No renderable structure data available
C1=CC(=C(C=C1Cl)C(F)(F)F)N=C=OChemical Intermediate
Structures, identifiers and computed properties have been matched to the database record by CAS.
| Intermediates | 4-chloro-1-isocyanato-2-(trifluoromethyl)benzene |
|---|---|
| IUPAC Name | — |
| CAS Number | 16588-69-5 |
| Database ID | 2733264 |
| Molecular Formula | — |
| Molecular Weight | — |
Product Information
4-chloro-1-isocyanato-2-(trifluoromethyl)benzene (CAS 16588-69-5) 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 2733264
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-fbff5b8685c547118fcdfe52242fb9abConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: 3-(4-Chloro-2-methyl-2H-pyrazol-3-yl)-4-methoxy-phenylamine was treated with 4-chloro-2-trifluoromethylphenyl isocyanate in a similar manner as described in Example 1.53, providing 4.4 mg (8%) of Compound 79 (Note: Compound 79 did not precipitate out. Therefore, the CH2Cl2 was removed under reduced pressure, the residue was dissolved in 5 mL DMSO, and purified by preparative HPLC): LCMS m/z (%)=461 (M+H37Cl, 60), 459 (M+H35Cl, 100). 1H NMR (400 MHz, acetone-d6) δ: 8.99 (s, 1H), 8.30 (s, 1H), 8.16 (dd, J1=8 Hz, J2=2 Hz, 1H), 8.01 (d, J=8 Hz, 1H), 7.66 (s, 1H), 7.64 (d, J=4 Hz, 1H), 7.45 (d, J=4 Hz, 1H), 7.43 (s, 1H), 7.12 (d, J=8 Hz, 1H), 3.79 (s, 3H), 3.63 (s, 3H).
Source ID: ord-8e06f2a50d4e4e5e96961e5441455f73Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: 3-(4-Chloro-2-methyl-2H-pyrazol-3-yl)-4-methoxy-phenylamine was treated with 4-chloro-2-trifluoromethylphenyl isocyanate in a similar manner as described in Example 1.53, providing 4.4 mg (8%) of Compound 79 (Note: Compound 79 did not precipitate out. Therefore, the CH2Cl2 was removed under reduced pressure, the residue was dissolved in 5 mL DMSO, and purified by preparative HPLC): LCMS m/z (%)=461 (M+H37Cl, 60), 459 (M+H35Cl, 100). 1H NMR (400 MHz, acetone-d6) δ: 8.99 (s, 1H), 8.30 (s, 1H), 8.16 (dd, J1=8 Hz, J2=2 Hz, 1H), 8.01 (d, J=8 Hz, 1H), 7.66 (s, 1H), 7.64 (d, J=4 Hz, 1H), 7.45 (d, J=4 Hz, 1H), 7.43 (s, 1H), 7.12 (d, J=8 Hz, 1H), 3.79 (s, 3H), 3.63 (s, 3H).
