Bromotoluene

Bromotoluene is a group of three isomeric chemical compounds. They (ortho-bromotoluene, meta-bromotoluene, and para-bromotoluene) consist of a disubstituted benzene ring with one bromine atom and one methyl group.

Not to be confused with Benzyl bromide.

Properties

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

Bromotoluene isomers[1][2][3]
General
Common name o-bromotoluene m-bromotoluene p-bromotoluene
Structure
Systematic name 1-bromo-2-methylbenzene 1-bromo-3-methylbenzene 1-bromo-4-methylbenzene
Molecular formula C7H7Br (C6H4BrCH3)
Molar mass 171.03 g/mol
Appearance colorless liquid, white crystalline solid
CAS number [95-46-5] [591-17-3] [106-38-7]
Properties
Density and phase 1.431 g/ml, liquid 1.4099 g/ml, liquid 1.3995 g/ml, solid
Solubility in water practically insoluble
Other solubilities very soluble in ethanol, ether, benzene, carbon tetrachloride, acetone, chloroform
Melting point -27.8 °C (-18.0 °F; -409.63 K) -39.8 °C (-39.6 °F; -388.03 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.[4]

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.[5] The methyl group may also be partially oxidized to form bromobenzaldehyde.[6]

See also

References
  1. "2-Bromotoluene". PubChem. National Center for Biotechnology Information. Retrieved January 19, 2023.
  2. "3-Bromotoluene". PubChem. National Center for Biotechnology Information. Retrieved January 19, 2023.
  3. "4-Bromotoluene". PubChem. National Center for Biotechnology Information. Retrieved January 19, 2023.
  4. Bigelow, L. A. (1925). "p-BROMOTOLUENE". Organic Syntheses. 5: 21. doi:10.15227/orgsyn.005.0021.
  5. Bigelow, L. A. (1922). "A Study of Side-Chain Oxidations with Potassium Permanganate. Ii". Journal of the American Chemical Society. 44 (9): 2010–2019. doi:10.1021/ja01430a020.
  6. Coleman, G. H.; Honeywell, G. E. (1937). "p-BROMOBENZALDEHYDE". Organic Syntheses. 17: 20. doi:10.15227/orgsyn.017.0020.
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