Aluminium chloride

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Aluminium chloride
Aluminium-trichloride-hexahydrate-white-and-yellow.jpg
Aluminium trichloride hexahydrate, pure (top), and contaminated with iron(III) chloride (bottom)
Aluminium trichloride dimer Aluminium-trichloride-dimer-3D-balls.png
Aluminium trichloride dimer
Aluminium trichloride unit cell Aluminium-chloride-xtal-unit-cell-3D-bs-17.png
Aluminium trichloride unit cell
Names
IUPAC name
Aluminium chloride
Other names
Aluminium(III) chloride
Aluminium trichloride
Trichloroaluminum
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.028.371 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 231-208-1
1876
PubChem CID
RTECS number
  • BD0530000
UNII
  • InChI=1S/Al.3ClH/h;3*1H/q+3;;;/p-3 Yes check.svgY
    Key: VSCWAEJMTAWNJL-UHFFFAOYSA-K Yes check.svgY
  • InChI=1/Al.3ClH/h;3*1H/q+3;;;/p-3
    Key: VSCWAEJMTAWNJL-DFZHHIFOAR
  • monomer:Cl[Al](Cl)Cl
  • dimer:Cl[Al-]1(Cl)[Cl+][Al-]([Cl+]1)(Cl)Cl
  • hexahydrate:[OH2+][Al-3]([OH2+])([OH2+])([OH2+])([OH2+])[OH2+].[Cl-].[Cl-].[Cl-]
Properties
AlCl3
Molar mass
  • 133.341 g/mol (anhydrous)
  • 241.432 g/mol (hexahydrate)
[1]
AppearanceColourless crystals, hygroscopic
Density
  • 2.48 g/cm3 (anhydrous)
  • 2.398 g/cm3 (hexahydrate)
[1]
Melting point
  • 180 °C (356 °F; 453 K) (anhydrous, sublimes) [1]
  • 100 °C (212 °F; 373 K) (hexahydrate, decomposes) [1]
  • 439 g/L (0 °C)
  • 449 g/L (10 °C)
  • 458 g/L (20 °C)
  • 466 g/L (30 °C)
  • 473 g/L (40 °C)
  • 481 g/L (60 °C)
  • 486 g/L (80 °C)
  • 490 g/L (100 °C)
Solubility
  • Soluble in hydrogen chloride, ethanol, chloroform, carbon tetrachloride
  • Slightly soluble in benzene
Vapor pressure
  • 133.3 Pa (99 °C)
  • 13.3 kPa (151 °C)
[2]
Viscosity
  • 0.35 cP (197 °C)
  • 0.26 cP (237 °C)
[2]
Structure
Monoclinic, mS16
C12/m1, No. 12 [3]
a = 0.591 nm, b = 0.591 nm, c = 1.752 nm [3]
0.52996 nm3
6
Octahedral (solid)
Tetrahedral (liquid)
Trigonal planar
(monomeric vapour)
Thermochemistry
91.1 J/(mol·K) [4]
Std molar
entropy (S⦵298)
109.3 J/(mol·K) [4]
−704.2 kJ/mol [4]
−628.8 kJ/mol [4]
Pharmacology
D10AX01 ( WHO )
Hazards
GHS labelling: [5]
GHS-pictogram-acid.svg
Danger
H314
P260, P280, P301+P330+P331, P303+P361+P353, P305+P351+P338+P310, P310
NFPA 704 (fire diamond)
NFPA 704.svgHealth 3: Short exposure could cause serious temporary or residual injury. E.g. chlorine gasFlammability 0: Will not burn. E.g. waterInstability 2: Undergoes violent chemical change at elevated temperatures and pressures, reacts violently with water, or may form explosive mixtures with water. E.g. white phosphorusSpecial hazards (white): no code
3
0
2
Lethal dose or concentration (LD, LC):
380 mg/kg, rat (oral, anhydrous)
3311 mg/kg, rat (oral, hexahydrate)
NIOSH (US health exposure limits):
PEL (Permissible)
None [6]
REL (Recommended)
2 mg/m3 [6]
IDLH (Immediate danger)
N.D. [6]
Related compounds
Other anions
Other cations
Related Lewis acids
Supplementary data page
Aluminium chloride (data page)
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 ?)
Aluminium chloride
Clinical data
AHFS/Drugs.com Monograph
License data
Routes of
administration 		Topical
ATC code
  • None
Identifiers
CompTox Dashboard (EPA)
ECHA InfoCard 100.028.371 OOjs UI icon edit-ltr-progressive.svg
Data page
Aluminium chloride (data page)

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.