Source ID: ord-29ed496b4a394335b067d9f2fc487c1bConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: Urea synthesis (General Procedure): To a stirred solution of 3-(4-bromo-2-methyl-2H-pyrazol-3-yl)-4-methoxy-phenylamine (0.034 g, 0.12 mol, Example 1.1) in CH2Cl2 (1 mL) was added 4-chloro-2-(trifluoromethyl)phenyl isocyanate (0.029 g, 20.0 μL, 0.13 mmol, 1.05 equiv.) at room temperature. White solid precipitated and was filtered and washed with cold CH2Cl2 to afford Compound 9 (0.037 g, 0.074 mmol, 60%) as a white solid. LCMS m/z (%)=503 (M+H79Br, 77), 439 (M+H81Br, 100). 1H NMR (400 MHz, acetone-d6) δ: 8.82 (s, 1H), 8.22 (d, J=9.6 Hz, 1H), 7.62-7.72 (m, 4H), 7.49 (s, 1H), 7.43 (d, J=2.6 Hz, 1H), 7.15 (d, J=9.0 Hz, 1H), 3.83 (s, 3H), 3.68 (s, 3H). White solid precipitated was filtered washed with cold CH2Cl2
Source ID: ord-bbbc1c473e054251aeebbc78936b1c73Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: 3-(4-Chloro-2-methyl-2H-pyrazol-3-yl)-4-methoxy-phenylamine was treated with 4-chloro-2-trifluoromethylphenyl isocyanate in a similar manner as described in Example 1.53, providing 4.4 mg (8%) of Compound 79 (Note: Compound 79 did not precipitate out. Therefore, the CH2Cl2 was removed under reduced pressure, the residue was dissolved in 5 mL DMSO, and purified by preparative HPLC): LCMS m/z (%)=461 (M+H37Cl, 60), 459 (M+H35Cl, 100). 1H NMR (400 MHz, acetone-d6) δ: 8.99 (s, 1H), 8.30 (s, 1H), 8.16 (dd, J1=8 Hz, J2=2 Hz, 1H), 8.01 (d, J=8 Hz, 1H), 7.66 (s, 1H), 7.64 (d, J=4 Hz, 1H), 7.45 (d, J=4 Hz, 1H), 7.43 (s, 1H), 7.12 (d, J=8 Hz, 1H), 3.79 (s, 3H), 3.63 (s, 3H).
Source ID: ord-b8bc0d83cf3b4ce89c1d70b9720a81e0Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: 3-(4-Chloro-2-methyl-2H-pyrazol-3-yl)-4-methoxy-phenylamine was treated with 4-chloro-2-trifluoromethylphenyl isocyanate in a similar manner as described in Example 1.53, providing 4.4 mg (8%) of Compound 79 (Note: Compound 79 did not precipitate out. Therefore, the CH2Cl2 was removed under reduced pressure, the residue was dissolved in 5 mL DMSO, and purified by preparative HPLC): LCMS m/z (%)=461 (M+H37Cl, 60), 459 (M+H35Cl, 100). 1H NMR (400 MHz, acetone-d6) δ: 8.99 (s, 1H), 8.30 (s, 1H), 8.16 (dd, J1=8 Hz, J2=2 Hz, 1H), 8.01 (d, J=8 Hz, 1H), 7.66 (s, 1H), 7.64 (d, J=4 Hz, 1H), 7.45 (d, J=4 Hz, 1H), 7.43 (s, 1H), 7.12 (d, J=8 Hz, 1H), 3.79 (s, 3H), 3.63 (s, 3H).
Source ID: ord-8e06f2a50d4e4e5e96961e5441455f73Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: 3-(4-Chloro-2-methyl-2H-pyrazol-3-yl)-4-methoxy-phenylamine was treated with 4-chloro-2-trifluoromethylphenyl isocyanate in a similar manner as described in Example 1.53, providing 4.4 mg (8%) of Compound 79 (Note: Compound 79 did not precipitate out. Therefore, the CH2Cl2 was removed under reduced pressure, the residue was dissolved in 5 mL DMSO, and purified by preparative HPLC): LCMS m/z (%)=461 (M+H37Cl, 60), 459 (M+H35Cl, 100). 1H NMR (400 MHz, acetone-d6) δ: 8.99 (s, 1H), 8.30 (s, 1H), 8.16 (dd, J1=8 Hz, J2=2 Hz, 1H), 8.01 (d, J=8 Hz, 1H), 7.66 (s, 1H), 7.64 (d, J=4 Hz, 1H), 7.45 (d, J=4 Hz, 1H), 7.43 (s, 1H), 7.12 (d, J=8 Hz, 1H), 3.79 (s, 3H), 3.63 (s, 3H).
