No renderable structure data available
C1=CC(=C(C=C1Cl)F)N=C=OChemical Intermediate
Structures, identifiers and computed properties have been matched to the database record by CAS.
| Intermediates | 4-chloro-2-fluoro-1-isocyanatobenzene |
|---|---|
| IUPAC Name | — |
| CAS Number | 51163-28-1 |
| Database ID | 4558203 |
| Molecular Formula | — |
| Molecular Weight | — |
Product Information
4-chloro-2-fluoro-1-isocyanatobenzene (CAS 51163-28-1) 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 4558203
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-3619b351ca7f446890240f40b9b9b214Conditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-ee2d2df3b68f4283b3a1f1107ecd25adConditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-3619b351ca7f446890240f40b9b9b214Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: The title compound was synthesized analogous to Example 23, using 4-chloro-2-fluoro-1-isocyanatobenzene and intermediate 3. 1HNMR (DMSO-d6, 300 MHz): δ 9.281 (s, 1H), 8.824-8.796 (d, J=8.4 Hz, 1H), 8.703 (s, 1H), 8.330 (s, 1H), 8.227-8.168 (t, J=8.7, 9 Hz, 1H), 8.069-8.040 (d, J=8.7 Hz, 2H), 7.589-7.560 (s, J=8.7 Hz, 2H), 7.508-7.463 (d, J=2.1, 11.1 Hz, 1H), 7.268-7.238 (d, J=9 Hz, 1H), 4.395-4.343 (t, J=7.8 Hz, 1H), 3.700 (s, 3H), 2.341-2.273 (m, 1H), 1.000-0.953 (t, J=6.9, 7.2 Hz, 6H); MS (ESI) m/z 503 (M−H), 505 (M+H)+.
Source ID: ord-17c79943ce314770bbbcd9d5dd8f03b9Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: The title compound was synthesized analogous to Example 23, using 4-chloro-2-fluoro-1-isocyanatobenzene and intermediate 3. 1HNMR (DMSO-d6, 300 MHz): δ 9.281 (s, 1H), 8.824-8.796 (d, J=8.4 Hz, 1H), 8.703 (s, 1H), 8.330 (s, 1H), 8.227-8.168 (t, J=8.7, 9 Hz, 1H), 8.069-8.040 (d, J=8.7 Hz, 2H), 7.589-7.560 (s, J=8.7 Hz, 2H), 7.508-7.463 (d, J=2.1, 11.1 Hz, 1H), 7.268-7.238 (d, J=9 Hz, 1H), 4.395-4.343 (t, J=7.8 Hz, 1H), 3.700 (s, 3H), 2.341-2.273 (m, 1H), 1.000-0.953 (t, J=6.9, 7.2 Hz, 6H); MS (ESI) m/z 503 (M−H), 505 (M+H)+.
Source ID: ord-17c79943ce314770bbbcd9d5dd8f03b9Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: The title compound was synthesized analogous to Example 1, using 4-chloro-2-fluoro-1-isocyanatobenzene (0.533 mmol) and intermediate 1. 1H-NMR (DMSO-d6, 300 MHz): δ 9.356 (s, 1H), 9.017-8.990 (d, 1H), 8.733 (s, 1H), 8.208-8.149 (m, 1H), 7.826 (s, 1H), 7.809-7.780 (d, J=8.7 Hz, 2H), 7.623-7.593 (d, J=9 Hz, 2H), 7.514-7.470 (d, J=2.1, 11.1 Hz, 1H), 7.270-7.241 (dd, J=0.6, 8.7 Hz, 1H), 4.328-4.277 (m, 1H), 3.680 (s, 3H), 2.286-2.217 (m, 1H), 0.979-0.957 (d, J=6.6 Hz, 6H); MS (ESI) m/z 487 (M−H), 489 (M+H).