The anhydrous form is commercially important. It has a low melting and boiling point. It is mainly produced and consumed in the production of aluminium, but large amounts are also used in other areas of the chemical industry. [7] The compound is often cited as a Lewis acid. It is an example of an inorganic compound that reversibly changes from a polymer to a monomer at mild temperature.

History

The salt was known in the 18th century as muriate of alumina, marine alum, argillaceous marine salt, [8] muriated clay. [9] It was first chemically studied in the 1830s. [10]

Structure

Illustration of structures of aluminium chloride Aluminium-trichloride-3D-structures.png
Illustration of structures of aluminium chloride

Anhydrous

AlCl3 adopts three structures, depending on the temperature and the state (solid, liquid, gas). Solid AlCl3 has a sheet-like layered structure with cubic close-packed chloride ions. In this framework, the Al centres exhibit octahedral coordination geometry. [11] Yttrium(III) chloride adopts the same structure, as do a range of other compounds. When aluminium trichloride is in its melted state, it exists as the dimer Al2Cl6, with tetracoordinate aluminium. This change in structure is related to the lower density of the liquid phase (1.78 g/cm3) versus solid aluminium trichloride (2.48 g/cm3). Al2Cl6 dimers are also found in the vapour phase. At higher temperatures, the Al2Cl6 dimers dissociate into trigonal planar AlCl3 monomer, which is structurally analogous to BF3. The melt conducts electricity poorly, [12] unlike more ionic halides such as sodium chloride.

Aluminium chloride monomer belongs to the point group D3h in its monomeric form and D2h in its dimeric form.

Hexahydrate

The hexahydrate consists of octahedral [Al(H2O)6]3+ cation centers and chloride anions (Cl−) as counterions. Hydrogen bonds link the cation and anions. [13] The hydrated form of aluminium chloride has an octahedral molecular geometry, with the central aluminium ion surrounded by six water ligand molecules. Being coordinatively saturated, the hydrate is of little value as a catalyst in Friedel-Crafts alkylation and related reactions.

Uses

Alkylation and acylation of arenes

AlCl3 is a common Lewis-acid catalyst for Friedel-Crafts reactions, both acylations and alkylations. [14] Important products are detergents and ethylbenzene. These types of reactions are the major use for aluminium chloride, for example, in the preparation of anthraquinone (used in the dyestuffs industry) from benzene and phosgene. [12] In the general Friedel-Crafts reaction, an acyl chloride or alkyl halide reacts with an aromatic system as shown: [14]

Benzene Friedel-Crafts alkylation-diagram.svg

The alkylation reaction is more widely used than the acylation reaction, although its practice is more technically demanding. For both reactions, the aluminium chloride, as well as other materials and the equipment, should be dry, although a trace of moisture is necessary for the reaction to proceed. [15] Detailed procedures are available for alkylation [16] and acylation [17] [18] of arenes.

A general problem with the Friedel-Crafts reaction is that the aluminium chloride catalyst sometimes is required in full stoichiometric quantities, because it complexes strongly with the products. This complication sometimes generates a large amount of corrosive waste. For these and similar reasons, the use of aluminium chloride has often been displaced by zeolites. [7]

Aluminium chloride can also be used to introduce aldehyde groups onto aromatic rings, for example via the Gattermann-Koch reaction which uses carbon monoxide, hydrogen chloride and a copper(I) chloride co-catalyst. [19]

AlCl3 formylation.gif

Other applications in organic and organometallic synthesis

Aluminium chloride finds a wide variety of other applications in organic chemistry. [20] For example, it can catalyse the ene reaction, such as the addition of 3-buten-2-one (methyl vinyl ketone) to carvone: [21]

AlCl3 ene rxn.gif

It is used to induce a variety of hydrocarbon couplings and rearrangements. [22] [23]

Aluminium chloride combined with aluminium in the presence of an arene can be used to synthesize bis(arene) metal complexes, e.g. bis(benzene)chromium, from certain metal halides via the Fischer–Hafner synthesis. Dichlorophenylphosphine is prepared by reaction of benzene and phosphorus trichloride catalyzed by aluminium chloride. [24]

Medical

Topical aluminum chloride hexahydrate is used for the treatment of hyperhidrosis (excessive sweating). [25] [26] [27]

Reactions

Anhydrous aluminium chloride is a powerful Lewis acid, capable of forming Lewis acid-base adducts with even weak Lewis bases such as benzophenone and mesitylene. [14] It forms tetrachloroaluminate ([AlCl4]−) in the presence of chloride ions.

