untitled


European	Journal	of	Chemistry	3	(4)	(2012)	404‐405	

European	Journal	of	Chemistry	
ISSN	2153‐2249	(Print)	/	ISSN	2153‐2257	(Online)		2012	EURJCHEM	

DOI:10.5155/eurjchem.3.4.404‐405.657	

	
	

	

	

European	Journal	of	Chemistry	
Journal	homepage:	www.eurjchem.com	

	 	 	

Synthesis	and	characterization	of		
1,3‐bis(4‐bromophenyl)‐5‐propyl‐1,3,5‐triazinane	

Leila	Lefrada	*,	Ahcene	Bouchemma,	Mustapha	Bouhenguel,	Amel	Ferhati	and	Mahmoud	Chebbah	

Laboratory	of	Applied	Chemistry	and	Materials	Technology,	Chemistry	Institute,	Larbi	Ben	M’hidi	University,	Oum	El	Bouaghi,	04000,	Algeria	

*Corresponding	author	at:	Laboratory	of	Applied	Chemistry	and	Materials	Technology,	Chemistry	Institute,	Larbi	Ben	M’hidi	University,	Oum	El	Bouaghi,	04000,	
Algeria.	Tel.:	+213.32421036;	Fax:	+213.32424213.	E‐mail	address:	aliel_2011@yahoo.fr	(L.	Lefrada).	

	
	

	 	

	 	 	
ARTICLE	INFORMATION	 	 ABSTRACT
Received:	01	July	2012	
Received	in	revised	form:	15	July	2012	
Accepted:	15	July	2012	
Online:	31	December	2012	

KEYWORDS	

	 Condensation	 of	 n‐propyl	 amine	 and	 4‐bromoaniline	with	 formaline	 in	 basic	 solution	 gives
1,3‐bis(4‐bromophenyl)‐5‐(propyl)‐1,3,5‐triazinane.	 Structure	 of	 the	 synthesized	 compound
was	characterized	by	FT‐IR	and	1H‐	and	13C‐NMR	spectroscopy.	

Formalin	
Schiff	base	
Propyl	amine	
4‐Bromoaniline	
Spectroscopic	methods		
Condensation	reactions	

	
1.	Introduction	
	

The	 formation	 of	 1,3,5‐triazacyclohexanes	 from	 primary	
amines	and	 formaldehyde	has	been	known	 for	over	a	 century	
[1].	 The	 different	 triazines	 were	 synthesized	 in	 the	 various	
laboratories	 according	 to	 the	 procedure	 described	 elsewhere	
[2].	 The	 1,3,5‐triazacyclohexane	 are	 the	 subject	 of	 several	
structural	 studies	 considering	 their	 use	 in	 the	 industrial	
chemistry.	 They	 can	be	used	as	 ligands	 for	 the	preparation	of	
new	 complexes	 that	 can	 be	 served	 as	 catalyst	 in	 the	
polymerization	 and	 trimerization	 of	 olefines	 [3].	 However,	
interest	 in	1,3,5‐triazacyclohexane	as	 ligand	seems	to	growing	
rapidly	[4‐8].		
	
2.	Experimental	
	
2.1.	Instrumentation	
	

Purity	 of	 the	 title	 compound	 was	 checked	 by	 thin	 layer	
chromatography	 (TLC)	 using	 CH2Cl2:n‐hexane	 (1:1)	 as	 an	
eluent.	IR	spectra	were	recorded	in	KBr	pellet	on	Shimadzu	FT‐
IR	8201	PC	(4000‐400	cm‐1).	1H‐	and	13C‐NMR	spectrum	of	the	
title	compound	were	recorded	on	a	Bruker	Advanced	DPX‐250	
(1H‐NMR	250	MHz	and	13C‐NMR	62.9	MHz)	spectrophotometer	
in	CDCl3	using	TMS	as	an	internal	standard.	
	
