1-Bromonaphthalene
Title: 1-Bromonaphthalene
CAS Registry Number: 90-11-9
Additional Names: a-Bromonaphthalene
Molecular Formula: C10H7Br
Molecular Weight: 207.07
Percent Composition: C 58.00%, H 3.41%, Br 38.59%
Literature References: Prepd by dropping bromine into a mixture of naphthalene and carbon tetrachloride, distilling the CCl4, heating the residue with NaOH, and fractionating the liquid under reduced pressure: Clarke, Schram, Org. Synth. 1, 35 (1921); Clarke, Brethen, ibid. coll. vol. I, 121 (2nd ed., 1941). Also prepd by heating naphthalene (liquid or gaseous) with bromine; 2-bromonaphthalene also being produced, esp with increasing temps: Wibaut, Chem. Weekbl. 39, 326, 328 (1942); Suyver, Wibaut, Rec. Trav. Chim. 64, 65 (1945).
Properties: Oily liquid at room temp. More pungent odor than naphthalene. d420 1.4834; d425 1.4785; d430 1.4732. When solid it exists in two forms: mp 0.2-0.7° and mp 6.2°. Darkens on standing when distilled at 760 mm, but remains colorless when distilled at 16 mm. Volatile with steam. bp760 281.1°; bp400 252.0°; bp200 224.2°; bp100 198.8°; bp60 183.5°; bp40 170.2°; bp20 150.2°; bp10 133.6°; bp5 117.5°; bp1.0 84.2°. nD16.5 1.66011. Slightly sol in water; miscible with alcohol, ether, benzene, chloroform. Absorption spectrum: DeLaszlo, Proc. R. Soc. London Ser. A 111, 356 (1926).
Melting point: mp 0.2-0.7° and mp 6.2°
Boiling point: bp760 281.1°; bp400 252.0°; bp200 224.2°; bp100 198.8°; bp60 183.5°; bp40 170.2°; bp20 150.2°; bp10 133.6°; bp5 117.5°; bp1.0 84.2°
Index of refraction: nD16.5 1.66011
Density: d420 1.4834; d425 1.4785; d430 1.4732
 
Derivative Type: Compd with 1,3,5-trinitrobenzene
Molecular Formula: C10H7Br.C6H3N3O6
Molecular Weight: 420.17
Percent Composition: C 45.74%, H 2.40%, Br 19.02%, N 10.00%, O 22.85%
Properties: Lemon-yellow needles, mp 137°.
Melting point: mp 137°
 
Use: Immersion fluid in the determination of the refractive index of crystals. For the determination of water in alc by the cloud point method. For refractometric fat determinations. Mixed with polymerized castor oil as a general immersion oil in microscopy.

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