Bromotoluene

Title: Bromotoluene
Molecular Formula: C7H7Br
Molecular Weight: 171.03
Percent Composition: C 49.16%, H 4.13%, Br 46.72%
Literature References: Prepn of o-isomer: Bourgeois, Ber. 28, 2312 (1895). Prepn of m-isomer: Acree, Ber. 37, 994 (1904). Kohn, Bum, Monatsh. Chem. 33, 924 (1912); Feitler, Z. Phys. Chem. 4, 77 (1889). Prepn of m-, o- and p-isomers: Bigelow et al., Org. Synth. coll. vol. I (2nd ed., 1941) pp 133, 135, 136 resp. Isomerization of p-isomer yields mixture of monobromotoluenes containing 48.2% of o-isomer: Crump, US 3077503 (1963 to Dow). Separation of o- and p-isomers by clathration: Coscia, US 3114784 (1963 to Am. Cyanamid).
Derivative Type: m-Bromotoluene
Additional Names: 1-Bromo-3-methylbenzene; 3-bromotoluene; m-tolylbromide
Properties: Liquid. d420 1.4099; d458 1.309; d4184 1.201. mp -39.8°. bp760 183.7°; bp400 160°; bp200 138°; bp100 117.8°; bp60 104.1°; bp40 93.9°; bp20 78.1°; bp10 64.0°; bp5 50.8°; bp1.0 14.8°. nD20 1.551. Absorption spectrum: Purvis, J. Chem. Soc. 99, 1706, 1710 (1911). Sol in alc, ether, benzene.
Melting point: mp -39.8°
Boiling point: bp760 183.7°; bp400 160°; bp200 138°; bp100 117.8°; bp60 104.1°; bp40 93.9°; bp20 78.1°; bp10 64.0°; bp5 50.8°; bp1.0 14.8°
Index of refraction: nD20 1.551
Density: d420 1.4099; d458 1.309; d4184 1.201
Derivative Type: o-Bromotoluene
Properties: Colorless liq. d1515 1.431. bp 181°. mp -26°. nD20 1.555. Practically insol in water; misc with alc, benzene.
Melting point: mp -26°
Boiling point: bp 181°
Index of refraction: nD20 1.555
Density: d1515 1.431
Derivative Type: p-Bromotoluene
Properties: Crystals from abs alc. d3535 1.3959; d5050 1.3856; d100100 1.3637; d184 1.1931. mp 28.5°. bp760 184.5°; bp100 116.4°; bp60 102.3°; bp40 91.8°; bp20 75.2°; bp10 61.1°; bp5 47.5°; bp1.0 10.3°. nD20 1.5490. Sol in alc, ether, benzene.
Melting point: mp 28.5°
Boiling point: bp760 184.5°; bp100 116.4°; bp60 102.3°; bp40 91.8°; bp20 75.2°; bp10 61.1°; bp5 47.5°; bp1.0 10.3°
Index of refraction: nD20 1.5490
Density: d3535 1.3959; d5050 1.3856; d100100 1.3637; d184 1.1931
CAUTION: Irritants!
Bromoxynil Bromperidol Brompheniramine Bromphenol Blue Bromthymol Blue

Benzyl bromide[1]
Skeletal structure of the benzyl bromide molecule 3D structure of the benzyl bromide molecule
Identifiers
CAS number 100-39-0 YesY
PubChem 7498
ChemSpider 13851576 YesY
ChEBI CHEBI:59858 YesY
ChEMBL CHEMBL1085946 YesY
Jmol-3D images Image 1
Image 2
Properties
Molecular formula C7H7Br
Molar mass 171.03 g mol−1
Appearance colorless liquid
Odor very sharp and pungent
Density 1.438 g/cm3
Melting point −3.9 °C; 25.0 °F; 269.2 K
Boiling point 201 °C; 394 °F; 474 K
Solubility soluble in benzene, CCl4
miscible in ethanol, ether
Refractive index (nD) 1.5752
Hazards
Flash point 70 °C; 158 °F; 343 K
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Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Infobox references

Benzyl bromide, or α-bromotoluene, is an organic compound consisting of a benzene ring substituted with a bromomethyl group. It can be prepared by the bromination of toluene at room temperature in air, using manganese(IV) oxide as a heterogeneous catalyst. It is a colorless liquid that is decomposed slowly in water.

Benzyl bromide is used in organic synthesis for the introduction of the benzyl protecting group for alcohols and carboxylic acids.

Benzyl bromide is a strong lachrymator and is also intensely irritating to skin and mucous membranes. Because of these properties, it has been used as a war gas.