2.2.	Synthesis	
	

The	 title	 compound	 was	 obtained	 by	 mixing	 a	 2:1:4:4	
stoichiometric	 ratio	 of	 n‐propyl	 amine,	 4‐bromo	 aniline,	
formaline	 and	 potassium	 hydroxide	 (in	 water	 15	 mL)	 in	
ethanol	 (25	mL)	 at	 293	K	 for	48h.	The	 resulting	 solution	was	
extracted	 with	 CH2Cl2,	 dried	 with	 MgSO4,	 evaporated	 on	 a	
rotary	evaporator	 to	dryness.	The	oil	 residue	was	 crystallized	
from	 cyclohexane	 [5‐8].	 1,3‐Bis(4‐bromophenyl)‐5‐(propyl)‐

1,3,5‐triazinane.	 Yield:	 95%.	 M.p.:	 115‐117	 oC.	 FT‐IR	 (KBr,	 ν,	
cm‐1):	 2925	 (C‐H),	 1583,	 1498	 (C=C),	 1276	 (C‐N),	 516	 (C‐Br),	
758	 (C‐H,	Ar).	 1H	NMR	 (250	MHz,	CDCl3,	 δ,	 ppm):	0.95	 (t,	 3H,	
CH3),	1.50	(m,	2H,	CH2),	2.51	(t,	2H,	CH2),	4.40	(s,	4H,	C2H5‐N‐
CH2‐N‐Ar),	 4.70	 (s,	 2H,	Ar‐N‐CH2‐N‐Ar),	 6.80‐7.00	 (m,	8H,	Ar).	
13C	 NMR	 (62.89	MHz,	 CDCl3,	 δ,	 ppm):	 11.87	 (CH3‐CH2),	 20.92	
(CH3‐CH2),	53.98	(C2H5‐CH2‐N),	68.26	(C3H7‐N‐CH2‐N‐Ar),	71.12	
(Ar‐N‐CH2‐N‐Ar),	112.97	(C‐Br)	119.10,	132.14 (CH=C‐),	148.38 
(N‐C=).	
	
3.	Results	and	discussion	
	

An	 unsymmetrically	 substituted	 triazinane,	 1,3‐bis(4‐
bromophenyl)‐5‐(propyl)‐1,3,5‐triazinane,	 was	 prepared	 from	
the	 condensation	 reaction	 of	 n‐propyl	 amine	 and																											
4‐bromoaniline	 with	 formaldehyde	 [6]	 (Scheme	 1).	 This	
compound	is	stable	at	room	temperature	and	high	yield	(95%)	
with	a	transparent	color.	

The	 mechanism	 of	 interaction	 is	 the	 production	 of	 Schiff	
base,	 which	 polymerize	 to	 give	 1,3‐bis(4‐bromophenyl)‐5‐
(propyl)‐1,3,5‐triazinane	(Scheme	2).	

Structure	of	the	title	compound	has	been	elucidated	by	FT‐
IR,	 1H‐NMR	 and	 13C‐NMR	 including	 2D,	 J‐mod,	 HSQC	
measurements.	 The	 infrared	 spectrum	 shows	 a	 strong	
stretching	 vibration	 at	 516	 cm‐1	 for	 characteristic	 C‐Br	 bond.	
Two	absorption	bands	at	1583	and	1498	cm‐1	are	shows	by	the	
six‐membered	aromatic	system	νC=C	an	absorption	bond	at	758	
cm‐1	 characteristic	 of	 the	 C‐H	 out	 of	 plane	 vibration	 of	 the	
aromatic	system.		

The	1H	NMR	spectrum	shows	protons	of	the	methyl	group	
resonate	 as	 a	 three	 proton	 triplet	 centered	 at	 0.95	 ppm,	 A	
triplet	 arises	 be	 cause	 the	 methyl	 group	 has	 two	 equivalent	
protons	 on	 an	 adjacent	 carbon	 atom.	 The	 two	protons	 of	 CH2	
group	adjacent	to	both	CH2	and	CH3	groups	appear	as	sexlet	at	
1.50	ppm	(CH3‐CH2‐CH2).		