Aluminium chloride reacts with calcium and magnesium hydrides in tetrahydrofuran forming tetrahydroaluminates.[ citation needed ]

Reactions with water

Anhydrous aluminium chloride is hygroscopic, having a very pronounced affinity for water. It fumes in moist air and hisses when mixed with liquid water as the Cl− ligands are displaced with H2O molecules to form the hexahydrate [Al(H2O)6]Cl3. The anhydrous phase cannot be regained on heating the hexahydrate. Instead HCl is lost leaving aluminium hydroxide or alumina (aluminium oxide):

[Al(H2O)6]Cl3 → Al(OH)3 + 3 HCl + 3 H2O

Like metal aquo complexes, aqueous AlCl3 is acidic owing to the ionization of the aquo ligands:

[Al(H2O)6]3+ ⇌ [Al(OH)(H2O)5]2+ + H+

Aqueous solutions behave similarly to other aluminium salts containing hydrated Al3+ ions, giving a gelatinous precipitate of aluminium hydroxide upon reaction with dilute sodium hydroxide:

AlCl3 + 3 NaOH → Al(OH)3 + 3 NaCl

Synthesis

Aluminium chloride is manufactured on a large scale by the exothermic reaction of aluminium metal with chlorine or hydrogen chloride at temperatures between 650 and 750 °C (1,202 and 1,382 °F). [12]

2 Al + 3 Cl2 → 2 AlCl3
2 Al + 6 HCl → 2 AlCl3 + 3 H2

Aluminium chloride may be formed via a single displacement reaction between copper(II) chloride and aluminium.

2 Al + 3 CuCl2 → 2 AlCl3 + 3 Cu

In the US in 1993, approximately 21,000 tons were produced, not counting the amounts consumed in the production of aluminium. [7]

Hydrated aluminium trichloride is prepared by dissolving aluminium oxides in hydrochloric acid. Metallic aluminium also readily dissolves in hydrochloric acid ─ releasing hydrogen gas and generating considerable heat. Heating this solid does not produce anhydrous aluminium trichloride, the hexahydrate decomposes to aluminium hydroxide when heated:

[Al(H2O)6]Cl3 → Al(OH)3 + 3 HCl + 3 H2O

Aluminium also forms a lower chloride, aluminium(I) chloride (AlCl), but this is very unstable and only known in the vapour phase. [12]

Natural occurrence

Anhydrous aluminium chloride is not found as a mineral. The hexahydrate, however, is known as the rare mineral chloraluminite. [28] A more complex, basic and hydrated aluminium chloride mineral is cadwaladerite. [29] [28]

Safety

Anhydrous AlCl3 reacts vigorously with bases, so suitable precautions are required. It can cause irritation to the eyes, skin, and the respiratory system if inhaled or on contact. [30]

See also

Related Research Articles

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

The Friedel–Crafts reactions are a set of reactions developed by Charles Friedel and James Crafts in 1877 to attach substituents to an aromatic ring. Friedel–Crafts reactions are of two main types: alkylation reactions and acylation reactions. Both proceed by electrophilic aromatic substitution.

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">Acyl halide</span> Oxoacid compound with an –OH group replaced by a halogen

In organic chemistry, an acyl halide is a chemical compound derived from an oxoacid by replacing a hydroxyl group with a halide group.

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

Triphenylmethane or triphenyl methane (sometimes also known as Tritan), is the hydrocarbon with the formula (C6H5)3CH. This colorless solid is soluble in nonpolar organic solvents and not in water. Triphenylmethane is the basic skeleton of many synthetic dyes called triarylmethane dyes, many of them are pH indicators, and some display fluorescence. A trityl group in organic chemistry is a triphenylmethyl group Ph3C, e.g. triphenylmethyl chloride (trityl chloride) and the triphenylmethyl radical (trityl radical).

