No renderable structure data available
CC(C)(C)OC(=O)NC1=CC=C(C=C1)CClChemical Intermediate
Structures, identifiers and computed properties have been matched to the database record by CAS.
| Intermediates | tert-butyl N-[4-(chloromethyl)phenyl]carbamate |
|---|---|
| IUPAC Name | — |
| CAS Number | 916578-53-5 |
| Database ID | 46835249 |
| Molecular Formula | — |
| Molecular Weight | — |
Product Information
tert-butyl N-[4-(chloromethyl)phenyl]carbamate (CAS 916578-53-5) 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 46835249
Safety Notice
For professional research and industrial use only. Review the supplier safety data sheet before handling.
Synthesis data
9 reactions · 9 references
Conditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-5981c143233d42edaac3f792d08d4c10Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: Following the procedure as described in Example 50, making variations as required to replace (2-bromoethoxy)(tert-butyl)dimethylsilane with tert-butyl 4-(chloromethyl)phenylcarbamate to react with ethyl 3-methyl-5-(2-oxoimidazolidin-1-yl)thiophene-2-carboxylate, the title compound was obtained as an off-white solid in 80% yield: 1H NMR (300 MHz, CDCl3) δ 7.34 (d, J=8.2 Hz, 2H), 7.22 (d, J=8.2 Hz, 2H), 6.49 (br s, 1H), 6.14 (s, 1H), 4.41 (s, 2H), 4.27 (q, J=7.1 Hz, 2H), 3.81-3.73 (m, 2H), 3.45-3.37 (m, 2H), 2.49 (s, 3H), 1.51 (s, 9H), 1.34 (t, J=7.1 Hz, 3H); MS (ES+) m/z 482.5 (M+23).
Source ID: ord-06c2b2386e9a494ab69a332f75ba04bbConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: Following the procedure as described in Example 50, making variations as required to replace (2-bromoethoxy)(tert-butyl)dimethylsilane with tert-butyl 4-(chloromethyl)phenylcarbamate to react with ethyl 3-methyl-5-(2-oxoimidazolidin-1-yl)thiophene-2-carboxylate, the title compound was obtained as an off-white solid in 80% yield: 1H NMR (300 MHz, CDCl3) δ 7.34 (d, J=8.2 Hz, 2H), 7.22 (d, J=8.2 Hz, 2H), 6.49 (br s, 1H), 6.14 (s, 1H), 4.41 (s, 2H), 4.27 (q, J=7.1 Hz, 2H), 3.81-3.73 (m, 2H), 3.45-3.37 (m, 2H), 2.49 (s, 3H), 1.51 (s, 9H), 1.34 (t, J=7.1 Hz, 3H); MS (ES+) m/z 482.5 (M+23).
Source ID: ord-06c2b2386e9a494ab69a332f75ba04bbConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a stirred solution of tert-butyl 4-(hydroxymethyl)phenylcarbamate (0.50 g, 2.24 mmol) in dichloromethane was added pyridine (3 drops), followed by the dropwise addition of thionyl chloride (0.35 mL, 4.98 mmol). The resulting reaction mixture was stirred for 30 minutes, and then quenched with water (25 mL). The aqueous layer was extracted with dichloromethane (50 mL), and the organic layer was dried over sodium sulfate, filtered and concentrated in vacuo to afford tert-butyl 4-(chloromethyl)phenylcarbamate as an orange solid in 50% yield (0.27 g, 50%): 1H NMR (300 MHz, CDCl3) δ 7.38-7.28 (m, 4H), 6.51 (br s, 1H), 4.55 (s, 2H), 1.52 (s, 9H). The resulting reaction mixture quenched with water (25 mL) The aqueous layer was extracted with dichloromethane (50 mL) the organic layer was dried over sodium sulfate filtered concentrated in vacuo
Source ID: ord-bd9476e09e6a4b41bb48685949e141e5Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a stirred solution of tert-butyl 4-(hydroxymethyl)phenylcarbamate (0.50 g, 2.24 mmol) in dichloromethane was added pyridine (3 drops), followed by the dropwise addition of thionyl chloride (0.35 mL, 4.98 mmol). The resulting reaction mixture was stirred for 30 minutes, and then quenched with water (25 mL). The aqueous layer was extracted with dichloromethane (50 mL), and the organic layer was dried over sodium sulfate, filtered and concentrated in vacuo to afford tert-butyl 4-(chloromethyl)phenylcarbamate as an orange solid in 50% yield (0.27 g, 50%): 1H NMR (300 MHz, CDCl3) δ 7.38-7.28 (m, 4H), 6.51 (br s, 1H), 4.55 (s, 2H), 1.52 (s, 9H). The resulting reaction mixture quenched with water (25 mL) The aqueous layer was extracted with dichloromethane (50 mL) the organic layer was dried over sodium sulfate filtered concentrated in vacuo
Source ID: ord-bd9476e09e6a4b41bb48685949e141e5Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: Following the procedure as described in Example 50, making variations as required to replace (2-bromoethoxy)(tert-butyl)dimethylsilane with tert-butyl 4-(chloromethyl)phenylcarbamate to react with ethyl 3-methyl-5-(2-oxoimidazolidin-1-yl)thiophene-2-carboxylate, the title compound was obtained as an off-white solid in 80% yield: 1H NMR (300 MHz, CDCl3) δ 7.34 (d, J=8.2 Hz, 2H), 7.22 (d, J=8.2 Hz, 2H), 6.49 (br s, 1H), 6.14 (s, 1H), 4.41 (s, 2H), 4.27 (q, J=7.1 Hz, 2H), 3.81-3.73 (m, 2H), 3.45-3.37 (m, 2H), 2.49 (s, 3H), 1.51 (s, 9H), 1.34 (t, J=7.1 Hz, 3H); MS (ES+) m/z 482.5 (M+23).
