No renderable structure data available
O(CCOC=C)N1C(C2=CC=CC=C2C1=O)=OChemical Intermediate
Structures, identifiers and computed properties have been matched to the database record by CAS.
| Intermediates | 2-[2-(Ethenyloxy)ethoxy]-1H-isoindole-1,3(2H)-dione |
|---|---|
| IUPAC Name | — |
| CAS Number | 391212-30-9 |
| Database ID | 22285907 |
| Molecular Formula | — |
| Molecular Weight | — |
Product Information
2-[2-(Ethenyloxy)ethoxy]-1H-isoindole-1,3(2H)-dione (CAS 391212-30-9) 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 22285907
Safety Notice
For professional research and industrial use only. Review the supplier safety data sheet before handling.
Synthesis data
7 reactions · 7 references
Conditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-f42e5dfe00a948428f829feaf90a2b07Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: Part A: Synthesis of 2-(2-Vinyloxy-ethoxy)-isoindole-1,3-dione Ethylene glycol vinyl ether (9.88 g, 112 mmol), triphenylphosphine (29.4 g, 112 mmol), and N-hydroxyphthalimide (18.22 g, 111.7 mmol) were combined in 300 mL of anhydrous tetrahydrofuran and cooled to 0° C. (ice bath). Diethylazodicarboxylate (18.0 mL, 114 mmol) was added dropwise over 15 min and the resultant reaction mixture was allowed to warm to ambient temperature over 18 h. The reaction mixture was concentrated to a paste and the solids were filtered and washed with chloroform. The filtrate was further concentrated and filtered again, washing the solids with chloroform. The remaining chloroform solution was concentrated to an oil. The oil was dissolved in absolute ethanol (75 mL). Scratching with a glass rod induced crystallization. The crystals were collected and recrystallized from hot ethanol to afford colorless needles of 2-(2-vinyloxy-ethoxy)-isoindole-1,3-dione (13.8 g, 53% yield): 1H NMR (400 MHz, CDCl3) δ 7.85 (m, 2H), 7.75 (m, 2H), 6.46 (dd, J=14.3, 6.7 Hz, 1H), 4.45 (m, 2H), 4.16 (dd, J=14.4, 2.2 Hz), 4.02 (m 3H). the resultant reaction mixture to warm to ambient temperature over 18 h The reaction mixture was concentrated to a paste the solids were filtered washed with chloroform The filtrate was further concentrated filtered again washing the solids with chloroform The remaining chloroform solution was concentrated to an oil The oil was dissolved in absolute ethanol (75 mL) crystallization The crystals were collected recrystallized from hot ethanol
Source ID: ord-a8aa1711942a4881a4ba500cd8766484Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: Part A: Synthesis of 2-(2-Vinyloxy-ethoxy)-isoindole-1,3-dione Ethylene glycol vinyl ether (9.88 g, 112 mmol), triphenylphosphine (29.4 g, 112 mmol), and N-hydroxyphthalimide (18.22 g, 111.7 mmol) were combined in 300 mL of anhydrous tetrahydrofuran and cooled to 0° C. (ice bath). Diethylazodicarboxylate (18.0 mL, 114 mmol) was added dropwise over 15 min and the resultant reaction mixture was allowed to warm to ambient temperature over 18 h. The reaction mixture was concentrated to a paste and the solids were filtered and washed with chloroform. The filtrate was further concentrated and filtered again, washing the solids with chloroform. The remaining chloroform solution was concentrated to an oil. The oil was dissolved in absolute ethanol (75 mL). Scratching with a glass rod induced crystallization. The crystals were collected and recrystallized from hot ethanol to afford colorless needles of 2-(2-vinyloxy-ethoxy)-isoindole-1,3-dione (13.8 g, 53% yield): 1H NMR (400 MHz, CDCl3) δ 7.85 (m, 2H), 7.75 (m, 2H), 6.46 (dd, J=14.3, 6.7 Hz, 1H), 4.45 (m, 2H), 4.16 (dd, J=14.4, 2.2 Hz), 4.02 (m 3H). the resultant reaction mixture to warm to ambient temperature over 18 h The reaction mixture was concentrated to a paste the solids were filtered washed with chloroform The filtrate was further concentrated filtered again washing the solids with chloroform The remaining chloroform solution was concentrated to an oil The oil was dissolved in absolute ethanol (75 mL) crystallization The crystals were collected recrystallized from hot ethanol
