|
|
| | 2,3,5-Triiodobenzoic acid Basic information |
| Product Name: | 2,3,5-Triiodobenzoic acid | | Synonyms: | 2,3,5-Tiba;2,3,5-TRIIODOBENZOIC ACID, TECH.;2,3,5-TRIIODOBENZOIC ACID PESTANAL, 250;2,3,5-TRIIODOBENZOIC ACID PLANT CELL*CUL TURE TESTED;Triiodobenzoicacid,98%;2.3.5-TriiodobenzoicAcidGr;2,3,5-TriiodobenzoicAcidGr(Tiba);1,3,5-TRIIODOBENZOIC ACID | | CAS: | 88-82-4 | | MF: | C7H3I3O2 | | MW: | 499.81 | | EINECS: | 201-859-6 | | Product Categories: | Pesticide intermediates;Auxins;Biochemistry;Plant Growth Regulators;Aromatic Carboxylic Acids, Amides, Anilides, Anhydrides & Salts;Benzoic acid;Acids & Esters;Iodine Compounds | | Mol File: | 88-82-4.mol |  |
| | 2,3,5-Triiodobenzoic acid Chemical Properties |
| Melting point | 220-222 °C (lit.) | | Boiling point | 456.7±45.0 °C(Predicted) | | density | 2.7985 (estimate) | | storage temp. | -20°C | | solubility | methanol: soluble5%, hazy, orange to very deep orange (light) | | pka | 2.16±0.10(Predicted) | | form | Solid | | color | Light brown | | Water Solubility | Insoluble in water. | | Sensitive | Light Sensitive | | BRN | 1955088 | | InChI | InChI=1S/C7H3I3O2/c8-3-1-4(7(11)12)6(10)5(9)2-3/h1-2H,(H,11,12) | | InChIKey | ZMZGFLUUZLELNE-UHFFFAOYSA-N | | SMILES | C(O)(=O)C1=CC(I)=CC(I)=C1I | | CAS DataBase Reference | 88-82-4(CAS DataBase Reference) | | NIST Chemistry Reference | 2,3,5-Triiodobenzoic acid(88-82-4) | | EPA Substance Registry System | 2,3,5-Triiodobenzoic acid (88-82-4) |
| | 2,3,5-Triiodobenzoic acid Usage And Synthesis |
| Description | 2,3,5-tri-iodobenzoic acid is an obsolete anti-auxin plant growth regulator. Litrtle information is available regarding its environmental fate or its toxicity to biodiversity. It has a moderate oral mammalian toxicity. | | Chemical Properties | beige powder | | Uses | 2,3,5-Triiodobenzoic Acid is a polar auxin transport inhibitor that inhibits and promotes endoreduplication in hypocotyls and cotyledons. | | Definition | ChEBI: 2,3,5-triiodobenzoic acid is a member of the class of benzoic acids that is benzoic acid in which the hydrogens at positions 2, 3 and 5 are replaced by iodine atoms. It is an auxin polar transport inhibitor. It has a role as a member of antiauxins. It is an organoiodine compound and a member of benzoic acids. | | Application | The 2,3,5-triiodobenzoic acid (TIBA) is a contrast agent used to improve the visualization of pathological tissues using X-ray techniques. 2, 3, 5-Triiodobenzoic Acid (syn: TIBA) is used as a plant growth regulator, defoliant, and agricultural herbicide. Several investigators have shown TIBA to be successful in causing the retention of buds, blooms, and pods of soybeans. Virtually no results have been reported on using TIBA to retain the 30 to 40% flower shed that occurs with cotton[1-2]. | | Production Methods | Commercial production of 2,3,5 triiodobenzoic acid (TIBA) is based on electrophilic iodination of a benzoic acid precursor, using controlled multi step halogenation to introduce iodine at the 2, 3, and 5 positions. Industry descriptions note that manufacturers typically start from benzoic acid or a suitably substituted benzoic acid, then carry out sequential iodination with iodine or iodine releasing reagents in the presence of oxidants or catalysts to drive substitution efficiently. Modern accounts emphasise optimised catalytic systems and reaction conditions that improve yield and reduce by products, reflecting advances in iodination technology. After iodination, the crude product is purified by crystallisation and drying to obtain technical grade TIBA. | | Biochem/physiol Actions | 2,3,5-Triiodobenzoic acid (TIBA) inhibits the translocation of indole-3-acetic acid transport.TIBA inhibits the colonization of the main root cortex by Laccaria bicolor S238 N and the formation of the Hartig net. | | Mechanism of action | Auxin-transport inhibitor | | Toxicology | 2,3,5-Triiodobenzoic acid induces physiological complications like increase in oxygen reactive species (ROS), and consequently, contrast-induced nephropathies[1].
| | References | [1] Jéssica Sodré Silva de Abreu, Janaína Fernandes. "The contrast agent 2,3,5-triiodobenzoic acid (TIBA) induces cell death in tumor cells through the generation of reactive oxygen species." Molecular Biology Reports 48.6 (2021): 5199–5207.
[2] Freytag, et al. "Effect of Multiple Applications of 2,3,5-Triiodobenzoic Acid (TIBA) on Yields of Stormproof and Nonstormproof Cotton." Agronomy Journal 65.4(1973):610-610. | | Pesticide Type | Plant Growth Regulator; Herbicide |
| | 2,3,5-Triiodobenzoic acid Preparation Products And Raw materials |
|