1,3,5-Tris(bromomethyl)benzene

Fernandes, José A.; Vilela, Sérgio M. F.; Ribeiro‐Claro, Paulo J. A.; Paz, Filipe A. Almeida

doi:10.1107/s0108270111013618

Cited by 3 publications

(2 citation statements)

References 15 publications

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“…Preparation of (benzene-1,3,5-triyltris(methylene)) triphosphonic acid (Benzene-1,3,5-triyltris(methylene))triphosphonic acid (H 6 bmt) was prepared by a two-step reaction according to published procedures with small modifications (Scheme 2). 20 Synthesis of H 6 bmt started with a Michaelis-Arbusov reaction of 1,3,5tris(bromomethyl)benzene 21 with triethyl phosphite at 120 C. Upon completion of the reaction the excess of triethyl phosphite was removed by distillation under reduced pressure. The intermediate compound L' [hexaethyl(benzene-1,3,5-triyltris-(methylene))tris(phosphonate)] was purified by flash column chromatography and isolated as a colorless oil in excellent yield (88%).…”

Section: Ligand Design Strategymentioning

confidence: 99%

Multi-functional metal–organic frameworks assembled from a tripodal organic linker

et al. 2012

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The reaction between (benzene-1,3,5-triyltris(methylene))triphosphonic acid (H 6 bmt) and lanthanide chlorides, under typical hydrothermal conditions (180 C for 3 days) or using microwave heating (5 minutes above 150 C), led to the isolation of an isotypical series of compounds formulated as 3+ (2), Pr 3+ (3), Nd 3+ (4), (La 0.95 Eu 0.05 ) 3+ ( 5) and (La 0.95 Tb 0.05 ) 3+ ( 6)]. Compounds 1 to 4 have been readily isolated as large single-crystals and their structures determined in the monoclinic C2/c space group using single-crystal X-ray diffraction. All compounds were thoroughly characterized in the solid-state using powder X-ray diffraction, FT-IR spectroscopy, thermogravimetry, scanning electron microscopy (SEM and EDS) and elemental analysis. Solid-state NMR ( 31 P MAS and 13 C{ 1 H} CP MAS) and thermodiffractometry studies have been performed on the La 3+ -based material. [Ln 2 (H 3 bmt) 2 (H 2 O) 2 ]$H 2 O were found to be threedimensional frameworks with water molecules (both of crystallization and coordinated to the lanthanide center), which could be reversibly removed by either heating the materials or by applying high vacuum. This typical zeolitic behaviour was confirmed experimentally by determining the crystal structure of the evacuated La 3+ -based material (1-dehyd) using single-crystal X-ray diffraction. This series of materials was found to exhibit dual functionality: photoluminescence and catalytic activity. Small amounts (5%) of Eu 3+ and Tb 3+ cations were engineered into the La 3+ -based matrices, promoting the isolation of optically active materials. The H 6Àx bmt xÀ residues were found to be good sensitizers of Tb 3+ , with 6 having the remarkable absolute emission quantum yield of ca. 46% (at 280 nm excitation). The zeolitic properties of the Eu 3+ -based material allowed an increase of the quantum efficiency from ca. 15% to 54% by removing under vacuum all water molecules in the material. Based on studies of the La 3+ -based material, these compounds can be employed as effective heterogeneous catalysts in the ring-opening reaction of styrene oxide with methanol, showing excellent regioselectivity, recyclability and structural stability in consecutive catalytic runs.

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Section: Ligand Design Strategymentioning

confidence: 99%

Multi-functional metal–organic frameworks assembled from a tripodal organic linker

et al. 2012

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“…Other papers have discussed the structures of all di(bromomethyl)naphthalene isomers [2], 1,6,7-tris(bromomethyl)naphthalene [3], 1,5-dibromo-2,6-dimethylnaphthalene [4], 2,5-bis(bromomethyl)-biphenyl [5], 2,2 -bis(bromomethyl)-p-terphenyl [6], mesitylene and dimesitylene compounds bearing bromomethyl units [7], a new polymorph of 1,4-dibromo-2,5-dimethylbenzene [8] and two polymorphs of 1,4-bis(tribromomethyl)benzene [9]. Other authors have reported the structure of 1,3,5-tris(bromomethyl)-benzene [10].…”

Section: Introductionmentioning

confidence: 99%

X-Ray Structure Determinations of Bromo- and/or Bromomethylsubstituted Benzenes: C–H···Br, C–Br···Br, and C–Br···π Interactions

Jones

Kuś

Dix

2012

Zeitschrift Für Naturforschung B

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The structures of seven benzene derivatives [1,2,3-tri(bromomethyl)benzene, (1); 3,5-di(bromomethyl)bromobenzene, (2); 2,5-di(bromomethyl)bromobenzene, (3); 4-(bromomethyl)-2,5-dibromotoluene, (4); 4-(bromomethyl)bromobenzene, (5); 2,3-di(bromomethyl)bromobenzene, (6) and (bromomethyl)-p-dibromobenzene, (7)] with bromo and bromomethyl (and in one case methyl) substituents are presented and analysed in terms of Br···Br interactions up to 4.0Å, supported by hydrogen bonds H···Br. Some interactions of the type Br···π and π···π are encountered and play a subordinate role in the packing. Despite the close chemical similarity of the compounds, some of which are isomers with permuted substituent positions, the packing motifs are highly variable. Compounds 2-5 are based on layer structures with Br n (n = 3, 4) and/or mixed Br/C rings. Compounds 1, 6 and 7 display three-dimensional packings of differing complexity, but with interpretable substructures; 1 can be analysed in terms of ribbons of linked Br 3 and Br 4 rings; 6 displays chains of linked Br 3 triangles; 7 consists of ribbons of linked Br 4 quadrilaterals.

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1,1′-[(5-Hydroxymethyl-1,3-phenylene)bis(methylene)]dipyridin-4(1H)-one monohydrate

et al. 2011

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The asymmetric unit of the title compound, C19H18N2O3, comprises a whole organic dipyridinone molecule plus a water molecule of crystallization. The planes of the pyridinone rings are approximately perpendicular with the plane of the central aromatic ring [dihedral angles = 80.68 (8) and 83.65 (8)°]. The C—O bond of the hydroxy group subtends an angle of 31.71 (10)° with the plane through the central aromatic ring. The crystal packing is mediated by the presence of several O—H⋯O hydrogen-bonding interactions and while the water molecules form a C 2 1(4) chain parallel to the c axis of the unit cell, the pendant hydroxy groups are engaged in O—H⋯O=C hydrogen bonds described by a C 1 1(12) graph-set motif which runs parallel to the a axis.

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1,3,5-Tris(bromomethyl)benzene

Cited by 3 publications

References 15 publications

Multi-functional metal–organic frameworks assembled from a tripodal organic linker

Multi-functional metal–organic frameworks assembled from a tripodal organic linker

X-Ray Structure Determinations of Bromo- and/or Bromomethylsubstituted Benzenes: C–H···Br, C–Br···Br, and C–Br···π Interactions

1,1′-[(5-Hydroxymethyl-1,3-phenylene)bis(methylene)]dipyridin-4(1H)-one monohydrate

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