organic compounds
of 2-(diphenylphosphanyl)phenyl 4-(hydroxymethyl)benzoate
aInstitut für Radiopharmazeutische Krebsforschung, Bautzner Landstr. 400, D-01328 Dresden, Germany, and bUniversität Rostock, Institut für Chemie, Anorganische Festkörperchemie, Albert-Einstein-Str. 3a, D-18059 Rostock, Germany
*Correspondence e-mail: c.mamat@hzdr.de
The title compound, C26H21O3P, was obtained as by-product due to the hydrolysis of the desired tosylated compound. The dihedral angles between the three aromatic rings attached to the P atom lie in the range 78.1 (1)–87.6 (1)°. The hydroxymethyl group is disordered between two conformations in a 0.719 (9):0.281 (9) ratio. The hydroxy H atom is not involved in intermolecular interactions, while the hydroxy O atom serves as a donor for weak C—H⋯O hydrogen bonds, which link the molecules into chains propagating in [0-11].
Keywords: crystal structure; benzoate functionalized 2-(diphenylphosphano)phenol derivative; hydrogen bonding.
CCDC reference: 1033495
1. Related literature
For a general introduction to the chemistry and et al. (2009); Pretze et al. (2010). For applications of chloromethyl and hydroxymethyl benzoates, see: Mamat et al. (2011); Wodtke et al. (2015).
of benzoate functionalized 2-(diphenylphosphanyl)phenol derivatives, see: Mamat2. Experimental
2.1. Crystal data
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2.3. Refinement
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Data collection: APEX2 (Bruker, 2007); cell SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014/1 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.
Supporting information
CCDC reference: 1033495
10.1107/S1600536814024623/cv5473sup1.cif
contains datablock I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536814024623/cv5473Isup2.hkl
2-(Diphenylphosphano)phenyl-4-(iodomethyl)benzoate was dissolved in acetonitrile and treated with AgOTs in the dark. After 16 h, the precipitate was filtered and the residue was purified by
after removal of the solvent. The title compound was obtained as by-product due to the hydrolysis of the desired tosylated compound during the purification step.Colorless crystals of the title compound were obtained by crystallization from ethyl acetate/petroleum ether after chromatographic separation.
All hydrogen atoms were placed on geometrically calculated positions [C—H 0.93–0.97 Å; O—H 0.82 Å], and refined using a riding model, with Uiso(H) = 1.2 – 1.5 Ueq of the parent atom.
The hydroxymethyl group disordered between two orientations was treated using a split model with the occupancies refined to 0.719 (9)/0.281 (9).
