Synthesis of 1-fluoro-2,4-dinitrobenzene

Preparation of 1-fluoro-2,4-dinitrobenzene

25.5 g of 1-chloro-2,4-dinitrobenzene and 14.5 g of dry potassium fluoride are allowed to react in 25.5 g of dimethylformamide for 30 min at 140-150° C or for 13 hours at 95-100°. The mixture is then diluted with water, and the resulting oil is washed well with water, dried, and distilled in a vacuum, giving 77% of 1-fluoro-2,4-dinitrobenzene, b.p. 122-124°/1 mm, 156-158°/12 mm. Alternatively, a mixture of 1-chloro-2,4-dinitrobenzene and dry potassium fluoride is heated for 7 hours at 180-200°, then cooled and taken up in hot, dry benzene. The benzene is removed and the  1-fluoro-2,4-dinitrobenzene is distilled in a vacuum and recrystallized from methanol yielding 92% yield of 1-fluoro-2,4-dinitrobenzene having m.p. 27° C.

J. Amer. Chem. Soc, 78, 6034 (1956).
Zh. Obshch. Khim., 27, 1672 (1957);
Angew. Chem., 63, 147 (1951)

IUPAC Name

1-fluoro-2,4-dinitrobenzene

InChI

InChI=1S/C6H3FN2O4/c7-5-2-1-4(8(10)11)3-6(5)9(12)13/h1-3H

InChI Key

LOTKRQAVGJMPNV-UHFFFAOYSA-N

Canonical SMILES

C1=CC(=C(C=C1[N+](=O)[O-])[N+](=O)[O-])F

MeSH Synonyms

1 Fluoro 2,4 dinitrobenzene, 1-Fluoro-2,4-dinitrobenzene, Dinitrofluorobenzene, DNFB, Fluorodinitrobenzene

Depositor-Supplied Synonyms

2,4-Dinitrofluorobenzene, 1-FLUORO-2,4-DINITROBENZENE, FDNB, DNFB, Dinitrofluorobenzene, 70-34-8, 2,4-Dinitro-1-fluorobenzene, Fluorodinitrobenzene, Fluoro-2,4-dinitrobenzene, 2,4-Dinitrobenzenefluoride, 2,4-Dinitrophenyl fluoride, Benzene, 1-fluoro-2,4-dinitro-, 2,4-Dinitrobenzene fluoride, Sanger’s Reagent, 2,4-DNFB, 1,2,4-Fluorodinitrobenzene, DNPF, 1-fluoro-2,4-dinitro-benzene, Benzene, 2,4-dinitro-1-fluoro-, NSC 33519, DFB (VAN), Fluorodinitrobenzene (VAN), Sanger reagent, CCRIS 1800, CHEBI:53049, HSDB 4342, LOTKRQAVGJMPNV-UHFFFAOYSA-N, EINECS 200-734-3, BRN 0398632, NCGC00091810-01, AI3-52653, DSSTox_CID_5331, DSSTox_RID_77753, DSSTox_GSID_25331, CAS-70-34-8, PubChem4416, 2,4-dinitroflurobenzene, 2.4-dinitrofluorobenzene, AC1Q5ANU, 1,4-Fluorodinitrobenzene, WLN: WNR BF ENW, 2,4-dinitriofluorobenzene, 2,4-dinitrophenylfluoride, 2,4,-dinitrofluorobenzene, 2,4-dinitro fluorobenzene, ACMC-209oe5, AC1L1M5C, 1-fluoro-2,4-dinitrobenzen, SCHEMBL35276, 42085_ALDRICH, Benzene,4-dinitro-1-fluoro-, D1529_SIGMA, CHEMBL167423, UNII-D241E059U6, 42085_FLUKA, CTK3J3799, MolPort-000-154-980, NSC33519, ZINC1665741, Tox21_111168, Tox21_200352, ANW-35883, AR-1J0738, KM1338, MFCD00007056, NSC-33519, SBB058863, STL453587, ZINC01665741, AKOS003652319, D241E059U6, LS-1598, MCULE-5865335842, RTR-032489, NCGC00091810-02, NCGC00257906-01, AK-86339, AN-23792, BP-13262, CJ-06047, CJ-26936, KB-17718, OR025731, OR110077, TR-032489, 2,4-Dinitrofluorobenzene (Sanger’s reagent), D0835, LT03328524, ST50826753, 1-Fluoro-2,4-dinitrobenzene: Sanger’s reagent, 141689-EP2277875A2, 141689-EP2292630A1, 4-05-00-00742 (Beilstein Handbook Reference), 3B3-033827, InChI=1/C6H3FN2O4/c7-5-2-1-4(8(10)11)3-6(5)9(12)13/h1-3

Removed Synonyms

Benzene,4-dinitro-, C6H3FN2O4, 1 Fluoro 2,4 dinitrobenzene, CID6264, A5512, T1229, D004139, DFB, 573-55-7, 726-62-5

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