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| | Methyl 4-amino-3-bromobenzoate Basic information | | Uses |
| | Methyl 4-amino-3-bromobenzoate Chemical Properties |
| Melting point | 105-109 °C | | Boiling point | 334.2±22.0 °C(Predicted) | | density | 1.6270 (rough estimate) | | refractive index | 1.6120 (estimate) | | storage temp. | under inert gas (nitrogen or Argon) at 2–8 °C | | pka | 0.41±0.10(Predicted) | | form | Crystalline Powder | | color | Brown | | InChI | InChI=1S/C8H8BrNO2/c1-12-8(11)5-2-3-7(10)6(9)4-5/h2-4H,10H2,1H3 | | InChIKey | AIUWAOALZYWQBX-UHFFFAOYSA-N | | SMILES | C(OC)(=O)C1=CC=C(N)C(Br)=C1 | | CAS DataBase Reference | 106896-49-5(CAS DataBase Reference) |
| Hazard Codes | Xn,Xi | | Risk Statements | 22-36-36/37/38 | | Safety Statements | 26-36/37-37/39 | | RIDADR | UN 2811 6.1/PG 3 | | WGK Germany | 3 | | Hazard Note | Irritant | | HS Code | 29163100 | | Storage Class | 6.1C - Combustible acute toxic Cat.3
toxic compounds or compounds which causing chronic effects | | Hazard Classifications | Acute Tox. 3 Oral
Eye Irrit. 2 |
| | Methyl 4-amino-3-bromobenzoate Usage And Synthesis |
| Uses | Methyl 4-amino-3-bromobenzoate is a carboxylic acid derivative and a commonly used pharmaceutical and chemical intermediate. | | Chemical Properties | brown crystalline powder | | Synthesis | General procedure for the preparation of methyl 4-amino-3-bromobenzoate: methyl 4-aminobenzoate (17 g, 0.1 mol) was dissolved in chloroform (250 mL). N-bromosuccinimide (20 g, 0.1 mol) was added slowly at 0 °C and the reaction mixture was stirred continuously for 3 h at this temperature. After completion of the reaction, the solvent was removed by distillation. Ethyl acetate (100 mL) was added to the residue for dissolution. Subsequently, the mixture was washed with aqueous sodium chloride to remove water-soluble impurities. The organic layer was separated and dried with anhydrous magnesium sulfate. After filtration, the product was purified by recrystallization from hexane to give the final methyl 4-amino-3-bromobenzoate (24.3 g, 93% yield). [1368] NMR data: 1H-NMR (CDCl3) δ 8.11 (1H, d), 7.79-7.77 (1H, m), 6.72 (1H, d), 4.51 (2H, br s), 3.85 (3H, s). | | References | [1] Journal of Organic Chemistry, 2014, vol. 79, # 21, p. 10410 - 10416
[2] Patent: WO2010/93191, 2010, A2. Location in patent: Paragraph 1365-1368
[3] Organic Letters, 2015, vol. 17, # 12, p. 2886 - 2889
[4] European Journal of Medicinal Chemistry, 2011, vol. 46, # 7, p. 2930 - 2936
[5] Synthesis (Germany), 2013, vol. 45, # 11, p. 1497 - 1504 |
| | Methyl 4-amino-3-bromobenzoate Preparation Products And Raw materials |
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