1798-11-4

Basic information

• Product Name: 4-Nitrophenoxyacetic acid
• Synonyms: (4-nitrophenoxy)-aceticaci;ba2690;p-nitrophenoxy-aceticaci;P-NITROPHENOXYACETIC ACID;RARECHEM AL BO 0661;TIMTEC-BB SBB000363;ART-CHEM-BB B000976;4-NITROPHENOXYACETIC ACID
• CAS NO: 1798-11-4
• Molecular Formula: C₈H₇NO₅
• Molecular Weight: 197.14
• EINECS: 217-283-3
• Product Categories: Phenoxyacetic Acids and Alcohols (substituted);Organic acids
• Mol File: 1798-11-4.mol
• Article Data: 52

Chemical Properties

• Melting Point: 182-188 °C
• Boiling Point: 334.23°C (rough estimate)
• Flash Point: 195.6 °C
• Appearance: yellow-beige crystalline powder
• Density: 1.5023 (rough estimate)
• Vapor Pressure: 4.12E-07mmHg at 25°C
• Refractive Index: 1.5700 (estimate)
• Solubility: soluble in Methanol
• PKA: pK1:2.893 (25°C)
• CAS DataBase Reference: 4-Nitrophenoxyacetic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Nitrophenoxyacetic acid(1798-11-4)
• EPA Substance Registry System: 4-Nitrophenoxyacetic acid(1798-11-4)

Safety Data

• Hazard Codes: Xn,Xi
• Statements: 44-36/37/38-22
• Safety Statements: 37/39-26
• RTECS: AJ1100000
• HazardClass: IRRITANT
• Hazardous Substances Data: 1798-11-4(Hazardous Substances Data)

Usage

Description

4-Nitrophenoxyacetic acid is a chemical compound that serves as a metabolite of butyl p-nitrophenyl ether. It is characterized by its yellow-beige crystalline powder appearance and possesses plant growth regulatory activity, making it a compound of interest in the agricultural and chemical industries.

Uses

Used in Plant Growth Regulation:
4-Nitrophenoxyacetic acid is used as a plant growth regulator for its ability to influence and control the growth and development of plants. This application is particularly relevant in the agricultural industry, where it can be employed to enhance crop yields, improve resistance to environmental stressors, and regulate the timing of growth stages.
Used in Chemical Synthesis:
In the chemical industry, 4-Nitrophenoxyacetic acid can be utilized as an intermediate in the synthesis of various compounds, taking advantage of its unique chemical properties and reactivity. This application allows for the creation of a wide range of products, from pharmaceuticals to specialty chemicals, that can benefit from the compound's specific characteristics.
Used in Research and Development:
Due to its plant growth regulatory activity, 4-Nitrophenoxyacetic acid is also used in research and development settings to study the underlying mechanisms of plant growth and development. This can lead to a better understanding of plant biology and the potential for developing new strategies to improve crop production and resilience.
Used in Environmental Applications:
4-Nitrophenoxyacetic acid may also find use in environmental applications, such as in the remediation of contaminated soils or water bodies. Its plant growth regulatory properties could be harnessed to stimulate the growth of specific plant species that can help in the removal of pollutants or the restoration of damaged ecosystems.

Safety Profile

Moderately toxic by intraperitoneal route. When heated to decomposition it emits toxic fumes of NOx.

InChI:InChI=1/C8H7NO5/c10-8(11)5-14-7-3-1-6(2-4-7)9(12)13/h1-4H,5H2,(H,10,11)