Data collection: APEX2 (Bruker, 2007); cell
SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014/1 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).Fig. 1. The molecular structure of the title compound, with the atom labels and 50% probability displacement ellipsoids. Only the major component of the disordered hydroxymethyl group is shown. Fig. 2. A portion of the crystal packing viewed approximately down the a axis. H atoms have been omitted for clarity. |
C26H21O3P | F(000) = 432 |
Mr = 412.40 | Dx = 1.274 Mg m−3 |
Triclinic, P1 | Melting point: 437 K |
a = 9.8197 (3) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 10.6503 (3) Å | Cell parameters from 9899 reflections |
c = 11.6744 (3) Å | θ = 2.7–35.0° |
α = 74.245 (1)° | µ = 0.15 mm−1 |
β = 80.428 (1)° | T = 296 K |
γ = 66.493 (1)° | Block, colourless |
V = 1075.23 (5) Å3 | 0.41 × 0.39 × 0.31 mm |
Z = 2 |
Bruker APEXII CCD diffractometer | 12072 independent reflections |
Radiation source: fine-focus sealed tube | 7599 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.019 |
ϕ and ω scans | θmax = 38.6°, θmin = 2.3° |
Absorption correction: multi-scan (SADABS; Bruker, 2007) | h = −17→17 |
Tmin = 0.940, Tmax = 0.954 | k = −18→18 |
40695 measured reflections | l = −20→20 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.051 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.176 | H-atom parameters constrained |
S = 1.02 | w = 1/[σ2(Fo2) + (0.0924P)2 + 0.0784P] where P = (Fo2 + 2Fc2)/3 |
12072 reflections | (Δ/σ)max = 0.001 |
292 parameters | Δρmax = 0.43 e Å−3 |
0 restraints | Δρmin = −0.20 e Å−3 |
C26H21O3P | γ = 66.493 (1)° |
Mr = 412.40 | V = 1075.23 (5) Å3 |
Triclinic, P1 | Z = 2 |
a = 9.8197 (3) Å | Mo Kα radiation |
b = 10.6503 (3) Å | µ = 0.15 mm−1 |
c = 11.6744 (3) Å | T = 296 K |
α = 74.245 (1)° | 0.41 × 0.39 × 0.31 mm |
β = 80.428 (1)° |
Bruker APEXII CCD diffractometer | 12072 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2007) | 7599 reflections with I > 2σ(I) |
Tmin = 0.940, Tmax = 0.954 | Rint = 0.019 |
40695 measured reflections |
R[F2 > 2σ(F2)] = 0.051 | 0 restraints |
wR(F2) = 0.176 | H-atom parameters constrained |
S = 1.02 | Δρmax = 0.43 e Å−3 |
12072 reflections | Δρmin = −0.20 e Å−3 |
292 parameters |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
P1 | 0.84403 (3) | 0.11854 (2) | 0.24387 (2) | 0.04106 (7) | |
C1 | 0.75048 (12) | 0.12573 (10) | 0.11847 (8) | 0.0442 (2) | |
C2 | 0.82426 (17) | 0.14309 (16) | 0.00583 (11) | 0.0667 (3) | |
H2A | 0.9184 | 0.1469 | −0.0018 | 0.080* | |
C3 | 0.7585 (2) | 0.1547 (2) | −0.09483 (13) | 0.0935 (6) | |
