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 OOjs UI icon edit-ltr-progressive.svg
PubChem CID
UNII
  • InChI=1S/C8H7BrO/c9-6-8(10)7-4-2-1-3-5-7/h1-5H,6H2 Yes check.svgY
    Key: LIGACIXOYTUXAW-UHFFFAOYSA-N Yes check.svgY
  • InChI=1/C8H7BrO/c9-6-8(10)7-4-2-1-3-5-7/h1-5H,6H2
    Key: LIGACIXOYTUXAW-UHFFFAOYAV
  • O=C(c1ccccc1)CBr
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
Occupational safety and health (OHS/OSH):
Main hazards
Toxic(T)
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 ?)

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

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Bromine is a chemical element; it has symbol Br and atomic number 35. It is a volatile red-brown liquid at room temperature that evaporates readily to form a similarly coloured vapour. Its properties are intermediate between those of chlorine and iodine. Isolated independently by two chemists, Carl Jacob Löwig and Antoine Jérôme Balard, its name was derived from Ancient Greek βρῶμος (bromos) 'stench', referring to its sharp and pungent smell.

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

Acetophenone is the organic compound with the formula C6H5C(O)CH3. It is the simplest aromatic ketone. This colorless, viscous liquid is a precursor to useful resins and fragrances.

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

Phenacyl chloride, also commonly known as chloroacetophenone, is a substituted acetophenone. It is a useful building block in organic chemistry. Apart from that, it has been historically used as a riot control agent, where it is designated CN. It should not be confused with cyanide, another agent used in chemical warfare, which has the chemical structure CN. Chloroacetophenone is thermally stable, and is the only tear agent that is distillable at ambient conditions.

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Carbon tetrabromide, CBr4, also known as tetrabromomethane, is a bromide of carbon. Both names are acceptable under IUPAC nomenclature.

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 odor.

α-Halo ketone

In organic chemistry, an α-halo ketone is a functional group consisting of a ketone group or more generally a carbonyl group with an α-halogen substituent. α-Halo ketones are alkylating agents. Prominent α-halo ketones include phenacyl bromide and chloroacetone.

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

Diphenylacetylene is the chemical compound C6H5C≡CC6H5. The molecule consists of two phenyl groups attached to a C2 unit. A colorless solid, it is used as a building block in organic synthesis and as a ligand in organometallic chemistry.

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

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

Phenylglyoxal is the organic compound with the formula C6H5C(O)C(O)H. It contains both an aldehyde and a ketone functional group. It is yellow liquid when anhydrous but readily forms a colorless crystalline hydrate. It has been used as a reagent to modify the amino acid, arginine. It has also been used to attach chemical payload (probes) to the amino acid citrulline and to peptides/proteins.

<span class="mw-page-title-main">1,2-Dibromopropane</span> Chemical compound

1,2-Dibromopropane, also known as propylene dibromide, is an organic compound with the formula CH3CHBrCH2Br. It is the simplest chiral hydrocarbon containing two bromine atoms:

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

Bromochloromethane or methylene bromochloride and Halon 1011 is a mixed halomethane. It is a heavy low-viscosity liquid with refractive index 1.4808.

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

Vinyl bromide is the organobromine compound with the formula CH2=CHBr. Classified as a vinyl halide, it is a colorless gas at room temperature. It is used as a reagent and a comonomer.

<span class="mw-page-title-main">Phenacyl group</span> 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 chemistry is the study of the synthesis and properties of organobromine compounds, also called organobromides, which are organic compounds that contain carbon bonded to bromine. The most pervasive is the naturally produced bromomethane.

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

Benzanilide is the organic compound with the formula C6H5C(O)NHC6H5. It is a white solid. Commercially available, it may be prepared by treating benzoic acid with aniline.

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

Dihydrochalcone (DHC) is the organic compound with the formula C6H5C(O)(CH2)2C6H5. It is the reduced derivative of chalcone (C6H5C(O)(CH)2C6H5). It is a white solid that is soluble in many organic solvents. Dihydrochalcone per se is often minor significance, but some derivatives occur in nature and have attracted attention as drugs.

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

Thiobenzoic acid is an organosulfur compound with molecular formula C6H5COSH. It is the parent of aryl thiocarboxylic acids. It is a pale yellow liquid that freezes just below room temperature.

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

Xylylene dibromide is an organic compound with the formula C6H4(CH2Br)2. It is an off-white solid that, like other benzyl halides, is strongly lachrymatory. It is a useful reagent owing to the convenient reactivity of the two C-Br bonds. Two other isomers are known, para- and meta-xylylene dibromide.

References

  1. 1 2 Phenacyl Bromide, TCI America
  2. R. M. Cowper and L. H. Davidson. "Phenacyl bromide". Organic Syntheses ; Collected Volumes, vol. 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.