Reaction #4116221
Related Literature (1)
openreactiondata ↗doi:10.1039/C8SC04228D
Conditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-c283622f07d74fbda4c9f09a398c0d2fNo renderable structure data available
C1=CC(=C(C=C1Br)N)COChemical Intermediate
Structures, identifiers and computed properties have been matched to the database record by CAS.
| Intermediates | (2-amino-4-bromophenyl)methanol |
|---|---|
| IUPAC Name | — |
| CAS Number | 946122-05-0 |
| Database ID | 53440895 |
| Molecular Formula | — |
| Molecular Weight | — |
Product Information
(2-amino-4-bromophenyl)methanol (CAS 946122-05-0) 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 53440895
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-c283622f07d74fbda4c9f09a398c0d2fConditions: temp:75.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A mixture of (4-bromo-2-nitro-phenyl)-methanol (1.85 g, 7.97 mmol), iron powder (2.23 g, 39.9 mmol), ammonium chloride (213 mg, 3.99 mmol), ethanol (20 mL), and water (10 mL) was heated at 75° C. for 1 h, then after cooling filtered through a pad of diatomaceous earth. The filtrate was evaporated and the residue partitioned between ethyl acetate and water, the organic layer was washed with brine, dried (MgSO4), and evaporated to produce (2-amino-4-bromo-phenyl)-methanol (1.53 g, 90%). Off-white solid, MS (EI)=201.0 (M+). after cooling filtered through a pad of diatomaceous earth The filtrate was evaporated the residue partitioned between ethyl acetate and water the organic layer was washed with brine dried (MgSO4) evaporated
Source ID: ord-fd49680148b04e8eadaabd019223b480Conditions: temp:75.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A mixture of (4-bromo-2-nitro-phenyl)-methanol (1.85 g, 7.97 mmol), iron powder (2.23 g, 39.9 mmol), ammonium chloride (213 mg, 3.99 mmol), ethanol (20 mL), and water (10 mL) was heated at 75° C. for 1 h, then after cooling filtered through a pad of diatomaceous earth. The filtrate was evaporated and the residue partitioned between ethyl acetate and water, the organic layer was washed with brine, dried (MgSO4), and evaporated to produce (2-amino-4-bromo-phenyl)-methanol (1.53 g, 90%). Off-white solid, MS (EI)=201.0 (M+). after cooling filtered through a pad of diatomaceous earth The filtrate was evaporated the residue partitioned between ethyl acetate and water the organic layer was washed with brine dried (MgSO4) evaporated
Source ID: ord-fd49680148b04e8eadaabd019223b480Conditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-c283622f07d74fbda4c9f09a398c0d2fConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A solution of (2-amino-4-bromo-phenyl)-methanol (1.53 g, 7.57 mmol) in pyridine (15 mL) was treated with 5-chloro-2-methoxybenzenesulfonyl chloride (1.85 g, 7.57 mmol) at room temperature and stirred for 72 h, then poured upon ice-cold 2 M aq. hydrochloric acid solution and extracted with ethyl acetate. The organic layer was washed with brine, dried (MgSO4), and evaporated to produce a gummy residue, from which the product was precipitated by addition of toluene. The precipitate was collected by filtration and dried to afford N-(5-bromo-2-hydroxymethyl-phenyl)-5-chloro-2-methoxy-benzenesulfonamide (2.51 g, 82%). Off-white solid, MS (ISP)=404.2 (M−H)−. extracted with ethyl acetate The organic layer was washed with brine dried (MgSO4) evaporated to produce a gummy residue from which the product was precipitated by addition of toluene The precipitate was collected by filtration dried
Source ID: ord-8ecfda0949a747b7897e65f00a34f470Conditions: temp:75.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A mixture of (4-bromo-2-nitro-phenyl)-methanol (1.85 g, 7.97 mmol), iron powder (2.23 g, 39.9 mmol), ammonium chloride (213 mg, 3.99 mmol), ethanol (20 mL), and water (10 mL) was heated at 75° C. for 1 h, then after cooling filtered through a pad of diatomaceous earth. The filtrate was evaporated and the residue partitioned between ethyl acetate and water, the organic layer was washed with brine, dried (MgSO4), and evaporated to produce (2-amino-4-bromophenyl)-methanol (1.53 g, 90%). Off-white solid, MS (EI)=201.0 (M+). after cooling filtered through a pad of diatomaceous earth The filtrate was evaporated the residue partitioned between ethyl acetate and water the organic layer was washed with brine dried (MgSO4) evaporated
Source ID: ord-08611a73a7db4a3fb2c2f74ef3e60cc9Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A solution of (2-amino-4-bromo-phenyl)-methanol (1.53 g, 7.57 mmol) in pyridine (15 mL) was treated with 5-chloro-2-methoxybenzenesulfonyl chloride (1.85 g, 7.57 mmol) at room temperature and stirred for 72 h, then poured upon ice-cold 2 M aq. hydrochloric acid solution and extracted with ethyl acetate. The organic layer was washed with brine, dried (MgSO4), and evaporated to produce a gummy residue, from which the product was precipitated by addition of toluene. The precipitate was collected by filtration and dried to afford N-(5-bromo-2-hydroxymethyl-phenyl)-5-chloro-2-methoxy-benzenesulfonamide (2.51 g, 82%). Off-white solid, MS (ISP)=404.2 (M−H)−. extracted with ethyl acetate The organic layer was washed with brine dried (MgSO4) evaporated to produce a gummy residue from which the product was precipitated by addition of toluene The precipitate was collected by filtration dried
Source ID: ord-d71509574d20457099894d504f9f341dConditions: temp:75.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A mixture of (4-bromo-2-nitro-phenyl)-methanol (1.85 g, 7.97 mmol), iron powder (2.23 g, 39.9 mmol), ammonium chloride (213 mg, 3.99 mmol), ethanol (20 mL), and water (10 mL) was heated at 75° C. for 1 h, then after cooling filtered through a pad of diatomaceous earth. The filtrate was evaporated and the residue partitioned between ethyl acetate and water, the organic layer was washed with brine, dried (MgSO4), and evaporated to produce (2-amino-4-bromo-phenyl)-methanol (1.53 g, 90%). Off-white solid, MS (EI)=201.0 (M+). after cooling filtered through a pad of diatomaceous earth The filtrate was evaporated the residue partitioned between ethyl acetate and water the organic layer was washed with brine dried (MgSO4) evaporated
Source ID: ord-750b8360f5894fb8a77b7e6101fc8346Conditions: temp:75.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A mixture of (4-bromo-2-nitro-phenyl)-methanol (1.85 g, 7.97 mmol), iron powder (2.23 g, 39.9 mmol), ammonium chloride (213 mg, 3.99 mmol), ethanol (20 mL), and water (10 mL) was heated at 75° C. for 1 h, then after cooling filtered through a pad of diatomaceous earth. The filtrate was evaporated and the residue partitioned between ethyl acetate and water, the organic layer was washed with brine, dried (MgSO4), and evaporated to produce (2-amino-4-bromo-phenyl)-methanol (1.53 g, 90%). Off-white solid, MS (EI)=201.0 (M+). after cooling filtered through a pad of diatomaceous earth The filtrate was evaporated the residue partitioned between ethyl acetate and water the organic layer was washed with brine dried (MgSO4) evaporated
Source ID: ord-fd49680148b04e8eadaabd019223b480PubChem References
These sources are listed in the compound's public database record.
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