H3A | 0.8084 | 0.1663 | −0.1696 | 0.112* | |
C4 | 0.6202 (2) | 0.1492 (2) | −0.08396 (16) | 0.0973 (7) | |
H4A | 0.5766 | 0.1564 | −0.1515 | 0.117* | |
C5 | 0.54466 (18) | 0.13304 (19) | 0.02639 (15) | 0.0779 (5) | |
H5A | 0.4503 | 0.1299 | 0.0328 | 0.094* | |
C6 | 0.60923 (13) | 0.12146 (14) | 0.12780 (11) | 0.0553 (3) | |
H6A | 0.5580 | 0.1108 | 0.2021 | 0.066* | |
C7 | 0.92219 (10) | −0.06956 (9) | 0.31351 (8) | 0.03940 (17) | |
C8 | 0.87987 (13) | −0.17150 (11) | 0.29290 (11) | 0.0512 (2) | |
H8A | 0.8029 | −0.1446 | 0.2438 | 0.061* | |
C9 | 0.95166 (15) | −0.31296 (12) | 0.34509 (12) | 0.0571 (3) | |
H9A | 0.9223 | −0.3801 | 0.3311 | 0.069* | |
C10 | 1.06669 (14) | −0.35384 (12) | 0.41781 (11) | 0.0541 (2) | |
H10A | 1.1150 | −0.4485 | 0.4521 | 0.065* | |
C11 | 1.10998 (14) | −0.25441 (12) | 0.43962 (10) | 0.0525 (2) | |
H11A | 1.1863 | −0.2820 | 0.4896 | 0.063* | |
C12 | 1.03918 (12) | −0.11301 (11) | 0.38674 (9) | 0.0459 (2) | |
H12A | 1.0701 | −0.0466 | 0.4003 | 0.055* | |
C13 | 0.68656 (10) | 0.18502 (9) | 0.34901 (8) | 0.03825 (16) | |
C14 | 0.60240 (11) | 0.32942 (10) | 0.32357 (8) | 0.03978 (17) | |
C15 | 0.48966 (13) | 0.39328 (12) | 0.40090 (11) | 0.0517 (2) | |
H15A | 0.4360 | 0.4897 | 0.3813 | 0.062* | |
C16 | 0.45770 (15) | 0.31154 (15) | 0.50816 (11) | 0.0601 (3) | |
H16A | 0.3827 | 0.3531 | 0.5616 | 0.072* | |
C17 | 0.53712 (15) | 0.16834 (15) | 0.53568 (11) | 0.0597 (3) | |
H17A | 0.5144 | 0.1137 | 0.6073 | 0.072* | |
C18 | 0.65102 (13) | 0.10505 (11) | 0.45706 (9) | 0.0482 (2) | |
H18A | 0.7039 | 0.0085 | 0.4768 | 0.058* | |
O1 | 0.62903 (8) | 0.40814 (7) | 0.21064 (6) | 0.04425 (15) | |
C19 | 0.71938 (11) | 0.47982 (10) | 0.20030 (9) | 0.04134 (18) | |
O2 | 0.76590 (12) | 0.48959 (11) | 0.28545 (8) | 0.0627 (2) | |
C20 | 0.75123 (11) | 0.54141 (9) | 0.07365 (8) | 0.04067 (17) | |
C21 | 0.82940 (13) | 0.63110 (12) | 0.04775 (11) | 0.0508 (2) | |
H21A | 0.8608 | 0.6509 | 0.1093 | 0.061* | |
C22 | 0.86029 (14) | 0.69063 (14) | −0.06974 (12) | 0.0574 (3) | |
H22A | 0.9117 | 0.7511 | −0.0867 | 0.069* | |
C23 | 0.81488 (13) | 0.66056 (13) | −0.16261 (10) | 0.0543 (2) | |
C24 | 0.73914 (15) | 0.56961 (14) | −0.13621 (10) | 0.0553 (3) | |
H24A | 0.7097 | 0.5483 | −0.1980 | 0.066* | |
C25 | 0.70666 (13) | 0.51005 (11) | −0.01914 (9) | 0.0477 (2) | |
H25A | 0.6554 | 0.4495 | −0.0025 | 0.057* | |
C26A | 0.8460 (5) | 0.7261 (4) | −0.2899 (3) | 0.0678 (9) | 0.719 (9) |
H26A | 0.9479 | 0.7215 | −0.3026 | 0.081* | 0.719 (9) |
H26B | 0.8320 | 0.6765 | −0.3427 | 0.081* | 0.719 (9) |
O3A | 0.7490 (5) | 0.8636 (4) | −0.3130 (3) | 0.126 (2) | 0.719 (9) |
