2-Phenylethyl bromide

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2-Phenylethyl bromide
2-Phenylethylbromide Structural Formula V1.svg
Names
Preferred IUPAC name
(2-Bromoethyl)benzene
Other names
Phenethyl bromide
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.002.846 OOjs UI icon edit-ltr-progressive.svg
PubChem CID
UNII
  • InChI=1S/C8H9Br/c9-7-6-8-4-2-1-3-5-8/h1-5H,6-7H2 Yes check.svgY
    Key: WMPPDTMATNBGJN-UHFFFAOYSA-N Yes check.svgY
  • InChI=1/C8H9Br/c9-7-6-8-4-2-1-3-5-8/h1-5H,6-7H2
    Key: WMPPDTMATNBGJN-UHFFFAOYAQ
  • BrCCc1ccccc1
Properties
C8H9Br
Molar mass 185.064 g·mol−1
AppearanceColorless liquid
Density 1.355 g/cm3
Melting point −56 °C (−69 °F; 217 K)
Boiling point 221 °C (430 °F; 494 K)
Insoluble in water
Hazards
Flash point 89 °C (192 °F; 362 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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2-Phenylethyl bromide is an organobromide with the formula C6H5CH2CH2Br. It is a colorless liquid, although older samples appear yellow. Analogous to the preparation of most 1-bromoalkanes, it is prepared by free-radical addition of hydrogen bromide to styrene. These conditions lead to anti-Markovnikov addition, giving the 1-bromo derivatives. [1]

Upon reaction with hydrazine, phenelzine is produced.

It can be used to produce fentanyl and is on the Special Surveillance List of the DEA. [2]

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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 the Ancient Greek βρῶμος (bromos) meaning "stench", referring to its sharp and pungent smell.

<span class="mw-page-title-main">Halogen</span> Group of chemical elements

The halogens are a group in the periodic table consisting of six chemically related elements: fluorine (F), chlorine (Cl), bromine (Br), iodine (I), and the radioactive elements astatine (At) and tennessine (Ts), though some authors would exclude tennessine as its chemistry is unknown and is theoretically expected to be more like that of gallium. In the modern IUPAC nomenclature, this group is known as group 17.

Bromomethane, commonly known as methyl bromide, is an organobromine compound with formula CH3Br. This colorless, odorless, nonflammable gas is produced both industrially and biologically. It is a recognized ozone-depleting chemical. It was used extensively as a pesticide until being phased out by most countries in the early 2000s. From the chemistry perspective, it is one of the halomethanes.

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

1,2-Dibromoethane, also known as ethylene dibromide (EDB), is an organobromine compound with the chemical formula C
2
H
4
Br
2
. Although trace amounts occur naturally in the ocean, where it is probably formed by algae and kelp, substantial amounts are produced industrially. It is a dense colorless liquid with a faint, sweet odor, detectable at 10 ppm. It is a widely used and sometimes-controversial fumigant. The combustion of 1,2-dibromoethane produces hydrogen bromide gas that is significantly corrosive.

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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 (255.7 °F). Boiling less concentrated solutions releases H2O until the constant-boiling mixture composition is reached.

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

Terephthalic acid is an organic compound with formula C6H4(CO2H)2. This white solid is a commodity chemical, used principally as a precursor to the polyester PET, used to make clothing and plastic bottles. Several million tons are produced annually. The common name is derived from the turpentine-producing tree Pistacia terebinthus and phthalic acid.

<span class="mw-page-title-main">Sodium bromide</span> Inorganic salt: NaBr

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.

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

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Phosphorus tribromide is a colourless liquid with the formula PBr3. The liquid fumes in moist air due to hydrolysis and has a penetrating odour. It is used in the laboratory for the conversion of alcohols to alkyl bromides.

A bromide ion is the negatively charged form (Br) of the element bromine, a member of the halogens group on the periodic table. Most bromides are colorless. Bromides have many practical roles, being found in anticonvulsants, flame-retardant materials, and cell stains. Although uncommon, chronic toxicity from bromide can result in bromism, a syndrome with multiple neurological symptoms. Bromide toxicity can also cause a type of skin eruption, see potassium bromide. The bromide ion has an ionic radius of 196 pm.

Benzyl chloride, or α-chlorotoluene, is an organic compound with the formula C6H5CH2Cl. This colorless liquid is a reactive organochlorine compound that is a widely used chemical building block.

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

Hypobromous acid is an inorganic compound with chemical formula of HOBr. It is a weak, unstable acid. It is mainly produced and handled in an aqueous solution. It is generated both biologically and commercially as a disinfectant. Salts of hypobromite are rarely isolated as solids.

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

Copper(II) bromide (CuBr2) is a chemical compound that forms an unstable tetrahydrate CuBr2·4H2O. It is used in photographic processing as an intensifier and as a brominating agent in organic synthesis.

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Organocadmium chemistry describes the physical properties, synthesis, reactions, and use of organocadmium compounds, which are organometallic compounds containing a carbon to cadmium chemical bond. Cadmium shares group 12 with zinc and mercury and their corresponding chemistries have much in common. The synthetic utility of organocadmium compounds is limited.

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Calcium bromide is the name for compounds with the chemical formula CaBr2(H2O)x. Individual compounds include the anhydrous material (x = 0), the hexahydrate (x = 6), and the rare dihydrate (x = 2). All are white powders that dissolve in water, and from these solutions crystallizes the hexahydrate. The hydrated form is mainly used in some drilling fluids.

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

Indium(I) bromide is a chemical compound of indium and bromine. It is a red crystalline compound that is isostructural with β-TlI and has a distorted rock salt structure. Indium(I) bromide is generally made from the elements, heating indium metal with InBr3. It has been used in the sulfur lamp. In organic chemistry, it has been found to promote the coupling of α, α-dichloroketones to 1-aryl-butane-1,4-diones. Oxidative addition reactions with for example alkyl halides to give alkyl indium halides and with NiBr complexes to give Ni-In bonds are known. It is unstable in water decomposing into indium metal and indium tribromide. When indium dibromide is dissolved in water, InBr is produced as a, presumably, insoluble red precipitate, that then rapidly decomposes.

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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.

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.

References

  1. Dagani, M. J.; Barda, H. J.; Benya, T. J.; Sanders, D. C. "Bromine Compounds". Ullmann's Encyclopedia of Industrial Chemistry . Weinheim: Wiley-VCH. doi:10.1002/14356007.a04_405. ISBN   978-3527306732.
  2. "Special Surveillance List of Chemicals, Products, Materials and Equipment Used in the Clandestine Production of Controlled Substances or Listed Chemicals". Archived from the original on April 20, 2011. Retrieved May 20, 2011.