No renderable structure data available
C1=CC(=CC(=C1)Br)CCC=OChemical Intermediate
Structures, identifiers and computed properties have been matched to the database record by CAS.
| Intermediates | 3-(3-bromophenyl)propanal |
|---|---|
| IUPAC Name | — |
| CAS Number | 210115-30-3 |
| Database ID | 21683806 |
| Molecular Formula | — |
| Molecular Weight | — |
Product Information
3-(3-bromophenyl)propanal (CAS 210115-30-3) 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 21683806
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-a8aaace735a9432c9812482aefe166aaConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: The title compound was prepared from 5-(3-amino-propyl)-thiophene-2-carboxylic acid tert-butyl ester hydrochloride and 3-(3-bromo-phenyl)-propionaldehyde following the method described in Step A of Example 141. 1H NMR (400 MHz, CDCl3) δ 7.50 (d, 1H), 7.28–7.30 (m, 2H), 7.06–7.14 (m, 2H), 6.75 (d, 1H), 2.85 (t, 2H), 2.65–2.78 (m, 4H), 2.60 (t, 2H), 1.92–2.04 (m, 4H), 1.52–1.54 (m, 9H); MS 438 (M+).
Source ID: ord-34f8eff4e325496ab39df3d509269ac5Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: The title compound was prepared from 5-(3-amino-propyl)-thiophene-2-carboxylic acid tert-butyl ester hydrochloride and 3-(3-bromo-phenyl)-propionaldehyde following the method described in Step A of Example 141. 1H NMR (400 MHz, CDCl3) δ 7.50 (d, 1H), 7.28-7.30 (m, 2H), 7.06-7.14 (m, 2H), 6.75 (d, 1H), 2.85 (t, 2H), 2.65-2.78 (m, 4H), 2.60 (t, 2H), 1.92-2.04 (m, 4H), 1.52-1.54 (m, 9H); MS 438 (M+).
Source ID: ord-a3209b43cd2f47398c3409515100ae66Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A solution of 1.34 gm (3.77 mmol) of methyltriphenylphosphonium bromide in THF at 0° C. was treated dropwise with 2.3 mL of 1.6 M n-BuLi in hexanes (3.77 mmol), stirred at 0° C. for 0.25 h, cooled to −78° C., treated dropwise with a solution of 3-(3-bromophenyl)propionaldehyde (0.7 gm, 3.28 mmol) in THF, stirred at −78° C. for 1 h, allowed to warm to room temperature, quenched with aqueous NH4Cl and concentrated under reduced pressure. The resultant residue was taken up in EtOAc, washed sequentially with water and brine, dried over Na2SO4 and concentrated under reduced pressure. Chromatography of this concentrate on silica gel with a gradient of 0.5% EtOAc-hexanes to 2.0% EtOAc-hexanes gave 1-bromo-3-but-3-enylbenzene as an oil, 0.35 gm (50% yield); 1H NMR (400 MHz, CDCl3) δ: 2.33 (m, 2H), 2.66 (t, 2H, J=7.4 Hz), 4.98 (m, 2H), 5.79 (m, 1H), 7.12 (m, 2H), 7.30 (m, 2H). cooled to −78° C. stirred at −78° C. for 1 h to warm to room temperature quenched with aqueous NH4Cl concentrated under reduced pressure washed sequentially with water and brine dried over Na2SO4 concentrated under reduced pressure Chromatography of this concentrate on silica gel with a gradient of 0.5% EtOAc-hexanes to 2.0% EtOAc-hexanes
Source ID: ord-deada4722d54478c8ba908846902f910Conditions: temp:22.01; pressure:0.00; stir:
Source ID: ord-9fc447a9162a4712be24e7a6269cb10eConditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-a8aaace735a9432c9812482aefe166aaConditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A solution of 1.34 gm (3.77 mmol) of methyltriphenylphosphonium bromide in THF at 0° C. was treated dropwise with 2.3 mL of 1.6 M n-BuLi in hexanes (3.77 mmol), stirred at 0° C. for 0.25 h, cooled to −78° C., treated dropwise with a solution of 3-(3-bromophenyl)propionaldehyde (0.7 gm, 3.28 mmol) in THF, stirred at −78° C. for 1 h, allowed to warm to room temperature, quenched with aqueous