Abstract
C10H12Br2, monoclinic, P21/c (no. 14), a = 8.1816(14) Å, b = 4.4288(7) Å, c = 15.2809(19) Å, β = 93.126(2)°, V = 516.10(14) Å3, Z = 2, R gt (F) = 0.0403, wR ref (F2) = 0.1011, T = 170 K.
Table 1 contains the crystallographic data. The list of the atoms including atomic coordinates and displacement parameters can be found in the cif-file attached to this article.

Data collection and handling.
| Crystal: | Needle, greenish |
| Size: | 0.22 × 0.12 × 0.1 mm |
| Wavelength: | Mo Kα radiation (0.71073 Å) |
| μ: | 7.8 mm−1 |
| Diffractometer, scan mode: | Bruker APEX-II, φ and ω-scans |
| θmax, completeness: | 26.4°, >99 % |
| N(hkl)measured, N(hkl)unique, Rint: | 1947, 1059, 0.047 |
| Criterion for Iobs, N(hkl)gt: | Iobs > 2 σ(Iobs), 781 |
| N(param)refined: | 56 |
| Programs: | CrysAlisPRO, 1 OLEX2, 2 SHELX 3 , 4 |
1 Source of materials
A mixture of 48 % hydrobromic acid (100 mL), paraformaldehyde (7.7 g), and p-xylene (15.5 mL) in a 500 mL round-bottom flask was stirred under reflux for 48 h. The white precipitate was collected by filtration to afford approximately 35 g of the crude title compound. Recrystallisation from carbon tetrachloride yielded pure product as white needles, suitable for single-crystal X-ray diffraction analysis.
2 Experimental details
The hydrogen atoms of the methyl group were located in difference Fourier maps and then placed in idealized positions with Uiso(H) = 1.5Ueq(C) and C–H distances constrained to 0.96 Å. The remaining hydrogen atoms were refined using a riding model with Uiso(H) = 1.2Ueq(C). Crystal data, data collection and structure refinement details are summarized in Table 1.
3 Comment
1,4-Bis(bromomethyl)-2,5-dimethylbenzene is widely used as a key intermediate in the organic synthesis of s-indacenes 5 and as a bridging building block for the preparation of novel macrocycles. 6 Its utility stems from its straightforward and high-yielding synthesis, exemplified by the bromomethylation of 1,4-dimethylbenzene, which unexpectedly affords the corresponding dibromo compound in nearly quantitative yield, significantly outperforming the typically low-yielding chloromethylation reaction. 5
The title compound, C10H12Br2, features a center of inversion situated at the centroid of the benzene ring. The asymmetric unit consists of one half of the molecule positioned on an inversion center, with its labeling shown in Figure (part a). Two bromomethyl groups are located on opposite sides of the benzene ring and are nearly perpendicular to it, as indicated by the Br1–C4–C1–C3 and Br1–C4–C1–C2 torsion angles of 98.4(4)° and 82.3(5)°, respectively. The carbon atom C4 is nearly coplanar with the benzene ring, supported by the C4–C1–C2–C3 and C4–C1–C2–C5 torsion angles of 179.4(4)° and 179.3(4)°, respectively. A comparison with the crystal structures of 1,1-bis(bromomethyl)benzene, 7 1,4-bis(bromomethyl)benzene, 8 and 1,2-bis(bromomethyl)benzene 9 reveals no unusual bond lengths or angles. However, the C–Br bond length in the title compound (1.988 Å) is slightly longer than those in 1,1-bis(bromomethyl)benzene (1.967 Å), 1,4-bis(bromomethyl)benzene (1.965 Å), 1,2-bis(bromomethyl)benzene (1.975 Å), and other bromomethyl-substituted benzenes (1.974–1.985 Å). 3 , 4 , 5 , 6 , 7 , 8 , 9 , 10
The crystal packing of the title compound features only weak C–H⋯π interactions, with no evidence of strong or weak hydrogen bonds, significant π⋯π interactions, or short Br⋯Br contacts. This behaviour contrasts with that of 1,4-bis(bromomethyl)benzene,
8
which exhibits short Br⋯Br contacts, but resembles the packing mode observed in 1,1-bis(bromomethyl)benzene.
