Phenacyl bromide

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Phenacyl bromide
Phenacyl bromide.svg
Phenacyl-bromide-3D-balls.png
Names
Preferred IUPAC name
2-Bromo-1-phenylethan-1-one
Other names
2-Bromo-1-phenylethanone
2-Bromoacetophenone
α-Bromoacetophenone
Bromomethyl phenyl ketone
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.000.659
PubChem CID
UNII
Properties
C8H7BrO
Molar mass 199.047 g·mol−1
AppearanceColorless solid
Melting point 50 °C (122 °F; 323 K) [1]
Boiling point 136 °C (277 °F; 409 K)18 mm Hg [1]
Hazards
Main hazards Toxic(T)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Phenacyl bromide is the organic compound with the formula C6H5C(O)CH2Br. This colourless solid is a powerful lachrymator as well as a useful precursor to other organic compounds.

It is prepared by bromination of acetophenone: [2]

C6H5C(O)CH3 + Br2 → C6H5C(O)CH2Br + HBr

The compound was first reported in 1871. [3]

Related Research Articles

Bromine Chemical element with atomic number 35

Bromine is a chemical element with the symbol Br and atomic number 35. It is the third-lightest halogen, and is a fuming red-brown liquid at room temperature that evaporates readily to form a similarly coloured gas. Its properties are thus intermediate between those of chlorine and iodine. Isolated independently by two chemists, Carl Jacob Löwig and Antoine Jérôme Balard, its name was derived from the Ancient Greek βρῶμος ("stench"), referencing its sharp and disagreeable smell.

Ether Class of organic compounds

Ethers are a class of organic compounds that contain an ether group—an oxygen atom connected to two alkyl or aryl groups. They have the general formula R–O–R′, where R and R′ represent the alkyl or aryl groups. Ethers can again be classified into two varieties: if the alkyl groups are the same on both sides of the oxygen atom, then it is a simple or symmetrical ether, whereas if they are different, the ethers are called mixed or unsymmetrical ethers. A typical example of the first group is the solvent and anesthetic diethyl ether, commonly referred to simply as "ether" (CH3–CH2–O–CH2–CH3). Ethers are common in organic chemistry and even more prevalent in biochemistry, as they are common linkages in carbohydrates and lignin.

Hydrogen bromide chemical compound

Hydrogen bromide is the diatomic molecular compound with the formula HBr, a hydrogen halide consisting of hydrogen and bromine. In pure form it is a colorless gas.

Sodium bromide chemical compound

Sodium bromide is an inorganic compound with the formula NaBr. It is a high-melting white, crystalline solid that resembles sodium chloride. It is a widely used source of the bromide ion and has many applications.

The phosphonium cation describes polyatomic cations with the chemical formula PR+
4
. They are tetrahedral and generally colorless.

1-Bromobutane chemical compound

1-Bromobutane is the organobromine compound with the formula CH3(CH2)3Br. It is a colorless liquid, although impure samples appear yellowish. It is insoluble in water, but soluble in organic solvents. It is a primarily used as a source of the butyl group in organic synthesis. It is one of several isomers of butyl bromide.

Bromoethane, also known as ethyl bromide, is a chemical compound of the haloalkanes group. It is abbreviated by chemists as EtBr. This volatile compound has an ether-like odour.

Nitrosobenzene chemical compound

Nitrosobenzene is the organic compound with the formula C6H5NO. It is one of the prototypical organic nitroso compounds. Characteristic of its functional group, it is a dark green species that exists in equilibrium with its pale yellow dimer. Both monomer and dimer are diamagnetic.

Zinc bromide chemical compound

Zinc bromide (ZnBr2) is an inorganic compound with the chemical formula ZnBr2. It is a colourless salt that shares many properties with zinc chloride (ZnCl2), namely a high solubility in water forming acidic solutions, and solubility in organic solvents. It is hygroscopic and forms a dihydrate ZnBr2 · 2H2O.

Methyllithium chemical compound

Methyllithium is the simplest organolithium reagent with the empirical formula CH3Li. This s-block organometallic compound adopts an oligomeric structure both in solution and in the solid state. This highly reactive compound, invariably used as a solution in ethers, is a reagent in organic synthesis as well as organometallic chemistry. Operations involving methyllithium require anhydrous conditions, because the compound is highly reactive toward water. Oxygen and carbon dioxide are also incompatible with MeLi. Methyllithium is usually not prepared, but purchased as a solution in various ethers.

Organomercury class of chemical compounds

Organomercury refers to the group of organometallic compounds that contain mercury. Typically the Hg–C bond is stable toward air and moisture but sensitive to light. Important organomercury compounds are the methylmercury(II) cation, CH3Hg+; ethylmercury(II) cation, C2H5Hg+; dimethylmercury, (CH3)2Hg, diethylmercury, and merbromin ("Mercurochrome"). Thiomersal is used as a preservative for vaccines and intravenous drugs.

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.

Phenethyl alcohol chemical compound

Phenethyl alcohol, or 2-phenylethanol, is the organic compound that consists of a phenethyl group (C6H5CH2CH2) group attached to OH. It is a colourless liquid that is slightly soluble in water (2 ml/100 ml H2O), but miscible with most organic solvents. It occurs widely in nature, being found in a variety of essential oils. It has a pleasant floral odor.

Dibromomethane chemical compound

Dibromomethane or methylene bromide, or methylene dibromide is a halomethane. It is slightly soluble in water but very soluble in organic solvents. It is a colorless liquid.

Cobalt(II) bromide chemical compound

Cobalt(II) bromide (CoBr2) is an inorganic compound. In its anhydrous form, it is a green solid that is soluble in water, used primarily as a catalyst in some processes.

Phenacyl functional group

In organic chemistry, a phenacyl group is an aromatic substituent that consists of a phenyl group attached to an acyl group. A molecule containing a phenacyl group has the formula RCH2(CO)C6H5 and the structure shown to the right. Here, R denotes the remainder of the molecule; for instance, if R is Br, then the compound could be called "phenacyl bromide". Note however that in the standard IUPAC nomenclature this compound would instead be called "2-bromo-1-phenylethanone".

Organobromine compounds, also called organobromides, are organic compounds that contain carbon bonded to bromine. The most pervasive is the naturally produced bromomethane.

Ethylmagnesium bromide chemical compound

Ethylmagnesium bromide is a Grignard reagent with formula C2H5MgBr. It is widely used in the laboratory synthesis of organic compounds.

tert-Butyl bromide (also referred to as 2-bromo-2-methylpropane) is an organic compound with the formula Me3CBr (Me = methyl). The molecule features a tert-butyl group attached to a bromide substituent. This organobromine compound is used as a standard reagent in synthetic organic chemistry. It is a colorless liquid.

Organorhenium chemistry describes the compounds with Re−C bonds. Because rhenium is a rare element, relatively few applications exist, but the area has been a rich source of concepts and a few useful catalysts.

References

  1. 1 2 Phenacyl Bromide, TCI America
  2. R. M. Cowper and L. H. Davidson. "Phenacyl bromide". Organic Syntheses .; Collective Volume, 2, p. 480
  3. A. Emmerling and C. Engler (1871). "Ueber einige Abkömmlinge des Acetophenons". Ber. 4 (1): 147–149. doi:10.1002/cber.18710040149.