4-Chlorophenoxyacetic acid - ≥98% , CAS No.122-88-3

CAS: 122-88-3 Cat. No.: C102890 Molecular Weight: 186.59 EC Number: 204-581-3

GRADE & PURITY ≥98%

Synonyms

4-CHLOROPHENOXYACETIC ACID | 4-Chlorophenoxyacetic acid, BioReagent, plant cell culture tested, crystalline | A50588 | Tomato hold | Kyselina 4-chlorfenoxyoctova [Czech] | AC-10963 | Acetic acid, 2-(4-chlorophenoxy)- | AI3-30799 | AKOS000103793 | EINECS 2

Storage

Desiccated,Room temperature

Shipped In

Normal

Overview

4-Chlorophenoxyacetic acid is a herbicide. Degradation of 4-chlorophenoxyacetic acid in aqueous medium by advanced electrochemical oxidation processes, using an undivided cell containing a Pt anode has been reported

4-Chlorophenoxyacetic acid has been used in para-chlorophenoxyacetic acid (p-CPA) residue assay.

4-chlorophenoxy acetic acid (4-CPA), a chlorine derivative of phenoxyacetic acid (PA), is a plant growth regulator used as a herbicide.

Specifications

Synonyms

4-CHLOROPHENOXYACETIC ACID | 4-Chlorophenoxyacetic acid, BioReagent, plant cell culture tested, crystalline | A50588 | Tomato hold | Kyselina 4-chlorfenoxyoctova [Czech] | AC-10963 | Acetic acid, 2-(4-chlorophenoxy)- | AI3-30799 | AKOS000103793 | EINECS 2

Specifications & Purity

≥98%

Biochemical and Physiological Mechanisms

4-Chlorophenoxyacetic acid is a synthetic auxin, that is used to induce parthenocarpic ovary growth on flowers of wild type plants.

Storage

Desiccated, Room temperature

Shipped In

Normal

Purity

≥98%

Names and Identifiers

• Canonical Smiles: C1=CC(=CC=C1OCC(=O)O)Cl
• IUPAC Name: 2-(4-chlorophenoxy)acetic acid
• InChIKey: SODPIMGUZLOIPE-UHFFFAOYSA-N
• INCHI: 1S/C8H7ClO3/c9-6-1-3-7(4-2-6)12-5-8(10)11/h1-4H,5H2,(H,10,11)
• Isomeric SMILES: C1=CC(=CC=C1OCC(=O)O)Cl
• WGK Germany: 1
• Molecular Weight: 186.59
• Reaxy-Rn: 1211804
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=1211804&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Benzenoids
    • Class Benzene and substituted derivatives
      • Subclass Phenoxyacetic acid derivatives

• Kingdom: Organic compounds
• Superclass: Benzenoids
• Class: Benzene and substituted derivatives
• Subclass: Phenoxyacetic acid derivatives
• Intermediate Tree Nodes: Not available
• Direct Parent: Chlorophenoxyacetates
• Alternative Parents: Phenoxy compounds Phenol ethers Chlorobenzenes Alkyl aryl ethers Aryl chlorides Monocarboxylic acids and derivatives Carboxylic acids Organochlorides Organic oxides Hydrocarbon derivatives Carbonyl compounds
• Molecular Framework: Aromatic homomonocyclic compounds
• Substituents: Chlorophenoxyacetate - Phenoxy compound - Phenol ether - Alkyl aryl ether - Chlorobenzene - Halobenzene - Aryl chloride - Aryl halide - Carboxylic acid derivative - Carboxylic acid - Ether - Monocarboxylic acid or derivatives - Organooxygen compound - Organic oxygen compound - Carbonyl group - Organic oxide - Organochloride - Hydrocarbon derivative - Organohalogen compound - Aromatic homomonocyclic compound
• Description: This compound belongs to the class of organic compounds known as chlorophenoxyacetates. These are compounds containing a phenoxyacetate that carries one or more chlorine atoms on the benzene ring.
• External Descriptors: Auxins

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Mechanisms of Action

Chemical and Physical Properties

• Solubility: Solubility in Methanol almost transparency
• Sensitivity: Moisture sensitive
• Melt Point(°C): 155-156°C
• Molecular Weight: 186.590 g/mol
• XLogP3: 2.200
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 186.008 Da
• Monoisotopic Mass: 186.008 Da
• Topological Polar Surface Area: 46.500 Ų
• Heavy Atom Count: 12
• Formal Charge: 0
• Complexity: 152.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 0
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1

