3590-84-9

Basic information

• Product Name: Tetraoctyltin
• Synonyms: tetra-n-octylstannane;tetraoctyl-stannan;tetraoctyl-ti;TIN TETRAOCTYL;TETRA-N-OCTYLTIN;TETRA-N-OCTYLTIN(IV);TETRAOCTYLSTANNANE;TETRAOCTYLTIN
• CAS NO: 3590-84-9
• Molecular Formula: C₃₂H₆₈Sn
• Molecular Weight: 571.59
• EINECS: 222-733-7
• Mol File: 3590-84-9.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 224°C 1mm
• Flash Point: 102°C
• Appearance: /
• Density: 0,98 g/cm3
• Vapor Pressure: 0Pa at 25℃
• Refractive Index: 1.4677
• Storage Temp.: Store below +30°C.
• Solubility: Chloroform (Soluble), Ethyl Acetate (Sparingly)
• CAS DataBase Reference: Tetraoctyltin(CAS DataBase Reference)
• NIST Chemistry Reference: Tetraoctyltin(3590-84-9)
• EPA Substance Registry System: Tetraoctyltin(3590-84-9)

Safety Data

• Statements: 36/37
• Safety Statements: 24
• TSCA: Yes
• Hazardous Substances Data: 3590-84-9(Hazardous Substances Data)

Usage

Uses

Tetraoctyltin was coupled to C-H bonds of 2-aryl- and 2-benzyl-substituted 4,4-?dimethyl-?2-?oxazolines and pyridines to give the benzene ring-?alkylated products in good yields by using 5 mol % Pd(OAc)?2 as the catalyst.

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

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

Downstream Products

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

Relevant articles and documents

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.

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.

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.