2-Amino-5-bromobenzoic acid
Synonym(s):5-Bromoanthranilic acid
- CAS NO.:5794-88-7
- Empirical Formula: C7H6BrNO2
- Molecular Weight: 216.03
- MDL number: MFCD00007823
- EINECS: 227-338-3
- SAFETY DATA SHEET (SDS)
- Update Date: 2024-01-25 16:49:20
What is 2-Amino-5-bromobenzoic acid?
Chemical properties
slight yellow to white powder
Physical properties
2-Amino-5-bromobenzoic acid has 17 atoms, meaning 45 vibrational modes in three main parts: Carboxyl group, amine group, and benzene. The molecule's most mechanically active parts are the carboxyl and amine groups. They exhibit rocking, swinging, and every kind of mechanical motion beside H immigrations between each other. For this reason, the molecule is not a simple carboxylic acid nor a primary amine[1].
The Uses of 2-Amino-5-bromobenzoic acid
2-Amino-5-bromobenzoic acid is a brominated derivative of Antharilinic Acid (A679222). 2-Amino-5-bromobenzoic acid displays plant growth-regulator activity. 2-Amino-5-bromobenzoic acid is used in the preparation of hepatitis C virus NS5b RNA polymerase inhibitors.
The Uses of 2-Amino-5-bromobenzoic acid
It is used in the preparation of hepatitis C virus NS5b RNA polymerase inhibitors. Also used in the determination of cobalt, copper, nickel, and zinc.
Preparation
2-Amino-5-bromobenzoic acid is synthesized from o-aminobenzoic acid by bromination.
Synthesis of 2-amino-5-bromobenzoic acid (4c, CAS: 5794-88-7) and 2-amino3,5-dibromobenzoic acid (4d, CAS: 609-85-8): A solution of bromine (7.2 g, 2 mL, 40 mmol) in 47 mL glacial acetic acid was added dropwise to sodium 2-aminobenzoate (6.4 g, 40 mmol) in 32 mL of glacial acetic acid at 15 °С and the mixture was stirred for 1 h at the same temperature. The product was filtered off, washed with benzene and dried in the dark. The bromobenzoic acids containing mixture (0.5 g) was added to 10 mL of boiling water followed by the addition of 1.3 mL of concentrated hydrochloric acid and hot filtration under vacuum. The insoluble material contained 2-amino-3,5-dibromobenzoic acid, whereas 2- amino-5-bromobenzoic acid precipitated upon cooling of the filtrate.
2-Amino-5-bromobenzoic acid (4c) IR (suspension in nujol, cm?1 ): 3497, 3383, 1675, 1616, 1587, 1548, 1423, 1377, 1316, 1292, 1239, 1160, 1127, 812, 748, 691.
References
[1] Kunduracioglu, Ahmet . "Tautomeric Forms of 2–Amino–5–Bromobenzoic Acid: A DFT Study for Structural and Molecular Orbital Analysis." (2021).
Properties of 2-Amino-5-bromobenzoic acid
Melting point: | 213-215 °C (lit.) |
Boiling point: | 265.51°C (rough estimate) |
Density | 1.6841 (rough estimate) |
refractive index | 1.6120 (estimate) |
storage temp. | Keep in dark place,Inert atmosphere,Room temperature |
solubility | Soluble in methanol and dimethyl sulfoxide. |
form | Powder |
pka | 4.55±0.10(Predicted) |
color | Beige |
Sensitive | Light Sensitive |
Merck | 14,1405 |
BRN | 639028 |
InChI | InChI=1S/C7H6BrNO2/c8-4-1-2-6(9)5(3-4)7(10)11/h1-3H,9H2,(H,10,11) |
CAS DataBase Reference | 5794-88-7(CAS DataBase Reference) |
NIST Chemistry Reference | 2-Amino-5-bromobenzoic acid(5794-88-7) |
Safety information for 2-Amino-5-bromobenzoic acid
Signal word | Danger |
Pictogram(s) |
Skull and Crossbones Acute Toxicity GHS06 |
GHS Hazard Statements |
H301:Acute toxicity,oral H315:Skin corrosion/irritation H319:Serious eye damage/eye irritation H335:Specific target organ toxicity, single exposure;Respiratory tract irritation |
Precautionary Statement Codes |
P261:Avoid breathing dust/fume/gas/mist/vapours/spray. P264:Wash hands thoroughly after handling. P264:Wash skin thouroughly after handling. P270:Do not eat, drink or smoke when using this product. P301+P310:IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician. P302+P352:IF ON SKIN: wash with plenty of soap and water. P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing. |
Computed Descriptors for 2-Amino-5-bromobenzoic acid
InChIKey | CUKXRHLWPSBCTI-UHFFFAOYSA-N |
SMILES | C(O)(=O)C1=CC(Br)=CC=C1N |
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