References

1. Wanwan Wang, Haiyun Rui, Lei Yu, Nuo Jin, Wan Liu, Chen Guo, Yumeng Cheng, Yonggen Lou.  (2023)  Four-Chlorophenoxyacetic Acid Treatment Induces the Defense Resistance of Rice to White-Backed Planthopper Sogatella furcifera.  INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES,  24  (21): (15722).  [PMID:37958711] [10.3390/ijms242115722]

2. Yifei Zhou, Qiuxiao Wang, Tao Wang, Haixiang Gao.  (2022)  Preparation and properties of multifunctional phenoxyacetate-based ionic liquids and their application in citrus bacteriostatic preservation.  NEW JOURNAL OF CHEMISTRY,  46  (47): (22621-22632).  [PMID:] [10.1039/D2NJ03461A]

3. Hailan Qin, Jingyu Sun, Dongsheng Xia, Haiming Xu, Qilin Yu, Yi Zheng, Yintao Shi.  (2022)  Boosting nonradical process in BiOI/BiOCl heterostructure by interface oxygen vacancies.  CHEMICAL ENGINEERING JOURNAL,      [PMID:] [10.1016/j.cej.2022.134847]

4. Xin-Qiao He, Yuan-Yuan Cui, Cheng-Xiong Yang.  (2021)  Thiol–Yne Click Postsynthesis of a Sulfonate Group-Enriched Magnetic Microporous Organic Network for Efficient Extraction of Benzimidazole Fungicides.  ACS Applied Materials & Interfaces,      [PMID:34374514] [10.1021/acsami.1c11148]

5. Xin-Qiao He, Yuan-Yuan Cui, Xiao-Hui Lin, Cheng-Xiong Yang.  (2021)  Fabrication of polyethyleneimine modified magnetic microporous organic network nanosphere for efficient enrichment of non-steroidal anti-inflammatory drugs from wastewater samples prior to HPLC-UV analysis.  TALANTA,      [PMID:34215105] [10.1016/j.talanta.2021.122471]

6. Yi Xu, Felix Y.H. Kutsanedzie, Md. Mehedi Hassan, Jiaji Zhu, Huanhuan Li, Quansheng Chen.  (2020)  Functionalized hollow Au@Ag nanoflower SERS matrix for pesticide sensing in food.  SENSORS AND ACTUATORS B-CHEMICAL,      [PMID:] [10.1016/j.snb.2020.128718]

7. Qi Wu, Wei Wu, Xue Zhan, Xiudan Hou.  (2020)  Three-dimensional chitosan/graphene oxide aerogel for high-efficiency solid-phase extraction of acidic herbicides in vegetables.  NEW JOURNAL OF CHEMISTRY,  44  (25): (10654-10661).  [PMID:] [10.1039/D0NJ01960G]

8. Xiudan Hou, Hui Yu, Shihai Yan, Junxia Xiao, Min Sun, Wei Wu.  (2020)  Cationic polyelectrolyte/graphene oxide as an efficient sorbent for the extraction and analysis of trace acidic herbicides in vegetables.  JOURNAL OF CHROMATOGRAPHY A,      [PMID:31973930] [10.1016/j.chroma.2020.460884]

9. Yehong Han, Zhiqiang Wang, Jun Jia, Ligai Bai, Haiyan Liu, Shigang Shen, Hongyuan Yan.  (2019)  Newly designed molecularly imprinted 3-aminophenol-glyoxal-urea resin as hydrophilic solid-phase extraction sorbent for specific simultaneous determination of three plant growth regulators in green bell peppers.  FOOD CHEMISTRY,      [PMID:31864185] [10.1016/j.foodchem.2019.125999]

10. Xiaoli Guo, Yanting Li, Bo Zhang, Lingling Yang, Xin Di, Xin Di.  (2019)  Development of dispersive solid phase extraction based on dissolvable Fe3O4-layered double hydroxide for high-performance liquid chromatographic determination of phenoxy acid herbicides in water samples.  MICROCHEMICAL JOURNAL,      [PMID:] [10.1016/j.microc.2019.104443]

