No renderable structure data available
CC1=C(C=CC(=C1)F)FChemical Intermediate
Structures, identifiers and computed properties have been matched to the database record by CAS.
| Intermediates | 1,4-difluoro-2-methylbenzene |
|---|---|
| IUPAC Name | — |
| CAS Number | 452-67-5 |
| Database ID | 67980 |
| Molecular Formula | — |
| Molecular Weight | — |
Product Information
1,4-difluoro-2-methylbenzene (CAS 452-67-5) product identity, structure identifiers and related reaction data for chemical intermediate research and sourcing review.
Potential Applications
For professional research and industrial use only
Database ID 67980
Safety Notice
For professional research and industrial use only. Review the supplier safety data sheet before handling.
Synthesis data
12 reactions · 12 references
Conditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-77e6a206323e475493ac04f9c807e63bConditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-77e6a206323e475493ac04f9c807e63bConditions: temp:28.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a stirred solution of 2,5-difluorotoluene (0.544 g, 4.25 mmol, Aldrich, used as received) in conc. H2SO4 (5.0 mL) at 0° C., KNO3 (0.430 g, 4.25 mmol) was added in one portion. The resulting pale yellow solution was warmed to 28° C. and stirred at that temperature overnight. It was then poured into ice (25 g) and extracted with ethyl acetate (40 mL). The extract was dried over Na2SO4 and evaporated to afford 0.555 g (91%) of the title compound as a light red oil; 1H NMR (CDCl3): 2.369 (d, 3H, J=1.8 Hz), 7.127 (dd, 1H, J1=8.1 Hz, J2=6.0 Hz), 7.734 (dd, 1H, J1=8.4 Hz, J2=6.3 Hz). extracted with ethyl acetate (40 mL) The extract was dried over Na2SO4 evaporated
Source ID: ord-c9f56cd72154474b850c24c99a95d818Conditions: temp:-5.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A mixture of 2,5-difluorotoluene (25 g, 0.20 mol) and iron powder (11 g, 0.2 mol) was cooled to −5° C. Bromine was added dropwise such that the internal temperature of the reaction did not rise above 0° C. After stirring for 3 hours, the mixture was diluted with ether, filtered and washed with aqueous sodium thiosulfate solution. The aqueous layer was extracted with ether, and the combined organic layers were dried over MgSO4, filtered and concentrated in vacuo. Distillation at atmospheric pressure gave 34 g of 1-bromo-2,5-difluoro-4-methyl-benzene as a colorless oil (b.p. 180 oC). 1H NMR (300 MHz, CDCl3) δ 7.20 (dd, 1H, J=6.0, 8.5 Hz), 6.93 (m, 1H), 2.23 (s, 3H) ppm. did not rise above 0° C filtered washed with aqueous sodium thiosulfate solution The aqueous layer was extracted with ether the combined organic layers were dried over MgSO4 filtered concentrated in vacuo Distillation at atmospheric pressure
Source ID: ord-3d2f98113a714585b552f54de4e08bc5Conditions: temp:-5.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A mixture of 2,5-difluorotoluene (25 g, 0.20 mol) and iron powder (11 g, 0.2 mol) was cooled to −5° C. Bromine was added dropwise such that the internal temperature of the reaction did not rise above 0° C. After stirring for 3 hours, the mixture was diluted with ether, filtered and washed with aqueous sodium thiosulfate solution. The aqueous layer was extracted with ether, and the combined organic layers were dried over MgSO4, filtered and concentrated in vacuo. Distillation at atmospheric pressure gave 34 g of 1-bromo-2,5-difluoro-4-methyl-benzene as a colorless oil (b.p. 180° C.). 1H NMR (300 MHz, CDCl3) δ7.20 (dd, 1H, J=6.0, 8.5 Hz), 6.93 (m, 1H), 2.23 (s, 3H) ppm. did not rise above 0° C filtered washed with aqueous sodium thiosulfate solution The aqueous layer was extracted with ether the combined organic layers were dried over MgSO4 filtered concentrated in vacuo Distillation at atmospheric pressure
Source ID: ord-fa007ed0c804469484a83281e06d6e7aConditions: temp:28.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a stirred solution of 2,5-difluorotoluene (0.544 g, 4.25 mmol, Aldrich, used as received) in conc. H2SO4 (5.0 mL) at 0° C., KNO3 (0.430 g, 4.25 mmol) was added in one portion. The resulting pale yellow solution was warmed to 28° C. and stirred at that temperature overnight. It was then poured into ice (25 g) and extracted with ethyl acetate (40 mL). The extract was dried over Na2SO4 and evaporated to afford 0.555 g (91%) of the title compound as a light red oil; 1H NMR (CDCl3): 2.369 (d, 3H, J=1.8 Hz), 7.127 (dd, 1H, J1 =8.1 Hz, J2 =6.0 Hz), 7.734 (dd, 1H, J1 =8.4 Hz, J2 =6.3 Hz). extracted with ethyl acetate (40 mL) The extract was dried over Na2SO4 evaporated
Source ID: ord-7a81ac6fc04949d2aa53239f919dfa9eConditions: temp:28.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a stirred solution of 2,5-difluorotoluene (0.544 g, 4.25 mmol, Aldrich, used as received) in conc. H2SO4 (5.0 mL) at 0° C., KNO3 (0.430 g, 4.25 mmol) was added in one portion. The resulting pale yellow solution was warmed to 28° C. and stirred at that temperature overnight. It was then poured into ice (25 g) and extracted with ethyl acetate (40 mL). The extract was dried over Na2SO4 and evaporated to afford 0.555 g (91%) of the title compound as a light red oil; 1H NMR (CDCl3): 2.369 (d, 3H, J=1.8 Hz), 7.127 (dd, 1H, J1 =8.1 Hz, J2 =6.0 Hz), 7.734 (dd, 1H, J1 =8.4 Hz, J2 =6.3 Hz). extracted with ethyl acetate (40 mL) The extract was dried over Na2SO4 evaporated