7
Such a packing environment is relatively uncommon among brominated compounds.
9
As shown in Figure, the crystal stability is primarily maintained by C4–H4⋯π interactions between the bromomethyl group and the centroid (C
g
) of a symmetry-related benzene ring [d(C4⋯
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Author contributions: All the authors have accepted responsibility for the entire content of this submitted manuscript and approved submission.
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Conflict of interest: The authors declare no conflicts of interest regarding this article.
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Research funding: This research was funded by the high-level talent research launch project of Zhoukou Normal University (project number: ZKNUC2024023, ZKNUC2023073).
References
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© 2025 the author(s), published by De Gruyter, Berlin/Boston
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Articles in the same Issue
- Frontmatter
- New Crystal Structures
- The crystal structure of (1Z, 2Z)-3-phenyl-2-propenal 2-(4-bromo-2-fluorophenyl)hydrazone, C15H12BrFN2
- Refinement of crystal structure of 2-(2,3-dihydro-3-oxo-1 H -inden-1-ylidene)-1 H -indene-1,3(2 H )-dione C18H10O3
- The crystal structure of 3-(1-fluoro-2-(naphthalen-2-yl)-2-oxoethyl)-2-methoxy-3,4-dihydroisoquinolin-1(2H)-one, C22H18FNO3
- Crystal structure of the dinuclear copper(II) complex bis(μ2-2,2′ -{[1,3-phenylenebis-(methylene)]bis(oxy)}dibenzoaot-κ4O,O′:O′′,O′′′)-bis(dimethylformamide-κ1O)dicopper(II), C50H44Cu2N2O14
- Crystal structure of poly[triaqua-(μ9-biphenyl-3,3′,5,5′-tetracarboxylic-κ8 O,O:O,O′: O,O″:O,O‴)samarium(III)sodium(I)], C16H12NaSmO11
- The crystal structure of 5-benzyl-1-(4-fluorobenzyl)-4-((4-fluorobenzyl)oxy)-1,5-dihydro-2H-pyrrol-2-one, C25H21F2NO2
- The crystal structure of diammonium 2,5-dihydroxyterephthalate, C8H12N2O6
- Crystal structure of (E)-4-(4-(1H-1,2,4-triazol-1-yl)benzylidene)-6,8-dimethoxy-3,4-dihydrobenzo[b]oxepin-5(2H)-one, C21H19N3O4
- Crystal structure of poly[oktakis(μ2-oxido-κ2O:O)-tetrakis(oxido-κ1O)-bis(μ2-1,1′-[1,4-phenylenebis(methylene)]di(1H-imidazole-κ2N:N′))-tetravanadium(V)-dizinc(II)] monohydrate, C28H30Zn2N8O13V4
- Crystal structure of acotiamide hydrochloride dimethylacetamide solvate (1/1), C25H40ClN5O6S
- Crystal structure of catena-poly[monoaqua (u2-(3-(3,5-dicarboxyphenyl)pyridine-2,6-dicarboxylic-k4O:O′:O″:N)zinc(II))] monohydrate, C15H11NO10Zn
- Crystal structure of dichlorido{2,6-bis(3,5-diisopropyl-N-pyrazolyl)pyridine}zinc(II), C23H33Cl2N5Zn
- Crystal structure of nitrato-κ2O,O′-[hydridotris(3,5-diethylpyrazol-1-yl)borato-κ3N,N′,N″]copper(II), C21H34BCuN7O3
