Asian Journal of Chemistry; Vol. 27, No. 8 (2015), 3127-3128
A
SIAN
J
OURNAL OF HEMISTRY
C
NOTE
Synthesis and Crystal Structure of 5-Bromoisophthalic Acid
*
R. ZHANG and M.Y. ZHANG
College of Chemistry and Chemical Engineering, Luoyang Normal University, Henan, P.R. China
Corresponding author: Tel: +86 379 65515113; Fax: +86 379 65515113; E-mail: zhangruihxx@126.com
Received: 5 June 2014; Accepted: 2 September 2014; Published online: 27 April 2015;
*
AJC-17206
A new compound viz., 5-bromoisophthalic acid with the molecular formula C
8
H
7
BrO has been successfully synthesized by the reaction
5
of isophthalic acid and N-bromosuccinimide (NBS). The compound has been characterized by X-ray single-crystal diffraction and shows
a one-dimensional framework. The 3D supramolecular structure is formed via hydrogen bonding connection.
Keywords: Coordination polymer, Crystal structure, Isophthalic acid.
Brominated benzene compounds have received wide
was then cooled slowly to room temperature and the solution
filtered. Yellow block-shaped crystals were obtained from
the filtrate after several days at room temperature. The
yellow crystals suitable for X-ray diffraction analysis were
collected.
Diffraction intensity data of the single crystal of the
compound were collected on a Bruker SMARTAPEXII CCD
diffractometer equipped with a graphite monochromated
attention as precursors in the synthesis of a variety of active
pharmaceutical ingredients, for example, citalopram,
1
-3
bromperidol, bromindione, ambroxol, tramadol , etc. Also
the bromarenes have been extensively used in the aromatic
bond formation reactions such as Heck arylation, Suzuki,
4
Buchwald, Negishi and Stille couplings , etc. for the synthesis
of biaryls some of which are the precursors for a few of the
antihypertensive agents. Bromoaromatic compounds find
application in the synthesis of dendrimers. Several procedures
are available for the synthesis of deactivated bromoarenes.
All reagent and solvents employed were commercially
available and used as received without further purification.
General procedure: 5-Bromoisophthalic acid was
prepared under the hydrothermal conditions. A mixture of
MoK radiation (λ = 0.71073 Å) by using a ω-scan mode.
α
All the structures were solved by direct methods and refined
2
by full-matrix least-squares methods on F using the program
5
SHELXL 97 . All non-hydrogen atoms were refined aniso-
tropically. The hydrogen atoms were located by geometrically
calculations and their positions and thermal parameters were
fixed during the structure refinement. The crystallographic
data and experimental details of structural analyses for
coordination polymers are summarized in Table-1. Selected
bond and angle parameters are listed in Table-2. CCDC:
911478.
isophthalic acid (16.6 mg, 0.1 mmol), H
mmol) and N-bromosuccinimide (NBS) (14.13 mg, 0.1 mmol),
O (12 mL) was sealed into a 25 mL stainless steel reactor
with a Teflon liner and heated at 333 K for 20 h. The reactor
2
SO
4
(9.8 mg, 0.2
H
2
TABLE-1
CRYSTALLOGRAPHIC DATA AND STRUCTURE REFINEMENT SUMMARY FOR 5-BROMOISOPHTHALIC ACID
3
Empirical formula
Formula weight
Crystal system space group
C H BrO
5
263.05
Z, Calculated density (mg/m )
4, 1.766
4.147
520
-15 ≤ h ≤ 17
11 ≤ k ≤ 11
8
7
-
1
Absorption coefficient (mm )
F(000)
Monoclinic, P2(1)/c
a = 14.384(3) Å
b = 9.626(2) Å
Unit cell dimensions
Limiting indices
-
c = 7.2062(16) Å
-8 ≤ l ≤ 8
3
3
Volume (Å )
989.4(4)
2.55 -25.50
Largest diff. peak and hole (e/Å )
1.000 and -0.691
1.184
R = 0.0530, wR = 0.1864
1 2
2
θ Range for data collection
Final R indices [I > 2σ(I)]
Goodness-of-fit on F
R
1
= 0.0494,wR
= 0.1831
R indices (all data)
2
Zhang
