No renderable structure data available
C1=CC(=CC(=C1)Br)CCCNChemical Intermediate
Structures, identifiers and computed properties have been matched to the database record by CAS.
| Intermediates | 3-(3-bromophenyl)propan-1-amine |
|---|---|
| IUPAC Name | — |
| CAS Number | 174689-12-4 |
| Database ID | 18367546 |
| Molecular Formula | — |
| Molecular Weight | — |
Product Information
3-(3-bromophenyl)propan-1-amine (CAS 174689-12-4) 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 18367546
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-d29ea5db254849ee9b427f04b41520c1Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a solution of 3-(3-bromophenyl)propionamide (94) (4.5 g, 19.7 mmol) in THF (50 ml) under argon was added BH3-THF complex (39.4 mL of a 1.0 M solution in THF, 39.4 mmol) and the mixture was stirred at room temperature for 18 h. The reaction was quenched with the cautious addition of 6 M HCl to pH 1. After stirring 4 h the solution was adjusted to pH>10 with the addition of 50% aqueous NaOH. This aqueous solution was extracted with EtOAc. The combined organics were washed with brine, dried over Na2SO4 and concentrated under reduced pressure to give 3-(3-bromophenyl)propan-1-amine (95) as an oil. This material was used in the next synthetic step without purification. 1H NMR (400 MHz, DMSO-d6) δ 7.40 (s, 1H), 7.35 (dt, J=6.4, 2.4 Hz, 1H), 7.26 (br s, 1H), 7.18-7.24 (m, 2H), 6.75 (br s, 1H), 2.78 (t, J=7.6 Hz, 2H), 2.34 (t, J=7.6 Hz, 2H). The reaction was quenched with the cautious addition of 6 M HCl to pH 1 After stirring 4 h the solution was adjusted to pH>10 with the addition of 50% aqueous NaOH This aqueous solution was extracted with EtOAc The combined organics were washed with brine dried over Na2SO4 concentrated under reduced pressure
Source ID: ord-08a834a0b0fe46a48ef40c9076665ca6Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a solution of 3-(3-bromophenyl)propionamide (94) (4.5 g, 19.7 mmol) in THF (50 ml) under argon was added BH3-THF complex (39.4 mL of a 1.0 M solution in THF, 39.4 mmol) and the mixture was stirred at room temperature for 18 h. The reaction was quenched with the cautious addition of 6 M HCl to pH 1. After stirring 4 h the solution was adjusted to pH>10 with the addition of 50% aqueous NaOH. This aqueous solution was extracted with EtOAc. The combined organics were washed with brine, dried over Na2SO4 and concentrated under reduced pressure to give 3-(3-bromophenyl)propan-1-amine (95) as an oil. This material was used in the next synthetic step without purification. 1H NMR (400 MHz, DMSO-d6) δ 7.40 (s, 1H), 7.35 (dt, J=6.4, 2.4 Hz, 1H), 7.26 (br s, 1H), 7.18-7.24 (m, 2H), 6.75 (br s, 1H), 2.78 (t, J=7.6 Hz, 2H), 2.34 (t, J=7.6 Hz, 2H). The reaction was quenched with the cautious addition of 6 M HCl to pH 1 After stirring 4 h the solution was adjusted to pH>10 with the addition of 50% aqueous NaOH This aqueous solution was extracted with EtOAc The combined organics were washed with brine dried over Na2SO4 concentrated under reduced pressure
Source ID: ord-f4dfc78902b247c68b45d0fa60a28ec0Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a solution of 3-(3-bromophenyl)propionamide (94) (4.5 g, 19.7 mmol) in THF (50 ml) under argon was added BH3-THF complex (39.4 mL of a 1.0 M solution in THF, 39.4 mmol) and the mixture was stirred at room temperature for 18 h. The reaction was quenched with the cautious addition of 6 M HCl to pH 1. After stirring 4 h the solution was adjusted to pH>10 with the addition of 50% aqueous NaOH. This aqueous solution was extracted with EtOAc. The combined organics were washed with brine, dried over Na2SO4 and concentrated under reduced pressure to give 3-(3-bromophenyl)propan-1-amine (95) as an oil. This material was used in the next synthetic step without purification. 1H NMR (400 MHz, DMSO-d6) δ 7.40 (s, 1H), 7.35 (dt, J=6.4, 2.4 Hz, 1H), 7.26 (br s, 1H), 7.18-7.24 (m, 2H), 6.75 (br s, 1H), 2.78 (t, J=7.6 Hz, 2H), 2.34 (t, J=7.6 Hz, 2H). The reaction was quenched with the cautious addition of 6 M HCl to pH 1 After stirring 4 h the solution was adjusted to pH>10 with the addition of 50% aqueous NaOH This aqueous solution was extracted with EtOAc The combined organics were washed with brine dried over Na2SO4 concentrated under reduced pressure
