EFFECT OF STRUCTURAL FACTORS AND SOLVENT NATURE
1575
Table 2. (Contd.)
substituent, to tetrabromo derivatives via formation of
mono-, di-, and tribromo derivatives.
Calculated, %
N
Comp.
no.
(2) The result of bromination in an aqueous
medium depends both on the nature of a substituent
and on its position in the aromatic ring. Presence of
electron-donor substituents in o- and p-positions leads
to formation of Aniline Black, whereas electron-
acceptor substituents yield mono-, di-, tri-, and
tetrabromo derivatives. m-Substituted anilines form,
irrespective of the properties of a substituent, 2,4,6-
tribromoanilines.
С
Н
Br
Cl
21.85
24.45
20.84
19.78
24.45
20.84
19.78
23.36
24.45
20.84
19.78
19.23
22.49
19.89
16.97
16.26
1.22
1.76
1.17
0.83
1.76
1.17
0.83
1.68
1.76
1.17
0.83
0.81
1.08
1.19
0.71
0.45
4.25
4.07
4.05
3.85
4.07
4.05
3.85
3.89
4.07
4.05
3.85
7.47
3.75
3.31
3.30
3.16
72.68
69.72
69.32
65.81
69.72
69.32
65.81
66.62
69.72
69.32
65.81
63.96
64.12
75.61
75.25
72.12
V
XXI
XXII
XXIII
XLI
XLII
XLIII
LI
LVII
LVIII
LIX
LX
LXI
XLIV
XLV
XLVI
9.73
9.73
REFERENCES
9.73
8.01
1. Gaevskii, B.D., Dorofeev, V.T., Matveeva, A.P., and
Rilo, R.P., Khimiya 2,4,6-tribromanilina. VNII
iodobrom, Saki (Chemistry of 2,4,6-Tribromoaniline,
All-Rissia Inst. IOdobromne, Saki), Available from
VINITI, no. 962, KhP-D84.
2. Bodische Anilin und Soda Fabrik, Chem. Industr. J.,
1954, vol. 72, no. 5, pp. 965–968.
3. USSR Inventor’s Certificate, no. 1398346.
4. Shishkin, V.N., Zh. Org. Khim., 1984, vol. 20, no. 12,
pp. 2588–2605.
5. Salakhov, M.S., Bagmanov, B.T., Umaeva, V.S., and
Bagmanova, M.I., Zh. Prikl. Khim., 2008, vol. 81, no. 8,
pp. 1404–1406.
6. Salakhov, M.S., Bagmanov, B.T., Nagiev, V.A., and
Mamedova, O.M., Abstracts of Papers, IX Vseso-
yuznaya konferentsiya “Sintez i issledovanie effektiv-
nosti khimikatov dlya polimernykh materialov” (IX All-
Union Conf. “Synthesis and Study of Efficiency of
Chemical Reagents for Polymeric Materials”), Tambov,
1990, pp. 166–167.
times washed with distilled water, and dried. The yield
of tribromoanilines was 85–99%. Selected physico-
chemical parameters of these compounds are listed in
Table 2.
b. Into a solution of 0.1 mol of a substituted aniline
in 250 ml of 25% HBr was added in the course of 3 h,
under vigorous agitation, 30.54 ml of a 30% H2O2
solution, with the temperature of the mixture
maintained at around 10°C (cooling with ice). The
resulting crystalline product was filtered off, several
times washed with distilled water, and dried in air.
Parameters of the compounds obtained V, XXI–
XXIII, XLI –XLIII, LI, and LVII–LXI are listed in
Table 2.
7. Islam, A.M. and Hassan, E.A., J. Chem. UAR, 1970,
vol. 13, no. 3, pp. 297–308.
8. Aseeva, R.M. and Zaikov, R.E., Snizhenie goryuchesti
polimernykh materialov (Lowering the Inflammability
of Polymeric Materials), Moscow: Znanie, 1981.
Tetrabromoanilines. To a solution of 0.1 mol of a
tribromoaniline, XLI –XLIII, in 250 ml of CCl4 was
added, under vigorous agitation, 0.1 mol of Br2 in
50 ml of CCl4. After the whole amount of bromine was
consumed, the reaction mixture was kept at room
temperature for additional 1 h and the solid product
was filtered off, several times washed with distilled
water, and dried. The yield of tetrabromoanilines
XLIV–XLVI was 85–93%; their characteristics are
listed in Table 2.
9. Bagmanov, B.T., Salakhov, M.S., Bagmanova, M.I.,
and Dostuyeva, V.M., VIth Int. Conf. “Ecology and
Security of Life Activity,” Sumgayit, December 6–7,
2007, p. 75.
10. Koptyug, V.A., Zh. Vses. Khim. O–va, 1976, vol. 21,
no. 3, pp. 247–255.
11. Bagmanov, B.T., Salakhov, M.S., Nagiev, V.A., and
Mamedova, O.M., Abstracts of Papers, IV Vseso-
yuznaya nauchnaya konferentsiya “Sovremennoe sos-
toyanie i perspektivy razvitiya khlororganicheskikh
produktov” (IV All-Union Sci. Conf. “Modern State
and prospects for Development of Organochlorine
Products”), Baku, 1991, p. 32.
CONCLUSIONS
(1) Bromination of substituted anilines in nonpolar
solvents leads, irrespective of the nature of a
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