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| | 2-Amino-5-bromobenzoic acid Basic information | | Synthesis |
| | 2-Amino-5-bromobenzoic acid Chemical Properties |
| 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 | | CAS DataBase Reference | 5794-88-7(CAS DataBase Reference) | | NIST Chemistry Reference | 2-Amino-5-bromobenzoic acid(5794-88-7) |
| Hazard Codes | Xn | | Risk Statements | 22-36/37 | | Safety Statements | 26-38-36/37 | | RIDADR | UN 2811 6.1/PG 3 | | WGK Germany | 3 | | RTECS | CB2557670 | | Hazard Note | Harmful | | PackingGroup | 6.1/PG 3 | | HS Code | 29224999 |
| | 2-Amino-5-bromobenzoic acid Usage And Synthesis |
| Synthesis | 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. IR (suspension in nujol, cm−1 ): 3497, 3383, 1675, 1616, 1587, 1548, 1423, 1377, 1316, 1292, 1239, 1160, 1127, 812, 748, 691. | | Chemical Properties | slight yellow to white powder | | Uses | 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.
| | Uses | 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. |
| | 2-Amino-5-bromobenzoic acid Preparation Products And Raw materials |
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