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!

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