4-Hydroxy­phenyl 4-fluoro­benzoate

Hyon Pil You; You-Soon Lee; Byung Hee Han; Sung Kwon Kang; Chang Keun Sung

doi:10.1107/S1600536809000129

. 2009 Jan 8;65(Pt 2):o252. doi: 10.1107/S1600536809000129

4-Hydroxyphenyl 4-fluorobenzoate

Hyon Pil You ^a, You-Soon Lee ^a, Byung Hee Han ^a, Sung Kwon Kang ^a,^*, Chang Keun Sung ^b

PMCID: PMC2968377 PMID: 21581868

Abstract

In the title compound, C₁₃H₉FO₃, the dihedral angle between the two benzene rings is 59.86 (4)°. In the crystal, intermolecular O—H⋯H hydrogen bonds lead to molecular chains propagating in [010].

Related literature

For general background to whitening agents, see: Ha et al. (2007 ▶); Dawley et al. (1993 ▶); Nerya et al. (2003 ▶); Hong et al. (2008 ▶); Lee et al. (2007 ▶); Hussain et al. (2003 ▶).

Experimental

Crystal data

C₁₃H₉FO₃
M _r = 232.2
Monoclinic,
a = 24.938 (5) Å
b = 5.4789 (11) Å
c = 7.6858 (15) Å
β = 93.59 (3)°
V = 1048.1 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.12 mm⁻¹
T = 174 (2) K
0.12 × 0.09 × 0.06 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: none
10972 measured reflections
2597 independent reflections
2054 reflections with I > 2σ(I)
R _int = 0.027

Refinement

R[F ² > 2σ(F ²)] = 0.041
wR(F ²) = 0.105
S = 1.05
2597 reflections
158 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.31 e Å⁻³
Δρ_min = −0.24 e Å⁻³

Data collection: SMART (Bruker, 2002 ▶); cell refinement: SAINT (Bruker, 2002 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809000129/bh2214sup1.cif

e-65-0o252-sup1.cif^{(13KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809000129/bh2214Isup2.hkl

e-65-0o252-Isup2.hkl^{(125KB, hkl)}

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O16—H16⋯O16ⁱ	0.82 (2)	2.12 (2)	2.9368 (9)	172 (2)

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Symmetry code: (i) Inline graphic .

Acknowledgments

This study was supported financially by the Research Fund of Chungnam National University in 2008

supplementary crystallographic information

Comment

Melanin is the pigment responsible for the color of human skin and hair. Tyrosinase is the key enzyme (Ha et al., 2007) that converts tyrosine to melanin and its inhibitors are the target molecules to develop and research anti-pigmentation agents for application to skin. Therefore, treatments using potent inhibitory agents on tyrosinase and melanin formation may be cosmetically useful. Most skin whitening agents currently on the market (Dawley et al., 1993; Nerya et al., 2003) are hydroquinone, ascorbic acid, kojic acid, arbutin, azealic acid, and glycyrrhetinic acid. They contain aromatic, methoxy, hydroxyl (Hong et al., 2008; Lee et al., 2007), or carbonyl functional groups in their structures, and act as a specific functional group to make the skin white by inhibiting the production of melanin. However, most skin whitening agents have some problems, due to toxicity, low stability of formulation and poor skin permeation. In the course of our work on the development of new whitening agents, to complement the inadequacy of current whitening agents and maximize the inhibitory effects of melanin creation, we have synthesized the title compound via a general chemical pathway (Hussain et al., 2003) between hydroquinone and 4-fluorobenzoyl chloride.

The 4-fluorobenzoic acid moiety and the 4-hydroxyphenyl ring are essentially planar, with mean deviations of 0.002 and 0.004 Å, respectively, from the corresponding least-squares planes. The dihedral angle between the two benzene rings is 59.86 (4)°. The intermolecular O16—H16···O16ⁱ [symmetry code: (i) -x+1, y-1/2, -z+3/2) hydrogen bond allows to form an extensive one-dimensional network, which stabilizes the crystal structure.

Experimental

Hydroquinone and 4-fluorobenzoyl chloride were purchased from Sigma Chemical Co. and used without further purification. The title compound was prepared from the reaction of 4-fluorobenzoyl chloride (0.159 g, 1 mmol) and hydroquinone (0.132 g, 1.2 mmol) in TEA (8.0 ml). After being stirred for 8 h at 333 K, the mixture was quenched and worked up with ethyl acetate. The mixture was chromatographed on silica gel (2/1 = dichloromethane / ethylacetate) to give the title compound as colorless solid (60%, m.p. 454 K). Single crystals were obtained by slow evaporation of a solution of the title compound in ethyl alcohol and methyl alcohol at room temperature.