Copper(II) tetrafluoroborate

Last updated • 1 min readFrom Wikipedia, The Free Encyclopedia
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), but this salt can be partially dehydrated to the tetrahydrate. [3] 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. [4] In the former two applications, the copper(II) is reduced to a copper(I) catalyst. [3] [5]

Related Research Articles

The term chromic acid is usually used for a mixture made by adding concentrated sulfuric acid to a dichromate, which may contain a variety of compounds, including solid chromium trioxide. This kind of chromic acid may be used as a cleaning mixture for glass. Chromic acid may also refer to the molecular species, H2CrO4 of which the trioxide is the anhydride. Chromic acid features chromium in an oxidation state of +6 (or VI). It is a strong and corrosive oxidising agent.

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.

Hydrogen bromide Chemical compound

Hydrogen bromide is the inorganic compound with the formula HBr. It is a hydrogen halide consisting of hydrogen and bromine. A colorless gas, it dissolves in water, forming hydrobromic acid, which is saturated at 68.85% HBr by weight at room temperature. Aqueous solutions that are 47.6% HBr by mass form a constant-boiling azeotrope mixture that boils at 124.3 °C. Boiling less concentrated solutions releases H2O until the constant-boiling mixture composition is reached.

Aluminium chloride Chemical compound

Aluminium chloride (AlCl3), also known as aluminium trichloride, describe compounds with the formula AlCl3(H2O)n (n = 0 or 6). They consist of aluminium and chlorine atoms in a 1:3 ratio, and one form also contains six waters of hydration. Both are white solids, but samples are often contaminated with iron(III) chloride, giving a yellow color.

Dimethylformamide is an organic compound with the formula (CH3)2NC(O)H. Commonly abbreviated as DMF (although this initialism is sometimes used for dimethylfuran, or dimethyl fumarate), this colourless liquid is miscible with water and the majority of organic liquids. DMF is a common solvent for chemical reactions. Dimethylformamide is odorless, but technical-grade or degraded samples often have a fishy smell due to impurity of dimethylamine. Dimethylamine degradation impurities can be removed by sparging samples with an inert gas such as argon or by sonicating the samples under reduced pressure. As its name indicates, it is structurally related to formamide. DMF is a polar (hydrophilic) aprotic solvent with a high boiling point. It facilitates reactions that follow polar mechanisms, such as SN2 reactions.

Copper(I) chloride Chemical compound

Copper(I) chloride, commonly called cuprous chloride, is the lower chloride of copper, with the formula CuCl. The substance is a white solid sparingly soluble in water, but very soluble in concentrated hydrochloric acid. Impure samples appear green due to the presence of copper(II) chloride (CuCl2).

Boron trifluoride is the inorganic compound with the formula BF3. This pungent colourless toxic gas forms white fumes in moist air. It is a useful Lewis acid and a versatile building block for other boron compounds.

The Sandmeyer reaction is a chemical reaction used to synthesize aryl halides from aryl diazonium salts using copper salts as reagents or catalysts. It is an example of a radical-nucleophilic aromatic substitution. The Sandmeyer reaction provides a method through which one can perform unique transformations on benzene, such as halogenation, cyanation, trifluoromethylation, and hydroxylation.

Copper chromite Chemical compound

Copper chromite is an inorganic compound with the formula Cu2Cr2O5. It is a black solid that is used to catalyze reactions in organic synthesis.

Copper(II) acetate 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. The mineral hoganite is a naturally occurring form of copper(II) acetate. A related mineral, also containing calcium, is paceite. Both are very rare.

Danishefsky Taxol total synthesis

The Danishefsky Taxol total synthesis in organic chemistry is an important third Taxol synthesis published by the group of Samuel Danishefsky in 1996 two years after the first two efforts described in the Holton Taxol total synthesis and the Nicolaou Taxol total synthesis. Combined they provide a good insight in the application of organic chemistry in total synthesis.

Tetrafluoroborate Anion

Tetrafluoroborate is the anion BF
4
. This tetrahedral species is isoelectronic with tetrafluoroberyllate (BeF2−
4
), tetrafluoromethane (CF4), and tetrafluoroammonium (NF+
4
) and is valence isoelectronic with many stable and important species including the perchlorate anion, ClO
4
, which is used in similar ways in the laboratory. It arises by the reaction of fluoride salts with the Lewis acid BF3, treatment of tetrafluoroboric acid with base, or by treatment of boric acid with hydrofluoric acid.

Organocopper compound Compound with carbon to copper bonds

Organocopper compounds in organometallic chemistry contain carbon to copper chemical bonds. Organocopper chemistry is the science of organocopper compounds describing their physical properties, synthesis and reactions. They are reagents in organic chemistry.

Copper(I) bromide Chemical compound

Copper(I) bromide is the chemical compound with the formula CuBr. This diamagnetic solid adopts a polymeric structure akin to that for zinc sulfide. The compound is widely used in the synthesis of organic compounds and as a lasing medium in copper bromide lasers.

Diethylaminosulfur trifluoride 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.

The Stieglitz rearrangement is a rearrangement reaction in organic chemistry which is named after the American chemist Julius Stieglitz (1867–1937) and was first investigated by him and Paul Nicholas Leech in 1913. It describes the 1,2-rearrangement of trityl amine derivatives to triaryl imines. It is comparable to a Beckmann rearrangement which also involves a substitution at a nitrogen atom through a carbon to nitrogen shift. As an example, triaryl hydroxylamines can undergo a Stieglitz rearrangement by dehydration and the shift of a phenyl group after activation with phosphorus pentachloride to yield the respective triaryl imine, a Schiff base.

Hexafluoropropylene oxide Chemical compound

Hexafluoropropylene oxide (HFPO) is an intermediate used in industrial organofluorine chemistry; specifically it is a monomer for fluoropolymers. This colourless gas is the epoxide of hexafluoropropylene, that is fluorinated analog of propylene oxide, HFPO is produced by DuPont and 3M and as a precursor to the lubricant Krytox and related materials. It is generated by oxidation of perfluoropropylene, e.g. with oxygen as well as other oxidants.

Trifluoroperacetic acid 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.

Bis(cyclopentadienyl)titanium(III) chloride 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. 1 2 Ilhyong Ryu, Noboru Sonoda, "Copper(II) Tetrafluoroborate" Encyclopedia of Reagents for Organic Synthesis 2001, John Wiley & Sons. doi : 10.1002/047084289X.rc249
  4. 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.
  5. Copper(II) Tetrafluorborate, chemicalland21.com