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1-bromo-4-(4-nitrophenoxy)benzene is a chemical compound with the molecular formula C12H8BrNO3. It is a benzene derivative featuring a bromine atom and a 4-nitrophenoxy group attached to the 1 and 4 positions, respectively. This white to beige crystalline solid has a melting point of approximately 85-87°C and is sparingly soluble in water but soluble in organic solvents. Due to its toxic nature upon ingestion or inhalation, and potential to cause skin and eye irritation, it requires careful handling and storage.

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  • 21969-04-0 Structure
  • Basic information

    1. Product Name: 1-Bromo-4-(4-nitrophenoxy)benzene
    2. Synonyms: 1-Bromo-4-(4-nitrophenoxy)benzene
    3. CAS NO:21969-04-0
    4. Molecular Formula: C12H8BrNO3
    5. Molecular Weight: 294.10082
    6. EINECS: N/A
    7. Product Categories: N/A
    8. Mol File: 21969-04-0.mol
  • Chemical Properties

    1. Melting Point: N/A
    2. Boiling Point: 365.1°Cat760mmHg
    3. Flash Point: 174.6°C
    4. Appearance: /
    5. Density: 1.563g/cm3
    6. Vapor Pressure: 3.38E-05mmHg at 25°C
    7. Refractive Index: 1.63
    8. Storage Temp.: Room temperature.
    9. Solubility: N/A
    10. CAS DataBase Reference: 1-Bromo-4-(4-nitrophenoxy)benzene(CAS DataBase Reference)
    11. NIST Chemistry Reference: 1-Bromo-4-(4-nitrophenoxy)benzene(21969-04-0)
    12. EPA Substance Registry System: 1-Bromo-4-(4-nitrophenoxy)benzene(21969-04-0)
  • Safety Data

    1. Hazard Codes: N/A
    2. Statements: N/A
    3. Safety Statements: N/A
    4. WGK Germany:
    5. RTECS:
    6. HazardClass: N/A
    7. PackingGroup: N/A
    8. Hazardous Substances Data: 21969-04-0(Hazardous Substances Data)

21969-04-0 Usage

Uses

Used in Organic Synthesis:
1-bromo-4-(4-nitrophenoxy)benzene is used as a reagent in organic synthesis for its ability to participate in various chemical reactions, facilitating the creation of new compounds and materials.
Used in Pharmaceutical Research:
In pharmaceutical research, 1-bromo-4-(4-nitrophenoxy)benzene serves as an intermediate, contributing to the development of new drugs by acting as a precursor in the synthesis of pharmaceutically active compounds.
Used in Agrochemical Production:
1-bromo-4-(4-nitrophenoxy)benzene is utilized as a key component in the production of agrochemicals, playing a role in the synthesis of substances that help protect crops from pests and diseases.
Used in Dye Manufacturing:
In the dye industry, 1-bromo-4-(4-nitrophenoxy)benzene is used as an intermediate in the manufacturing process, contributing to the creation of dyes with specific color properties and applications.

Check Digit Verification of cas no

The CAS Registry Mumber 21969-04-0 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 2,1,9,6 and 9 respectively; the second part has 2 digits, 0 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 21969-04:
(7*2)+(6*1)+(5*9)+(4*6)+(3*9)+(2*0)+(1*4)=120
120 % 10 = 0
So 21969-04-0 is a valid CAS Registry Number.
InChI:InChI=1/C12H8BrNO3/c13-9-1-5-11(6-2-9)17-12-7-3-10(4-8-12)14(15)16/h1-8H

21969-04-0SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 17, 2017

Revision Date: Aug 17, 2017

1.Identification

1.1 GHS Product identifier

Product name 1-(4-bromophenoxy)-4-nitrobenzene

1.2 Other means of identification

Product number -
Other names (4-bromo-phenyl)-(4-nitro-phenyl)-ether

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:21969-04-0 SDS

21969-04-0Relevant articles and documents

Cu(I)-PNF, an organic-based nanocatalyst, catalyzed C-O and C-S cross-coupling reactions

Taherinia, Zahra,Ghorbani-Choghamarani, Arash

, p. 46 - 52 (2019/01/10)

Peptide nanofiber has been prepared via a self-assembly protocol and decorated with Cu(I) to prepare a nanostructural catalyst. The catalytic activity of this prepared nanomaterial (Cu(I)-PNF) was examined in C-O and C-S cross-coupling reactions. Compared with conventional copper-ligand catalytic systems, CuNP-PNF has unique advantages such as water solubility, high efficiency, and low cost, which makes it a highly efficient and beneficial catalyst to reuse in cross-coupling reactions.

