Anthranilamide
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| Names | |
|---|---|
| Preferred IUPAC name
2-Aminobenzamide | |
| Systematic IUPAC name
2-Aminobenzamide | |
Other names
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| Identifiers | |
3D model (JSmol) |
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| ChEBI | |
| ChEMBL | |
| ChemSpider | |
| ECHA InfoCard | 100.001.683 |
| EC Number |
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PubChem CID |
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| UNII | |
CompTox Dashboard (EPA) |
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| Properties | |
| C7H8N2O | |
| Molar mass | 136.154 g·mol−1 |
| Appearance | white or yellow solid |
| Odor | odorless |
| Density | 1.17 g/cm3 |
| Melting point | 111 to 113 °C (232 to 235 °F; 384 to 386 K)[1] |
| Boiling point | 300 °C (572 °F; 573 K) |
| 5 g/L (20 °C) | |
| Solubility | very soluble in ethyl acetate soluble in hot water, ethanol slightly soluble in diethyl ether, benzene |
| Hazards | |
| GHS labelling: | |
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| Danger | |
| H318 | |
| P280, P305+P351+P338, P310 | |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Anthranilamide is a chemical compound of the group of amides.
Synthesis and production
[edit]Anthranilamide can be obtained by reacting ammonia, ammonium carbonate and ammonium chloride with isatoic anhydride.[2]
Properties
[edit]Anthranilamide is a flammable, flame-retardant, crystalline, colorless to yellowish, odorless solid that is poorly soluble in water.[1]
Use
[edit]Anthranilamide is used as an acetaldehyde scavenger in PET bottles for water. It is not required for sweet beverages, juices and beer, as the concentration of acetaldehyde in the bevereage is higher than what might migrate from the PET.[3] Anthranilamide is also for non-selective, efficient fluorescence labeling of glycans.[4] It is also used as an intermediate for dyes, pharmaceuticals, blowing agents and other chemicals. In lubricating oils for engines, it prevents copper and magnesium corrosion.[5]
1-Naphthaldehyde [66-77-3] is reacted with anthranilamide to give a 75% yield of U-29409 [31785-60-1]. This antispermatogenic agent also has antiarthritic properties.[6][7]
References
[edit]- 1 2 "Anthranilamid".
- ↑ "Synthesis of Anthranilamide". Thomas’ Chemistry. Archived from the original on 5 August 2018.
- ↑ DLG:>"DLG Expert report 04/2016: Packaging material made from polyethylene terephthalate (PET)". DLG e.V. 28 August 2025. Retrieved 1 September 2025.
- ↑ "Anthranilamide, matrix substance for MALDI-MS, ≥99.0% (HPLC)". Sigma-Aldrich. Retrieved 2018-08-05.
- ↑ "2-Aminobenzamide, 98+%". Retrieved 2018-08-05.
- ↑ Glenn, E. M., Lyster, S. C., Rohloff, N. A. (1 October 1971). "Antiarthritic Effects of the Antispermatogenic Agent 2,3-Dihydro-(1-naphthyl)-4-(1H)-quinazolinone (U-29,409)". Experimental Biology and Medicine. 138 (1): 244–248. doi:10.3181/00379727-138-35871.
- ↑ Ericsson, R. J. (1 June 1971). "Antispermatogenic Properties of 2,3-Dihydro-2-(1-naphthyl)-4(1H)-quinazolinone (U-29,409)". Experimental Biology and Medicine. 137 (2): 532–535. doi:10.3181/00379727-137-35614.
Attribution: translated from de:Anthranilamid in August 2025