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

Manganese(II) chloride is the dichloride salt of manganese, MnCl2. This inorganic chemical exists in the anhydrous form, as well as the dihydrate (MnCl2·2H2O) and tetrahydrate (MnCl2·4H2O), with the tetrahydrate being the most common form. Like many Mn(II) species, these salts are pink, with the paleness of the color being characteristic of transition metal complexes with high spin d5 configurations.

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

Dysprosium(III) chloride (DyCl3), also known as dysprosium trichloride, is a compound of dysprosium and chlorine. It is a white to yellow solid which rapidly absorbs water on exposure to moist air to form a hexahydrate, DyCl3·6H2O. Simple rapid heating of the hydrate causes partial hydrolysis to an oxychloride, DyOCl.

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

Chromium(III) chloride (also called chromic chloride) is an inorganic chemical compound with the chemical formula CrCl3. It forms several hydrates with the formula CrCl3·nH2O, among which are hydrates where n can be 5 (chromium(III) chloride pentahydrate CrCl3·5H2O) or 6 (chromium(III) chloride hexahydrate CrCl3·6H2O). The anhydrous compound with the formula CrCl3 are violet crystals, while the most common form of the chromium(III) chloride are the dark green crystals of hexahydrate, CrCl3·6H2O. Chromium chlorides find use as catalysts and as precursors to dyes for wool.

Iron(II) chloride, also known as ferrous chloride, is the chemical compound of formula FeCl2. It is a paramagnetic solid with a high melting point. The compound is white, but typical samples are often off-white. FeCl2 crystallizes from water as the greenish tetrahydrate, which is the form that is most commonly encountered in commerce and the laboratory. There is also a dihydrate. The compound is highly soluble in water, giving pale green solutions.

<span class="mw-page-title-main">Benzoyl chloride</span> Organochlorine compound (C7H5ClO)

Benzoyl chloride, also known as benzenecarbonyl chloride, is an organochlorine compound with the formula C7H5ClO. It is a colourless, fuming liquid with an irritating odour, and consists of a benzene ring with an acyl chloride substituent. It is mainly useful for the production of peroxides but is generally useful in other areas such as in the preparation of dyes, perfumes, pharmaceuticals, and resins.

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

Rhodium(III) chloride refers to inorganic compounds with the formula RhCl3(H2O)n, where n varies from 0 to 3. These are diamagnetic red-brown solids. The soluble trihydrated (n = 3) salt is the usual compound of commerce. It is widely used to prepare compounds used in homogeneous catalysis.

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

Gold(III) chloride, traditionally called auric chloride, is an inorganic compound of gold and chlorine with the molecular formula Au2Cl6. The "III" in the name indicates that the gold has an oxidation state of +3, typical for many gold compounds. It has two forms, the monohydrate (AuCl3·H2O) and the anhydrous form, which are both hygroscopic and light-sensitive solids. This compound is a dimer of AuCl3. This compound has a few uses, such as an oxidizing agent and for catalyzing various organic reactions.

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

Gadolinium(III) chloride, also known as gadolinium trichloride, is GdCl3. It is a colorless, hygroscopic, water-soluble solid. The hexahydrate GdCl3∙6H2O is commonly encountered and is sometimes also called gadolinium trichloride. Gd3+ species are of special interest because the ion has the maximum number of unpaired spins possible, at least for known elements. With seven valence electrons and seven available f-orbitals, all seven electrons are unpaired and symmetrically arranged around the metal. The high magnetism and high symmetry combine to make Gd3+ a useful component in NMR spectroscopy and MRI.

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

Ruthenium(III) chloride is the chemical compound with the formula RuCl3. "Ruthenium(III) chloride" more commonly refers to the hydrate RuCl3·xH2O. Both the anhydrous and hydrated species are dark brown or black solids. The hydrate, with a varying proportion of water of crystallization, often approximating to a trihydrate, is a commonly used starting material in ruthenium chemistry.

<span class="mw-page-title-main">Trimethylsilyl chloride</span> Organosilicon compound with the formula (CH3)3SiCl

Trimethylsilyl chloride, also known as chlorotrimethylsilane is an organosilicon compound, 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.

Titanium(III) chloride is the inorganic compound with the formula TiCl3. At least four distinct species have this formula; additionally hydrated derivatives are known. TiCl3 is one of the most common halides of titanium and is an important catalyst for the manufacture of polyolefins.

