No renderable structure data available
C1=CC=C(C(=C1)N=C=O)IChemical Intermediate
Structures, identifiers and computed properties have been matched to the database record by CAS.
| Intermediates | 1-iodo-2-isocyanatobenzene |
|---|---|
| IUPAC Name | — |
| CAS Number | 128255-31-2 |
| Database ID | 2733385 |
| Molecular Formula | — |
| Molecular Weight | — |
Product Information
1-iodo-2-isocyanatobenzene (CAS 128255-31-2) 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 2733385
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-3b662e9a79684bac941632ad10454f39Conditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-0d3878c175744a5fb2b588db0b37c099Conditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-76a7d64266d64d6297697d2b41fef744Conditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-00a6a02467f94dd3ab39e74e89da3480Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a stirred solution of tert-butyl 4-amino-3-methoxyphenylacetate (1.94 g, 8.16 mmol) in THF (20 ml) was added 2-iodophenylisocyanate (2.0 g, 8.16 mmol) and Et3N (114 ul, 0.816 mmol). After stirring overnight, the mixture was poured into 1 N HCl (200 ml). The resulting precipitate was collected by filtration and dissolved in CHCl3 (200 ml). The solution was dried over MgSO4 and evaporated to give tert-butyl 4-[N′-(2-iodophenyl)ureido]-3-methoxyphenylacetate (3.93 g, quant) as a pale yellow amorphous solid 1H-NMR (CDCl3) δ1.44 (s, 9 H), 3.49 (s, 2 H), 3.85 (s, 3 H), 6.78-6.88 (m, 4 H), 7.07 (s, 1 H), 7.31-7.35 (m, 1 H), 7.76 (dd, J=7.8, 1.5 Hz, 1 H), 7.95 (d, J=8.3 Hz, 1 H), 7.99 (dd, J=8.3, 1.5 Hz, 1 H). MS (ESI), m/z 483 (M++1). The resulting precipitate was collected by filtration dissolved in CHCl3 (200 ml) The solution was dried over MgSO4 evaporated
Source ID: ord-cbdbbb956a0e4f33b58cd41a703415baConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a stirred solution of tert-butyl 4-amino-3-methoxyphenylacetate (1.94 g, 8.16 mmol) in THF (20 ml) was added 2-iodophenylisocyanate (2.0 g, 8.16 mmol) and Et3 N (114 μl, 0.816 mmol). After stirring overnight, the mixture was poured into 1 N HCl (200 ml). The resulting precipitate was collected by filtration and dissolved in CHCl3 (200 ml). The solution was dried over MgSO4 and evaporated to give tert-butyl 4-[N′-(2-iodophenyl)ureido]-3-methoxyphenylacetate (3.93 g, quant) as a pale yellow amorphous solid. 1H-NMR (CDCl3)δ 1.44 (s, 9 H), 3.49 (s, 2 H), 3.85 (s, 3 H), 6.78–6.88 (m, 4 H), 7.07 (s, 1 H), 7.31–7.35 (m, 1 H), 7.76 (dd, J=7.8, 1.5 Hz, 1 H), 7.95 (d, J=8.3 Hz, 1 H), 7.99 (dd, J=8.3, 1.5 Hz, 1 H). MS (ESI), m/z 483 (M++1). The resulting precipitate was collected by filtration dissolved in CHCl3 (200 ml) The solution was dried over MgSO4 evaporated
Source ID: ord-5256959e56bd4ddcba30bb442bf6dec7Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a solution of 2-iodophenyl isocyanate (3.36 g, 13.7 mmol) in THF (250 mL) was added ethyl 2-aminobenzoate (5.1 mL, 34.5 mmol). The resulting mixture was stirred at room temperature for 8 hours, evaporated and chromatographed (silica gel, 10% EtOAc in hexanes) to give 4.4 g (78%) of ethyl 2-(2-iodophenylureido)benzoate as a white solid, mp 162°-164° C. evaporated chromatographed (silica gel, 10% EtOAc in hexanes)
Source ID: ord-313a4509f53a45f882ea62ba6133800bConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a solution of 2-iodophenyl isocyanate (3.36 g, 13.7 mmol) in THF (250 mL) was added ethyl 2-aminobenzoate (5.1 mL, 34.5 mmol). The resulting mixture was stirred at room temperature for 8 hours, evaporated and chromatographed (silica gel, 10% EtOAc in hexanes) to give 4.4 g (78%) of ethyl 2-(2-iodophenylureido)benzoate as a white solid, mp 162°-164° C. evaporated chromatographed (silica gel, 10% EtOAc in hexanes)