- Crystal structure of 2,7-bis(3,5-diethyl-1H-pyrazol-4-yl)-benzo[lmn][3,8]phenanthroline-1,3,6,8(2H,7H)-tetrone, C28H26N6O4
- Crystal structure of 2-(4-chlorophenyl)benzothiazole, C13H8ClNS
- Synthesis and crystal structure (3R,4′S)-4′-(3,5-dibromophenyl)-1′-methyl-2H-dispiro [benzofuran-3,3′-pyrrolidine-2′,2″-indene]-1″,2,3″-trione, C26H17Br2NO4
- Crystal structure of bis(((3a,7a-dihydro-1H-benzo[d][1,2,3]triazol-1-yl)methyl) triphenylphosphonium) tetrachloridomanganate(II), C50H42Cl4MnN6P2
- The crystal structure of 4,9-bis(4-chlorophenyl)-1,6-bis(2-cyanobenzyl)-2,4a,5,6,7,7a-hexahydro-1H-2,7,5-(epiprop[2]ene[1,1,3]triyl)pyrrolo[3,4-b]pyridine-3,10-dicarbonitrile, C40H26Cl2N6
- The crystal structure of poly((μ2-3-(3-nitro-4-carboxylphenyl)benzoate-κ3O, O′:O″)-μ2-1,4-bis(1-imidazolyl)benzene-κ2N:N′-cadmium(II)), C26H17N5O6Cd
- The crystal structure of 6-hydroxy-5H-pyrrolo[3,4-b]pyridine-5,7(6H)-dione monohydrate, C7H6N2O4
- Crystal structure of 4-((cyclohexylsulfonyl)methyl)-1,2,3,4-tetrahydrobenzo [4,5]imidazo[1,2-a]pyridine, C18H24N2O2S
- Crystal structure of 4,7-diphenyl-1,10-phenanthroline-κ2N,N′)-bis(2,4-di(fluorine)-1-phenylpyridine-κ2C,N)-iridium(III) hexafluorophosphate–dichloromethane (1/1), C47H30Cl2F10IrN4P
- Crystal structure of (4-(1-phenyl-1H-benzo[d]imidazol-2-yl)phenyl)boronic acid, C19H15BN2O2
- The crystal structure of (E)-(2-((pyridin-2-ylmethylene)amino)phenyl)arsonic acid, C12H11AsN2O3
- The crystal structure of N(benzyl(phenyl)carbomothioyl)benzamide, C21H18N2OS
- The crystal structure of bis(2-picolinium) hexachlorostannate dichloromethane monosolvate, C13H18Cl8N2Sn
- Crystal structure of poly[tetraaqua-bis(μ4-3–1-(carboxylatomethyl)-1H-1,2,4-triazole-3-carboxylato)-κ4O:O′,O″,N)zinc(II)], C5H7N3O6Zn
- The crystal structure of the co-crystal isonicotinamide – 2-(nitrophenyl)methanol (1/1), C6H6N2O·C7H7NO3
- The crystal structure of 4-(3-carboxy-1-ethyl-6-fluoro-4-oxo-1,4-dihydroquinolin-7-yl)piperazin-1-ium 2-fluorobenzoate hydrate, C23H25F2N3O6
- Crystal structure of [diaqua-{1H-benzo[d]imidazol-3-ium-5,6-dicarboxylato-κ2O,O′}magnesium(II)] C18H14MgN4O10
- Crystal structure of (3-(dimethoxymethyl)-5-methoxy-1H-indol-1-yl) (2-iodo-5-methoxyphenyl)methanone, C20H20INO5
- The crystal structure of 3,7,11-trimethylbenzo[5,6][1,4]thiazino[2,3,4-kl]phenothiazine 5,5,9,9-tetraoxide, C21H17NO4S2
- Crystal structure of tris(piperazine-1,4-diium)bis(2-hydroxy-1,2,3-propane-tricarboxylate) pentahydrate, C24H56N6O19
- Crystal structure of 2-chloro-5-((5-isopropyl-2-methylphenoxy)methyl)pyridine, C16H18ClNO
- Crystal structure of (E)-4-(4-(1H-pyrrol-1-yl)benzylidene)-6,8-dimethoxy-3,4-dihydrobenzo[(b)]oxepin-5(2H)-one, C23H21NO4
- Crystal structure of (E)-N′-(3,4-dichlorobenzylidene)-3,4,5-trimethoxybenzohydrazide, C17H16Cl2N2O4
