4-Bromoanisole - ≥99% , CAS No.104-92-7

CAS: 104-92-7 Cat. No.: B108656 Molecular Weight: 187.03 Beilstein Registry Number: 1237590 EC Number: 203-252-1

GRADE & PURITY ≥99%

Synonyms

InChI=1/C7H7BrO/c1-9-7-4-2-6(8)3-5-7/h2-5H,1H | 4-anisyl bromide | CHEBI:47257 | STR04213 | B0547 | p-Bromophenyl methyl ether | AKOS000119001 | AM20020130 | F0001-0093 | para-bromoanisole | parabromo-anisole | 1-methoxy-4-bromobenzene | p-Methoxyphenyl b

Storage

Protected from light,Room temperature

Shipped In

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Overview

4-Bromoanisole is a useful brominating reagent.It is formed as reaction product in the reaction between HOBr and anisole.Suzuki coupling of 4-bromoanisole with phenylboronic acid catalyzed by palladium pincer complexes has been studied. Heck Reaction of 4-bromoanisole with ethyl acrylates in room-temperature ionic liquids is reported to afford ethyl 4-methoxycinnamate

Specifications

Synonyms

InChI=1/C7H7BrO/c1-9-7-4-2-6(8)3-5-7/h2-5H, 1H | 4-anisyl bromide | CHEBI:47257 | STR04213 | B0547 | p-Bromophenyl methyl ether | AKOS000119001 | AM20020130 | F0001-0093 | para-bromoanisole | parabromo-anisole | 1-methoxy-4-bromobenzene | p-Methoxyphenyl b

Specifications & Purity

≥99%

Storage

Protected from light, Room temperature

Shipped In

FedEx DG Service

This product requires cold chain shipping. Ground and other economy services are not available.

Purity

≥99%

Names and Identifiers

• Pubchem Sid: 488180543
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/488180543
• Canonical Smiles: COC1=CC=C(C=C1)Br
• IUPAC Name: 1-bromo-4-methoxybenzene
• InChIKey: QJPJQTDYNZXKQF-UHFFFAOYSA-N
• INCHI: 1S/C7H7BrO/c1-9-7-4-2-6(8)3-5-7/h2-5H,1H3
• Isomeric SMILES: COC1=CC=C(C=C1)Br
• WGK Germany: 2
• RTECS: BZ8501000
• Molecular Weight: 187.03
• Beilstein: 1237590
• Reaxy-Rn: 1237590
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=1237590&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Benzenoids
    • Class Phenol ethers
      • Subclass Anisoles

• Kingdom: Organic compounds
• Superclass: Benzenoids
• Class: Phenol ethers
• Subclass: Anisoles
• Intermediate Tree Nodes: Not available
• Direct Parent: Anisoles
• Alternative Parents: Phenoxy compounds Methoxybenzenes Bromobenzenes Alkyl aryl ethers Aryl bromides Organobromides Hydrocarbon derivatives
• Molecular Framework: Aromatic homomonocyclic compounds
• Substituents: Phenoxy compound - Anisole - Methoxybenzene - Alkyl aryl ether - Bromobenzene - Halobenzene - Monocyclic benzene moiety - Aryl halide - Aryl bromide - Ether - Organohalogen compound - Organic oxygen compound - Organobromide - Organooxygen compound - Hydrocarbon derivative - Aromatic homomonocyclic compound
• Description: This compound belongs to the class of organic compounds known as anisoles. These are organic compounds containing a methoxybenzene or a derivative thereof.
• External Descriptors: organobromine compound - monomethoxybenzene

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Chemical and Physical Properties