Source ID: ord-200e8bbf6c6b4eba9c12c4e3ec5524f9Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a stirred solution of tert-butyl 4-(hydroxymethyl)phenylcarbamate (0.50 g, 2.24 mmol) in dichloromethane was added pyridine (3 drops), followed by the dropwise addition of thionyl chloride (0.35 mL, 4.98 mmol). The resulting reaction mixture was stirred for 30 minutes, and then quenched with water (25 mL). The aqueous layer was extracted with dichloromethane (50 mL), and the organic layer was dried over sodium sulfate, filtered and concentrated in vacuo to afford tert-butyl 4-(chloromethyl)-phenylcarbamate as an orange solid in 50% yield (0.27 g, 50%): 1H NMR (300 MHz, CDCl3) δ 7.38-7.28 (m, 4H), 6.51 (br s, 1H), 4.55 (s, 2H), 1.52 (s, 9H). The resulting reaction mixture quenched with water (25 mL) The aqueous layer was extracted with dichloromethane (50 mL) the organic layer was dried over sodium sulfate filtered concentrated in vacuo
Source ID: ord-3e98fc89cd874f068a4dfc2132c2176bConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: Following the procedure as described in Example 50, making variations as required to replace (2-bromoethoxy)(tert-butyl)dimethylsilane with tert-butyl 4-(chloromethyl)phenylcarbamate to react with ethyl 3-methyl-5-(2-oxoimidazolidin-1-yl)thiophene-2-carboxylate, the title compound was obtained as an off-white solid in 80% yield: 1H NMR (300 MHz, CDCl3) δ 7.34 (d, J=8.2 Hz, 2H), 7.22 (d, J=8.2 Hz, 2H), 6.49 (br s, 1H), 6.14 (s, 1H), 4.41 (s, 2H), 4.27 (q, J=7.1 Hz, 2H), 3.81-3.73 (m, 2H), 3.45-3.37 (m, 2H), 2.49 (s, 3H), 1.51 (s, 9H), 1.34 (t, J=7.1 Hz, 3H); MS (ES+) m/z 482.5 (M+23).
Source ID: ord-06c2b2386e9a494ab69a332f75ba04bbConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a stirred solution of tert-butyl 4-(hydroxymethyl)phenylcarbamate (0.50 g, 2.24 mmol) in dichloromethane was added pyridine (3 drops), followed by the dropwise addition of thionyl chloride (0.35 mL, 4.98 mmol). The resulting reaction mixture was stirred for 30 minutes, and then quenched with water (25 mL). The aqueous layer was extracted with dichloromethane (50 mL), and the organic layer was dried over sodium sulfate, filtered and concentrated in vacuo to afford tert-butyl 4-(chloromethyl)phenylcarbamate as an orange solid in 50% yield (0.27 g, 50%): 1H NMR (300 MHz, CDCl3) δ 7.38-7.28 (m, 4H), 6.51 (br s, 1H), 4.55 (s, 2H), 1.52 (s, 9H). The resulting reaction mixture quenched with water (25 mL) The aqueous layer was extracted with dichloromethane (50 mL) the organic layer was dried over sodium sulfate filtered concentrated in vacuo
Source ID: ord-bd9476e09e6a4b41bb48685949e141e5PubChem References
These sources are listed in the compound's public database record.
Related Products
12 related records
CAS 239074-27-2
CAS 301548-32-3
CAS 231958-04-6
CAS 1233249-35-8
CAS 111331-82-9
CAS 161117-84-6
CAS 54840-15-2
CAS 2164-13-8
CAS 387360-95-4
CAS 885270-73-5
CAS 79537-70-5
CAS 186663-74-1
Request a Quote
Send the required specification, quantity, destination and intended use. The CATO team will review availability and respond.