Source ID: ord-f4dfc78902b247c68b45d0fa60a28ec0Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a solution of 3-(3-bromophenyl)propionamide (94) (4.5 g, 19.7 mmol) in THF (50 ml) under argon was added BH3-THF complex (39.4 mL of a 1.0 M solution in THF, 39.4 mmol) and the mixture was stirred at room temperature for 18 h. The reaction was quenched with the cautious addition of 6 M HCl to pH 1. After stirring 4 h the solution was adjusted to pH>10 with the addition of 50% aqueous NaOH. This aqueous solution was extracted with EtOAc. The combined organics were washed with brine, dried over Na2SO4 and concentrated under reduced pressure to give 3-(3-bromophenyl)propan-1-amine (95) as an oil. This material was used in the next synthetic step without purification. 1H NMR (400 MHz, DMSO-d6) δ 7.40 (s, 1H), 7.35 (dt, J=6.4, 2.4 Hz, 1H), 7.26 (br s, 1H), 7.18-7.24 (m, 2H), 6.75 (br s, 1H), 2.78 (t, J=7.6 Hz, 2H), 2.34 (t, J=7.6 Hz, 2H). The reaction was quenched with the cautious addition of 6 M HCl to pH 1 After stirring 4 h the solution was adjusted to pH>10 with the addition of 50% aqueous NaOH This aqueous solution was extracted with EtOAc The combined organics were washed with brine dried over Na2SO4 concentrated under reduced pressure
Source ID: ord-08a834a0b0fe46a48ef40c9076665ca6Conditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-d29ea5db254849ee9b427f04b41520c1Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A mixture of 3-(3-bromophenyl)-propylamine (7.86 g, 36.7 mmol), 2-bromomethyl-benzoic acid methyl ester (8.45 g, 36.7 mmol), and K2CO3 (6.91 g, 50 mmol) in toluene (100 mL) was heated at reflux with stirring for 1.5 h. Workup and silica gel column chromatography using a gradient of hexanes to 50% ethyl acetate in hexanes afforded 2-[3-(3-bromophenyl)-propyl]-2,3-dihydroisoindol-1-one (8.81 g, 73%). GC/MS gave: m/z (rel.int.) 331 (M+, 10), 329 (M+, 10), 147-(100), 146 (72) 119 (25), and 91 (38). 1H NMR (300 MHz, CDCl3): δ 2.00 (dt, 2H), 2.67 (t, 2H), 3.67 (t, 2H), 4.36 (s, 2H), 7.14 (dd, 2H), 7.31 (m, 1H), 7.35 (br s, 1H), 7.45 (m, 2H), 7.51 (dt, 1H), 7.85 (d, 1H). 13C NMR (300 MHz, CDCl3): δ 29.9, 32.8, 42.0, 49.9, 122.4, 122.7, 123.6, 127.1, 128.0, 129.1, 130.0, 131.2, 131.3 132.8, 141.1, 143.7, 168.6. was heated at reflux
Source ID: ord-fd85e45984fb44a7bf9fa405c00dac00Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A mixture of 3-(3-bromophenyl)-propylamine (7.86 g, 36.7 mmol), 2-bromomethyl-benzoic acid methyl ester (8.45 g, 36.7 mmol), and K2CO3 (6.91 g, 50 mmol) in toluene (100 mL) was heated at reflux with stirring for 1.5 h. Workup and silica gel column chromatography using a gradient of hexanes to 50% ethyl acetate in hexanes afforded 2-[3-(3-bromophenyl)-propyl]-2,3-dihydroisoindol-1-one (8.81 g, 73%). GC/MS gave: m/z (rel.int.) 331 (M+, 10), 329 (M+, 10), 147-(100), 146 (72) 119 (25), and 91 (38). 1H NMR (300 MHz, CDCl3): δ 2.00 (dt, 2H), 2.67 (t, 2H), 3.67 (t, 2H), 4.36 (s, 2H), 7.14 (dd, 2H), 7.31 (m, 1H), 7.35 (br s, 1H), 7.45 (m, 2H), 7.51 (dt, 1H), 7.85 (d, 1H). 13C NMR (300 MHz, CDCl3): δ 29.9, 32.8, 42.0, 49.9, 122.4, 122.7, 123.6, 127.1, 128.0, 129.1, 130.0, 131.2, 131.3 132.8, 141.1, 143.7, 168.6. was heated at reflux
Source ID: ord-fd85e45984fb44a7bf9fa405c00dac00Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a solution of 3-(3-bromophenyl)propionamide (94) (4.5 g, 19.7 mmol) in THF (50 ml) under argon was added BH3-THF complex (39.4 mL of a 1.0 M solution in THF, 39.4 mmol) and the mixture was stirred at room temperature for 18 h. The reaction was quenched with the cautious addition of 6 M HCl to pH 1. After stirring 4 h the solution was adjusted to pH>10 with the addition of 50% aqueous NaOH. This aqueous solution was extracted with EtOAc. The combined organics were washed with brine, dried over Na2SO4 and concentrated under reduced pressure to give 3-(3-bromophenyl)propan-1-amine (95) as an oil. This material was used in the next synthetic step without purification. 1H NMR (400 MHz, DMSO-d6) δ 7.40 (s, 1H), 7.35 (dt, J=6.4, 2.4 Hz, 1H), 7.26 (br s, 1H), 7.18-7.24 (m, 2H), 6.75 (br s, 1H), 2.78 (t, J=7.6 Hz, 2H), 2.34 (t, J=7.6 Hz, 2H). The reaction was quenched with the cautious addition of 6 M HCl to pH 1 After stirring 4 h the solution was adjusted to pH>10 with the addition of 50% aqueous NaOH This aqueous solution was extracted with EtOAc The combined organics were washed with brine dried over Na2SO4 concentrated under reduced pressure