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

Indium(III) chloride is the chemical compound with the formula InCl3 which forms a tetrahydrate. 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. This is one of three known indium chlorides.

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

Gallium(III) chloride is an inorganic chemical compound with the formula GaCl3 which forms a monohydrate, GaCl3·H2O. Solid gallium(III) chloride is a deliquescent white solid and 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">Aluminium compounds</span>

Aluminium (British and IUPAC spellings) or aluminum (North American spelling) combines characteristics of pre- and post-transition metals. Since it has few available electrons for metallic bonding, like its heavier group 13 congeners, it has the characteristic physical properties of a post-transition metal, with longer-than-expected interatomic distances. Furthermore, as Al3+ is a small and highly charged cation, it is strongly polarizing and aluminium compounds tend towards covalency; this behaviour is similar to that of beryllium (Be2+), an example of a diagonal relationship. However, unlike all other post-transition metals, the underlying core under aluminium's valence shell is that of the preceding noble gas, whereas for gallium and indium it is that of the preceding noble gas plus a filled d-subshell, and for thallium and nihonium it is that of the preceding noble gas plus filled d- and f-subshells. Hence, aluminium does not suffer the effects of incomplete shielding of valence electrons by inner electrons from the nucleus that its heavier congeners do. Aluminium's electropositive behavior, high affinity for oxygen, and highly negative standard electrode potential are all more similar to those of scandium, yttrium, lanthanum, and actinium, which have ds2 configurations of three valence electrons outside a noble gas core: aluminium is the most electropositive metal in its group. Aluminium also bears minor similarities to the metalloid boron in the same group; AlX3 compounds are valence isoelectronic to BX3 compounds (they have the same valence electronic structure), and both behave as Lewis acids and readily form adducts. Additionally, one of the main motifs of boron chemistry is regular icosahedral structures, and aluminium forms an important part of many icosahedral quasicrystal alloys, including the Al–Zn–Mg class.

Lanthanide trichlorides are a family of inorganic compound with the formula LnCl3, where Ln stands for a lanthanide metal. The trichlorides are standard reagents in applied and academic chemistry of the lanthanides. They exist as anhydrous solids and as hydrates.

