Xylylene dibromide

Last updated
Xylylene dibromide
C6H4(CH2Br)2.svg
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.001.857 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 202-042-7
PubChem CID
UNII
  • InChI=1S/C8H8Br2/c9-5-7-3-1-2-4-8(7)6-10/h1-4H,5-6H2
    Key: KGKAYWMGPDWLQZ-UHFFFAOYSA-N
  • C1=CC=C(C(=C1)CBr)CBr
Properties
C8H8Br2
Molar mass 263.960 g·mol−1
Appearanceoff-white solid
Melting point 93–94 °C (199–201 °F; 366–367 K)
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
lachrymator
GHS labelling:
GHS-pictogram-acid.svg GHS-pictogram-exclam.svg
Danger
H302, H314
P260, P264, P270, P280, P301+P312, P301+P330+P331, P303+P361+P353, P304+P340, P305+P351+P338, P310, P321, P330, P363, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Xylylene dibromide is an organic compound with the formula C6H4(CH2Br)2. It is an off-white solid that, like other benzyl halides, a strong lachrymator. It is a useful reagent owing to the convenient reactivity of the two C-Br bonds. [1] Two other isomers are known, para- and meta-xylylene dibromide.

Contents

Synthesis

It is prepared by the photochemical reaction of ortho-xylene with bromine: [2]

C6H4(CH3)2 + 2 Br2 → C6H4(CH2Br)2 + 2 HBr

Reactions

Further bromination gives the tetrabromide: [3]

C6H4(CH2Br)2 + 2 Br2 → C6H4(CHBr2)2 + 2 HBr

Upon reaction with thiourea followed by hydrolysis of the intermediate bisisothiouronium salts, xylylene dibromide can be converted to the dithiol C6H4(CH2SH)2. [4]

Xylylene dibromide is a precursor to the ephemeral molecule ortho-quinonedimethane, also known as xylylene. This species can be trapped when the dehalogenation is conducted in the presence of iron carbonyl. [5]

Coupling of xylylene dibromide by treatment with lithium metal gives dibenzocyclooctane, precursor to dibenzocyclooctadiene. [6]

Related Research Articles

Imine Chemical compound

An imine is a functional group or organic compound containing a carbon–nitrogen double bond. The nitrogen atom can be attached to a hydrogen or an organic group (R). The carbon atom has two additional single bonds. Imines are common in synthetic and naturally occurring compounds and they participate in many reactions.

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.

Phosphorus tribromide Chemical compound

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.

Aluminium bromide Chemical compound

Aluminium bromide is any chemical compound with the empirical formula AlBrx. Aluminium tribromide is the most common form of aluminium bromide. It is a colorless, sublimable hygroscopic solid; hence old samples tend to be hydrated, mostly as aluminium tribromide hexahydrate (AlBr3·6H2O).

Dichlorocarbene is the reactive intermediate with chemical formula CCl2. Although this chemical species has not been isolated, it is a common intermediate in organic chemistry, being generated from chloroform. This bent diamagnetic molecule rapidly inserts into other bonds.

(<i>E</i>)-Stilbene Chemical compound

(E)-Stilbene, commonly known as trans-stilbene, is an organic compound represented by the condensed structural formula C6H5CH=CHC6H5. Classified as a diarylethene, it features a central ethylene moiety with one phenyl group substituent on each end of the carbon–carbon double bond. It has an (E) stereochemistry, meaning that the phenyl groups are located on opposite sides of the double bond, the opposite of its geometric isomer, cis-stilbene. Trans-stilbene occurs as a white crystalline solid at room temperature and is highly soluble in organic solvents. It can be converted to cis-stilbene photochemically, and further reacted to produce phenanthrene.

<i>o</i>-Xylene Chemical compound

o-Xylene (ortho-xylene) is an aromatic hydrocarbon with the formula C6H4(CH3)2. with two methyl substituents bonded to adjacent carbon atoms of a benzene ring (the ortho configuration). It is a constitutional isomer of m-xylene and p-xylene, the mixture being called xylene or xylenes. o-Xylene is a colorless slightly oily flammable liquid.

Benzyl bromide is an organic compound with the formula C6H5CH2Br. The molecule consists of a benzene ring substituted with a bromomethyl group. It is a colorless liquid with lachrymatory properties. The compound is a reagent for introducing benzyl groups.

Alpha-Haloketone

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

Hell–Volhard–Zelinsky halogenation Chemical reaction

The Hell–Volhard–Zelinsky halogenation reaction is a chemical transformation that involves the halogenation of a carboxylic acid at the α carbon. For this reaction to occur the α carbon must bear at least one proton. The reaction is named after the German chemists Carl Magnus von Hell (1849–1926) and Jacob Volhard (1834–1910) and the Russian chemist Nikolay Zelinsky (1861–1953).