NH4Cl and concentrated under reduced pressure. The resultant residue was taken up in EtOAc, washed sequentially with water and brine, dried over Na2SO4 and concentrated under reduced pressure. Chromatography of this concentrate on silica gel with a gradient of 0.5% EtOAc-hexanes to 2.0% EtOAc-hexanes gave 1-bromo-3-but-3-enylbenzene as an oil, 0.35 gm (50% yield); 1H NMR (400 MHz, CDCl3) δ: 2.33 (m, 2H), 2.66 (t, 2H, J=7.4 Hz), 4.98 (m, 2H), 5.79 (m, 1H), 7.12 (m, 2H), 7.30 (m, 2H). cooled to −78° C. stirred at −78° C. for 1 h to warm to room temperature quenched with aqueous NH4Cl concentrated under reduced pressure washed sequentially with water and brine dried over Na2SO4 concentrated under reduced pressure Chromatography of this concentrate on silica gel with a gradient of 0.5% EtOAc-hexanes to 2.0% EtOAc-hexanes
Source ID: ord-deada4722d54478c8ba908846902f910Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: The title compound was prepared from 5-(3-amino-propyl)-thiophene-2-carboxylic Acid tert-butyl ester hydrochloride and 3-(3-bromo-phenyl)-propionaldehyde following the method described in Step A of Example 141. 1H NMR (400 MHz, CDCl3) δ 7.50 (d, 1H), 7.28-7.30 (m, 2H), 7.06-7.14 (m, 2H), 6.75 (d, 1H), 2.85 (t, 2H), 2.65-2.78 (m, 4H), 2.60 (t, 2H), 1.92-2.04 (m, 4H), 1.52-1.54 (m, 9H); MS 438 (M+).
Source ID: ord-adbd72dcf32d4cd39c136fef4700481eConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: The title compound was prepared from 5-(3-amino-propyl)-thiophene-2-carboxylic Acid tert-butyl ester hydrochloride and 3-(3-bromo-phenyl)-propionaldehyde following the method described in Step A of Example 141. 1H NMR (400 MHz, CDCl3) δ 7.50 (d, 1H), 7.28-7.30 (m, 2H), 7.06-7.14 (m, 2H), 6.75 (d, 1H), 2.85 (t, 2H), 2.65-2.78 (m, 4H), 2.60 (t, 2H), 1.92-2.04 (m, 4H), 1.52-1.54 (m, 9H); MS 438 (M+).
Source ID: ord-adbd72dcf32d4cd39c136fef4700481eConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: The title compound was prepared from 5-(3-amino-propyl)-thiophene-2-carboxylic Acid tert-butyl ester hydrochloride and 3-(3-bromo-phenyl)-propionaldehyde following the method described in Step A of Example 141. 1H NMR (400 MHz, CDCl3) δ 7.50 (d, 1H), 7.28-7.30 (m, 2H), 7.06-7.14 (m, 2H), 6.75 (d, 1H), 2.85 (t, 2H), 2.65-2.78 (m, 4H), 2.60 (t, 2H), 1.92-2.04 (m, 4H), 1.52-1.54 (m, 9H); MS 438 (M+).
Source ID: ord-adbd72dcf32d4cd39c136fef4700481eConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: The title compound was prepared from 5-(3-amino-propyl)-thiophene-2-carboxylic acid tert-butyl ester hydrochloride and 3-(3-bromo-phenyl)-propionaldehyde following the method described in Step A of Example 141. 1H NMR (400 MHz, CDCl3) δ7.50 (d, 1H), 7.28-7.30 (m, 2H), 7.06-7.14 (m, 2H), 6.75 (d, 1H), 2.85 (t, 2H), 2.65-2.78 (m, 4H), 2.60 (t, 2H), 1.92-2.04 (m, 4H), 1.52-1.54 (m, 9H); MS 438 (M+).
Source ID: ord-3b3917ae1e7d4fcdbb53a133200c866dConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: The title compound was prepared from 5-(3-amino-propyl)-thiophene-2-carboxylic acid tert-butyl ester hydrochloride and 3-(3-bromo-phenyl)-propionaldehyde following the method described in Step A of Example 141. 1H NMR (400 MHz, CDCl3) δ 7.50 (d, 1H), 7.28-7.30 (m, 2H), 7.06-7.14 (m, 2H), 6.75 (d, 1H), 2.85 (t, 2H), 2.65-2.78 (m, 4H), 2.60 (t, 2H), 1.92-2.04 (m, 4H), 1.52-1.54 (m, 9H); MS 438 (M+).
Source ID: ord-4eb0cab92ace4e58b015433466bf2649PubChem References
These sources are listed in the compound's public database record.
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