Bromotoluene

{{Short description|Isomers of the organic compound bromotoluene}}

{{Distinguish|Benzyl bromide}} '''Bromotoluenes''' are aryl bromides based on toluene in which at least one aromatic hydrogen atom is replaced with a bromine atom. They have the general formula C₇H_8–''n''Br_''n'', where ''n'' = 1–5 is the number of bromine atoms.

==Monobromotoluene==

Monobromotoluenes are bromotoluenes containing one bromine atom. There are three isomers, each with the formula C₇H₇Br.

=== Properties === The isomers differ in the location of the bromine, but have the same chemical formula.

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! {{Chemical datatable header}} align="center" colspan="4" | Monobromotoluene isomers<ref>{{Cite PubChem|cid=7236|title=2-Bromotoluene|access-date=January 19, 2023}}</ref><ref>{{Cite PubChem|cid=11560|title=3-Bromotoluene|access-date=January 19, 2023}}</ref><ref>{{Cite PubChem|cid=7805|title=4-Bromotoluene|access-date=January 19, 2023}}</ref> |- | Common name | {{no redirect|2-Bromotoluene|'''''o''-bromotoluene'''}} | {{no redirect|3-Bromotoluene|'''''m''-bromotoluene'''}} | {{no redirect|4-Bromotoluene|'''''p''-bromotoluene'''}} |- | Structure | align="center" | 90px | align="center" | 90px | align="center" | 55px |- | Systematic name | 1-bromo-2-methylbenzene | 1-bromo-3-methylbenzene | 1-bromo-4-methylbenzene |- | Molecular formula | align="center" colspan="3" | C₇H₇Br (C₆H₄BrCH₃) |- | Molar mass | align="center" colspan="3" | 171.03 g/mol |- | Appearance | colorless liquid | colorless liquid | white crystalline solid |- | CAS number | [95-46-5] | [591-17-3] | [106-38-7] |- ! {{Chemical datatable header}} align="center" colspan="5" | Properties |- | Density and phase | 1.431 g/ml, liquid | 1.4099 g/ml, liquid | 1.3995 g/ml, solid |- | Solubility in water | align="center" colspan="3" | practically insoluble |- | Other solubilities | align="center" colspan="4" | very soluble in ethanol, ether, benzene, carbon tetrachloride, acetone, chloroform |- | Melting point | −27.8 °C (−18.0 °F; 245.35 K) | −39.8 °C (−39.6 °F; 233.35 K) | 28.5 °C (83.3 °F; 301.7 K) |- | Boiling point | 181.7 °C (359.1 °F; 454.9 K) | 183.7 °C (362.7 °F; 456.9 K) | 184.5 °C (364.1 °F; 457.7 K) |}

Benzyl bromide is an isomer, which has a bromine substituted for one of the hydrogens of toluene's methyl group, and it is sometimes named α-bromotoluene.

==Preparation== A laboratory route to ''p''-bromotoluene proceeds from ''p''-toluidine, which is diazotiized followed by treatment with copper(I) bromide.<ref>{{cite journal |last=Bigelow |first=L. A. |date=1925 |title=''p''-BROMOTOLUENE |journal=Organic Syntheses |volume=5 |pages=21 |doi=10.15227/orgsyn.005.0021}}</ref>

==Uses== Bromotoluenes are precursors to many organic building blocks. For example, the methyl group may be oxidized using potassium permanganate to form the corresponding bromobenzoic acid.<ref>{{cite journal |last=Bigelow |first=L. A. |title=A Study of Side-Chain Oxidations with Potassium Permanganate. Ii |date=1922 |journal=Journal of the American Chemical Society |volume=44 |issue=9 |pages=2010–2019 |doi=10.1021/ja01430a020}}</ref> The methyl group may also be partially oxidized to form bromobenzaldehyde.<ref>{{cite journal |last1=Coleman |first1=G. H. |last2=Honeywell |first2=G. E. |date=1937 |title=''p''-BROMOBENZALDEHYDE |journal=Organic Syntheses |volume=17 |pages=20 |doi=10.15227/orgsyn.017.0020}}</ref>

==See also== *Chlorotoluene *Iodotoluene

== References ==

{{reflist}}

Category:Bromobenzene derivatives Category:Toluenes Category:Multiple compounds, tabular