Upstream product

• 28341-54-0 4-(4-nitrophenoxy)butanoic acid 
• 105-39-5 chloroacetic acid ethyl ester 
• 19076-89-2 ethyl 4-nitrophenoxyacetate 
• 3926-62-3 sodium monochloroacetic acid 
• 2272-12-0 (4-nitro-phenoxy)-malonic acid 
• 100-02-7 4-nitro-phenol 
• 824-78-2 4-nitrophenol sodium salt 
• 20768-14-3 (4-nitrophenoxy)acetic acid tert-butyl ester 
• 79-11-8 chloroacetic acid 
• 79-08-3 bromoacetic acid 
• 19786-48-2 methyl 2-(4-nitrophenoxy)acetate 
• 122-59-8 2-phenoxyacetic acid 
• 105-36-2 ethyl bromoacetate 
• 139024-36-5 1-Imidazol-1-yl-2-(4-nitro-phenoxy)-ethanone 

Downstream Products

• 19076-89-2 ethyl 4-nitrophenoxyacetate 
• 443902-49-6 3'-Nitro-<2-(4-nitrophenoxy)>acetanilid 
• 106272-93-9 (4-nitro-phenoxy)-acetic acid cyclohexyl ester 
• 100537-61-9 2-((4-nitrophenoxy)methyl)benzothiazole 
• 105377-54-6 (4-Nitro-phenoxy)-acetic acid; compound with 2-[bis-(2-hydroxy-ethyl)-amino]-ethanol 
• 130837-06-8 2-(4-Nitrophenoxy)methyl-1,4-naphthoquinone 
• 5513-42-8 <2-Chlormethyl-4-nitro-phenoxy>-essigsaeure 
• 20916-16-9 N-benzyl-2-(4-nitrophenoxy)acetamide 
• 85430-03-1 4-dimethylamino-4'-nitro-2-phenylsulfonyldiphenylamine 

Relevant articles and documents

Application of magnetic Fe3O4 nanoparticles as a reusable heterogeneous catalyst in the synthesis of β-lactams containing amino groups

Herein we report the catalytic activity of magnetic Fe3O4 nanoparticles to promote the reduction of β-lactams containing nitroaryl groups to β-lactams containing aminoaryl groups in ethanol. The catalytic experimental conditions have

Design and synthesis of α-phenoxy-N-sulfonylphenyl acetamides as Trypanosoma brucei Leucyl-tRNA synthetase inhibitors

Human African trypanosomiasis (HAT), caused by the parasitic protozoa Trypanosoma brucei, is one of the fatal diseases in tropical areas and current medicines are insufficient. Thus, development of new drugs for HAT is urgently needed. Leucyl-tRNA synthetase (LeuRS), a recently clinically validated antimicrobial target, is an attractive target for development of antitrypanosomal drugs. In this work, we report a series of α-phenoxy-N-sulfonylphenyl acetamides as T. brucei LeuRS inhibitors. The most potent compound 28g showed an IC50 of 0.70 μM which was 250-fold more potent than the starting hit compound 1. The structure-activity relationship was also discussed. These acetamides provided a new scaffold and lead compounds for the further development of clinically useful antitrypanosomal agents.

Structure-based modification of carbonyl-diphenylpyrimidines (Car-DPPYs) as a novel focal adhesion kinase (FAK) inhibitor against various stubborn cancer cells

A family of carbonyl-substituted diphenylpyrimidine derivatives (Car-DPPYs) with strong activity against focal adhesion kinase (FAK), were described in this manuscript. Among them, compounds 7a (IC50 = 5.17 nM) and 7f (IC50 = 2.58 nM) displayed equal anti-FAK enzymatic activity to the lead compound TAE226 (6.79 nM). In particular, compound 7a also exhibited strong antiproliferative activity against several stubborn cancer cells, including AsPC-1 cells (IC50 = 0.105 μM), BxPC-3 cells (IC50 = 0.090 μM), and MCF-7/ADR cells (IC50 = 0.59 μM). Additionally, compound 7a also showed great antitumor efficacy in vivo via aAsPC-1 cancer Xenograft mouse model. The preliminary mechanism study by Western blot analysis revealed that 7a repressed FAK phosphorylation in AsPC cancer cells. Taken together, the results indicate that compound 7a may serve as a promising preclinical candidate for treatment of stubborn cancers.