Indium(III) chloride

Last updated
Indium(III) chloride
Kristallstruktur Chrom(III)-chlorid.png
Names
Other names
Indium chloride
Indium trichloride
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.030.027 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 233-043-0
PubChem CID
RTECS number
  • NL1400000
UNII
UN number 3260
  • InChI=1S/3ClH.In/h3*1H;/q;;;+3/p-3 Yes check.svgY
    Key: PSCMQHVBLHHWTO-UHFFFAOYSA-K Yes check.svgY
  • InChI=1/3ClH.In/h3*1H;/q;;;+3/p-3
    Key: PSCMQHVBLHHWTO-DFZHHIFOAF
  • Cl[In](Cl)Cl
Properties
InCl3
Molar mass 221.18 g/mol
Appearancewhite flakes
Density 3.46 g/cm3
Melting point 586 °C (1,087 °F; 859 K)
Boiling point 800 °C (1,470 °F; 1,070 K)
195 g/100 mL, exothermic
Solubility in other solvents THF, Ethanol
Structure
Monoclinic, mS16
C12/m1, No. 12
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
Corrosive
GHS labelling:
GHS-pictogram-acid.svg GHS-pictogram-exclam.svg [1]
Danger [1]
H302, H314 [1]
P260, P301+P330+P331, P303+P361+P353, P305+P351+P338, P405, P501 [1]
NFPA 704 (fire diamond)
NFPA 704.svgHealth 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroformFlammability 0: Will not burn. E.g. waterInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
2
0
0
Safety data sheet (SDS) External SDS
Related compounds
Other anions
Indium(III) fluoride
Indium(III) bromide
Indium(III) iodide
Other cations
Aluminium chloride
Gallium trichloride
Thallium(III) chloride
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Yes check.svgY  verify  (what is  Yes check.svgYX mark.svgN ?)

Indium(III) chloride is the chemical compound with the formula In Cl3. This salt is a white, flaky solid with applications in organic synthesis as a Lewis acid. It is also the most available soluble derivative of indium. [2] This is one of three known indium chlorides.

Contents

Synthesis and structure

Being a relatively electropositive metal, indium reacts quickly with chlorine to give the trichloride. Indium trichloride is very soluble and deliquescent. [3] A synthesis has been reported using an electrochemical cell in a mixed methanol-benzene solution. [4]

Like AlCl3 and TlCl3, InCl3 crystallizes as a layered structure consisting of a close-packed chloride arrangement containing layers of octahedrally coordinated In(III) centers, [5] a structure akin to that seen in YCl3. [6] In contrast, GaCl3 crystallizes as dimers containing Ga2Cl6. [6] Molten InCl3 conducts electricity, [5] whereas AlCl3 does not as it converts to the molecular dimer, Al2Cl6. [7]

Reactions

InCl3 is a Lewis acid and forms complexes with donor ligands, L, InCl3L, InCl3L2, InCl3L3. For example, with the chloride ion it forms tetrahedral InCl4−, trigonal bipyramidal InCl52−, and octahedral InCl63−. [5]

In diethyl ether solution, InCl3 reacts with lithium hydride, LiH, to form . This unstable compound decomposes below 0 °C, [8] and is reacted in situ in organic synthesis as a reducing agent [9] and to prepare tertiary amine and phosphine complexes of InH3. [10]

Trimethylindium, InMe3, can be produced by reacting InCl3 in diethyl ether solution either with the Grignard reagent or methyllithium, LiMe. Triethylindium can be prepared in a similar fashion but with the grignard reagent EtMgBr. [11]

InCl3 reacts with indium metal at high temperature to form the lower valent indium chlorides In5Cl9, In2Cl3 and InCl. [5]

Catalyst in chemistry

Indium chloride is a Lewis acid catalyst in organic reactions such as Friedel-Crafts acylations and Diels-Alder reactions. As an example of the latter, [12] the reaction proceeds at room temperature, with 1 mole% catalyst loading in an acetonitrile-water solvent mixture. The first step is a Knoevenagel condensation between the barbituric acid and the aldehyde; the second step is a reverse electron-demand Diels-Alder reaction, which is a multicomponent reaction of N,N'-dimethyl-barbituric acid, benzaldehyde and ethyl vinyl ether. With the catalyst, the reported chemical yield is 90% and the percentage trans isomer is 70%. Without the catalyst added, the yield drops to 65% with 50% trans product.

IndiumChlorideApplication.png

Related Research Articles

Iron(III) chloride describes the inorganic compounds with the formula FeCl3(H2O)x. Also called ferric chloride, these compounds are available both in anhydrous and hydrated forms which are both hygroscopic. They are common sources of iron in its +3 oxidation state. The anhydrous derivative is a Lewis acid, while the hydrate is a mild oxidizing agent. It is used as a water cleaner and as an etchant for metals.