- The crystal structure of 2-(2-hydroxyphenyl)-3-(pyridin-2-yl)-2,3- dihydroquinazolin-4(1H)-one, C19H15N3O2
- Crystal structure of 5-hydroxy-2-(4-hydroxyphenyl)-7-methoxy-8-methylchroman-4-one, C17H16O5
- Crystal structure of bis[(3,4-dimethoxybenzyl)triphenylphosphonium]di-μ2-bromido-dibromidodicopper(I)
- Crystal structure of bis [(1,3-dioxolan-2-ylmethyl)triphenylphosphonium] tetrabromidodicopper(I), C22H22Br2CuO2P
- Crystal structure of [1-(4-carboxyphenyl)-4-oxo-1,4-dihydropyridazine-3-carboxylic acid], C12H8N2O5
- The crystal structure of one-dimensional cooridnation polymer bis(thiocyanato)-bis((1E,2E)-1,2-bis(1-(pyridin-3-yl)ethylidene)-hydrazine κ2N:N)iron(II), (C30H28N10S2Fe)n
- Crystal structure of ((4-acetamidophenyl)sulfonyl)-l-alanine, C11H14N2O5S
- Crystal structure of [(1-naphthalen-1-yl-methyl)triphenylphosphonium] dichloridocopper(I), [C29H24P]+[CuCl2]−
- RbTm3S5: the first rubidium lanthanoid(III) sulfide with CsEr3Se5-type crystal structure
- Crystal structure of 2,2′-((ethane-1,2-diylbis(methylammoniumdiyl))bis(methylene))bis(pyridin-1-ium) diiodido-tris(μ2-iodido-κ2I:I)dicopper(II) chloride dihydrate, C16H30Cu2I6N4O2
- The crystal structure of 4-(trifluoromethyl)pyridine-2-carboxylic acid, C7H4F3NO2
- The crystal structure of (E)-2-ethoxy-1-methoxy-4-(2-(methylsulfonyl)vinyl)benzene, C12H16O4S
- Crystal structure of potassium 1H,1H,2H,2H-perfluorooctanesulfonate, C8H4O3F13SK
- Crystal structure of 4-(4-(quinolin-8-yloxy)-1,2,5-thiadiazol-3-yl)morpholine, C15H14O2N4S
- The crystal structure of 1,4-bis(bromomethyl)-2,5-dimethylbenzene, C10H12Br2
- The crystal structure of imidazo[4,5-e][1,3]diazepine-4,6,8-triamine methanol solvate, C7H11N7O
- The crystal structure of chlorido-bis(1,10-phenantroline-κ2N,N′)-(2-formylphenoxyacetato-κ2O,O) lead(II), C33H23N4O4ClPb
- Crystal structure of pyridinium tetrakis(1,1,1-trifluoro-2,4-pentadionato-κ2O,O′)yttrium(III) C20F12H16YO8C5H6N
Articles in the same Issue
- Frontmatter
- New Crystal Structures
- The crystal structure of (1Z, 2Z)-3-phenyl-2-propenal 2-(4-bromo-2-fluorophenyl)hydrazone, C15H12BrFN2
- Refinement of crystal structure of 2-(2,3-dihydro-3-oxo-1 H -inden-1-ylidene)-1 H -indene-1,3(2 H )-dione C18H10O3
- The crystal structure of 3-(1-fluoro-2-(naphthalen-2-yl)-2-oxoethyl)-2-methoxy-3,4-dihydroisoquinolin-1(2H)-one, C22H18FNO3
- Crystal structure of the dinuclear copper(II) complex bis(μ2-2,2′ -{[1,3-phenylenebis-(methylene)]bis(oxy)}dibenzoaot-κ4O,O′:O′′,O′′′)-bis(dimethylformamide-κ1O)dicopper(II), C50H44Cu2N2O14
- Crystal structure of poly[triaqua-(μ9-biphenyl-3,3′,5,5′-tetracarboxylic-κ8 O,O:O,O′: O,O″:O,O‴)samarium(III)sodium(I)], C16H12NaSmO11
- The crystal structure of 5-benzyl-1-(4-fluorobenzyl)-4-((4-fluorobenzyl)oxy)-1,5-dihydro-2H-pyrrol-2-one, C25H21F2NO2
