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C1CC1CCBrChemical Intermediate
Structures, identifiers and computed properties have been matched to the database record by CAS.
| Intermediates | 2-bromoethylcyclopropane |
|---|---|
| IUPAC Name | — |
| CAS Number | 36982-56-6 |
| Database ID | 22636989 |
| Molecular Formula | — |
| Molecular Weight | — |
Product Information
2-bromoethylcyclopropane (CAS 36982-56-6) 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 22636989
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-7570dd6430f444e4b81d501c2bca7fd1Conditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-6fbc40ac55d741a99b465afdb4d1cf9dConditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-11723e1c0b36412db66e1a7bcd6eeb4cConditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-e198f55668ed45e89a14c196baca3861Conditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-9169a86890f540e1a380de46ee25edbdConditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-672c0afc483f4cbda66255f8770ecc36Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: Following the procedure as described in PREPARATION 2A, and making non-critical variations to replace isatin with 5-chloro-1H-indole-2,3-dione, and (2-bromoethyl)cyclopropane with ethyl 2-bromoacetate, the title compound was obtained (98%) as solid: 1H NMR (300 MHz, CDCl3) δ 7.60 (d, 1H), 7.54 (dd, 1H), 6.74 (d, 1H), 4.46 (s, 2H), 4.23 (q, 2H), 1.27 (t, 3H); MS (ES+) m/z 268.6 (M+1).
Source ID: ord-373bb5dbb03f436ca84e3ca26969a72fConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: Following the procedure as described in PREPARATION 2A, and making non-critical variations to replace isatin with 5-methylisatin, and (2-bromoethyl)cyclopropane with 1,1′-(bromomethylene)dibenzene, the title compound was obtained (74%) as a bright orange solid: 1H NMR (300 MHz, CDCl3) δ 7.42-7.26 (m, 11H), 7.09 (d, 1H), 6.95 (s, 1H), 6.37 (d, 1H), 2.24 (s, 3H).
Source ID: ord-a395496f2d4a4a459af74af53d28849bConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: Following the procedure as described in PREPARATION 2A, and making non-critical variations to replace isatin with 5-fluoroisatin, and (2-bromoethyl)cyclopropane with 2-(bromomethyl)-5-(trifluoromethyl)furan, the title compound was obtained (59%) as a red solid: 1H NMR (300 MHz, DMSO-d6) δ 7.54-7.50 (m, 1H), 7.47-7.44 (m, 1H), 7.20 (dd, 1H), 7.14-7.13 (m, 1H), 6.75 (d, 1H), 4.99 (s, 2H); 13C NMR (75 MHz, DMSO-d6) δ 182.4 (d), 160.7, 158.5 (d), 157.5, 153.0 (d), 146.5 (d), 139.9 (q), 124.3, 119.3 (d), 114.5 (d), 112.7 (d), 112.0 (d), 110.5, 36.8.
Source ID: ord-6688fe29b5454f82b914962e4e7e692cConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: Following the procedure as described in PREPARATION 2A, and making non-critical variations to replace isatin with 4-chloro-1H-indole-2,3-dione, and (2-bromoethyl)cyclopropane with ethyl bromoacetate, the title compound was obtained (95%) as a colorless solid: 1H NMR (300 MHz, CDCl3) δ 7.48 (t, 1H), 7.08 (d, 1H), 6.67 (d, 1H), 4.47 (s, 2H), 4.23 (q, 2H), 1.27 (t, 3H); MS (ES+) m/z 268.6 (M+1).
Source ID: ord-b5b55faa1ceb48b7a44501bcba9e098aConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: Following the procedure as described in PREPARATION 2A, and making non-critical variations to replace isatin with 4-bromoisatin and (2-bromoethyl)cyclopropane with ethyl bromoacetate, the title compound was obtained as a yellow solid (68%): 1H NMR (300 MHz, CDCl3) δ 7.39 (t, 1H), 7.27(dd, 1H), 6.71 (dd, 1H), 4.47 (s, 2H), 4.23 (q, 2H), 1.27 (t, 3H); MS (ES+) m/z 312 (M+1), 314 (M+1), 334 (M+23) 336 (M+23).
Source ID: ord-38c8d5db552b477e8d9385b7cf784229Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a suspension of sodium hydride (1.61 g, 41.9 mmol, 60% dispersion in mineral oil) in anhydrous N,N-dimethylformamide (25.0 mL) was added isatin (6.17 g, 41.9 mmol) at 0° C. The reaction mixture was stirred for 0.5 h followed by the addition of (2-bromoethyl)cyclopropane (Maercker, A., et al, Justus Liebigs Ann. Chem. (1972), 759:132-157) (9.25 g, 61.2 mmol). The resulting mixture was stirred at ambient temperature for 16 h and quenched with water (50.0 mL). The mixture was extracted with ethyl acetate (3×100 mL). The combined organic layers was washed with water (3×50.0 mL), dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated in vacuo to dryness to yield the title compound (6.50 g, 90%) as a viscous gum: 1H NMR (300 MHz, CDCl3) δ 7.57-7.51 (m, 2H), 7.05 (t, 1H), 6.88 (d, 1H), 3.79-3.74 (m, 2H), 1.59-1.52 (m, 2H), 0.70-0.61 (m, 1H), 0.44-0.38 (m, 2H), 0.05-0.02 (m, 2H); 13C NMR (75 MHz, CDCl3) δ 183.7, 158.2, 151.2, 138.4, 125.4, 123.6, 117.5, 110.3, 40.3, 32.2, 8.6, 4.3. The resulting mixture was stirred at ambient temperature for 16 h quenched with water (50.0 mL) The mixture was extracted with ethyl acetate (3×100 mL) The combined organic layers was washed with water (3×50.0 mL) dried over anhydrous sodium sulfate filtered The filtrate was concentrated in vacuo to dryness
Source ID: ord-9589c6804c3445f5b65b89090d876057PubChem References
These sources are listed in the compound's public database record.
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