<span class="mw-page-title-main">Gilman reagent</span> Class of chemical compounds

A Gilman reagent is a lithium and copper (diorganocopper) reagent compound, R2CuLi, where R is an alkyl or aryl. These reagents are useful because, unlike related Grignard reagents and organolithium reagents, they react with organic halides to replace the halide group with an R group (the Corey–House reaction). Such displacement reactions allow for the synthesis of complex products from simple building blocks.

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

Lithium aluminium hydride, commonly abbreviated to LAH, is an inorganic compound with the chemical formula Li[AlH4] or LiAlH4. It is a white solid, discovered by Finholt, Bond and Schlesinger in 1947. This compound is used as a reducing agent in organic synthesis, especially for the reduction of esters, carboxylic acids, and amides. The solid is dangerously reactive toward water, releasing gaseous hydrogen (H2). Some related derivatives have been discussed for hydrogen storage.

In organic chemistry, an acyl chloride is an organic compound with the functional group −C(=O)Cl. Their formula is usually written R−COCl, where R is a side chain. They are reactive derivatives of carboxylic acids. A specific example of an acyl chloride is acetyl chloride, CH3COCl. Acyl chlorides are the most important subset of acyl halides.

<span class="mw-page-title-main">Titanium tetrachloride</span> Inorganic chemical compound

Titanium tetrachloride is the inorganic compound with the formula TiCl4. It is an important intermediate in the production of titanium metal and the pigment titanium dioxide. TiCl4 is a volatile liquid. Upon contact with humid air, it forms thick clouds of titanium dioxide and hydrochloric acid, a reaction that was formerly exploited for use in smoke machines. It is sometimes referred to as "tickle" or "tickle 4" due to the phonetic resemblance of its molecular formula to the word.

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

Cerium(III) chloride (CeCl3), also known as cerous chloride or cerium trichloride, is a compound of cerium and chlorine. It is a white hygroscopic salt; it rapidly absorbs water on exposure to moist air to form a hydrate, which appears to be of variable composition, though the heptahydrate CeCl3·7H2O is known. It is highly soluble in water, and (when anhydrous) it is soluble in ethanol and acetone.

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

Aluminium chloride, also known as aluminium trichloride, is an inorganic compound with the formula AlCl3. It forms a hexahydrate with the formula [Al(H2O)6]Cl3, containing six water molecules of hydration. Both the anhydrous form and the hexahydrate are colourless crystals, but samples are often contaminated with iron(III) chloride, giving them a yellow colour.

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

Nickel(II) chloride (or just nickel chloride) is the chemical compound NiCl2. The anhydrous salt is yellow, but the more familiar hydrate NiCl2·6H2O is green. Nickel(II) chloride, in various forms, is the most important source of nickel for chemical synthesis. The nickel chlorides are deliquescent, absorbing moisture from the air to form a solution. Nickel salts have been shown to be carcinogenic to the lungs and nasal passages in cases of long-term inhalation exposure.

<span class="mw-page-title-main">Thionyl chloride</span> Inorganic compound (SOCl2)

Thionyl chloride is an inorganic compound with the chemical formula SOCl2. It is a moderately volatile, colourless liquid with an unpleasant acrid odour. Thionyl chloride is primarily used as a chlorinating reagent, with approximately 45,000 tonnes per year being produced during the early 1990s, but is occasionally also used as a solvent. It is toxic, reacts with water, and is also listed under the Chemical Weapons Convention as it may be used for the production of chemical weapons.

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

Phosphorus trichloride is an inorganic compound with the chemical formula PCl3. A colorless liquid when pure, it is an important industrial chemical, being used for the manufacture of phosphites and other organophosphorus compounds. It is toxic and reacts readily with water to release hydrogen chloride.

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

Triphenylphosphine (IUPAC name: triphenylphosphane) is a common organophosphorus compound with the formula P(C6H5)3 and often abbreviated to PPh3 or Ph3P. It is widely used in the synthesis of organic and organometallic compounds. PPh3 exists as relatively air stable, colorless crystals at room temperature. It dissolves in non-polar organic solvents such as benzene and diethyl ether.

<span class="mw-page-title-main">18-Crown-6</span> Chemical compound

18-Crown-6 is an organic compound with the formula [C2H4O]6 and the IUPAC name of 1,4,7,10,13,16-hexaoxacyclooctadecane. It is a white, hygroscopic crystalline solid with a low melting point. Like other crown ethers, 18-crown-6 functions as a ligand for some metal cations with a particular affinity for potassium cations (binding constant in methanol: 106 M−1). The point group of 18-crown-6 is S6. The dipole moment of 18-crown-6 varies in different solvent and under different temperature. Under 25 °C, the dipole moment of 18-crown-6 is 2.76 ± 0.06 D in cyclohexane and 2.73 ± 0.02 in benzene. The synthesis of the crown ethers led to the awarding of the Nobel Prize in Chemistry to Charles J. Pedersen.

