16738-00-4

Basic information

• Product Name: (4-BROMO-PHENOXY)-ACETIC ACID HYDRAZIDE
• Synonyms: 2-(4-bromophenoxy)ethanehydrazide
• CAS NO: 16738-00-4
• Molecular Formula: C₈H₉BrN₂O₂
• Molecular Weight: 245.08
• Mol File: 16738-00-4.mol
• Article Data: 19

Chemical Properties

• Melting Point: 171-172 °C(Solv: ethanol (64-17-5))
• Boiling Point: 444.7°C at 760 mmHg
• Flash Point: 222.7°C
• Appearance: /
• Density: 1.573g/cm³
• Vapor Pressure: 4.2E-08mmHg at 25°C
• Refractive Index: 1.588
• PKA: 12.10±0.35(Predicted)
• CAS DataBase Reference: (4-BROMO-PHENOXY)-ACETIC ACID HYDRAZIDE(CAS DataBase Reference)
• NIST Chemistry Reference: (4-BROMO-PHENOXY)-ACETIC ACID HYDRAZIDE(16738-00-4)
• EPA Substance Registry System: (4-BROMO-PHENOXY)-ACETIC ACID HYDRAZIDE(16738-00-4)

Safety Data

• Hazardous Substances Data: 16738-00-4(Hazardous Substances Data)

Usage

General Description

(4-Bromo-phenoxy)-acetic acid hydrazide is a chemical compound with the molecular formula C8H9BrN2O2. It is a hydrazide derivative of (4-Bromo-phenoxy)-acetic acid and is used in organic synthesis and as a reagent for the determination of Ni(II) by spectrophotometry. The compound is also used in the synthesis of potential antiviral agents and has been studied for its antimicrobial and herbicidal properties. It is a white to off-white crystalline powder and should be handled and stored with care due to its potential health and environmental hazards.

InChI:InChI=1/C8H9BrN2O2/c9-6-1-3-7(4-2-6)13-5-8(12)11-10/h1-4H,5,10H2,(H,11,12)

Upstream product

• 106-41-2 4-bromo-phenol 
• 105-39-5 chloroacetic acid ethyl ester 
• 6964-29-0 ethyl 2-(4-bromophenoxy)acetate 
• 7803-57-8 hydrazine hydrate 
• 1878-91-7 (4-bromophenoxy)acetic acid 
• 4841-23-0 (4-bromophenoxy)acetic acid methyl ester 

Downstream Products

• 1000019-93-1 5-3-[(4-bromophenoxy)methyl]-1H-1,2,4-triazol-5-yl-N-butyl-1H-imidazol-4-amine 
• 304447-18-5 C₁₅H₁₂BrClN₂O₂ 
• 118794-67-5 3-(4-Bromo-phenoxymethyl)-6-(5-nitro-furan-2-yl)-7H-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazine 
• 118794-60-8 5-(4-Bromo-phenoxymethyl)-4-{[1-(5-nitro-furan-2-yl)-meth-(E)-ylidene]-amino}-4H-[1,2,4]triazole-3-thiol 
• 118794-56-2 4-amino-3-(4-bromophenoxymethyl)-5-mercapto-1,2,4-triazole 
• 120353-42-6 5-(4-bromophenoxy)methyl-3-(2-ethoxyphenyl)aminomethyl-1,3,4-oxadiazole-2-thione 
• 120353-40-4 5-(4-bromophenoxy)methyl-3-(2,4-dichlorophenyl)aminomethyl-1,3,4-oxadiazole-2-thione 
• 120353-41-5 5-(4-bromophenoxy)methyl-3-(2-methoxyphenyl)aminomethyl-1,3,4-oxadiazole-2-thione 
• 120353-43-7 5-(4-bromophenoxy)methyl-3-(2,5-dimethylphenyl)aminomethyl-1,3,4-oxadiazole-2-thione 
• 120353-38-0 5-(4-bromophenoxy)methyl-3-(2-chlorophenyl)aminomethyl-1,3,4-oxadiazole-2-thione 
• 120353-39-1 5-(4-bromophenoxy)methyl-3-(4-chlorophenyl)aminomethyl-1,3,4-oxadiazole-2-thione 

Relevant articles and documents

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.

Molecular docking and synthesis of caffeic acid analogous and its anti-inflammatory, analgesic and ulcerogenic studies

A series of caffeic acid (CA) derivatives 7a-j were synthesized via etherification and coupling action and their chemical structures were elucidated spectroscopically. Motivated by the various biological activities displayed by CA derivatives such as anti-inflammatory, antiviral, anticancer and antioxidant and also based on its extensively consumption in the human diet. In the present work, the newly synthesized compounds 7a-j were evaluated for anti-inflammatory and analgesic action and most of them exerted comparable activity to the reference compound celecoxib. Further, ulcer indexes for the most active compounds were calculated and most of them showed less ulcerogenic effect than the reference drug. Among the title series 7a-j, compounds 7f and 7g with electron withdrawing bromo and chloro group respectively, at the para position of the phenoxy ring was showed good activity compared to all other compounds. Interestingly, the COX-I/COX-II activity ratio of potent compounds 7f and7g showed an almost equal inhibitory effect on both isoenzymes. Further, molecular docking studies have been performed for the potent compounds which showed statistically significant result.

Synthesis and luminescence properties of novel 8-hydroxyquinoline derivatives and their Eu(III) complexes

Six novel 8-hydroxyquinoline derivatives were synthesized using 2-methyl-8-hydroxyquinoline and para-substituted phenol as the main starting materials, and were characterized by 1H nuclear magnetic resonance (NMR), mass spectrometry (MS), ultraviolet (UV) light analysis and infra-red (IR) light analysis. Their complexes with Eu(III) were also prepared and characterized by elemental analysis, molar conductivity, UV light analysis, IR light analysis, and thermogravimetric–differential thermal analysis (TG–DTA). The results showed that the ligand coordinated well with Eu(III) ions and had excellent thermal stability. The structure of the target complex was EuY1–6(NO3)3.2H2O. The luminescence properties of the target complexes were investigated, the results indicated that all target complexes had favorable luminescence properties and that the introduction of an electron-donating group could enhance the luminescence intensity of the corresponding complexes, but the addition of an electron-withdrawing group had the opposite effect. Among all the target complexes, the methoxy-substituted complex (–OCH3) had the highest fluorescence intensity and the nitro-substituted complex (–NO2) had the weakest fluorescence intensity. The results showed that 8-hydroxyquinoline derivatives had good energy transfer efficiency for the Eu(III) ion. All the target complexes had a relatively high fluorescence quantum yield. The fluorescence quantum yield of the complex EuY3(NO3)3.2H2O was highest among all target complexes and was up to 0.628. Because of excellent luminescence properties and thermal stabilities of the Eu(III) complexes, they could be used as promising candidate luminescent materials.