Phenoxyacetic acid
In this article, we will delve into the fascinating world of Phenoxyacetic acid, a topic that has aroused the interest and curiosity of countless people over time. Phenoxyacetic acid is an element present in various facets of daily life, from history to science, through art and culture. Along these lines, we will explore the different aspects that make Phenoxyacetic acid a topic worthy of being addressed and analyzed in detail. From its origins to its impact on today's society, we will immerse ourselves in a journey of discovery and knowledge that will allow us to better understand the importance and relevance of Phenoxyacetic acid in the world around us.
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| Names | |
|---|---|
| Preferred IUPAC name
Phenoxyacetic acid | |
| Identifiers | |
3D model (JSmol)
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| 907949 | |
| ChEBI | |
| ChEMBL | |
| ChemSpider | |
| ECHA InfoCard | 100.004.143 |
| EC Number |
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| 142730 | |
| KEGG | |
PubChem CID
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| UNII | |
| UN number | 3347 |
CompTox Dashboard (EPA)
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| Properties | |
| C8H8O3 | |
| Molar mass | 152.15 g/mol |
| Appearance | White solid or tan powder |
| Odor | Sweet and sour |
| Melting point | 98–99 °C (208–210 °F; 371–372 K) |
| log P | 1.48 |
| Acidity (pKa) | 3.7 |
| Hazards | |
| GHS labelling: | |
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| Warning | |
| H302, H315, H319, H335 | |
| P261, P264, P270, P271, P280, P301+P312, P302+P352, P304+P340, P305+P351+P338, P312, P321, P330, P332+P313, P337+P313, P362, P403+P233, P405, P501 | |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa).
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Phenoxyacetic acid, POA, is a white solid with the formula of C8H8O3.[1][2] Although not itself usefully active as an herbicide, it forms the part-structure of many phenoxy herbicide derivatives including MCPA and 2,4-D.
Structure and synthesis
Phenoxyacetic acid is an O-phenyl derivative of glycolic acid. It is both a monocarboxylic acid and an aryl ether. Its preparation from sodium phenolate and sodium chloroacetate in hot water was first reported in 1880.[3]
- 1) C6H5O−Na+ + ClCH2COO−Na+ → C6H5OCH2COO−Na+ + NaCl
- 2) C6H5OCH2COO−Na+ + HCl → C6H5OCH2COOH + NaCl
The phenolate anion reacts via nucleophilic attack on the methylene carbon of the chloroacetic acid, forming an ether bond.
Properties
Phenoxyacetic acid is a white or clear crystalline compound at room temperature.[2] When impure, it can appear to be a light tan to brown. The compound has a solubility in water of 12 g/L and is highly soluble in organic solvents including ethanol, diethyl ether and benzene. Phenoxyacetic acid is a weak acid and weak base with a pKa of 3.7.[1][4]
Uses
Phenoxyacetic acid has found minor uses as a food additive and perfume component and is categorised as "generally recognised as safe" in these applications.[5][6]
References
- ^ a b Wishart, David S.; Guo, An Chi; Oler, Eponine; Wang, Fel; Anjum, Afia; Peters, Harrison; Dizon, Raynard; Sayeeda, Zinat; Tian, Siyang; Lee, Brian L.; Berjanskii, Mark; Mah, Robert; Yamamoto, Mai; Jovel Castillo, Juan; Torres Calzada, Claudia; Hiebert Giesbrecht, Mickel; Lui, Vicki W.; Varshavi, Dorna; Varshavi, Dorsa; Allen, Dana; Arndt, David; Khetarpal, Nitya; Sivakumaran, Aadhavya; Harford, Karxena; Sanford, Selena; Yee, Kristen; Cao, Xuan; Budinsky, Zachary; Liigand, Jaanus; Zhang, Lun; Zheng, Jiamin; Mandal, Rupasri; Karu, Naama; Dambrova, Maija; Schiöth, Helgi B.; Gautam, Vasuk. "Showing metabocard for Phenoxyacetic acid (HMDB0031609)". Human Metabolome Database, HMDB. 5.0.
- ^ a b "Phenoxyacetic acid". Sigmaaldrich. 2021. Retrieved 2021-02-17.
- ^ "Phenoxyacetic Acid". Journal of the Chemical Society, Abstracts. 38: 318–319. 1880. doi:10.1039/CA8803800307.
- ^ Freed, V. H.; Chiou, C. T.; Schmedding, D.; Kohnert, R. (1979). "Some physical factors in toxicological assessment tests". Environmental Health Perspectives. 30: 75–80. Bibcode:1979EnvHP..30...75F. doi:10.1289/ehp.793075. PMC 1637710. PMID 446460.
- ^ "Phenoxyacetic acid". The Good Scents Company. Retrieved 2021-02-17.
- ^ "Opinion of the Scientific Panel on food additives, flavourings, processing aids and materials in contact with food (AFC) related to Flavouring Group Evaluation 23 (FGE.23): Aliphatic, alicyclic and aromatic ethers including anisole derivatives from chemical groups 15, 16 and 26 (Commission Regulation (EC) No 1565/2000 of 18 July 2000". EFSA Journal. 5 (5). 2007. doi:10.2903/j.efsa.2007.417.