No renderable structure data available
C1=CC(=C(C=C1Br)CO)NChemical Intermediate
Structures, identifiers and computed properties have been matched to the database record by CAS.
| Intermediates | (2-amino-5-bromophenyl)methanol |
|---|---|
| IUPAC Name | — |
| CAS Number | 226713-43-5 |
| Database ID | 11030874 |
| Molecular Formula | — |
| Molecular Weight | — |
Product Information
(2-amino-5-bromophenyl)methanol (CAS 226713-43-5) 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 11030874
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-ea30b29563984088a3e0a06ff0781673Conditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-3bc65b03f9824a1fb0cb0ef63655e3feConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To acetone (300 ml) were added (2-amino-5-bromophenyl)methanol (23.32 g) and active manganese dioxide (58.5 g), and the mixture was stirred at room temperature for 17.5 hours and filtered. The solvent was evaporated under reduced pressure to give 2-amino-5-bromobenzaldehyde (16.41 g, 71%). filtered The solvent was evaporated under reduced pressure
Source ID: ord-65c40bbacbb4473ebb9494df3de6cedbConditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: In THF (350 ml) was dissolved 5-bromoanthranilic acid (40.06 g), and the mixture was cooled to 0° C. To the mixture was added dropwise a solution of 10.0M borane dimethylsulfide in THF (54.5 ml), and the mixture was stirred at room temperature for 4.5 hours. The mixture was cooled to 0° C., and to the mixture was added dropwise 3N sodium hydroxide solution. The mixture was stirred at room temperature overnight, and to the mixture was added granulated sodium hydroxide to adjust the mixture to pH 11. The aqueous layer was saturated with potassium carbonate, and the THF layer was separated. The aqueous layer was extracted with ether (100 ml×5). The organic layers were combined and dried with magnesium sulfate. The solvent was evaporated under reduced pressure to give (2-amino-5-bromophenyl)methanol (36.66 g, 100%). The mixture was cooled to 0° C. The mixture was stirred at room temperature overnight to the mixture was added the THF layer was separated The aqueous layer was extracted with ether (100 ml×5) dried with magnesium sulfate The solvent was evaporated under reduced pressure
Source ID: ord-fcbadb8ff6c24675b5fd143234943411Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: In THF (350 ml) was dissolved 5-bromoanthranilic acid (40.06 g), and the mixture was cooled to 0° C. To the mixture was added dropwise a solution of 10.0M borane dimethylsulfide in THF (54.5 ml), and the mixture was stirred at room temperature for 4.5 hours. The mixture was cooled to 0° C., and to the mixture was added dropwise 3N sodium hydroxide solution. The mixture was stirred at room temperature overnight, and to the mixture was added granulated sodium hydroxide to adjust the mixture to pH 11. The aqueous layer was saturated with potassium carbonate, and the THF layer was separated. The aqueous layer was extracted with ether (100 ml×5). The organic layers were combined and dried with magnesium sulfate. The solvent was evaporated under reduced pressure to give (2-amino-5-bromophenyl)methanol (36.66 g, 100%). The mixture was cooled to 0° C. The mixture was stirred at room temperature overnight to the mixture was added the THF layer was separated The aqueous layer was extracted with ether (100 ml×5) dried with magnesium sulfate The solvent was evaporated under reduced pressure
Source ID: ord-fcbadb8ff6c24675b5fd143234943411Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A mixture of (2-amino-5-bromophenyl)methanol (10 g, 49.5 mmol) and MnO2 (25.8 g, 296.6 mmol) in CH2Cl2 (400 mL) was stirred at RT overnight. LCMS showed the reaction was completed. The solid was filtered off, and the filtrate was concentrated to give the title compound as a light yellow solid (8 g, 81%), which was directly used in next step without further purification. MS (ES+) C7H6BrNO requires: 199. found: 200, 202 [M+H]+. The solid was filtered off the filtrate was concentrated
Source ID: ord-cce5a4d41af44cbe996d2618a96c8642Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a solution of 2-amino-5-bromobenzoic acid (10.0 g, 46.3 mmol) in THF (150 mL) was added BH3-THF (1 M, 231 mL) at room temperature, and the reaction mixture was stirred overnight. An aliquot of the reaction mixture was analyzed by LCMS and indicated that the reaction had proceeded to completion. The reaction was quenched with water (150 mL) and extracted with EtOAc (3×500 mL). The organic layers were separated, combined, washed with water (200 mL) and brine (200 mL), dried over sodium sulfate, filtered, and concentrated to afford the title compound (10 g, crude), which was directly used in the next step without further purification. MS (ES+) C7H8BrNO requires: 201. found: 202, 204 [M+H]+. The reaction was quenched with water (150 mL) extracted with EtOAc (3×500 mL) The organic layers were separated washed with water (200 mL) and brine (200 mL) dried over sodium sulfate filtered concentrated