Quinoline derivative as well as preparation method and application thereof (by machine translation)

-

Paragraph 0255-0257, (2019/11/28)

The invention provides a quinoline derivative and a composition containing the same. The invention also provides a method for preparing the derivative and application of the derivative and the composition to kill pests. (by machine translation)

Synthesis, SAR and molecular docking study of novel non-β-lactam inhibitors of TEM type β-lactamase

Antipin, Roman L.,Beshnova, Daria A.,Petrov, Rostislav A.,Shiryaeva, Anna S.,Andreeva, Irina P.,Grigorenko, Vitaly G.,Rubtsova, Maya Yu.,Majouga, Alexander G.,Lamzin, Victor S.,Egorov, Alexey M.

supporting information, p. 1588 - 1592 (2017/03/17)

The novel classes of acylated phenoxyanilide and thiourea compounds were investigated for their ability to inhibit TEM type β-lactamase enzyme. Two compounds 4g and 5c reveal the inhibition potency in micromolar range and show their action by non-covalent binding in the vicinity of the TEM-171 active site. The structure activity relationship around carbon chain length and different substituents in ortho- and para-positions of acylated phenoxyanilide as well as molecular modelling study has been performed.

CsF/clinoptilolite: An efficient solid base in SNAr and copper-catalyzed Ullmann reactions

Keipour, Hoda,Hosseini, Abolfazl,Afsari, Amir,Oladee, Razieh,Khalilzadeh, Mohammad A.,Ollevier, Thierry

, p. 95 - 104 (2016/01/16)

CsF/clinoptilolite was found to be an efficient solid base catalyst for both SNAr and Ullmann ether reactions. A general and efficient one-step procedure was developed for the synthesis of biaryl ethers via direct coupling of electron-deficient aryl halides to phenols using CsF/clinoptilolite. The protocol was also applied to electron-rich aryl halides by addition of a catalytic amount of copper oxide nanoparticles. Both SNAr and Ullmann reactions were rapid and provided good to excellent yields.

Synthesis and biological evaluation of pentanedioic acid derivatives as farnesyltransferase inhibitors

Yang, Liuqing,Liu, Wei,Mei, Hanbing,Zhang, Yuan,Yu, Xiaojuan,Xu, Yufang,Li, Honglin,Huang, Jin,Zhao, Zhenjiang

supporting information, p. 671 - 676 (2015/04/27)

Structure-based virtual screening of a commercial library identified pentanedioic acid derivatives (6 and 13b) as a kind of novel scaffold farnesyltransferase inhibitors (FTIs). Chemical modifications of the lead compounds, biological assays and analysis of the structure-activity relationships (SAR) were conducted to discover more potent FTIs. Some of them displayed excellent inhibition against FTase, and among them, the most active compound 13n with an IC50 value of 0.0029 μM and SAR analysis might be helpful to the discovery of more potent FTIs. This journal is

Discovery of 1,2,4-triazole-1,3-disulfonamides as dual inhibitors of mitochondrial complex II and complex III

Cheng, Hua,Shen, Yan-Qing,Pan, Xia-Yan,Hou, Yi-Ping,Wu, Qiong-You,Yang, Guang-Fu

, p. 7281 - 7292 (2015/09/02)

Respiratory chain succinate-ubiquinone oxidoreductase (SQR or complex II) and ubihydroquinone-cytochrome (cyt) c oxidoreductase (cyt bc1 or complex III) have been demonstrated as the promising targets of numerous antibiotics and fungicides. As a continuation of our research work on the development of new fungicides, a series of 1,2,4-triazole-1,3-disulfonamide derivatives with dual functions targeting both SQR and cyt bc1 were designed and synthesized by coupling diverse diphenyl ether moieties with triazolesulfonamide units. These newly synthesized compounds were characterized by elemental analyses, 1H NMR and ESI-MS spectrometry. The in vitro assay indicated that most of the synthesized compounds displayed good inhibition against porcine succinate-cytochrome reductase (SCR) with IC50 values ranging from 3.2 to 81.8 μM, revealing much higher activity than that of the commercial control amisulbrom whose IC50 value is 93.0 μM. Further evaluation against the respective SQR and cyt bc1 indicated that most compounds exhibited SQR-inhibiting activity as well as cyt bc1-inhibiting activity, but the inhibition potency against SQR is much higher than that against cyt bc1, showing that the SCR inhibition might be contributed greatly by the SQR inhibition. The further antibacterial evaluation against Xanthomonas oryzae pv. oryzae revealed that four compounds showed excellent potency at the concentration of 20 μg mL-1. In particular, compounds 6h and 6j exhibited much better antibacterial activity than the commercial control bismerthiazol in terms of their EC50. Impressively, 6j has an EC90 of 33.62 μg mL-1, more than 10-fold higher than that of bismerthiazol.

