| Identification | Back Directory | [Name]
2-Amino-6-bromobenzoic acid | [CAS]
20776-48-1 | [Synonyms]
20776-48-1
2-AMino-6-broMobenzoic
6-BroMoanthranilic Acid
2-Nitro-5-broMobenzoic acid
2-Amino-6-bromobenzoic acid
Benzoic acid, 2-amino-6-bromo-
2-Amino-6-bromobenzoic acid 97%
BP11632-amino-6-bromobenzoicacid
2-AMINO-6-BROMOBENZOIC ACID(RS20012390)
3-Bromo-2-carboxyaniline, 6-Bromoanthranilic acid | [EINECS(EC#)]
630-293-6 | [Molecular Formula]
C7H6BrNO2 | [MDL Number]
MFCD03618455 | [MOL File]
20776-48-1.mol | [Molecular Weight]
216.03 |
| Chemical Properties | Back Directory | [Melting point ]
136 °C | [Boiling point ]
348.9±32.0 °C(Predicted) | [density ]
1.793±0.06 g/cm3(Predicted) | [storage temp. ]
Keep in dark place,Sealed in dry,Room Temperature | [form ]
powder | [pka]
0.85±0.10(Predicted) | [color ]
Light brown to beige | [Sensitive ]
Light Sensitive | [InChI]
InChI=1S/C7H6BrNO2/c8-4-2-1-3-5(9)6(4)7(10)11/h1-3H,9H2,(H,10,11) | [InChIKey]
BNQPROAXWQCNKO-UHFFFAOYSA-N | [SMILES]
C(O)(=O)C1=C(Br)C=CC=C1N |
| Hazard Information | Back Directory | [Uses]
2-Amino-6-bromobenzoic acid serves as a precursor to 5-bromo-2H-3,1-benzoxazine-2,4(1H)-dione (6-bromoisatoic anhydride), formed by treatment with sodium hydroxide and phosgene at 0 °C[1]. The compound condenses with 2-fluorobenzaldehyde to give 5-bromo-2-(2-fluorophenyl)-1,2-dihydro-4H-benzo[d][1,3]oxazin-4-one in 88% yield, and with methylamine in the presence of EDCI and HOBt to afford an amide intermediate that undergoes self-condensation en route to anthranilic diamide analogues. Its hydrochloride is reacted with N,O-dimethylhydroxylamine hydrochloride in DMF under nitrogen to synthesize 2-amino-X-bromo-N-methoxy-N-methylbenzamides[2]. | [Synthesis]
General procedure for the synthesis of 2-amino-6-bromobenzoic acid from 4-bromoindoline-2,3-dione: Commercially available 4-bromoindigo (2.50 g, 11.1 mmol) was dissolved in 1.5 mol/L aqueous sodium hydroxide solution (20 mL), and 33% aqueous hydrogen peroxide solution (1 mL) was added slowly and dropwise at 55 °C. The reaction mixture was stirred continuously at 55 °C for 30 min and then cooled to room temperature. Subsequently, the reaction solution was neutralized with 2.0 mol/L hydrochloric acid solution and finally purified by HP-20 resin column to obtain the target product 2-amino-6-bromobenzoic acid (1.60 g, 67% yield). | [References]
[1] Patent: EP2708540, 2014, A1. Location in patent: Paragraph 0092
[2] Proceedings of the Royal Society of London, Series B: Biological Sciences, 1958, vol. 148, p. 481,488
[3] Patent: WO2011/28741, 2011, A1. Location in patent: Page/Page column 202
[4] ACS Medicinal Chemistry Letters, 2016, vol. 7, # 9, p. 831 - 834 | [Synthesis Reference(s)]
[1] Patent: EP2708540, 2014, A1. Location in patent: Paragraph 0092
[2] Proceedings of the Royal Society of London, Series B: Biological Sciences, 1958, vol. 148, p. 481,488
[3] Patent: WO2011/28741, 2011, A1. Location in patent: Page/Page column 202
[4] ACS Medicinal Chemistry Letters, 2016, vol. 7, # 9, p. 831 - 834 |
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