Source ID: ord-4df10ea1c0474a85af91badd245917c5Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a solution of 3-(3-bromophenyl)propionamide (94) (4.5 g, 19.7 mmol) in THF (50 ml) under argon was added BH3-THF complex (39.4 mL of a 1.0 M solution in THF, 39.4 mmol) and the mixture was stirred at room temperature for 18 h. The reaction was quenched with the cautious addition of 6 M HCl to pH 1. After stirring 4 h the solution was adjusted to pH>10 with the addition of 50% aqueous NaOH. This aqueous solution was extracted with EtOAc. The combined organics were washed with brine, dried over Na2SO4 and concentrated under reduced pressure to give 3-(3-bromophenyl)propan-1-amine (95) as an oil. This material was used in the next synthetic step without purification. 1H NMR (400 MHz, DMSO-d6) δ 7.40 (s, 1H), 7.35 (dt, J=6.4, 2.4 Hz, 1H), 7.26 (br s, 1H), 7.18-7.24 (m, 2H), 6.75 (br s, 1H), 2.78 (t, J=7.6 Hz, 2H), 2.34 (t, J=7.6 Hz, 2H). The reaction was quenched with the cautious addition of 6 M HCl to pH 1 After stirring 4 h the solution was adjusted to pH>10 with the addition of 50% aqueous NaOH This aqueous solution was extracted with EtOAc The combined organics were washed with brine dried over Na2SO4 concentrated under reduced pressure
Source ID: ord-497b8270b2e04602907b2cdbebc0462aConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a solution of 3-(3-bromophenyl)propionamide (94) (4.5 g, 19.7 mmol) in THF (50 ml) under argon was added BH3-THF complex (39.4 mL of a 1.0 M solution in THF, 39.4 mmol) and the mixture was stirred at room temperature for 18 h. The reaction was quenched with the cautious addition of 6 M HCl to pH 1. After stirring 4 h the solution was adjusted to pH>10 with the addition of 50% aqueous NaOH. This aqueous solution was extracted with EtOAc. The combined organics were washed with brine, dried over Na2SO4 and concentrated under reduced pressure to give 3-(3-bromophenyl)propan-1-amine (95) as an oil. This material was used in the next synthetic step without purification. 1H NMR (400 MHz, DMSO-d6) δ 7.40 (s, 1H), 7.35 (dt, J=6.4, 2.4 Hz, 1H), 7.26 (br s, 1H), 7.18-7.24 (m, 2H), 6.75 (br s, 1H), 2.78 (t, J=7.6 Hz, 2H), 2.34 (t, J=7.6 Hz, 2H). The reaction was quenched with the cautious addition of 6 M HCl to pH 1 After stirring 4 h the solution was adjusted to pH>10 with the addition of 50% aqueous NaOH This aqueous solution was extracted with EtOAc The combined organics were washed with brine dried over Na2SO4 concentrated under reduced pressure
Source ID: ord-f4dfc78902b247c68b45d0fa60a28ec0Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a solution of 3-(3-bromophenyl)propionamide (94) (4.5 g, 19.7 mmol) in THF (50 ml) under argon was added BH3-THF complex (39.4 mL of a 1.0 M solution in THF, 39.4 mmol) and the mixture was stirred at room temperature for 18 h. The reaction was quenched with the cautious addition of 6 M HCl to pH 1. After stirring 4 h the solution was adjusted to pH>10 with the addition of 50% aqueous NaOH. This aqueous solution was extracted with EtOAc. The combined organics were washed with brine, dried over Na2SO4 and concentrated under reduced pressure to give 3-(3-bromophenyl)propan-1-amine (95) as an oil. This material was used in the next synthetic step without purification. 1H NMR (400 MHz, DMSO-d6) δ 7.40 (s, 1H), 7.35 (dt, J=6.4, 2.4 Hz, 1H), 7.26 (br s, 1H), 7.18-7.24 (m, 2H), 6.75 (br s, 1H), 2.78 (t, J=7.6 Hz, 2H), 2.34 (t, J=7.6 Hz, 2H). The reaction was quenched with the cautious addition of 6 M HCl to pH 1 After stirring 4 h the solution was adjusted to pH>10 with the addition of 50% aqueous NaOH This aqueous solution was extracted with EtOAc The combined organics were washed with brine dried over Na2SO4 concentrated under reduced pressure
Source ID: ord-08a834a0b0fe46a48ef40c9076665ca6PubChem References
These sources are listed in the compound's public database record.
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