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Chemistry
Organic Building Blocks
Aryls
3-Amino-5-bromophenol
Chemistry
Organic Building Blocks
Aryls
Amines Bromides Phenols Benzene Compounds

[ CAS No. 100367-38-2 ] {[proInfo.proName]}

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Cat. No.: {[proInfo.prAm]}
Chemical Structure| 100367-38-2
Chemical Structure| 100367-38-2
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Product Details of [ 100367-38-2 ]

CAS No. :100367-38-2 MDL No. :MFCD16999374
Formula : C6H6BrNO Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W : 188.02 Pubchem ID :-
Synonyms :

Safety of [ 100367-38-2 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 100367-38-2 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 100367-38-2 ]

[ 100367-38-2 ] Synthesis Path-Downstream   1~2

  • 1
  • [ 116632-23-6 ]
  • [ 100367-38-2 ]
YieldReaction ConditionsOperation in experiment
87% 3-amino-5-bromophenol3-Bromo-5-nitrophenol (8.5 g, 39.0 mmol) was dissolved in ethanol (100 mL) and acetic acid (100 mL) and iron powder (8.71 g, 156 mmol) were added. The mixture was stirred at reflux for 2 h before it was cooled to room temperature, diluted with water (400 mL), and neutralized with solid Na2C03. The mixture was extracted with methylene chloride (4 x 200 mL). The combined organic extracts were washed with brine, passed over a phase separator, and concentrated to afford 3-amino-5-bromophenol (6.75 g, 87percent yield) which was used without further purification. MS (m/z) 189.9 (M+H+).
Reference： [1]Patent: WO2011/119704,2011,A1 .Location in patent: Page/Page column 45
[2]Journal of Medicinal Chemistry,2015,vol. 58,p. 2135 - 2148
  • 2
  • [ 16618-68-1 ]
  • [ 100367-38-2 ]
YieldReaction ConditionsOperation in experiment
With boron tribromide; In dichloromethane; at 0 - 20℃; for 24h; General procedure: A solution of BBr3 in dichloromethane (1.0 M, 12 mL,12 mmol) was added slowly to a solution of 4-bromo-3-methoxyaniline (800 mg, 3.96 mmol) in methylene chloride(15 mL) at 0C. The resulting brown solution was warmed toroom temperature and stirred for 24 h. After saturated aqueousNaHCO3 (30 mL) was added at 0C, the solution was extractedwith EtOAc (20 mL × 3). The combined organic layer wasdried with anhydrous Na2SO4, filtered and concentrated invacuum. The residue was purified by flash chromatographyover silica gel (petroleum-EtOAc = 2 : 1) to give 5-amino-2-bromophenol (665 mg, 88%). To a solution of 5-amino-2-bromophenol (55 mg, 0.29 mmol)and triethylamine (53 muL, 0.38 mmol) in tetrahydrofuran (THF)(3 mL) was added slowly benzoyl chloride (0.32 mmol) at 0C.The reaction mixture was then stirred at room temperature for30 min. After the reaction was quenched with water (10 mL),the solution was extracted with EtOAc (10 mL × 2). The combinedorganic layer was dried over anhydrous Na2SO4, filteredand concentrated in vacuum. The residue was purified bycolumn chromatography to afford the product 3 (74 mg, 87%).
Reference： [1]Chemical and Pharmaceutical Bulletin,2019,vol. 67,p. 372 - 381

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