Tetraethyltin

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Tetraethyltin
Tetraethyltin Structure.svg
Tetraethyltin-3D-spacefill.png
Names
IUPAC name
Tetraethyltin
Other names
Tetraethyl tin
Tetraethylstannane
Identifiers
3D model (JSmol)
AbbreviationsTET
ChemSpider
ECHA InfoCard 100.009.007 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 209-906-2
MeSH Tetraethyltin
PubChem CID
UNII
UN number 3384 2788
  • InChI=1S/4C2H5.Sn/c4*1-2;/h4*1H2,2H3; Yes check.svgY
    Key: RWWNQEOPUOCKGR-UHFFFAOYSA-N Yes check.svgY
  • CC[Sn](CC)(CC)CC
Properties
(CH3CH2)4Sn
Molar mass 234.958 g·mol−1
AppearanceColourless liquid
Density 1.187 g cm−3
Melting point −112 °C (−170 °F; 161 K)
Boiling point 181 °C (358 °F; 454 K)
Hazards
GHS labelling:
GHS-pictogram-flamme.svg GHS-pictogram-skull.svg GHS-pictogram-pollu.svg
Danger
H226, H300, H310, H330, H410
P210, P233, P240, P241, P242, P243, P260, P262, P264, P270, P271, P273, P280, P284, P301+P310, P302+P350, P303+P361+P353, P304+P340, P310, P320, P321, P322, P330, P361, P363, P370+P378, P391, P403+P233, P403+P235, P405, P501
NFPA 704 (fire diamond)
NFPA 704.svgHealth 3: Short exposure could cause serious temporary or residual injury. E.g. chlorine gasFlammability 2: Must be moderately heated or exposed to relatively high ambient temperature before ignition can occur. Flash point between 38 and 93 °C (100 and 200 °F). E.g. diesel fuelInstability 3: Capable of detonation or explosive decomposition but requires a strong initiating source, must be heated under confinement before initiation, reacts explosively with water, or will detonate if severely shocked. E.g. hydrogen peroxideSpecial hazards (white): no code
3
2
3
Flash point 53 °C (127 °F; 326 K)
Related compounds
Related Tetraalkylstannanes
Related compounds
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
X mark.svgN  verify  (what is  Yes check.svgYX mark.svgN ?)

Tetraethyltin or tetraethyl tin is a chemical compound with the formula (CH3CH2)4Sn, that is, a tin atom attached to four ethyl groups. It is an important example of an organotin compound, often abbreviated as TET.

Tetraethyltin is a colourless flammable liquid, soluble in diethyl ether and insoluble in water, that freezes at −112 °C and boils at 181 °C. [1] [2] It is used in the electronics industry.

Tetraethyltin can be obtained by reacting ethylmagnesium bromide with tin(IV) chloride: [1]

SnCl4 + 4 CH3CH2MgBr → (CH3CH2)4Sn + 4 MgBrCl

The same reaction can be used to obtain tetra-n-propyltin and tetra-n-butyltin. [1]

Tetraethyltin is converted in the body to the more toxic triethylstannylium ions. [3]

See also

Related Research Articles

<span class="mw-page-title-main">Tin</span> Chemical element with atomic number 50 (Sn)

Tin is a chemical element; it has symbol Sn and atomic number 50. A silvery-colored metal, tin is soft enough to be cut with little force, and a bar of tin can be bent by hand with little effort. When bent, the so-called "tin cry" can be heard as a result of twinning in tin crystals.

<span class="mw-page-title-main">Carbon group</span> Periodic table group

The carbon group is a periodic table group consisting of carbon (C), silicon (Si), germanium (Ge), tin (Sn), lead (Pb), and flerovium (Fl). It lies within the p-block.

The Stille reaction is a chemical reaction widely used in organic synthesis. The reaction involves the coupling of two organic groups, one of which is carried as an organotin compound (also known as organostannanes). A variety of organic electrophiles provide the other coupling partner. The Stille reaction is one of many palladium-catalyzed coupling reactions.

Tin(IV) chloride, also known as tin tetrachloride or stannic chloride, is an inorganic compound of tin and chlorine with the formula SnCl4. It is a colorless hygroscopic liquid, which fumes on contact with air. It is used as a precursor to other tin compounds. It was first discovered by Andreas Libavius (1550–1616) and was known as spiritus fumans libavii.

<span class="mw-page-title-main">Cobalt(II) chloride</span> Chemical compound

Cobalt(II) chloride is an inorganic compound, a salt of cobalt and chlorine, with the formula CoCl
2
. The compound forms several hydrates CoCl
2
·nH
2
O
, for n = 1, 2, 6, and 9. Claims of the formation of tri- and tetrahydrates have not been confirmed. The anhydrous form is a blue crystalline solid; the dihydrate is purple and the hexahydrate is pink. Commercial samples are usually the hexahydrate, which is one of the most commonly used cobalt salts in the lab.

<span class="mw-page-title-main">Organotin chemistry</span> Branch of organic chemistry

Organotin chemistry is the scientific study of the synthesis and properties of organotin compounds or stannanes, which are organometallic compounds containing tin–carbon bonds. The first organotin compound was diethyltin diiodide, discovered by Edward Frankland in 1849. The area grew rapidly in the 1900s, especially after the discovery of the Grignard reagents, which are useful for producing Sn–C bonds. The area remains rich with many applications in industry and continuing activity in the research laboratory.

