| Identification | Back Directory | [Name]
3-AMINO-5-BROMOBENZOIC ACID | [CAS]
42237-85-4 | [Synonyms]
3-Amino-6-bromobenzoic acid
Benzoicacid,3-aMino-5-broMo-
3-AMINO-5-BROMOBENZOIC ACID USP/EP/BP | [Molecular Formula]
C7H6BrNO2 | [MDL Number]
MFCD00227745 | [MOL File]
42237-85-4.mol | [Molecular Weight]
216.03 |
| Chemical Properties | Back Directory | [Melting point ]
217-221 °C | [Boiling point ]
398.3±32.0 °C(Predicted) | [density ]
1.793 | [storage temp. ]
Keep in dark place,Inert atmosphere,Room temperature | [form ]
solid | [pka]
3.97±0.10(Predicted) | [Appearance]
White to off-white Solid | [Major Application]
peptide synthesis | [InChI]
InChI=1S/C7H6BrNO2/c8-5-1-4(7(10)11)2-6(9)3-5/h1-3H,9H2,(H,10,11) | [InChIKey]
RQSXRGSPGHZKFT-UHFFFAOYSA-N | [SMILES]
C(O)(=O)C1=CC(Br)=CC(N)=C1 |
| Safety Data | Back Directory | [Hazard Codes ]
Xn | [Risk Statements ]
22 | [RIDADR ]
UN 2811 6.1/PG 3 | [WGK Germany ]
3 | [HazardClass ]
6.1 | [PackingGroup ]
Ⅲ | [HS Code ]
2922498590 | [Storage Class]
6.1C - Combustible acute toxic Cat.3
toxic compounds or compounds which causing chronic effects | [Hazard Classifications]
Acute Tox. 3 Oral |
| Hazard Information | Back Directory | [Uses]
peptide synthesis | [reaction suitability]
reaction type: solution phase peptide synthesis | [Synthesis]
The general procedure for the synthesis of 3-amino-5-bromobenzoic acid from 3-bromo-5-nitrobenzoic acid was as follows: concentrated hydrochloric acid (30 mL) was slowly added to a solution containing 3-bromo-5-nitrobenzoic acid (7.02 g, 28.54 mmol) and ethanol (150 mL), and the mixture was stirred for 5 min at room temperature. Subsequently, tin (II) chloride was added and the reaction mixture was stirred at 50 °C for 2 hours. After completion of the reaction, the mixture was cooled to room temperature. The pH was adjusted to 9 with 8 M sodium hydroxide solution, at which point a solid precipitated. The solids were removed by filtration. The filtrate was acidified to pH 5 with hydrochloric acid and the target product 3-amino-5-bromobenzoic acid was precipitated, which was filtered to give 5.8 g (94% yield). The product was analyzed by HPLC/MS with a retention time of 4.67 min, LRMS: m/z 216 (M-1). | [References]
[1] Patent: EP2196465, 2010, A1. Location in patent: Page/Page column 42; 43
[2] Patent: EP2394998, 2011, A1. Location in patent: Page/Page column 22-23
[3] Journal of Medicinal Chemistry, 2016, vol. 59, # 23, p. 10479 - 10497
[4] Justus Liebigs Annalen der Chemie, 1884, vol. 222, p. 169
[5] Organic and Biomolecular Chemistry, 2005, vol. 3, # 20, p. 3757 - 3766 |
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