1737-62-8

Basic information

• Product Name: 4-FLUOROPHENOXYACETIC ACID HYDRAZIDE
• Synonyms: 4-FLUOROPHENOXYACETIC ACID HYDRAZIDE;AKOS B015229;AKOS AU36-M58;2-(4-FLUOROPHENOXY)ACETIC ACID HYDRAZIDE;2-(4-FLUOROPHENOXY)ACETOHYDRAZIDE;4-Fluorophenoxyacetic acid hydrazide;2-(4-fluorophenoxy)ethanehydrazide
• CAS NO: 1737-62-8
• Molecular Formula: C₈H₉FN₂O₂
• Molecular Weight: 184.17
• Product Categories: Aromatic Hydrazides, Hydrazines, Hydrazones and Oximes;Carbonyl Compounds;Hydrazides;Organic Building Blocks
• Mol File: 1737-62-8.mol
• Article Data: 10

Chemical Properties

• Melting Point: 129-134 °C(lit.)
• Boiling Point: 408.8 °C at 760 mmHg
• Flash Point: 201 °C
• Appearance: /
• Density: 1.281 g/cm³
• Vapor Pressure: 6.84E-07mmHg at 25°C
• Refractive Index: 1.534
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• PKA: 13.33±0.37(Predicted)
• BRN: 2526730
• CAS DataBase Reference: 4-FLUOROPHENOXYACETIC ACID HYDRAZIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-FLUOROPHENOXYACETIC ACID HYDRAZIDE(1737-62-8)
• EPA Substance Registry System: 4-FLUOROPHENOXYACETIC ACID HYDRAZIDE(1737-62-8)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 1737-62-8(Hazardous Substances Data)

Usage

Uses

4-Fluorophenoxyacetic acid hydrazide (4-FH) may be used as one of the reactants in the synthesis of: symmetrical 2,5-bis(2,4-dichloro-5-fuorophenyl)-1,3,4-oxadiazole (DCFPO) [Pd(4-FH)2Cl2] complex.N-trimethylacetyl-N′-(4-fluorophenoxyacetyl)hydrazine

InChI:InChI=1/C8H9FN2O2/c9-6-1-3-7(4-2-6)13-5-8(12)11-10/h1-4H,5,10H2,(H,11,12)

Upstream product

• 371-41-5 4-Fluorophenol 
• 105-39-5 chloroacetic acid ethyl ester 
• 777-87-7 ethyl 2-(4-fuorophenoxy)acetate 
• 55444-93-4 (4-fluorophenoxy)acetic acid methyl ester 
• 405-79-8 2-(4-fluorophenoxy)ethanoic acid 

Downstream Products

• 1489287-71-9 1-(4-fluorophenoxyacetyl)-4-(4-phenylbenzyl)-thiosemicarbazide 

Relevant articles and documents

Expedient discovery for novel antifungal leads: 1,3,4-Oxadiazole derivatives bearing a quinazolin-4(3H)-one fragment

Developing novel fungicide candidates are intensively promoted by the rapid emergences of resistant fungi that outbreak on agricultural production. Aiming to discovery novel antifungal leads, a series of 1,3,4-oxadiazole derivatives bearing a quinazolin-4(3H)-one fragment were constructed for evaluating their inhibition effects against phytopathogenic fungi in vitro and in vivo. Systematically structural optimizations generated the bioactive molecule I32 that was identified as a promising inhibitor against Rhizoctonia solani with the in vivo preventative effect of 58.63% at 200 μg/mL. The observations that were captured by scanning electron microscopy and transmission electron microscopy demonstrated that the bioactive molecule I32 could induce the sprawling growth of hyphae, the local shrinkage and rupture on hyphal surfaces, the extreme swelling of vacuoles, the striking distortions on cell walls, and the reduction of mitochondria numbers. The above results provided an indispensable complement for the discovery of antifungal lead bearing a quinazolin-4(3H)-one and 1,3,4-oxadiazole fragment.

Synthesis, Nematicidal Activity, and 3D-QSAR of Novel 1,3,4-Oxadiazole/ Thiadiazole Thioether Derivatives

Forty one novel 1,3,4-oxadiazole/thiadiazole thioether derivatives containing phenoxy moiety were designed and synthesized. Bioassay demonstrated that some of them showed remarkable activities against Tylenchulus semipenetrans in vitro and in vivo. Compounds 20, 21, 35 and 39 showed excellent lethal activities after treatment for 48?h in vitro, with LC50 values of 13.4?±?1.8, 11.7?±?2.5, 13.7?±?2.4 and 13.3?±?1.1?mg·L–1, respectively, which were obviously superior to fosthiazate (49.1?±?2.8?mg·L–1) and avermectin (26.6?±?2.3?mg·L–1). Compound 21 can effectively control the citrus nematode disease caused by T. semipenetrans at 200?mg·L–1 in vivo with (68?±?3)% inhibitory effect, which was even better than that of avermectin ((63?±?2)%). The CoMFA and CoMSIA models of three-dimensional quantitative structure-activity relationships (3D-QSARs) were established. The compound 33 was designed based on the 3D-QSAR models with more vigorous nematicidal activities in vitro (LC50?=?9.8?±?1.4?mg·L–1) and in vivo ((70?±?5)%). These results demonstrated that compound 33 can be considered as a potential nematicide.

Synthesis and antibacterial evaluation of new sulfone derivatives containing 2-aroxymethyl-1,3,4-oxadiazole/thiadiazole moiety

Sulfones are one of the most important classes of agricultural fungicides. To discover new lead compounds with high antibacterial activity, a series of new sulfone derivatives were designed and synthesized by introducing the aroxymethyl moiety into the scaffold of 1,3,4-oxadiazole/thiadiazole sulfones. Antibacterial activities against three phytopathogens (Xanthomonas oryzae pv. oryzae, Ralstonia solanacearum, Xanthomonas axonopodis pv. citri.) were assayed in vitro. As compared to the control of commercial fungicides and some reported sulfone fungicides, seven compounds 5I-1-5I-7 exerted remarkably higher activities with EC50 values ranging from 0.45-1.86 μg/mL against X. oryzae and 1.97-20.15 μg/mL against R. solanacearum. Exhilaratingly, 5I-1, 5I-2 and 5I-4 displayed significant in vivo activity against X. oryzae with protective effect of 90.4%, 77.7%, and 81.1% at 200 μg/mL, respectively, much higher than that exhibited by Bismerthiazol (25.6%) and Thiadiazole-copper (32.0%). And the differential phytotoxicity of active derivatives was preliminarily checked. The results demonstrated that derivative of 2-aroxymethyl-1,3,4-oxadiazole/thiadiazole sulfone can serve as potential alternative bactericides for the management of plant bacterial diseases.