References

  1. 1 2 3 4 Haynes WM, ed. (2011). CRC Handbook of Chemistry and Physics (92nd ed.). Boca Raton, FL: CRC Press. p. 4.45. ISBN   1-4398-5511-0.
  2. 1 2 "Properties of substance: Aluminium chloride". Chemister.ru. 2007-03-19. Archived from the original on 2014-05-05. Retrieved 2017-03-17.
  3. 1 2 Ketelaar JA (1935). "Die Kristallstruktur der Aluminiumhalogenide II". Zeitschrift für Kristallographie – Crystalline Materials. 90 (1–6): 237–255. doi:10.1524/zkri.1935.90.1.237. S2CID   100796636.
  4. 1 2 3 4 Haynes WM, ed. (2011). CRC Handbook of Chemistry and Physics (92nd ed.). Boca Raton, FL: CRC Press. p. 5.5. ISBN   1-4398-5511-0.
  5. ↑ Sigma-Aldrich Co., Aluminium chloride.
  6. 1 2 3 NIOSH Pocket Guide to Chemical Hazards. "#0024". National Institute for Occupational Safety and Health (NIOSH).
  7. 1 2 3 Helmboldt O, Keith Hudson L, Misra C, Wefers K, Heck W, Stark H, et al. (2007). "Aluminum Compounds, Inorganic". Ullmann's Encyclopedia of Industrial Chemistry . Weinheim: Wiley-VCH. doi:10.1002/14356007.a01_527.pub2. ISBN   978-3527306732.
  8. ↑ FOURCROY AF (1790). Elements of natural history, and of chemistry: being the second edition of the elementary lectures on those sciences ... enlarged and improved by the author ... Translated into English, with ... notes; and an historical preface by the translator W. Nicholson.
  9. ↑ Berthollet CL (1791). Elements of the Art of Dyeing ... Translated ... by William Hamilton. Stephen Couchman; sold by J. Johnson.
  10. ↑ Gambold M (1835). The American Journal of Science. Kline Geology Laboratory, Yale University.
  11. ↑ Wells AF (1984). Structural Inorganic Chemistry. Oxford, United Kingdom.: Oxford Press. ISBN   0198553706. In contrast, AlBr3 has a more molecular structure, with the Al3+ centers occupying adjacent tetrahedral holes of the close-packed framework of Br− ions.
  12. 1 2 3 4 Greenwood NN, Earnshaw A (1984). Chemistry of the Elements. Oxford: Pergamon Press. ISBN   978-0-08-022057-4.
  13. ↑ Andress KR, Carpenter C (1934). "Kristallhydrate II. Die Struktur von Chromchlorid- und Aluminiumchloridhexahydrat". Zeitschrift für Kristallographie – Crystalline Materials. 87. doi:10.1524/zkri.1934.87.1.446. S2CID   263857074.
  14. 1 2 3 Olah GA, ed. (1963). Friedel-Crafts and Related Reactions. Vol. 1. New York City: Interscience.
  15. ↑ Nenitzescu CD, Cantuniari IP (1933). "Durch Aluminiumchlorid Katalysierte Reaktion, VI. Mitteil.: Die Umlagerung des Cyclohexans in Metyl-cyclopentan". Berichte der Deutschen Chemischen Gesellschaft (A and B Series). 66 (8): 1097–1100. doi:10.1002/cber.19330660817. ISSN   1099-0682.
  16. ↑ Reeves JT, Tan Z, Fandrick DR, Song JJ, Yee NK, Senanayake CH (2012). "Synthesis of Trifluoromethyl Ketones from Carboxylic Acids: 4-(3,4-Dibromophenyl)-1,1,1-trifluoro-4-methylpentan-2-one". Organic Syntheses. 89: 210. doi: 10.15227/orgsyn.089.0210 .
  17. ↑ Paruch K, Vyklicky L, Katz TJ (2003). "Preparation of 9,10-Dimethoxyphenanthrene and 3,6-Diacetyl-9,10-Dimethoxyphenanthrene". Organic Syntheses. 80: 227. doi:10.15227/orgsyn.080.0227.
  18. ↑ Seed AJ, Sonpatki V, Herbert MR (2002). "3-(4-Bromobenzoyl)propanoic Acid". Organic Syntheses. 79: 204. doi:10.15227/orgsyn.079.0204.
  19. ↑ Wade LG (2003). Organic Chemistry (5th ed.). Upper Saddle River, New Jersey: Prentice Hall. ISBN   013033832X.
  20. ↑ Galatsis P (1999). "Aluminum Chloride". In Reich HJ, Rigby JH (eds.). Acidic and Basic Reagents. Handbook of Reagents for Organic Synthesis. New York City: Wiley. pp. 12–15. ISBN   978-0-471-97925-8.
  21. ↑ Snider BB (1980). "Lewis-acid catalyzed ene reactions". Acc. Chem. Res. 13 (11): 426. doi:10.1021/ar50155a007.
  22. ↑ Rieke RD, Bales SE, Hudnall PM, Burns TP, Poindexter GS (1979). "Highly Reactive Magnesium for the Preparation of Grignard Reagents: 1-Norbornanecarboxylic Acid". Organic Syntheses. 59: 85. doi:10.15227/orgsyn.059.0085.
  23. ↑ Shama SA, Wamser CC (1983). "Hexamethyl Dewar Benzene". Organic Syntheses. 61: 62. doi:10.15227/orgsyn.061.0062.
  24. ↑ Buchner B, Lockhart Jr LB (1951). "Phenyldichlorophosphine". Organic Syntheses. 31: 88. doi:10.15227/orgsyn.031.0088.
  25. ↑ McConaghy JR, Fosselman D (June 2018). "Hyperhidrosis: Management Options". American Family Physician. 97 (11): 729–734. PMID   30215934.
  26. ↑ Nawrocki S, Cha J (September 2019). "The etiology, diagnosis, and management of hyperhidrosis: A comprehensive review: Therapeutic options". Journal of the American Academy of Dermatology. 81 (3): 669–680. doi:10.1016/j.jaad.2018.11.066. PMID   30710603.
  27. ↑ "Aluminum Chloride (Topical) (Monograph)". American Society of Health System Pharmacists (ASHP). drugs.com.
  28. 1 2 "List of Minerals". www.ima-mineralogy.org. International Mineralogical Association. March 21, 2011.
  29. ↑ "Cadwaladerite". www.mindat.org.
  30. ↑ Aluminium Chloride. solvaychemicals.us
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