Source ID: ord-8e06f2a50d4e4e5e96961e5441455f73Conditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-fbff5b8685c547118fcdfe52242fb9abConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: 3-(4-Chloro-2-methyl-2H-pyrazol-3-yl)-4-methoxy-phenylamine was treated with 4-chloro-2-trifluoromethylphenyl isocyanate in a similar manner as described in Example 1.53, providing 4.4 mg (8%) of Compound 79 (Note: Compound 79 did not precipitate out. Therefore, the CH2Cl2 was removed under reduced pressure, the residue was dissolved in 5 mL DMSO, and purified by preparative HPLC): LCMS m/z (%)=461 (M+H37Cl, 60), 459 (M+H35Cl, 100). 1H NMR (400 MHz, acetone-d6) δ: 8.99 (s, 1H), 8.30 (s, 1H), 8.16 (dd, J1=8 Hz, J2=2 Hz, 1H), 8.01 (d, J=8 Hz, 1H), 7.66 (s, 1H), 7.64 (d, J=4 Hz, 1H), 7.45 (d, J=4 Hz, 1H), 7.43 (s, 1H), 7.12 (d, J=8 Hz, 1H), 3.79 (s, 3H), 3.63 (s, 3H).
Source ID: ord-29ed496b4a394335b067d9f2fc487c1bConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: 3-(4-Chloro-2-methyl-2H-pyrazol-3-yl)-4-methoxy-phenylamine was treated with 4-chloro-2-trifluoromethylphenyl isocyanate in a similar manner as described in Example 1.53, providing 4.4 mg (8%) of Compound 79 (Note: Compound 79 did not precipitate out. Therefore, the CH2Cl2 was removed under reduced pressure, the residue was dissolved in 5 mL DMSO, and purified by preparative HPLC): LCMS m/z (%)=461 (M+H37Cl, 60), 459 (M+H35Cl, 100). 1H NMR (400 MHz, acetone-d6) δ: 8.99 (s, 1H), 8.30 (s, 1H), 8.16 (dd, J1=8 Hz, J2=2 Hz, 1H), 8.01 (d, J=8 Hz, 1H), 7.66 (s, 1H), 7.64 (d, J=4 Hz, 1H), 7.45 (d, J=4 Hz, 1H), 7.43 (s, 1H), 7.12 (d, J=8 Hz, 1H), 3.79 (s, 3H), 3.63 (s, 3H).
Source ID: ord-b8bc0d83cf3b4ce89c1d70b9720a81e0Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: 1-(4-Chloro-2-trifluoromethylphenyl)-3-[2-(6,7-dimethoxyquinazolin-4-ylamino)benzothiazol-6-yl]urea was prepared from 4-chloro-2-(trifluoromethyl)phenyl isocyanate (17 μL, 0.113 mmol) and N2-(6,7-dimethoxyquinazolin-4-yl)benzothiazole-2,6-diamine (40 mg, 0.113 mmol) according to GP 3. The solid was filtered off and washed thoroughly with dichloromethane to obtain a yellow solid (27 mg, 48 μmol, 42%). LC/ESI-MS: m/z=575 [M(35Cl)+H]+; m/z=573 [M(35Cl)−H]−; Rt=3.79 min. The solid was filtered off washed thoroughly with dichloromethane
Source ID: ord-8f9189dced77400b9340f2039c60b129Conditions: temp:24.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: 4-Chloro-2-(trifluoromethyl)phenyl carbamic fluoride was prepared in situ by the reaction of 221 parts of 4-chloro-2-(trifluoromethyl)-isocyanatobenzene and 380 parts of hydrogen fluoride added over a period of about 15 minutes at about 4° C. The reaction mixture was then sealed in a polytetrafluoroethylene reactor, heated to about 24° C. and maintained at about that temperature, with agitation, for about 96 hours. The reactor was then opened to atmospheric pressure and most of the hydrogen fluoride and carbonyl fluoride gases removed. Analysis of the remaining organic product by gas chromatographic techniques, using n-pentadecane as an internal standard, indicated as yield of 55 parts of 4-chloro-2-(trifluoromethyl)benzenamine. added over a period of about 15 minutes at about 4° C The reaction mixture was then sealed in a polytetrafluoroethylene reactor maintained at about that temperature, with agitation, for about 96 hours removed
Source ID: ord-3992da07c5554303858bc646bce42752PubChem References
These sources are listed in the compound's public database record.
Request a Quote
Send the required specification, quantity, destination and intended use. The CATO team will review availability and respond.