- The crystal structure of diammonium 2,5-dihydroxyterephthalate, C8H12N2O6
- Crystal structure of (E)-4-(4-(1H-1,2,4-triazol-1-yl)benzylidene)-6,8-dimethoxy-3,4-dihydrobenzo[b]oxepin-5(2H)-one, C21H19N3O4
- Crystal structure of poly[oktakis(μ2-oxido-κ2O:O)-tetrakis(oxido-κ1O)-bis(μ2-1,1′-[1,4-phenylenebis(methylene)]di(1H-imidazole-κ2N:N′))-tetravanadium(V)-dizinc(II)] monohydrate, C28H30Zn2N8O13V4
- Crystal structure of acotiamide hydrochloride dimethylacetamide solvate (1/1), C25H40ClN5O6S
- Crystal structure of catena-poly[monoaqua (u2-(3-(3,5-dicarboxyphenyl)pyridine-2,6-dicarboxylic-k4O:O′:O″:N)zinc(II))] monohydrate, C15H11NO10Zn
- Crystal structure of dichlorido{2,6-bis(3,5-diisopropyl-N-pyrazolyl)pyridine}zinc(II), C23H33Cl2N5Zn
- Crystal structure of nitrato-κ2O,O′-[hydridotris(3,5-diethylpyrazol-1-yl)borato-κ3N,N′,N″]copper(II), C21H34BCuN7O3
- Crystal structure of 2,7-bis(3,5-diethyl-1H-pyrazol-4-yl)-benzo[lmn][3,8]phenanthroline-1,3,6,8(2H,7H)-tetrone, C28H26N6O4
- Crystal structure of 2-(4-chlorophenyl)benzothiazole, C13H8ClNS
- Synthesis and crystal structure (3R,4′S)-4′-(3,5-dibromophenyl)-1′-methyl-2H-dispiro [benzofuran-3,3′-pyrrolidine-2′,2″-indene]-1″,2,3″-trione, C26H17Br2NO4
- Crystal structure of bis(((3a,7a-dihydro-1H-benzo[d][1,2,3]triazol-1-yl)methyl) triphenylphosphonium) tetrachloridomanganate(II), C50H42Cl4MnN6P2
- The crystal structure of 4,9-bis(4-chlorophenyl)-1,6-bis(2-cyanobenzyl)-2,4a,5,6,7,7a-hexahydro-1H-2,7,5-(epiprop[2]ene[1,1,3]triyl)pyrrolo[3,4-b]pyridine-3,10-dicarbonitrile, C40H26Cl2N6
- The crystal structure of poly((μ2-3-(3-nitro-4-carboxylphenyl)benzoate-κ3O, O′:O″)-μ2-1,4-bis(1-imidazolyl)benzene-κ2N:N′-cadmium(II)), C26H17N5O6Cd
- The crystal structure of 6-hydroxy-5H-pyrrolo[3,4-b]pyridine-5,7(6H)-dione monohydrate, C7H6N2O4
- Crystal structure of 4-((cyclohexylsulfonyl)methyl)-1,2,3,4-tetrahydrobenzo [4,5]imidazo[1,2-a]pyridine, C18H24N2O2S
- Crystal structure of 4,7-diphenyl-1,10-phenanthroline-κ2N,N′)-bis(2,4-di(fluorine)-1-phenylpyridine-κ2C,N)-iridium(III) hexafluorophosphate–dichloromethane (1/1), C47H30Cl2F10IrN4P
- Crystal structure of (4-(1-phenyl-1H-benzo[d]imidazol-2-yl)phenyl)boronic acid, C19H15BN2O2
- The crystal structure of (E)-(2-((pyridin-2-ylmethylene)amino)phenyl)arsonic acid, C12H11AsN2O3
- The crystal structure of N(benzyl(phenyl)carbomothioyl)benzamide, C21H18N2OS
- The crystal structure of bis(2-picolinium) hexachlorostannate dichloromethane monosolvate, C13H18Cl8N2Sn
- Crystal structure of poly[tetraaqua-bis(μ4-3–1-(carboxylatomethyl)-1H-1,2,4-triazole-3-carboxylato)-κ4O:O′,O″,N)zinc(II)], C5H7N3O6Zn
- The crystal structure of the co-crystal isonicotinamide – 2-(nitrophenyl)methanol (1/1), C6H6N2O·C7H7NO3
- The crystal structure of 4-(3-carboxy-1-ethyl-6-fluoro-4-oxo-1,4-dihydroquinolin-7-yl)piperazin-1-ium 2-fluorobenzoate hydrate, C23H25F2N3O6
