl) oxide (2787-93-1) → tetraoctyltin (3590-84-9) + hexaoctyldistannane (21227-24-7)

Conditions	Yield
With magnesium In tetrahydrofuran a soln. of ditin oxide in dry THF was added dropwise to a suspn. of a magnesium powder, activated by BrCH2CH2Br or I2, in dry THF, mixt. was heated at reflux for 15 h; petroleum ether was added, filtered, solvents evapd., residue was distilled;	A 0% B 82%
With sodium In neat (no solvent) stoich. amt. of sodium (2 mol for 1 mol of ditin oxide), 120°C, 48 h; unreacted n-Oct6Sn2O was removed by filtration in pentane through a short SiO2 column, n-Oct4Sn was removed by distn.;	A 1-5 B 68%

tin(IV) chloride (7646-78-8) + n-octylmagnesium chloride (38841-98-4) → tetraoctyltin (3590-84-9)

Conditions	Yield
	64.9%
	64.9%

Upstream product

• 7440-31-5 tin 
• 111-85-3 n-chlorooctane 
• 17049-49-9 octylmagnesium bromide 
• 7646-78-8 tin(IV) chloride 
• 38841-98-4 n-octylmagnesium chloride 
• 24219-37-2 di-n-octylmagnesium 
• 7440-31-5 stannane 
• 111-66-0 oct-1-ene 
• 2787-93-1 bis(trioctylstannyl) oxide 
• 3542-36-7 di-n-octyltin dichloride 
• 1070-00-4 trioctylaluminum 

Downstream Products

• 3091-29-0 trioctyltin bromide 
• 111-83-1 1-bromo-octane 
• 2787-93-1 bis(trioctylstannyl) oxide 
• 2587-76-0 trioctyltin chloride 
• 26674-66-8 octylmercury ⁽¹⁺⁾; chloride 
• 3542-36-7 di-n-octyltin dichloride 
• 63348-82-3 (n-octyl)dichloroborane 
• 3091-25-6 n-octyltin trichloride 
• 111-65-9 octane 
• 919-28-8 trioctyltin acetate 

Relevant academic research and scientific papers

Continuous organomagnesium synthesis of organometallic compounds

Continuous organomagnesium synthesis of a number of organic derivatives of 14th group elements of the periodic table was examined in a column apparatus with an agitator. An effect of a molar ratio of reactants, temperature in a reaction zone, and other factors was studied on the yield and composition of the products.

Diorganomagnesium Compounds from Magnesium, Hydrogen, and 1-Alkenes and Their Application in Synthesis

1-Alkenes are converted in high yields to the corresponding primary diorganomagnesium compounds by transition metal-catalyzed hydromagnesation reaction using catalytically prepared suspended (MgH2*) or dissolved magnesium hydride (MgH2').The most active hydromagnesation catalysts have been found to be combinations of zirconium tetrahalides with MgH2* or MgH2'.The reaction is highly regio- and chemoselective.The diorganomagnesium compounds prepared in situ from magnesium, hydrogen, and 1-alkenes can be applied to the synthesis of organic and organometallic compounds just as Grignard compounds (Scheme 3, reactions 3-11).Dioctylmagnesium undergoes the growth reaction with ethene in the presence of quinuclidine and is oxidized by molecular oxygen in high yield to 1-octanol. Key Words: Magnesium hydride, catalytically prepared / Hydromagnesation reactions / Magnesium, diorgano compounds, preparation from magnesium, hydrogen and 1-alkenes / Magnesium, diorgano compounds, application in syntheses / Magnesium, diorgano compounds, oxidation of

Reduction of bis(triorganotin) oxides by metals: An easy route to hexaorganoditins

Bis(triorganotin) oxides have been reduced in high yield to hexaorganoditins by titanium, magnesium, potassium, and sodium.

A NEW PREPARATION OF HEXAALKYLDITINS. 119Sn NMR AND CHROMATOGRAPHIC DATA ON LINEAR POLYTINS

The reaction of triorganotin oxides and formic acid provides a good route to ditin derivatives.Several new linear polytin compounds have been isolated, and the vicinal and long range 119Sn-119Sn coupling constants determined.A linear relationship has been demonstrated between the logarithm of the HPLC retention time and the number of tin atoms in the compounds.

THE USE OF ORGANOSODIUM INTERMEDIATES IN THE SYNTHESIS OF ALKYLTIN CHLORIDES

The synthesis of various RxSnCl4-x compounds (R=butyl, octyl, dodecyl) from reaction between tin(IV) chloride, or a dialkyltin dichloride, and alkylsodium compounds RNa was investigated.Optimum conditions were established and some competing side-reactions identified.

A NEW ROUTE TO TETRAORGANOTIN COMPOUNDS

A new direct synthesis suitable for the preparation of straight-chain tetraalkyltins is described.