Copper(II) tetrafluoroborate

Last updated
Copper(II) tetrafluoroborate [1]
Copper tetrafluoroborate.svg
Names
IUPAC name
Copper(II) tetrafluoroborate
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.049.037 OOjs UI icon edit-ltr-progressive.svg
PubChem CID
  • InChI=1S/2BF4.Cu.H2O/c2*2-1(3,4)5;;/h;;;1H2/q2*-1;+2; Yes check.svgY
    Key: JYLPBVRGTDBGBM-UHFFFAOYSA-N Yes check.svgY
  • InChI=1/2BF4.Cu.H2O/c2*2-1(3,4)5;;/h;;;1H2/q2*-1;+2;
    Key: JYLPBVRGTDBGBM-UHFFFAOYAF
  • [Cu+2].F[B-](F)(F)F.F[B-](F)(F)F.O
Properties
Cu(BF4)2
Molar mass 237.155 g/mol
Appearanceblue crystal
soluble in water
Hazards
NIOSH (US health exposure limits):
PEL (Permissible)
TWA 1 mg/m3 (as Cu) [2]
REL (Recommended)
TWA 1 mg/m3 (as Cu) [2]
IDLH (Immediate danger)
TWA 100 mg/m3 (as Cu) [2]
Related compounds
Other anions
Copper(II) chloride
Copper(II) oxide
Copper(II) triflate
Other cations
Sodium tetrafluoroborate
Lithium tetrafluoroborate
Silver tetrafluoroborate
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 ?)

Copper(II) tetrafluoroborate is any inorganic compound with the formula Cu(H2O)x (BF4)2. As usually encountered, it is assumed to be the hexahydrate (x = 6) [3] , but this salt can be partially dehydrated to the tetrahydrate. [4] Regardless, these compounds are aquo complexes of copper in its +2 oxidation state, with two weakly coordinating tetrafluoroborate anions.

The compound is used in organic synthesis, e.g. as a Lewis acid for Diels Alder reactions, for cyclopropanation of alkenes with diazo reagents, and as a Lewis Acid in Meinwald Rearrangement reactions on Epoxides. [5] In the former two applications, the copper(II) is reduced to a copper(I) catalyst. [4] [6] The compound is also used for copper electroplating in fluoroborate-based plating baths. [7]

Related Research Articles

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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.

An ylide or ylid is a neutral dipolar molecule containing a formally negatively charged atom (usually a carbanion) directly attached to a heteroatom with a formal positive charge (usually nitrogen, phosphorus or sulfur), and in which both atoms have full octets of electrons. The result can be viewed as a structure in which two adjacent atoms are connected by both a covalent and an ionic bond; normally written X+–Y. Ylides are thus 1,2-dipolar compounds, and a subclass of zwitterions. They appear in organic chemistry as reagents or reactive intermediates.

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

Copper(II) nitrate describes any member of the family of inorganic compounds with the formula Cu(NO3)2(H2O)x. The hydrates are hygroscopic blue solids. Anhydrous copper nitrate forms blue-green crystals and sublimes in a vacuum at 150-200 °C. Common hydrates are the hemipentahydrate and trihydrate.

<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">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.

<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.

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

Copper(II) acetate, also referred to as cupric acetate, is the chemical compound with the formula Cu(OAc)2 where AcO is acetate (CH
3
CO
2
). The hydrated derivative, Cu2(OAc)4(H2O)2, which contains one molecule of water for each copper atom, is available commercially. Anhydrous copper(II) acetate is a dark green crystalline solid, whereas Cu2(OAc)4(H2O)2 is more bluish-green. Since ancient times, copper acetates of some form have been used as fungicides and green pigments. Today, copper acetates are used as reagents for the synthesis of various inorganic and organic compounds. Copper acetate, like all copper compounds, emits a blue-green glow in a flame.

<span class="mw-page-title-main">Cyclopropanation</span> Chemical process which generates cyclopropane rings

In organic chemistry, cyclopropanation refers to any chemical process which generates cyclopropane rings. It is an important process in modern chemistry as many useful compounds bear this motif; for example pyrethroid insecticides and a number of quinolone antibiotics. However, the high ring strain present in cyclopropanes makes them challenging to produce and generally requires the use of highly reactive species, such as carbenes, ylids and carbanions. Many of the reactions proceed in a cheletropic manner.

<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">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">Diethylaminosulfur trifluoride</span> Chemical compound

Diethylaminosulfur trifluoride (DAST) is the organosulfur compound with the formula Et2NSF3. This liquid is a fluorinating reagent used for the synthesis of organofluorine compounds. The compound is colourless; older samples assume an orange colour.

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<span class="mw-page-title-main">Jones oxidation</span> Oxidation of alcohol

The Jones oxidation is an organic reaction for the oxidation of primary and secondary alcohols to carboxylic acids and ketones, respectively. It is named after its discoverer, Sir Ewart Jones. The reaction was an early method for the oxidation of alcohols. Its use has subsided because milder, more selective reagents have been developed, e.g. Collins reagent.

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

Trifluoroperacetic acid is an organofluorine compound, the peroxy acid analog of trifluoroacetic acid, with the condensed structural formula CF
3
COOOH
. It is a strong oxidizing agent for organic oxidation reactions, such as in Baeyer–Villiger oxidations of ketones. It is the most reactive of the organic peroxy acids, allowing it to successfully oxidise relatively unreactive alkenes to epoxides where other peroxy acids are ineffective. It can also oxidise the chalcogens in some functional groups, such as by transforming selenoethers to selones. It is a potentially explosive material and is not commercially available, but it can be quickly prepared as needed. Its use as a laboratory reagent was pioneered and developed by William D. Emmons.

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

Bis(cyclopentadienyl)titanium(III) chloride, also known as the Nugent–RajanBabu reagent, is the organotitanium compound which exists as a dimer with the formula [(C5H5)2TiCl]2. It is an air sensitive green solid. The complex finds specialized use in synthetic organic chemistry as a single electron reductant.

References

  1. Lide, David R. (1998), Handbook of Chemistry and Physics (87 ed.), Boca Raton, Florida: CRC Press, pp. 4–56, ISBN   0-8493-0594-2
  2. 1 2 3 NIOSH Pocket Guide to Chemical Hazards. "#0150". National Institute for Occupational Safety and Health (NIOSH).
  3. Vakulka, A., Goreshnik, E. Copper(II) Tetrafluoroborate Hexahydrate: Preparation, Structure and Raman Spectrum. J Chem Crystallogr 54, 157–162 (2024). https://doi.org/10.1007/s10870-024-01008-3
  4. 1 2 Ilhyong Ryu, Noboru Sonoda, "Copper(II) Tetrafluoroborate" Encyclopedia of Reagents for Organic Synthesis 2001, John Wiley & Sons. doi : 10.1002/047084289X.rc249
  5. Robinson, Mathew W.C.; Pillinger, Kathryn S.; Graham, Andrew E. (August 2006). "Highly efficient Meinwald rearrangement reactions of epoxides catalyzed by copper tetrafluoroborate". Tetrahedron Letters. 47 (33): 5919–5921. doi:10.1016/j.tetlet.2006.06.055.
  6. Copper(II) Tetrafluorborate, chemicalland21.com
  7. Barauskas, Romualdas "Ron" (January 1, 2000). "Copper plating". Metal Finishing. 98 (1): 234–247. doi:10.1016/S0026-0576(00)80330-X. ISSN   0026-0576 . Retrieved July 21, 2022.