Source ID: ord-33c9351b9654442ea0e6150c1762fb18Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: The title compound was synthesized analogous to Example 1, using 4-chloro-2-fluoro-1-isocyanatobenzene (0.533 mmol) and intermediate 1. 1H-NMR (DMSO-d6, 300 MHz): δ 9.356 (s, 1H), 9.017-8.990 (d, 1H), 8.733 (s, 1H), 8.208-8.149 (m, 1H), 7.826 (s, 1H), 7.809-7.780 (d, J=8.7 Hz, 2H), 7.623-7.593 (d, J=9 Hz, 2H), 7.514-7.470 (d, J=2.1, 11.1 Hz, 1H), 7.270-7.241 (dd, J=0.6, 8.7 Hz, 1H), 4.328-4.277 (m, 1H), 3.680 (s, 3H), 2.286-2.217 (m, 1H), 0.979-0.957 (d, J=6.6 Hz, 6H); MS (ESI) m/z 487 (M−H), 489 (M+H).
Source ID: ord-33c9351b9654442ea0e6150c1762fb18Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A stirred solution of 17.1 grams (0.10 mole) of 4-chloro-2-fluorophenyl isocyanate and 20.0 grams (0.17 mole) of azidotrimethylsilane was heated under reflux for 16 hours. The reaction mixture was cooled to ambient temperature and 60 ml of toluene and 100 ml of water were added. The mixture was allowed to stand for two hours and the resultant solid collected by filtration. The filter cake was washed with petroleum ether to yield 14.5 grams of 1-(4-chloro-2-fluorophenyl)-1,4-dihydro-5H-tetrazol-5-one; m.p. 185°-187° C. The reaction was repeated several times. under reflux for 16 hours the resultant solid collected by filtration The filter cake was washed with petroleum ether
Source ID: ord-a4b596b4e33649ad8cef5419040e6c32Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a stirred solution of 20.0 grams (0.13 mole) of 4-chloro-2-fluoroaniline in 250 ml of toluene was added dropwise a solution of 17.2 ml (0.13 mole) of trichloromethyl chloroformate in 40 ml of toluene. Upon completion of addition the reaction mixture was heated to reflux where it stirred for 16 hours. The solvent was separated from the reaction mixture by distillation to yield 21.8 grams of 4-chloro-2-fluorophenyl isocyanate as an oil. The reaction was repeated several times. Upon completion of addition the reaction mixture was heated to reflux where it The solvent was separated from the reaction mixture by distillation
Source ID: ord-8100e6eb8a6942ee91490dd4284198b3Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A solution of 8.6 g of 4-chloro-2-fluorophenylisocyanate in 20 ml of anhydrous ether was added dropwise to a mixture of 9.8 g of crude 3-carbethoxy-5,6-dihydro-1,4-thiazine and 10 drops of triethylamine in 20 ml of ether. After the addition, 30 ml of hexane was added dropwise in 20 min. The solution was stirred at room temperature for 3 hrs. The solution was concentrated in vacuo to remove solvent. The resulting oil was crystallized from ether to give 10 g of 2-(4-chloro-2-fluorophenyl)-5,6-dihydro-1H-imidazo[5,1-c][1,4]thiazine-1,3(2H)-dione, m.p. 117.5°-120.5° C. was added dropwise in 20 min The solution was concentrated in vacuo to remove solvent The resulting oil was crystallized from ether
Source ID: ord-717bfbb6b90c4d1aae73fb1d40032188Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: An emulsion of 14 g of 3-carbethoxythiomorpholine in 50 ml of n-hexane was added dropwise to a solution of 14 g of 4-chloro-2-fluorophenylisocyanate in 60 ml of anhydrous ether at 15° to 28° C. with stirring. A heavy oil formed after the addition. The oil crystallized after stirring at room temperature for 15 min. The precipitate was collected by filtration to give 24.3 g of 3-carbethoxy-4-(4-chloro-2-fluorophenylaminocarbonyl)thiomorpholine, m.p. 111.5°-112.5° C. A heavy oil formed after the addition The oil crystallized after stirring at room temperature for 15 min The precipitate was collected by filtration
Source ID: ord-95b0801eb1af422b91d722b853fc31cfConditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-ee2d2df3b68f4283b3a1f1107ecd25adPubChem References
These sources are listed in the compound's public database record.
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