Palladium nanoparticles supported on natural nanozeolite clinoptilolite as a catalyst for ligand and copper-free C-C and C-O cross coupling reactions in aqueous medium

Baghbanian, Seyed Meysam,Yadollahy, Horieh,Tajbakhsh, Mahmood,Farhang, Maryam,Biparva, Pourya

, p. 62532 - 62543 (2015/02/19)

In this article, Pd0-nanoparticles supported on natural nanozeolite clinoptilolite (CP) were successfully synthesized, and the catalytic activity of the nanocatalyst was investigated in C-C and C-O coupling reactions, namely the Sonogashira and Ullmann condensation reactions in an aqueous medium. The nanocatalyst was characterized by various techniques such as powder-XRD, BET, SEM, TEM, HRTEM, TEM-EDS, ICP-OES and XPS. From an electron microscopy (SEM) study it can be inferred that the particles are mostly spherical or of ellipsoidal shape and have diameters ranging from 25 to 80 nm. A HRTEM study reveals that Pd0-nanoparticles supported on nanozeolite CP have an average diameter of ~10 nm. The supported palladium nanoparticles showed excellent catalytic activity in the synthesis of aryl alkynes and diaryl ethers in high yields. In addition, the nanocatalyst could be recycled and reused several times without significant loss of catalytic activity.

Palladium supported on zinc ferrite: An efficient catalyst for ligand free C-C and C-O cross coupling reactions

Singh, Abhilash S.,Shendage, Suresh S.,Nagarkar, Jayashree M.

, p. 6319 - 6323 (2013/11/06)

An efficient superparamagnetic Pd-ZnFe2O4 solid catalyst has been synthesized by loading Pd(0) species on zinc ferrite nanoparticles. Sonogashira cross couplings between terminal alkynes and aryl halides were achieved in the absence of any Cu co-catalyst. A Heck-Matsuda coupling reaction of structurally different aryldiazonium tetrafluoroborate substrates was preceded at 40 C in water. Cyanation of aryl halides was successfully done using K4[Fe(CN)6] as the cyanide source over Pd-ZnFe2O4. The catalyst was also employed for Ullmann type cross coupling reactions. Excellent yield of the products, reusability, and uncomplicated work-up make this catalyst efficient for C-C and C-O coupling reactions. Good yield of products, easy separation, and negligible leaching of Pd from the catalyst surface confirm the true heterogeneity in these catalytic reactions.

First palladium-catalyzed denitrated coupling reaction of nitroarenes with phenols

Wang, Hailei,Yu, Ajuan,Cao, Aijuan,Chang, Junbiao,Wu, Yangjie

, p. 611 - 614 (2013/10/21)

The first palladium-catalyzed protocol for the denitrated coupling reaction of nitroarenes with phenols has been developed, achieving unsymmetrical diaryl ethers in moderate to excellent yields. The cyclopalladated ferrocenylimine (catalyst Ic) exhibited highly catalytic activity for this transformation with low catalyst loading (0.75 mol%) and short reaction time (2 h). The efficiency of this reaction was demonstrated by its compatibility with a range of groups. Moreover, the rigorous exclusion of air or moisture was not required in these transformations. Copyright

Open air O-arylation reaction of phenols with aryl halides catalyzed by polymer-anchored copper(II) complexes

Islam, Manirul,Mondal, Sanchita,Mondal, Paramita,Roy, Anupam Singha,Hossain, Dildar,Mobarak, Manir

experimental part, p. 1 - 11 (2012/02/01)

Two copper complexes were synthesized from macroporous chloromethylated polystyrene beads. The first one was prepared by sequential attachment of imidazole and copper acetate with chloromethylated polystyrene-divinyl benzene copolymer, and the second one was prepared from 4-vinylpyridine and copper acetate with chloromethylated polystyrene-divinyl benzene copolymer. These catalysts showed excellent catalytic activity in O-arylation reaction of aryl halides with phenol in dimethylsulfoxide using potassium carbonate at 130 °C under open air conditions to give diaryl ethers in high yields. Less reactive aryl bromides and aryl chlorides have also been shown to react with phenols to give good yields of the diaryl ethers. The effects of various parameters such as solvent, catalyst from different copper salt and base on the reaction system were studied. The reaction is applicable to a wide variety of substituted aryl halides and phenols with different steric and electronic properties. These catalysts were recovered by simple filtration, and the reusability experiments showed that these catalysts can be used five times without much loss in the catalytic activity.

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