1-Bromo-4-phenoxybenzene

Base Information

• Chemical Name: 1-Bromo-4-phenoxybenzene
• CAS No.: 101-55-3
• Molecular Formula: C12H9BrO
• Molecular Weight: 249.107
• Hs Code.: 29093090
• European Community (EC) Number: 202-952-4
• NSC Number: 5619
• UN Number: 3082
• UNII: N19SE3QCFN
• DSSTox Substance ID: DTXSID8023927
• Nikkaji Number: J47.554H
• Wikidata: Q27146950
• ChEMBL ID: CHEMBL1873236
• Mol file: 101-55-3.mol

Synonyms:4-bromodiphenyl ether

Chemical Property of 1-Bromo-4-phenoxybenzene

Chemical Property:

• Appearance/Colour: light yellow liquid
• Vapor Pressure: 0.00112mmHg at 25°C
• Melting Point: 18 °C(lit.)
• Refractive Index: n20/D 1.607(lit.)
• Boiling Point: 310.1 °C at 760 mmHg
• Flash Point: 118.4 °C
• PSA: 9.23000
• Density: 1.413 g/cm³
• LogP: 4.24140
• Storage Temp.: 2-8°C
• Solubility.: Soluble in ether (Weast, 1986) and many other solvents including 1,4-dioxane, benzene, and toluene.
• XLogP3: 4.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 2
• Exact Mass: 247.98368
• Heavy Atom Count: 14
• Complexity: 158
• Transport DOT Label: Class 9

Purity/Quality:

99% ^*data from raw suppliers

1-Bromo-4-phenoxybenzene ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn; F; N
• Hazard Codes: N,Xn,F
• Statements: 50/53-67-65-38-11-43-41-22
• Safety Statements: 60-61-62-36/37/39-26-33-29-16-9

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Other Classes -> Halogenated Polyaromatics
• Canonical SMILES: C1=CC=C(C=C1)OC2=CC=C(C=C2)Br

Technology Process of 1-Bromo-4-phenoxybenzene

There total 32 articles about 1-Bromo-4-phenoxybenzene which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 99.0%

para-nitrophenyl bromide (586-78-7) + phenol (108-95-2,27073-41-2) → 4-Bromodiphenyl ether (101-55-3)

Guidance literature:

With [Pd((η5-C5H5)Fe[(η5-C5H3)C(Me)=N(C6H4-4-Me)])(μ-Cl)]2; caesium carbonate; In N,N-dimethyl-formamide; at 100 ℃; for 2h;

DOI:10.1002/aoc.3043

Reference yield: 98.0%

diphenylether (101-84-8) → 4-Bromodiphenyl ether (101-55-3)

Guidance literature:

With ammonium nitrate; N-Bromosuccinimide; In acetonitrile; for 0.5h;

DOI:10.1246/cl.2003.932

Reference yield: 97.0%

1,4-bromoiodobenzene (589-87-7) + phenol (108-95-2,27073-41-2) → 4-Bromodiphenyl ether (101-55-3)

Guidance literature:

With caesium carbonate; copper(l) iodide; In N,N-dimethyl-formamide; at 110 ℃; for 13h;

DOI:10.1002/chem.200501473

upstream raw materials:

diphenylether

4-phenoxyanilin

1.4-dibromobenzene

phenol

Downstream raw materials:

2-phenoxy-5-bromobenzoic acid

N,N-Diethyl-4-phenoxy-benzamide

N,N-Diethyl-2-oxo-2-(4-phenoxy-phenyl)-acetamide

diphenyl ether-4-phosphonic acid diethyl ester

Refernces

• 1、 Qian, Ding-Quan,Shine, Henry J.,Thurston, John H.,Whitmire, Kenton H.. "Nucleophilic reactions of 5-(aryl)thianthrenium bromides with sodium aryl oxides". . p. 142 - 147. Retrieved 2003.
• 2、 Zhou, Zhongshi,He, Xuehan. "An efficient and regioselective monobromination of electron-rich aromatic compounds using catalytic hypervalent iodine(III) reagent". . p. 207 - 209. Retrieved 2011.
• 3、 Zysman-Colman, Eli,Arias, Karla,Siegel, Jay S.. "Synthesis of arylbromides from arenes and Nbromosuccinimide bromosuccinimide (NBS) in acetonitrile - A convenient method for aromatic bromination". . p. 440 - 447. Retrieved 2009.
• 4、 Yang, Li,Yang, Qichao,Shi, Jianxin,Wang, Yufang,Zhang, Mingjie. "Betti base as an efficient ligand for copper-catalyzed ullmann coupling of phenol with aryl halides". . p. 2468 - 2477. Retrieved 2014.
• 5、 Olah, George A.,Ohannesian, Lena,Arvanaghi, Massoud. "Synthetic Methods and Reactions; 127. Regioselective para Halogenation of Phenols, Phenol Ethers and Anilines with Halodimethylsulfonium Halides". . p. 868 - 870. Retrieved 1986.
• 6、 Saberi, Dariush,Sheykhan, Mehdi,Niknam, Khodabakhsh,Heydari, Akbar. "Preparation of carbon nanotube-supported α-Fe2O 3@CuO nanocomposite: A highly efficient and magnetically separable catalyst in cross-coupling of aryl halides with phenols". . p. 2025 - 2031. Retrieved 2013.
• 7、 Firouzabadi,Iranpoor,Shiri. "Direct and regioselective iodination and bromination of benzene, naphthalene and other activated aromatic compounds using iodine and bromine". . p. 8781 - 8785. Retrieved 2003.
• 8、 Aghili, Nora,Hosseinzadeh, Rahman,Mavvaji, Mohammad. "Synthesis and characterization of nano-cellulose immobilized phenanthroline-copper (I) complex as a recyclable and efficient catalyst for preparation of diaryl ethers, N-aryl amides and N-aryl heterocycles". . . Retrieved 2022/01/03.
• 9、 Ding, Zhiqiang,Nie, Nan,Chen, Tian,Meng, Lingxin,Wang, Gongshu,Chen, Zhangpei,Hu, Jianshe. "L-Proline N-oxide dihydrazides as an efficient ligand for cross-coupling reactions of aryl iodides and bromides with amines and phenols". supporting information. . Retrieved 2020/12/21.