H3B | 0.7261 | 0.8919 | −0.2511 | 0.189* | 0.719 (9) |
C26B | 0.840 (2) | 0.751 (3) | −0.2877 (14) | 0.141 (8) | 0.281 (9) |
H26C | 0.8470 | 0.8364 | −0.2786 | 0.170* | 0.281 (9) |
H26D | 0.9335 | 0.6990 | −0.3263 | 0.170* | 0.281 (9) |
O3B | 0.7332 (11) | 0.7830 (17) | −0.3523 (7) | 0.132 (5) | 0.281 (9) |
H3C | 0.7558 | 0.7259 | −0.3940 | 0.198* | 0.281 (9) |
U11 | U22 | U33 | U12 | U13 | U23 | |
P1 | 0.04208 (13) | 0.03810 (12) | 0.04163 (12) | −0.01697 (9) | 0.00118 (9) | −0.00612 (9) |
C1 | 0.0481 (5) | 0.0389 (4) | 0.0357 (4) | −0.0074 (3) | 0.0001 (3) | −0.0079 (3) |
C2 | 0.0682 (8) | 0.0736 (8) | 0.0416 (5) | −0.0141 (6) | 0.0117 (5) | −0.0146 (5) |
C3 | 0.1029 (13) | 0.1108 (14) | 0.0398 (6) | −0.0092 (11) | 0.0030 (7) | −0.0262 (8) |
C4 | 0.0991 (13) | 0.1105 (14) | 0.0591 (8) | 0.0073 (11) | −0.0291 (8) | −0.0398 (9) |
C5 | 0.0613 (7) | 0.0883 (10) | 0.0766 (9) | 0.0000 (7) | −0.0249 (7) | −0.0375 (8) |
C6 | 0.0486 (5) | 0.0615 (6) | 0.0498 (5) | −0.0094 (5) | −0.0064 (4) | −0.0187 (5) |
C7 | 0.0392 (4) | 0.0384 (4) | 0.0395 (4) | −0.0136 (3) | −0.0019 (3) | −0.0088 (3) |
C8 | 0.0527 (5) | 0.0437 (5) | 0.0597 (6) | −0.0194 (4) | −0.0186 (5) | −0.0047 (4) |
C9 | 0.0675 (7) | 0.0415 (5) | 0.0664 (7) | −0.0238 (5) | −0.0177 (6) | −0.0052 (4) |
C10 | 0.0591 (6) | 0.0421 (5) | 0.0527 (6) | −0.0129 (4) | −0.0110 (5) | −0.0021 (4) |
C11 | 0.0551 (6) | 0.0546 (6) | 0.0439 (5) | −0.0159 (5) | −0.0145 (4) | −0.0051 (4) |
C12 | 0.0523 (5) | 0.0484 (5) | 0.0404 (4) | −0.0188 (4) | −0.0078 (4) | −0.0125 (4) |
C13 | 0.0449 (4) | 0.0381 (4) | 0.0344 (3) | −0.0188 (3) | −0.0009 (3) | −0.0081 (3) |
C14 | 0.0463 (4) | 0.0383 (4) | 0.0375 (4) | −0.0177 (3) | −0.0045 (3) | −0.0089 (3) |
C15 | 0.0520 (5) | 0.0481 (5) | 0.0541 (6) | −0.0131 (4) | −0.0014 (4) | −0.0199 (4) |
C16 | 0.0589 (6) | 0.0716 (8) | 0.0518 (6) | −0.0237 (6) | 0.0120 (5) | −0.0274 (6) |
C17 | 0.0692 (7) | 0.0698 (7) | 0.0421 (5) | −0.0342 (6) | 0.0117 (5) | −0.0121 (5) |
C18 | 0.0588 (6) | 0.0457 (5) | 0.0397 (4) | −0.0242 (4) | 0.0025 (4) | −0.0050 (4) |
O1 | 0.0553 (4) | 0.0405 (3) | 0.0401 (3) | −0.0223 (3) | −0.0096 (3) | −0.0036 (2) |
C19 | 0.0464 (4) | 0.0369 (4) | 0.0414 (4) | −0.0154 (3) | −0.0063 (3) | −0.0081 (3) |
O2 | 0.0853 (6) | 0.0788 (6) | 0.0444 (4) | −0.0514 (5) | −0.0092 (4) | −0.0111 (4) |
C20 | 0.0429 (4) | 0.0364 (4) | 0.0407 (4) | −0.0136 (3) | −0.0069 (3) | −0.0050 (3) |
C21 | 0.0548 (6) | 0.0529 (5) | 0.0501 (5) | −0.0273 (5) | −0.0088 (4) | −0.0057 (4) |
C22 | 0.0560 (6) | 0.0610 (7) | 0.0574 (6) | −0.0317 (5) | −0.0044 (5) | −0.0010 (5) |