11. Shuang Song, Qiuxiang Liu, Jinhui Fang, Weiting Yu.  (2019)  Enhanced electrocatalytic dechlorination of 2,4-dichlorophenoxyacetic acid on in situ prepared Pd-anchored Ni(OH)2 bifunctional electrodes: synergistic effect between H* formation on Ni(OH)2 and dechlorination steps on Pd.  Catalysis Science & Technology,  9  (18): (5130-5141).  [PMID:] [10.1039/C9CY01359H]

12. Shijuan Zhang, Ting Xu, Qian Liu, Jiammin Liu, Fengli Lu, Mingbo Yue, Yanxin Li, Zhiwei Sun, Jinmao You.  (2018)  Cationic gemini surfactant-resorcinol-aldehyde resin and its application in the extraction of endocrine disrupting compounds from food contacting materials.  FOOD CHEMISTRY,      [PMID:30502164] [10.1016/j.foodchem.2018.10.132]

13. Xiudan Hou, Sheng Tang, Xingxiang Guo, Licheng Wang, Xia Liu, Xiaofeng Lu, Yong Guo.  (2018)  Preparation and application of guanidyl-functionalized graphene oxide-grafted silica for efficient extraction of acidic herbicides by Box-Behnken design.  JOURNAL OF CHROMATOGRAPHY A,      [PMID:30150113] [10.1016/j.chroma.2018.08.030]

14. Dong-Xue Zhang, Shuai Qu, Yu-Han Liu, Chen Xu, Xiao-Ying Liu, Hong Kan, Kai Dong, Ying-Ping Wang.  (2024)  Application of three-dimensional material CZIF-8/CS-MS as adsorbents for the determination of plant growth regulators in Schisandra chinensis.  JOURNAL OF CHROMATOGRAPHY A,      [PMID:38359689] [10.1016/j.chroma.2024.464727]

15. Ertai Zhang, Shuyan Guan, Haojun Fan, Yongxin Wang, Hui Yan, Lei Guo, Xuedong Zhai, Carlos A. Martínez Huitle, Jing Ding.  (2024)  Boosting organics degradation via sulfite activation by Fe/Mn@CF composite electrode: Performance and mechanism.  CHEMICAL ENGINEERING JOURNAL,      [PMID:] [10.1016/j.cej.2024.152342]

16. Junying Ge, Jianzhi Dou, Xifeng Yu, Haiyan Song, Yue Sun, Dazhong Shen.  (2024)  Elimination of the interference from non-specific adsorption on molecularly imprinted sensors in capacitive and piezoelectric microgravimetry dual-mode via a differential strategy demonstrated by 2,4-dichlorophenoxyacetic acid determination.  JOURNAL OF ELECTROANALYTICAL CHEMISTRY,      [PMID:] [10.1016/j.jelechem.2024.118542]

17. Fang Wen, Yao Liu, Hehe Yang, Xu Yan, YanDong Zhang, Zhimei Zhong.  (2024)  Preparation, characterization, antioxidant, and antifungal activity of phenyl/indolyl-acyl chitooligosaccharides.  CARBOHYDRATE RESEARCH,      [PMID:38479043] [10.1016/j.carres.2024.109077]

18. Jiaxiao Niu, Yanhui Zhang, Hongbo Li, Xiaoqin Hai, Qingxin Lu, Ruiyu Fu, Tingze Ren, Xiaoli Guo, Xin Di.  (2024)  Switchable deep eutectic solvent as green and efficient media for liquid-phase microextraction of phenoxyacetic acid herbicides in water and food matrices.  FOOD CHEMISTRY,      [PMID:38237292] [10.1016/j.foodchem.2024.138433]

19. Mingwei Wang, Yanan Yuan, Yehong Han, Fengxia Qiao, Jinliang Li, Hongyuan Yan.  (2024)  Two-dimensional hydrophilic imprinted resin–graphene oxide composite for selective extraction and rapid determination of gibberellin traces in licorice samples.  FOOD CHEMISTRY,      [PMID:38733687] [10.1016/j.foodchem.2024.139553]

20. Xin-Qiao He, Yuan-Yuan Cui, Cheng-Xiong Yang.  (2020)  Engineering of amino microporous organic network on zeolitic imidazolate framework-67 derived nitrogen-doped carbon for efficient magnetic extraction of plant growth regulators.  TALANTA,      [PMID:33379085] [10.1016/j.talanta.2020.121876]