The Finkelstein reaction named after the German chemist Hans Finkelstein, is an SN2 reaction that involves the exchange of one halogen atom for another. It is an equilibrium reaction, but the reaction can be driven to completion by exploiting the differential solubility of halide salts, or by using a large excess of the halide salt.

Allyl bromide Chemical compound

Allyl bromide (3-bromopropene) is an organic halide. It is an alkylating agent used in synthesis of polymers, pharmaceuticals, synthetic perfumes and other organic compounds. Physically, allyl bromide is a colorless liquid with an irritating and persistent smell, however, commercial samples are yellow or brown. Allyl bromide is more reactive but more expensive than allyl chloride, and these considerations guide its use.

Disodium tetracarbonylferrate Chemical compound

Disodium tetracarbonylferrate is the organoiron compound with the formula Na2[Fe(CO)4]. It is always used as a solvate, e.g., with tetrahydrofuran or dimethoxyethane, which bind to the sodium cation. An oxygen-sensitive colourless solid, it is a reagent in organometallic and organic chemical research. The dioxane solvated sodium salt is known as Collman's reagent, in recognition of James P. Collman, an early popularizer of its use.

Dimethylbenzylamine Chemical compound

Dimethylbenzylamine is the organic compound with the formula C6H5CH2N(CH3)2. The molecule consists of a benzyl group, C6H5CH2, attached to a dimethylamino functional group. It is a colorless liquid. It is used as a catalyst for the formation of polyurethane foams and epoxy resins.

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

Xylylene

Xylylene (sometimes quinone-dimethides) comprises two isomeric organic compounds with the formula C6H4(CH2)2. These compounds are related to the corresponding quinones and quinone methides by replacement of the oxygen atoms by CH2 groups. ortho- and para-xylylene are best known, although neither is stable in solid or liquid form. The meta form is a diradical. Certain substituted derivatives of xylylenes are however highly stable, an example being tetracyanoquinodimethane.

Diethylphosphite Chemical compound

Diethylphosphite is the organophosphorus compound with the formula (C2H5O)2P(O)H. It is a popular reagent for generating other organophosphorus compounds, exploiting the high reactivity of the P-H bond. Diethylphosphite is a colorless liquid. The molecule is tetrahedral.

<i>meso</i>-Stilbene dibromide Organic molecule

meso-Stilbene dibromide is an organic compound with a formula of (C6H5CH(Br))2.

Tetrabromo-<i>o</i>-xylene Chemical compound

α,α,α',α'-Tetrabromo-o-xylene is an organobromine compound with the formula C6H4(CHBr2)2. Three isomers of α,α,α',α'-Tetrabromoxylene exist, but the ortho derivative is most widely studied. It is an off-white solid. The compound is prepared by the photochemical reaction of o-xylene with elemental bromine:

Mesityl bromide Chemical compound

Mesityl bromide is an organic compound with the formula (CH3)3C6H2Br. It is a derivative of mesitylene (1,3,5-trimethylbenzene) with one ring H replaced by Br. The compound is a colorless oil. It is a standard electron-rich aryl halide substrate for cross coupling reactions. With magnesium it reacts to give the Grignard reagent, which is used in the preparation of tetramesityldiiron.

References

  1. Bornstein, J.; Shields, J. E. (1967). "2-(p-Tolylsulfonyl)dihydroisoindole". Organic Syntheses. 47: 110. doi:10.15227/orgsyn.047.0110.
  2. Emily F. M. Stephenson (1954). "o-Xylylene Dibromide". Organic Syntheses. 34: 100. doi:10.15227/orgsyn.034.0100.
  3. Bill, J. C.; Tarbell, D. S. (1954). "o-Phthalaldehyde". Organic Syntheses. 34: 82. doi:10.15227/orgsyn.034.0082.
  4. Mayerle, J. J.; Denmark, S. E.; Depamphilis, B. V.; Ibers, James A.; Holm, R. H. (1975). "Synthetic Analogs of the Active Sites of Iron-Sulfur Proteins. XI. Synthesis and Properties of Complexes Containing the Iron Sulfide (Fe2S2) Core and the Structures of Bis[o-Xylyl-α,α'-Dithiolato-μ-Sulfido-Ferrate(III)] and bis[p-Tolylthiolato-μ-Sulfido-Ferrate(III)] Dianions". Journal of the American Chemical Society. 97 (5): 1032–1045. doi:10.1021/ja00838a015.
  5. Kerber, Robert C.; Ribakove, Everett C. (1991). "Formation of Iron Carbonyl Complexes of Reactive Polyenes from Dihalides involving the Free Polyene". Organometallics. 10 (8): 2848–2853. doi:10.1021/om00054a059.
  6. Géraldine Franck, Marcel Brill, Günter Helmchen (2012). "Dibenzo[a,e]cyclooctene: Multi-gram Synthesis of a Bidentate Ligand". Organic Syntheses. 89: 55. doi:10.15227/orgsyn.089.0055.{{cite journal}}: CS1 maint: multiple names: authors list (link)