C23 | 0.0505 (5) | 0.0569 (6) | 0.0452 (5) | −0.0173 (5) | −0.0019 (4) | −0.0005 (4) |
C24 | 0.0649 (7) | 0.0610 (6) | 0.0405 (5) | −0.0248 (5) | −0.0080 (4) | −0.0074 (4) |
C25 | 0.0570 (6) | 0.0466 (5) | 0.0428 (5) | −0.0229 (4) | −0.0076 (4) | −0.0072 (4) |
C26A | 0.075 (2) | 0.0728 (15) | 0.0438 (12) | −0.0333 (13) | 0.0023 (11) | 0.0108 (10) |
O3A | 0.141 (3) | 0.0907 (19) | 0.0719 (14) | −0.0052 (16) | −0.0068 (16) | 0.0415 (13) |
C26B | 0.086 (9) | 0.26 (2) | 0.086 (8) | −0.061 (11) | −0.008 (6) | −0.061 (10) |
O3B | 0.136 (5) | 0.201 (11) | 0.070 (4) | −0.120 (6) | −0.056 (4) | 0.069 (5) |
P1—C1 | 1.823 (1) | C15—H15A | 0.9300 |
P1—C7 | 1.8330 (9) | C16—C17 | 1.3805 (19) |
P1—C13 | 1.8347 (9) | C16—H16A | 0.9300 |
C1—C6 | 1.391 (2) | C17—C18 | 1.3931 (16) |
C1—C2 | 1.3950 (15) | C17—H17A | 0.9300 |
C2—C3 | 1.387 (2) | C18—H18A | 0.9300 |
C2—H2A | 0.9300 | O1—C19 | 1.356 (1) |
C3—C4 | 1.366 (3) | C19—O2 | 1.205 (1) |
C3—H3A | 0.9300 | C19—C20 | 1.4824 (13) |
C4—C5 | 1.380 (3) | C20—C21 | 1.3943 (14) |
C4—H4A | 0.9300 | C20—C25 | 1.3955 (14) |
C5—C6 | 1.3881 (18) | C21—C22 | 1.3850 (17) |
C5—H5A | 0.9300 | C21—H21A | 0.9300 |
C6—H6A | 0.9300 | C22—C23 | 1.3930 (18) |
C7—C8 | 1.3944 (14) | C22—H22A | 0.9300 |
C7—C12 | 1.3973 (13) | C23—C24 | 1.3866 (18) |
C8—C9 | 1.3911 (15) | C23—C26A | 1.498 (3) |
C8—H8A | 0.9300 | C23—C26B | 1.560 (18) |
C9—C10 | 1.3828 (17) | C24—C25 | 1.3847 (15) |
C9—H9A | 0.9300 | C24—H24A | 0.9300 |
C10—C11 | 1.3815 (17) | C25—H25A | 0.9300 |
C10—H10A | 0.9300 | C26A—O3A | 1.372 (5) |
C11—C12 | 1.3911 (15) | C26A—H26A | 0.9700 |
C11—H11A | 0.9300 | C26A—H26B | 0.9700 |
C12—H12A | 0.9300 | O3A—H3B | 0.8200 |
C13—C18 | 1.3949 (13) | C26B—O3B | 1.28 (2) |
C13—C14 | 1.3986 (13) | C26B—H26C | 0.9700 |
C14—C15 | 1.3796 (15) | C26B—H26D | 0.9700 |
C14—O1 | 1.403 (1) | O3B—H3C | 0.8200 |
C15—C16 | 1.3856 (19) | ||
C1—P1—C7 | 103.65 (4) | C17—C16—C15 | 120.01 (10) |
C1—P1—C13 | 102.01 (4) | C17—C16—H16A | 120.0 |
C7—P1—C13 | 102.34 (4) | C15—C16—H16A | 120.0 |
C6—C1—C2 | 118.77 (11) | C16—C17—C18 | 120.54 (11) |
C6—C1—P1 | 124.24 (8) | C16—C17—H17A | 119.7 |
C2—C1—P1 | 116.93 (10) | C18—C17—H17A | 119.7 |
C3—C2—C1 | 120.59 (16) | C17—C18—C13 | 120.66 (10) |
C3—C2—H2A | 119.7 | C17—C18—H18A | 119.7 |
C1—C2—H2A | 119.7 | C13—C18—H18A | 119.7 |
C4—C3—C2 | 119.88 (15) | C19—O1—C14 | 118.46 (7) |
C4—C3—H3A | 120.1 | O2—C19—O1 | 122.61 (9) |
C2—C3—H3A | 120.1 | O2—C19—C20 | 126.05 (9) |
C3—C4—C5 | 120.58 (14) | O1—C19—C20 | 111.34 (8) |
C3—C4—H4A | 119.7 | C21—C20—C25 | 119.77 (10) |
C5—C4—H4A | 119.7 | C21—C20—C19 | 118.68 (9) |
C4—C5—C6 | 120.09 (17) | C25—C20—C19 | 121.54 (9) |
