| Identification | More | [Name]
5-AMINO-2-BROMOBENZOIC ACID | [CAS]
2840-02-0 | [Synonyms]
5-AMINO-2-BROMOBENZOIC
4-Bromo-3-carboxyaniline
5-AMINO-2-BROMOBENZOIC ACID
2-Bromo-5-aminobenzoic acid
Benzoic acid, 5-amino-2-bromo-
5-Amino-2-bromobenzoic acid 94%
5-AMINO-2-BROMOBENZOIC ACID USP/EP/BP | [Molecular Formula]
C7H6BrNO2 | [MDL Number]
MFCD07368968 | [Molecular Weight]
216.03 | [MOL File]
2840-02-0.mol |
| Chemical Properties | Back Directory | [Melting point ]
171-179 °C | [storage temp. ]
Keep in dark place,Inert atmosphere,Room temperature | [solubility ]
DMSO (Slightly), Methanol (Slightly) | [form ]
Solid | [color ]
Brown | [Water Solubility ]
Slightly soluble in water. | [InChI]
InChI=1S/C7H6BrNO2/c8-6-2-1-4(9)3-5(6)7(10)11/h1-3H,9H2,(H,10,11) | [InChIKey]
FEXDUVBQBNYSQV-UHFFFAOYSA-N | [SMILES]
C(O)(=O)C1=CC(N)=CC=C1Br | [CAS DataBase Reference]
2840-02-0(CAS DataBase Reference) |
| Safety Data | Back Directory | [Hazard Codes ]
Xn | [Risk Statements ]
R22:Harmful if swallowed.
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36/37:Wear suitable protective clothing and gloves . | [RIDADR ]
UN 2811 6.1/PG 3 | [WGK Germany ]
3 | [Hazard Note ]
Harmful | [HS Code ]
2922498590 |
| Hazard Information | Back Directory | [Chemical Properties]
White crystalline solid | [Uses]
It is an important raw material and intermediate used in organic synthesis, pharmaceuticals, agrochemicals and dyestuffs and is also used in medicine. | [reaction suitability]
reaction type: solution phase peptide synthesis | [Synthesis]
General procedure for the synthesis of 5-amino-2-bromobenzoic acid from 3-aminobenzoic acid: 3-aminobenzoic acid (3.00 g, 21.9 mmol) was dissolved in N,N-dimethylformamide (18.0 mL) and cooled to below 5 °C. In another vessel, a solution was prepared by mixing N,N-dimethylformamide (9.00 mL) with N-bromosuccinimide (4.09 g, 23.0 mmol). This solution was slowly added to the cooled 3-aminobenzoic acid solution, keeping the reaction temperature at 5 °C or lower. The reaction mixture was stirred at 5 °C for 1 h. After the reaction mixture was stirred for 1 h, water (60.0 mL) was added and the stirring was continued for 12 h at 5 °C. Upon completion of the reaction, the solid product was collected by filtration, and the filtrate was washed with water (5.00 mL) and dried to give 5-amino-2-bromobenzoic acid (3.68 g, 78% yield). The structure of the product was confirmed by 1H-NMR (400 MHz, DMSO-D6): δ 5.49 (s, 2H), 6.59 (dd, J = 8.5,2.9Hz, 1H), 6.93 (d, J = 2.9Hz, 1H), 7.25 (d, J = 8.5Hz, 1H), 13.04 (s, 1H). | [Purification Methods]
Crystallise the acid from H2O or *C6H6 (m 128o). The acetyl derivative crystallises from H2O (as monohydrate) or absolute EtOH with m 196-197o (anhydrous). [Koopal Rec Trav Chim, Pays Bas 34 148 1915, Bamberger Chem Ber 57 2090 1924, Beilstein 14 H 413, 14 II 245.] | [References]
[1] Patent: US2013/310576, 2013, A1. Location in patent: Paragraph 0151 |
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