ChemicalBook Product Catalog Organic Chemistry Hydrocarbons and derivatives Hydrocarbon nitrification 2-Chloro-4-fluoro-5-nitrophenol

2-Chloro-4-fluoro-5-nitrophenol

Product Name2-Chloro-4-fluoro-5-nitrophenol
CAS84478-75-1
MFC6H3ClFNO3
MW191.54
EINECS671-719-0
MOL File84478-75-1.mol

Chemical Properties

Melting point	105-108°C
Boiling point	298.7±40.0 °C(Predicted)
Density	1.653±0.06 g/cm3(Predicted)
storage temp.	Inert atmosphere,Room Temperature
solubility	soluble in Methanol
form	powder to crystal
pka	6.58±0.24(Predicted)
color	Light orange to Yellow to Green
InChI	InChI=1S/C6H3ClFNO3/c7-3-1-4(8)5(9(11)12)2-6(3)10/h1-2,10H
InChIKey	NAWVMCKMQMJQMF-UHFFFAOYSA-N
SMILES	C1(O)=CC([N+]([O-])=O)=C(F)C=C1Cl
CAS DataBase Reference	84478-75-1(CAS DataBase Reference)

Safety Information

Hazard Codes	Xi
Risk Statements	36/37/38
Safety Statements	26-36/37/39
HazardClass	IRRITANT
HS Code	2908990000

Usage And Synthesis

Uses

2-Chloro-4-fluoro-5-nitrophenol is a multi-substituted nitrophenol compound, primarily used as a key intermediate in the production of herbicides. It can be utilised in the synthesis of PPO-inhibiting pyrimidinedione derivatives, a class of herbicides suitable for use on cotton. It is also used in the synthesis of 5-(1-amino-4-phenoxyadibutyl)barbituric acid derivatives containing an enylaminedione structural unit, which exhibit herbicidal activity[6-7].

Synthesis

2-chloro-4-fluoro-5-nitrophenyl methyl carbonate

84478-89-7

84478-75-1

2-Chloro-4-fluoro-5-nitrophenyl methyl carbonate (120 g, 0.48 mol) was mixed with sodium hydroxide (22.7 g, 0.57 mol) in water (300 mL) and the reaction was carried out at reflux for 4 hrs. Upon completion of the reaction, the insoluble solids were removed by filtration and the filtrate was acidified with dilute hydrochloric acid to pH < 7. Subsequently, the precipitated solid product was collected by filtration, washed with water and dried to afford 2-chloro-4-fluoro-5-nitrophenol (90 g, 98% yield). The product was characterized by 1H NMR (400 MHz, DMSO-d6): δ 11.18 (s, 1H), 8.10 (d, J=10.4 Hz, 1H), 7.62 (d, J=7.2 Hz, 1H); mass spectrum (ESI) m/z: 192.1 ([M+H]+).

References

[1] Patent: US2008/90856, 2008, A1. Location in patent: Page/Page column 38
[2] Patent: WO2010/51373, 2010, A1. Location in patent: Page/Page column 75
[3] Patent: WO2013/36232, 2013, A2. Location in patent: Paragraph 00252
[4] Organic Process Research and Development, 2014, vol. 18, # 1, p. 122 - 134
[5] Patent: US2008/234267, 2008, A1. Location in patent: Page/Page column 15
[6] Wu, X., Song, C., Zhu, Y., Wang, X., Zhang, H., Hu, D., Song, R. (2023). Design and synthesis of novel PPO-inhibiting pyrimidinedione derivatives safed towards cotton. Pesticide Biochemistry and Physiology, 193, 105449. https://doi.org/10.1016/j.pestbp.2023.105449
[7] Chen, K., Wang, S., Fu, S., Zhang, Y., Gao, W., Liu, J., Liu, R., Lei, K. (2025). Design, Synthesis and Herbicidal Activity of 5-(1-Amino-4-phenoxybutylidene)barbituric Acid Derivatives Containing an Enamino Diketone Motif. Molecules, 30(16), 3445. https://doi.org/10.3390/molecules30163445

2-Chloro-4-fluoro-5-nitrophenol

Chemical Properties

Safety Information

Usage And Synthesis

Preparation Products And Raw materials

2-Chloro-4-fluoro-5-nitrophenol Supplier

2-Chloro-4-fluoro-5-nitrophenol manufacturers

Related Product Information