C4—C5—H5A | 120.0 | C22—C21—C20 | 119.97 (10) |
C6—C5—H5A | 120.0 | C22—C21—H21A | 120.0 |
C5—C6—C1 | 120.08 (13) | C20—C21—H21A | 120.0 |
C5—C6—H6A | 120.0 | C21—C22—C23 | 120.42 (11) |
C1—C6—H6A | 120.0 | C21—C22—H22A | 119.8 |
C8—C7—C12 | 118.45 (9) | C23—C22—H22A | 119.8 |
C8—C7—P1 | 124.96 (7) | C24—C23—C22 | 119.28 (11) |
C12—C7—P1 | 116.47 (7) | C24—C23—C26A | 120.0 (2) |
C9—C8—C7 | 120.66 (10) | C22—C23—C26A | 120.7 (2) |
C9—C8—H8A | 119.7 | C24—C23—C26B | 126.8 (7) |
C7—C8—H8A | 119.7 | C22—C23—C26B | 113.4 (8) |
C10—C9—C8 | 120.04 (10) | C25—C24—C23 | 120.91 (11) |
C10—C9—H9A | 120.0 | C25—C24—H24A | 119.5 |
C8—C9—H9A | 120.0 | C23—C24—H24A | 119.5 |
C11—C10—C9 | 120.18 (10) | C24—C25—C20 | 119.63 (10) |
C11—C10—H10A | 119.9 | C24—C25—H25A | 120.2 |
C9—C10—H10A | 119.9 | C20—C25—H25A | 120.2 |
C10—C11—C12 | 119.87 (10) | O3A—C26A—C23 | 107.7 (3) |
C10—C11—H11A | 120.1 | O3A—C26A—H26A | 110.2 |
C12—C11—H11A | 120.1 | C23—C26A—H26A | 110.2 |
C11—C12—C7 | 120.78 (10) | O3A—C26A—H26B | 110.2 |
C11—C12—H12A | 119.6 | C23—C26A—H26B | 110.2 |
C7—C12—H12A | 119.6 | H26A—C26A—H26B | 108.5 |
C18—C13—C14 | 117.14 (9) | C26A—O3A—H3B | 109.5 |
C18—C13—P1 | 125.19 (8) | O3B—C26B—C23 | 110.1 (12) |
C14—C13—P1 | 117.47 (7) | O3B—C26B—H26C | 109.6 |
C15—C14—C13 | 122.70 (9) | C23—C26B—H26C | 109.6 |
C15—C14—O1 | 119.88 (9) | O3B—C26B—H26D | 109.6 |
C13—C14—O1 | 117.26 (8) | C23—C26B—H26D | 109.6 |
C14—C15—C16 | 118.95 (11) | H26C—C26B—H26D | 108.2 |
C14—C15—H15A | 120.5 | C26B—O3B—H3C | 109.5 |
C16—C15—H15A | 120.5 |
D—H···A | D—H | H···A | D···A | D—H···A |
C18—H18A···O3Ai | 0.93 | 2.52 | 3.143 (5) | 125 |
C18—H18A···O3Bi | 0.93 | 2.62 | 3.408 (9) | 143 |
Symmetry code: (i) x, y−1, z+1. |
D—H···A | D—H | H···A | D···A | D—H···A |
C18—H18A···O3Ai | 0.93 | 2.52 | 3.143 (5) | 125 |
C18—H18A···O3Bi | 0.93 | 2.62 | 3.408 (9) | 143 |
Symmetry code: (i) x, y−1, z+1. |
References
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Benzoate functionalized 2-(diphenylphosphano)phenol derivatives are important starting materials for various labeling purposes using the traceless Staudinger Ligation (Mamat et al., 2009). 4-(Halomethyl) and 4-(hydroxymethyl)benzoates were developed, especially, for the insertion of fluorescence markers (Wodtke et al., 2015) or for the introduction of radiolabels such as fluorine-18 (Mamat et al., 2011). For the later purpose, good leaving groups were required. The title compound was obtained as by-product after the tosylation step during the preparation of the tosylated title compound which was further used as precursor for radiofluorinations.