Source ID: ord-a8aa1711942a4881a4ba500cd8766484Conditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-f42e5dfe00a948428f829feaf90a2b07Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: Ethylene glycol vinyl ether (9.88 g, 112 mmol), triphenylphosphine (29.4 g, 112 mmol), and N-hydroxyphthalimide (18.22 g, 111.7 mmol) were combined in 300 mL of anhydrous tetrahydrofuran and cooled to 0° C. (ice bath). Diethylazodicarboxylate (18.0 mL, 114 mmol) was added dropwise over 15 min and the resultant reaction mixture was allowed to warm to ambient temperature over 18 h. The reaction mixture was concentrated to a paste and the solids were filtered and washed with chloroform. The filtrate was further concentrated and filtered again, washing the solids with chloroform. The remaining chloroform solution was concentrated to an oil. The oil was dissolved in absolute ethanol (75 mL). Scratching with a glass rod induced crystallization. The crystals were collected and recrystallized from hot ethanol to afford colorless needles of 2-(2-vinyloxy-ethoxy)-isoindole-1,3-dione (13.8 g, 53% yield): 1H NMR (400 MHz, CDCl3) δ 7.85 (m, 2 H), 7.75 (m, 2 H), 6.46 (dd, J=14.3, 6.7 Hz, 1 H), 4.45 (m, 2H), 4.16 (dd, J=14.4, 2.2 Hz), 4.02 (m 3 H). the resultant reaction mixture to warm to ambient temperature over 18 h The reaction mixture was concentrated to a paste the solids were filtered washed with chloroform The filtrate was further concentrated filtered again washing the solids with chloroform The remaining chloroform solution was concentrated to an oil The oil was dissolved in absolute ethanol (75 mL) crystallization The crystals were collected recrystallized from hot ethanol
Source ID: ord-7b4e648515c74e31beefb8132ab9a184Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: Ethylene glycol vinyl ether (9.88 g, 112 mmol), triphenylphosphine (29.4 g, 112 mmol), and N-hydroxyphthalimide (18.22 g, 111.7 mmol) were combined in 300 mL of anhydrous tetrahydrofuran and cooled to 0° C. (ice bath). Diethylazodicarboxylate (18.0 mL, 114 mmol) was added dropwise over 15 min and the resultant reaction mixture was allowed to warm to ambient temperature over 18 h. The reaction mixture was concentrated to a paste and the solids were filtered and washed with chloroform. The filtrate was further concentrated and filtered again, washing the solids with chloroform. The remaining chloroform solution was concentrated to an oil. The oil was dissolved in absolute ethanol (75 mL). Scratching with a glass rod induced crystallization. The crystals were collected and recrystallized from hot ethanol to afford colorless needles of 2-(2-vinyloxy-ethoxy)-isoindole-1,3-dione (13.8 g, 53% yield): 1H NMR (400 MHz, CDCl3) δ 7.85 (m, 2 H), 7.75 (m, 2 H), 6.46 (dd, J=14.3, 6.7 Hz, 1 H), 4.45 (m, 2H), 4.16 (dd, J=14.4, 2.2 Hz), 4.02 (m 3 H). the resultant reaction mixture to warm to ambient temperature over 18 h The reaction mixture was concentrated to a paste the solids were filtered washed with chloroform The filtrate was further concentrated filtered again washing the solids with chloroform The remaining chloroform solution was concentrated to an oil The oil was dissolved in absolute ethanol (75 mL) crystallization The crystals were collected recrystallized from hot ethanol
Source ID: ord-7b4e648515c74e31beefb8132ab9a184Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: Part A: Synthesis of 2-(2-Vinyloxy-ethoxy)-isoindole-1,3-dione Ethylene glycol vinyl ether (9.88 g, 112 mmol), triphenylphosphine (29.4 g, 112 mmol), and N-hydroxyphthalimide (18.22 g, 111.7 mmol) were combined in 300 mL of anhydrous tetrahydrofuran and cooled to 0° C. (ice bath). Diethylazodicarboxylate (18.0 mL, 114 mmol) was added dropwise over 15 min and the resultant reaction mixture was allowed to warm to ambient temperature over 18 h. The reaction mixture was concentrated to a paste and the solids were filtered and washed with chloroform. The filtrate was further concentrated and filtered again, washing the solids with chloroform. The remaining chloroform solution was concentrated to an oil. The oil was dissolved in absolute ethanol (75 mL). Scratching with a glass rod induced crystallization. The crystals were collected and recrystallized from hot ethanol to afford colorless needles of 2-(2-vinyloxy-ethoxy)-isoindole-1,3-dione (13.8 g, 53% yield): 1H NMR (400 MHz, CDCl3) δ 7.85 (m, 2H), 7.75 (m, 2H), 6.46 (dd, J=14.3, 6.7 Hz, 1H), 4.45 (m, 2H), 4.16 (dd, J=14.4, 2.2 Hz), 4.02 (m 3H). the resultant reaction mixture to warm to ambient temperature over 18 h The reaction mixture was concentrated to a paste the solids were filtered washed with chloroform The filtrate was further concentrated filtered again washing the solids with chloroform The remaining chloroform solution was concentrated to an oil The oil was dissolved in absolute ethanol (75 mL) crystallization The crystals were collected recrystallized from hot ethanol
Source ID: ord-a8aa1711942a4881a4ba500cd8766484PubChem References
These sources are listed in the compound's public database record.
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