Source ID: ord-313a4509f53a45f882ea62ba6133800bConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A solution of methylamine in THF (2 M, 19 mL, 39 mmol) was cooled to 0° C. and 2-iodophenylisocyanate (0.68 g, 12.6 mmol) was added dropwise over 5 minutes. The solution was stirred for 30 minutes, after which it was evaporated to dryness in vacuo to yield a white solid (2.05 g) 1H NMR (400 MHz, d6-DMSO): δ 7.81-7.77 (2H, m), 7.53 (1H, s), 7.30-7.26 (1H, m), 6.87 (1H, d, J=4.3 Hz), 6.77-6.73 (1H, m), 2.65 (3H, d, J=4.6 Hz). after which it was evaporated to dryness in vacuo
Source ID: ord-c57c7e981afa44a383f954763034f31eConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a stirred solution of tert-butyl 4-amino-3-methoxyphenylacetate (1.94 g, 8.16 mmol) in THF (20 ml) was added 2-iodophenylisocyanate (2.0 g, 8.16 mmol) and Et3N (114 ul, 0.816 mmol). After stirring overnight, the mixture was poured into 1 N HCl (200 ml). The resulting precipitate was collected by filtration and dissolved in CHCl3 (200 ml). The solution was dried over MgSO4 and evaporated to give tert-butyl 4-[N′-(2-iodophenyl)ureido]-3-methoxyphenylacetate (3.93 g, quant) as a pale yellow amorphous solid 1H-NMR (CDCl3) δ1.44 (s, 9 H), 3.49 (s, 2 H), 3.85 (s, 3 H), 6.78-6.88 (m, 4 H), 7.07 (s, 1 H), 7.31-7.35 (m, 1 H), 7.76 (dd, J=7.8, 1.5 Hz, 1 H), 7.95 (d, J=8.3 Hz, 1 H), 7.99 (dd, J=8.3, 1.5 Hz, 1 H). MS (ESI), m/z 483 (M++1). The resulting precipitate was collected by filtration dissolved in CHCl3 (200 ml) The solution was dried over MgSO4 evaporated
Source ID: ord-cbdbbb956a0e4f33b58cd41a703415baConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a stirred solution of tert-butyl 4-amino-3-methoxyphenylacetate (1.94 g, 8.16 mmol) in THF (20 ml) was added 2-iodophenylisocyanate (2.0 g, 8.16 mmol) and Et3N (114 ul, 0.816 mmol). After stirring overnight, the mixture was poured into 1 N HCl (200 ml). The resulting precipitate was collected by filtration and dissolved in CHCl3 (200 ml). The solution was dried over MgSO4 and evaporated to give tert-butyl 4-[N′-(2-iodophenyl)ureido]-3-methoxyphenylacetate (3.93 g, quant) as a pale yellow amorphous solid 1H-NMR (CDCl3) δ1.44 (s, 9 H), 3.49 (s, 2 H), 3.85 (s, 3 H), 6.78-6.88 (m, 4 H), 7.07 (s, 1 H), 7.31-7.35 (m, 1 H), 7.76 (dd, J=7.8, 1.5 Hz, 1 H), 7.95 (d, J=8.3 Hz, 1 H), 7.99 (dd, J=8.3, 1.5 Hz, 1 H). MS (ESI), m/z 483 (M++1). The resulting precipitate was collected by filtration dissolved in CHCl3 (200 ml) The solution was dried over MgSO4 evaporated
Source ID: ord-cbdbbb956a0e4f33b58cd41a703415baConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a stirred solution of tert-butyl 4-amino-3-methoxyphenylacetate (1.94 g, 8.16 mmol) in THF (20 ml) was added 2-iodophenylisocyanate (2.0 g, 8.16 mmol) and Et3 N (114 μl, 0.816 mmol). After stirring overnight, the mixture was poured into 1 N HCl (200 ml). The resulting precipitate was collected by filtration and dissolved in CHCl3 (200 ml). The solution was dried over MgSO4 and evaporated to give tert-butyl 4-[N′-(2-iodophenyl)ureido]-3-methoxyphenylacetate (3.93 g, quant) as a pale yellow amorphous solid. 1H-NMR (CDCl3)δ 1.44 (s, 9 H), 3.49 (s, 2 H), 3.85 (s, 3 H), 6.78–6.88 (m, 4 H), 7.07 (s, 1 H), 7.31–7.35 (m, 1 H), 7.76 (dd, J=7.8, 1.5 Hz, 1 H), 7.95 (d, J=8.3 Hz, 1 H), 7.99 (dd, J=8.3, 1.5 Hz, 1 H). MS (ESI), m/z 483 (M++1). The resulting precipitate was collected by filtration dissolved in CHCl3 (200 ml) The solution was dried over MgSO4 evaporated
Source ID: ord-5256959e56bd4ddcba30bb442bf6dec7PubChem References
These sources are listed in the compound's public database record.
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