The Hiyama coupling is a palladium-catalyzed cross-coupling reaction of organosilanes with organic halides used in organic chemistry to form carbon–carbon bonds. This reaction was discovered in 1988 by Tamejiro Hiyama and Yasuo Hatanaka as a method to form carbon-carbon bonds synthetically with chemo- and regioselectivity. The Hiyama coupling has been applied to the synthesis of various natural products.

<span class="mw-page-title-main">Fluoroboric acid</span> Chemical compound

Fluoroboric acid or tetrafluoroboric acid is an inorganic compound with the simplified chemical formula H+[BF4]. Solvent-free tetrafluoroboric acid has not been reported. The term "fluoroboric acid" usually refers to a range of compounds including hydronium tetrafluoroborate, which are available as solutions. The ethyl ether solvate is also commercially available, where the fluoroboric acid can be represented by the formula [H( 2O)n]+[BF4], where n is 2.

<span class="mw-page-title-main">Tributyltin hydride</span> Chemical compound

Tributyltin hydride is an organotin compound with the formula (C4H9)3SnH. It is a colorless liquid that is soluble in organic solvents. The compound is used as a source of hydrogen atoms in organic synthesis.

<span class="mw-page-title-main">Thiophosphoryl chloride</span> Chemical compound

Thiophosphoryl chloride is an inorganic compound with the chemical formula PSCl3. It is a colorless pungent smelling liquid that fumes in air. It is synthesized from phosphorus chloride and used to thiophosphorylate organic compounds, such as to produce insecticides.

<span class="mw-page-title-main">Trimethyltin chloride</span> Chemical compound

Trimethyltin chloride is an organotin compound with the formula (CH3)3SnCl. It is a white solid that is highly toxic and malodorous. It is susceptible to hydrolysis.

<span class="mw-page-title-main">Carbon diselenide</span> Chemical compound

Carbon diselenide is an inorganic compound with the chemical formula CSe2. It is a yellow-orange oily liquid with pungent odor. It is the selenium analogue of carbon disulfide and carbon dioxide. This light-sensitive compound is insoluble in water and soluble in organic solvents.

<span class="mw-page-title-main">Tetramethyltin</span> Chemical compound

Tetramethyltin is an organometallic compound with the formula (CH3)4Sn. This liquid, one of the simplest organotin compounds, is useful for transition-metal mediated conversion of acid chlorides to methyl ketones and aryl halides to aryl methyl ketones. It is volatile and toxic, so care should be taken when using it in the laboratory.

Zinc compounds are chemical compounds containing the element zinc which is a member of the group 12 of the periodic table. The oxidation state of zinc in most compounds is the group oxidation state of +2. Zinc may be classified as a post-transition main group element with zinc(II). Zinc compounds are noteworthy for their nondescript appearance and behavior: they are generally colorless, do not readily engage in redox reactions, and generally adopt symmetrical structures.

A stannide can refer to an intermetallic compound containing tin combined with one or more other metals; an anion consisting solely of tin atoms or a compound containing such an anion, or, in the field of organometallic chemistry an ionic compound containing an organotin anion

<span class="mw-page-title-main">Sodium selenide</span> Chemical compound

Sodium selenide is an inorganic compound of sodium and selenium with the chemical formula Na2Se.

<span class="mw-page-title-main">High-valent iron</span> Iron in an oxidation state higher than III

High-valent iron commonly denotes compounds and intermediates in which iron is found in a formal oxidation state > 3 that show a number of bonds > 6 with a coordination number ≤ 6. The term is rather uncommon for hepta-coordinate compounds of iron. It has to be distinguished from the terms hypervalent and hypercoordinate, as high-valent iron compounds neither necessarily violate the 18-electron rule nor necessarily show coordination numbers > 6. The ferrate(VI) ion [FeO4]2− was the first structure in this class synthesized. The synthetic compounds discussed below contain highly oxidized iron in general, as the concepts are closely related.

<span class="mw-page-title-main">Stannole</span> Organotin compound

Stannole is an organotin compound with the formula (CH)4SnH2. It is classified as a metallole, i.e. an unsaturated five-membered ring containing a heteroatom. It is a structural analog of cyclopentadiene, with tin replacing the saturated carbon atom. Substituted derivatives, which have been synthesized, are also called stannoles.

Polyhalogen ions are a group of polyatomic cations and anions containing halogens only. The ions can be classified into two classes, isopolyhalogen ions which contain one type of halogen only, and heteropolyhalogen ions with more than one type of halogen.

<span class="mw-page-title-main">Sodium tetrapropylborate</span> Chemical compound

Sodium tetrapropylborate is an ionic organoboron compound used as a derivatization reagent for chromatography of organometallic pollutants. It is a white hygroscopic powder. It is stable in aqueous solution, but pyrophoric in air; it can be stored as a solution in tetrahydrofuran for multiple weeks.

References

  1. 1 2 3 G. J. M. Van Der Kerk and J. G. A. Luijten (1956), "Tetraethyltin". Organic Syntheses, volume 36, page 86; Coll. Vol. 4, p.881 (1963)
  2. SAFC corp, tetraethyltin catalog page. Accessed on 2011-01-18.
  3. Jill E. Cremer (1958), "The biochemistry of organotin compounds. The conversion of tetraethyltin into triethyltin in mammals". Biochem J. volume 68, issue 4, pages 685–692. Cremer refers to the ions as the ambiguous "triethyltin", but cites H. B. Stoner, J. M. Barnes, and J. I. Duff (1955), Brit. J. Pharmacol. volume 10, issue 16, which indicates that the compounds in question are triethyltin hydroxide and sulfate.