2-Amino-5-bromo-benzoic acid ethyl ester

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2-Amino-5-bromo-benzoic acid ethyl ester Basic information
Product Name:2-Amino-5-bromo-benzoic acid ethyl ester
Synonyms:Benzoic acid, 2-aMino-5-broMo-, ethyl ester;ETHYL 2-AMINO-5-BROMOBENZOATE;2-Amino-5-bromo-benzoic acid ethyl ester
CAS:63243-76-5
MF:C9H10BrNO2
MW:244.09
EINECS:
Product Categories:Aromatic Esters;pharmacetical;Acids & Esters;Anilines, Amides & Amines;Bromine Compounds
Mol File:63243-76-5.mol
2-Amino-5-bromo-benzoic acid ethyl ester Structure
2-Amino-5-bromo-benzoic acid ethyl ester Chemical Properties
Melting point 187 °C(Solv: ethanol (64-17-5))
Boiling point 301.2±22.0 °C(Predicted)
density 1.503±0.06 g/cm3(Predicted)
storage temp. under inert gas (nitrogen or Argon) at 2–8 °C
pka1.77±0.10(Predicted)
AppearanceWhite to off-white Solid
Safety Information
MSDS Information
2-Amino-5-bromo-benzoic acid ethyl ester Usage And Synthesis
Synthesis
Ethanol

64-17-5

2-Amino-5-bromobenzoic acid

5794-88-7

2-AMINO-5-BROMO-BENZOIC ACID ETHYL ESTER

63243-76-5

To a 100 mL three-necked round-bottomed flask was added 2-amino-5-bromobenzoic acid (5 g, 23.14 mmol, 1.00 equiv) and anhydrous ethanol (100 mL). Dry hydrogen chloride gas was passed to saturation and the reaction mixture was subsequently heated to reflux for 12 hours. Upon completion of the reaction, saturated sodium bicarbonate solution was slowly added to neutralize the reaction system. The solvent was removed by distillation under reduced pressure to give the crude product. The crude product was purified by fast column chromatography (silica gel, eluent ratio was adjusted according to the TLC results) to give ethyl 2-amino-5-bromobenzoate (2.5 g, 44% yield) as a yellow solid.

References[1] Bioorganic and Medicinal Chemistry Letters, 2009, vol. 19, # 19, p. 5746 - 5752
[2] Patent: WO2014/182951, 2014, A1. Location in patent: Paragraph 00281
[3] Bioorganic and Medicinal Chemistry Letters, 2007, vol. 17, # 23, p. 6481 - 6488
[4] Patent: EP1180514, 2002, A1. Location in patent: Example 75
[5] Journal of Organic Chemistry, 2018, vol. 83, # 3, p. 1154 - 1159
2-Amino-5-bromo-benzoic acid ethyl ester Preparation Products And Raw materials
Raw materialsEthanol-->2-Amino-5-bromobenzoic acid
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