- Crystal structure of [diaqua-{1H-benzo[d]imidazol-3-ium-5,6-dicarboxylato-κ2O,O′}magnesium(II)] C18H14MgN4O10
- Crystal structure of (3-(dimethoxymethyl)-5-methoxy-1H-indol-1-yl) (2-iodo-5-methoxyphenyl)methanone, C20H20INO5
- The crystal structure of 3,7,11-trimethylbenzo[5,6][1,4]thiazino[2,3,4-kl]phenothiazine 5,5,9,9-tetraoxide, C21H17NO4S2
- Crystal structure of tris(piperazine-1,4-diium)bis(2-hydroxy-1,2,3-propane-tricarboxylate) pentahydrate, C24H56N6O19
- Crystal structure of 2-chloro-5-((5-isopropyl-2-methylphenoxy)methyl)pyridine, C16H18ClNO
- Crystal structure of (E)-4-(4-(1H-pyrrol-1-yl)benzylidene)-6,8-dimethoxy-3,4-dihydrobenzo[(b)]oxepin-5(2H)-one, C23H21NO4
- Crystal structure of (E)-N′-(3,4-dichlorobenzylidene)-3,4,5-trimethoxybenzohydrazide, C17H16Cl2N2O4
- The crystal structure of 2-(2-hydroxyphenyl)-3-(pyridin-2-yl)-2,3- dihydroquinazolin-4(1H)-one, C19H15N3O2
- Crystal structure of 5-hydroxy-2-(4-hydroxyphenyl)-7-methoxy-8-methylchroman-4-one, C17H16O5
- Crystal structure of bis[(3,4-dimethoxybenzyl)triphenylphosphonium]di-μ2-bromido-dibromidodicopper(I)
- Crystal structure of bis [(1,3-dioxolan-2-ylmethyl)triphenylphosphonium] tetrabromidodicopper(I), C22H22Br2CuO2P
- Crystal structure of [1-(4-carboxyphenyl)-4-oxo-1,4-dihydropyridazine-3-carboxylic acid], C12H8N2O5
- The crystal structure of one-dimensional cooridnation polymer bis(thiocyanato)-bis((1E,2E)-1,2-bis(1-(pyridin-3-yl)ethylidene)-hydrazine κ2N:N)iron(II), (C30H28N10S2Fe)n
- Crystal structure of ((4-acetamidophenyl)sulfonyl)-l-alanine, C11H14N2O5S
- Crystal structure of [(1-naphthalen-1-yl-methyl)triphenylphosphonium] dichloridocopper(I), [C29H24P]+[CuCl2]−
- RbTm3S5: the first rubidium lanthanoid(III) sulfide with CsEr3Se5-type crystal structure
- Crystal structure of 2,2′-((ethane-1,2-diylbis(methylammoniumdiyl))bis(methylene))bis(pyridin-1-ium) diiodido-tris(μ2-iodido-κ2I:I)dicopper(II) chloride dihydrate, C16H30Cu2I6N4O2
- The crystal structure of 4-(trifluoromethyl)pyridine-2-carboxylic acid, C7H4F3NO2
- The crystal structure of (E)-2-ethoxy-1-methoxy-4-(2-(methylsulfonyl)vinyl)benzene, C12H16O4S
- Crystal structure of potassium 1H,1H,2H,2H-perfluorooctanesulfonate, C8H4O3F13SK
- Crystal structure of 4-(4-(quinolin-8-yloxy)-1,2,5-thiadiazol-3-yl)morpholine, C15H14O2N4S
- The crystal structure of 1,4-bis(bromomethyl)-2,5-dimethylbenzene, C10H12Br2
- The crystal structure of imidazo[4,5-e][1,3]diazepine-4,6,8-triamine methanol solvate, C7H11N7O
- The crystal structure of chlorido-bis(1,10-phenantroline-κ2N,N′)-(2-formylphenoxyacetato-κ2O,O) lead(II), C33H23N4O4ClPb
- Crystal structure of pyridinium tetrakis(1,1,1-trifluoro-2,4-pentadionato-κ2O,O′)yttrium(III) C20F12H16YO8C5H6N