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

Trimethylsilyl chloride, also known as chlorotrimethylsilane is an organosilicon compound (silyl halide), with the formula (CH3)3SiCl, often abbreviated Me3SiCl or TMSCl. It is a colourless volatile liquid that is stable in the absence of water. It is widely used in organic chemistry.

Boron trichloride is the inorganic compound with the formula BCl3. This colorless gas is a reagent in organic synthesis. It is highly reactive toward water.

<span class="mw-page-title-main">Grignard reagent</span> Organometallic compounds used in organic synthesis

A Grignard reagent or Grignard compound is a chemical compound with the general formula R−Mg−X, where X is a halogen and R is an organic group, normally an alkyl or aryl. Two typical examples are methylmagnesium chloride Cl−Mg−CH3 and phenylmagnesium bromide (C6H5)−Mg−Br. They are a subclass of the organomagnesium compounds.

<span class="mw-page-title-main">Indium(III) bromide</span> Chemical compound

Indium(III) bromide, (indium tribromide), InBr3, is a chemical compound of indium and bromine. It is a Lewis acid and has been used in organic synthesis.

In inorganic chemistry, sulfonyl halide groups occur when a sulfonyl functional group is singly bonded to a halogen atom. They have the general formula RSO2X, where X is a halogen. The stability of sulfonyl halides decreases in the order fluorides > chlorides > bromides > iodides, all four types being well known. The sulfonyl chlorides and fluorides are of dominant importance in this series.

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

Gallium trichloride is the chemical compound with the formula GaCl3. Solid gallium trichloride exists as a dimer with the formula Ga2Cl6. It is colourless and soluble in virtually all solvents, even alkanes, which is truly unusual for a metal halide. It is the main precursor to most derivatives of gallium and a reagent in organic synthesis.

<span class="mw-page-title-main">Organocopper chemistry</span> Compound with carbon to copper bonds

Organocopper chemistry is the study of the physical properties, reactions, and synthesis of organocopper compounds, which are organometallic compounds containing a carbon to copper chemical bond. They are reagents in organic chemistry.

<span class="mw-page-title-main">Group 2 organometallic chemistry</span>

Group 2 organometallic chemistry refers to the chemistry of compounds containing carbon bonded to any group 2 element. By far the most common group 2 organometallic compounds are the magnesium-containing Grignard reagents which are widely used in organic chemistry. Other organmetallic group 2 compounds are rare and are typically limited to academic interests.

References

  1. 1 2 3 4 "Indium(III) Chloride". American Elements . Retrieved May 15, 2019.
  2. ↑ Araki, S.; Hirashita, T. "Indium trichloride" in Encyclopedia of Reagents for Organic Synthesis (Ed: L. Paquette) 2004, J. Wiley & Sons, New York. doi : 10.1002/047084289X.
  3. ↑ Indium Trichloride
  4. ↑ Habeeb, J. J.; Tuck, D. G. "Electrochemical Synthesis of Indium(III) Complexes" Inorganic Syntheses, 1979, volume XIX, ISBN   0-471-04542-X
  5. 1 2 3 4 Egon Wiberg, Arnold Frederick Holleman (2001) Inorganic Chemistry, Elsevier ISBN   0123526515
  6. 1 2 Wells, A.F. Structural Inorganic Chemistry, Oxford: Clarendon Press, 1984. ISBN   0-19-855370-6.
  7. ↑ Greenwood, Norman N.; Earnshaw, Alan (1997). Chemistry of the Elements (2nd ed.). Butterworth-Heinemann. ISBN   978-0-08-037941-8.
  8. ↑ Anthony John Downs (1993). Chemistry of aluminium, gallium, indium, and thallium. Springer. ISBN   0-7514-0103-X.
  9. ↑ Main Group Metals in Organic Synthesis vol 1, ed. Hisashi Yamamoto, Koichiro Oshima, Wiley VCH, 2004, ISBN   3527305084
  10. ↑ The Group 13 Metals Aluminium, Gallium, Indium and Thallium: Chemical Patterns and Peculiarities, Simon Aldridge, Anthony J. Downs, Wiley, 2011, ISBN   978-0-470-68191-6
  11. ↑ Main Group compounds in Inorganic Syntheses, vol 31, By Schultz, Neumayer, Marks; Ed., Alan H. Cowley, John Wiley & Sons, Inc., 1997, ISBN   0471152889
  12. ↑ An efficient synthesis of novel pyrano[2,3-d]- and furopyrano[2,3-d]pyrimidines via Indium-Catalyzed Multicomponent Domino Reaction Prajapati, D. Mukut Gohain, M. Beilstein Journal of Organic Chemistry 2006, 2:11 doi : 10.1186/1860-5397-2-11
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