Source ID: ord-c070473595ab44adbb5b496789489738Conditions: temp:-5.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A mixture of 2,5-difluorotoluene (25 g, 0.20 mol) and iron powder (11 g, 0.2 mol) was cooled to −5° C. Bromine was added dropwise such that the internal temperature of the reaction did not rise above 0° C. After stirring for 3 hours, the mixture was diluted with ether, filtered and washed with aqueous sodium thiosulfate solution. The aqueous layer was extracted with ether, and the combined organic layers were dried over MgSO4, filtered and concentrated in vacuo. Distillation at atmospheric pressure gave 34 g of 1-bromo-2,5-difluoro-4-methyl-benzene as a colorless oil (b.p. 180° C.). 1H NMR (300 MHz, CDCl3) δ 7.20 (dd, 1H, J=6.0, 8.5 Hz), 6.93 (m, 1H), 2.23 (s, 3H) ppm. did not rise above 0° C filtered washed with aqueous sodium thiosulfate solution The aqueous layer was extracted with ether the combined organic layers were dried over MgSO4 filtered concentrated in vacuo Distillation at atmospheric pressure
Source ID: ord-2f345a5ee7ef4e88a2bfb39279dde47fConditions: temp:28.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a stirred solution of 2,5-difluorotoluene (0.544 g, 4.25 mmol, Aldrich, used as received) in conc. H2SO4 (5.0 mL) at 0° C., KNO3 (0.430 g, 4.25 mmol) was added in one portion. The resulting pale yellow solution was warmed to 28° C. and stirred at that temperature overnight. It was then poured into ice (25 g) and extracted with ethyl acetate (40 mL). The extract was dried over Na2SO4 and evaporated to afford 0.555 g (91%) of the title compound as a light red oil; 1H NMR (CDCl3): 2.369 (d, 3H, J=1.8 Hz), 7.127 (dd, 1H, J1 =8.1 Hz, J2 =6.0 Hz), 7.734 (dd, 1H, J1 =8.4 Hz, J2 =6.3 Hz). extracted with ethyl acetate (40 mL) The extract was dried over Na2SO4 evaporated
Source ID: ord-49434420ea2548069bc94d84b49bbd99Conditions: temp:-5.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A mixture of 2,5-difluorotoluene (25 g, 0.20 mol) and iron powder (11 g, 0.2 mol) was cooled to −5° C. Bromine was added dropwise such that the internal temperature of the reaction did not rise above 0° C. After stirring for 3 hours, the mixture was diluted with ether, filtered and washed with aqueous sodium thiosulfate solution. The aqueous layer was extracted with ether, and the combined organic layers were dried over MgSO4, filtered and concentrated in vacuo. Distillation at atmospheric pressure gave 34 g of 1-bromo-2,5-difluoro-4-methyl-benzene as a colorless oil (b.p. 180 oC). 1H NMR (300 MHz, CDCl3) δ 7.20 (dd, 1H, J=6.0, 8.5 Hz), 6.93 (m,1H), 2.23 (s, 3H) ppm. did not rise above 0° C filtered washed with aqueous sodium thiosulfate solution The aqueous layer was extracted with ether the combined organic layers were dried over MgSO4 filtered concentrated in vacuo Distillation at atmospheric pressure
Source ID: ord-5ef447a9a28b4d398da3ece6d96d7f4dConditions: temp:28.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a stirred solution of 2,5-difluorotoluene (0.544 g, 4.25 mmol, Aldrich, used as received) in conc. H2SO4 (5.0 mL) at 0° C., KNO3 (0.430 g, 4.25 mmol) was added in one portion. The resulting pale yellow solution was warmed to 28° C. and stirred at that temperature overnight. It was then poured into ice (25 g) and extracted with ethyl acetate (40 mL). The extract was dried over Na2SO4 and evaporated to afford 0.555 g (91%) of the title compound as a light red oil; 1H NMR (CDCl3): 2.369 (d, 3H, J=1.8 Hz), 7.127 (dd, 1H, J1=8.1 Hz, J2=6.0 Hz), 7.734 (dd, 1H, J1=8.4 Hz, J2=6.3 Hz). extracted with ethyl acetate (40 mL) The extract was dried over Na2SO4 evaporated
Source ID: ord-c9f56cd72154474b850c24c99a95d818Conditions: temp:-5.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A mixture of 2,5-difluorotoluene (25 g, 0.20 mol) and iron powder (11 g, 0.2 mol) was cooled to −5° C. Bromine was added dropwise such that the internal temperature of the reaction did not rise above 0° C. After stirring for 3 hours, the mixture was diluted with ether, filtered and washed with aqueous sodium thiosulfate solution. The aqueous layer was extracted with ether, and the combined organic layers were dried over MgSO4, filtered and concentrated in vacuo. Distillation at atmospheric pressure gave 34 g of 1-bromo-2,5-difluoro-4-methyl-benzene as a colorless oil (b.p. 180 oC). 1H NMR (300 MHz, CDCl3) δ 7.20 (dd, 1H, J=6.0, 8.5 Hz), 6.93 (m, 1H), 2.23 (s, 3H) ppm. did not rise above 0° C filtered washed with aqueous sodium thiosulfate solution The aqueous layer was extracted with ether the combined organic layers were dried over MgSO4 filtered concentrated in vacuo Distillation at atmospheric pressure
Source ID: ord-3d2f98113a714585b552f54de4e08bc5PubChem References
These sources are listed in the compound's public database record.
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