Lefrada	et	al.	/	European	Journal	of	Chemistry	3	(4)	(2012)	404‐405	 405	
 

	

	
	

Scheme	1
	
	
	

	
	

Scheme	2
	
	

	
The	two	protons	of	the	CH2	group	attached	to	the	nitrogen	

atom	 (CH2‐CH2‐N)	 shows	 a	 triplet	 centered	 at	 2.51	 ppm.	 The	
protons	of	 the	heterocyclic	triazinane	appear	as	two	singlet	at	
4.40	 ppm	 (C3H7‐N‐CH2‐N‐Ar)	 and	 4.70	 (Ar‐N‐CH2‐N‐Ar),	 the	
protons	 of	 the	 aromatic	 system	 appear	 as	 multiple	 signal	 at	
6.80‐7.00	ppm.		

The	 carbon	 atoms	 of	 the	 propyl	 group	 appear	 at	 11.87,	
20.92,	 53.98	 ppm,	 the	 carbon	 atoms	 of	 the	 triazinane	 group	
appears	at	68.26	and	71.12	ppm,	 the	carbon	atoms	of	 the	aryl	
group	 appears	 at	 119.10,	 132.14	 and	148.38	ppm,	 the	 carbon	
ring	aryl	which	has	a	bromine	atom	appears	at	112.97	ppm.	
	
4.	Conclusion	
	

We	 have	 synthesized	 and	 characterized	 a	 new	
unsymmetrical	 1,3,5‐triazinane	 derivative.	 The	 synthesis	 was	
achieved	 by	 condensation	 of	 n‐propyl	 amine	 and	 4‐bromo	
aniline	with	formalin.	The	synthesized	compound	is	very	stable	
in	 air	 and	 can	 be	 a	 useful	 ligand	 for	 the	 preparation	 of	 new	
metal	 complexes	 that	 can	 be	 served	 as	 catalyst	 in	 the	
polymerization	and	trimerization.	
	
Acknowledgements	
	

We	 thank	 the	 Mustapha	 Bouhenguel	 director	 of	 the	
Laboratory	of	Applied	Chemistry	 and	Materials	Technology	of	
the	University	Larbi	Ben	M’hidi	of	Oum	El	Bouaghi,	Algeria.	
	
References	
	
[1]. Franchimont,	A.	P.	N.;	Erp,	H.	Rec.	Trav.	Chim.	1896,	15,	66‐68.	
[2]. Miller,	J.	G.;	Wagner,	E.	C.	J.	Am.	Chem.	Soc.	1932,	54(9),	3698‐3706.	
[3]. Baker,	M.	V.;	Palermo,	M.	C.;	Skelton,	B.	W.;	White,	A.	H.	Aust.	J.	Chem.	

1999,	52(3),	179‐184.	

[4]. Guide,	 S.	 Phd	 Thesis,	 Synthesis	 and	 Coordination	 Chemistry	 of	
Traizacyclohexane	and	Orthoamides.	Technischen	Universitat,	Berlin,	
1999.		

[5]. Bouchemma,	A.;	McCabe,	P.	H.;	Sim,	G.	A.	J.	Chem.	Soc.,	Perkin	Trans.	2	
1989,	585‐587.	

[6]. Latreche,	S.;	Bouchemma,	A.;	Bouacida,	S.;	Bouhenguel,	M.;	Mousser,	A.	
Acta	Cryst.	E	2006,	62,	o4676‐o4678.		

[7]. Latreche,	S.;	Bouchemma,	A.;	Bouacida,	S.;	Bouhenguel,	M.;	Mousser,	A.	
Acta	Cryst.	E	2006,	62,	o4674‐o4675.	

[8]. Latreche,	S.;	Bouchemma,	A.;	Bouacida,	S.;	 	Mousserd,	H.;	Mousser,	A.	
Acta	Cryst.	E	2006,	62,	o4960‐o4962.