Source ID: ord-5b3952c678a14f01ad3ab86da6a6cc0cConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a solution of 2-amino-5-bromobenzoic acid (10.0 g, 46.3 mmol) in THF (150 mL) was added BH3-THF (1 M, 231 mL) at room temperature, and the reaction mixture was stirred overnight. An aliquot of the reaction mixture was analyzed by LCMS and indicated that the reaction had proceeded to completion. The reaction was quenched with water (150 mL) and extracted with EtOAc (3×500 mL). The organic layers were separated, combined, washed with water (200 mL) and brine (200 mL), dried over sodium sulfate, filtered, and concentrated to afford the title compound (10 g, crude), which was directly used in the next step without further purification. MS (ES+) C7H8BrNO requires: 201. found: 202, 204 [M+H]+. The reaction was quenched with water (150 mL) extracted with EtOAc (3×500 mL) The organic layers were separated washed with water (200 mL) and brine (200 mL) dried over sodium sulfate filtered concentrated
Source ID: ord-5b3952c678a14f01ad3ab86da6a6cc0cConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: (2-Amino-5-bromophenyl)methanol (22 g, 109 mmol), 3,5-dimethylacetophenone (24.2 g, 163 mmol), RuCl2(PPh3)3 (1.05 g, 1.09 mmol), KOH (11.0 g, 196 mmol) were refluxed in 270 mL of toluene for 18 h. Water was collected from the reaction using a Dean-stark trap. The reaction mixture was allowed to cool to room temperature and filtered through a silica gel plug and eluted with 5% ethyl acetate in hexanes. The product was further purified by Kugelrohr distillation and crystallization from methanol. Water was collected from the reaction filtered through a silica gel plug eluted with 5% ethyl acetate in hexanes The product was further purified by Kugelrohr distillation and crystallization from methanol
Source ID: ord-986066fbfc4944dcb4e0b6e1519ba014Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: (2-Amino-5-bromophenyl)methanol (22 g, 109 mmol), 3,5-dimethylacetophenone (24.2 g, 163 mmol), RuCl2(PPh3)3 (1.05 g, 1.09 mmol), KOH (11.0 g, 196 mmol) were refluxed in 270 mL of toluene for 18 h. Water was collected from the reaction using a Dean-stark trap. The reaction mixture was allowed to cool to room temperature and filtered through a silica gel plug and eluted with 5% ethyl acetate in hexanes. The product was further purified by Kugelrohr distillation and crystallization from methanol. Water was collected from the reaction filtered through a silica gel plug eluted with 5% ethyl acetate in hexanes The product was further purified by Kugelrohr distillation and crystallization from methanol
Source ID: ord-986066fbfc4944dcb4e0b6e1519ba014Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: (2-Amino-5-bromophenyl)methanol (22 g, 109 mmol), 3,5-dimethylacetophenone (24.2 g, 163 mmol), RuCl2(PPh3)3 (1.05 g, 1.09 mmol), KOH (11.0 g, 196 mmol) were refluxed in 270 mL of toluene for 18 h. Water was collected from the reaction using a Dean-stark trap. The reaction mixture was allowed to cool to room temperature and filtered through a silica gel plug and eluted with 5% ethyl acetate in hexanes. The product was further purified by Kugelrohr distillation and crystallization from methanol. Water was collected from the reaction filtered through a silica gel plug eluted with 5% ethyl acetate in hexanes The product was further purified by Kugelrohr distillation and crystallization from methanol
Source ID: ord-a9c36c0959304e91a3bb17824f1f1a89Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: (2-Amino-5-bromophenyl)methanol (22 g, 109 mmol), 3,5-dimethylacetophenone (24.2 g, 163 mmol), RuCl2(PPh3)3 (1.05 g, 1.09 mmol), KOH (11.0 g, 196 mmol) were refluxed in 270 mL of toluene for 18 h. Water was collected from the reaction using a Dean-stark trap. The reaction mixture was allowed to cool to room temperature and filtered through a silica gel plug and eluted with 5% ethyl acetate in hexanes. The product was further purified by Kugelrohr distillation and crystallization from methanol. Water was collected from the reaction filtered through a silica gel plug eluted with 5% ethyl acetate in hexanes The product was further purified by Kugelrohr distillation and crystallization from methanol
Source ID: ord-a9c36c0959304e91a3bb17824f1f1a89PubChem References
These sources are listed in the compound's public database record.
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