• Solubility: Immiscible with water.
• Sensitivity: Light sensitive.
• Freezing Point(°C): 12 °C
• Refractive Index: 1.564
• Flash Point(°F): 208.4 °F
• Flash Point(°C): 94℃
• Boil Point(°C): 223 °C
• Melt Point(°C): 9-10°C
• Molecular Weight: 187.030 g/mol
• XLogP3: 2.800
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 1
• Exact Mass: 185.968 Da
• Monoisotopic Mass: 185.968 Da
• Topological Polar Surface Area: 9.200 Ų
• Heavy Atom Count: 9
• Formal Charge: 0
• Complexity: 77.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 0
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1

References

1. Chengyi Zhu, Jianxiong Liu, Xiaohua Yu, Yingjie Zhang, Xiaodong Jiang, Peng Dong, Yannan Zhang.  (2023)  4-Bromoanisole (4BA) as Additive for Overcharge Protection of Lithium-Ion Batteries.  International Journal of Electrochemical Science,      [PMID:] [10.20964/2019.05.17]

2. Lijing Zhang, Jiaqi Han, Yuchao Wang, Wenbo Yang, Shengyang Tao.  (2022)  Pd/Mg(OH)2/MgO–ZrO2 Nanocomposite Systems for Highly Efficient Suzuki–Miyaura Coupling Reaction at Room Temperature: Implications for Low-Carbon Green Organic Synthesis.  ACS Applied Nano Materials,      [PMID:] [10.1021/acsanm.2c01179]

3. Fangfang Ren, Simin Li, Wenqing Zheng, Qianyi Song, Wenhui Jia, Yaqin Nan, Haijiao Jia, Jia Liu, James Jianmin Bao, Youxin Li.  (2022)  Preparation of a novel heterogeneous palladium nanocatalyst based on carboxyl modified magnetic nanoparticles and its applications in Suzuki-Miyaura coupling reactions.  COLLOIDS AND SURFACES A-PHYSICOCHEMICAL AND ENGINEERING ASPECTS,      [PMID:] [10.1016/j.colsurfa.2022.128611]

4. Chunfeng Mao, Kai Yin, Chenghan Yang, Guomeng Dong, Guokai Tian, Yiwei Zhang, Yuming Zhou.  (2021)  Fe-based MOFs@Pd@COFs with spatial confinement effect and electron transfer synergy of highly dispersed Pd nanoparticles for Suzuki-Miyaura coupling reaction.  JOURNAL OF COLLOID AND INTERFACE SCIENCE,      [PMID:34785458] [10.1016/j.jcis.2021.10.055]

5. Kaitao Zhang, Minggui Shen, He Liu, Shibin Shang, Dan Wang, Henrikki Liimatainen.  (2018)  Facile synthesis of palladium and gold nanoparticles by using dialdehyde nanocellulose as template and reducing agent.  CARBOHYDRATE POLYMERS,      [PMID:29455970] [10.1016/j.carbpol.2018.01.048]

6. Qinrui Fu, Yuan Meng, Zilin Fang, Quanqin Hu, Liang Xu, Wenhua Gao, Xiaochun Huang, Qiao Xue, Ya-Ping Sun, Fushen Lu.  (2017)  Boron Nitride Nanosheet-Anchored Pd–Fe Core–Shell Nanoparticles as Highly Efficient Catalysts for Suzuki–Miyaura Coupling Reactions.  ACS Applied Materials & Interfaces,      [PMID:28051299] [10.1021/acsami.6b13570]

7. Liang Ren, Fan Yang, Chunxia Wang, Yongfeng Li, Hailing Liu, Zhiqiang Tu, Liqiang Zhang, Zhichang Liu, Jinsen Gao, Chunming Xu.  (2014)  Plasma synthesis of oxidized graphene foam supporting Pd nanoparticles as a new catalyst for one-pot synthesis of dibenzyls.  RSC Advances,  4  (108): (63048-63054).  [PMID:] [10.1039/C4RA11060A]

8. Mingxi Chen, Zhe Zhang, Lingzhi Li, Yu Liu, Wei Wang, Jianping Gao.  (2014)  Fast synthesis of Ag–Pd@reduced graphene oxide bimetallic nanoparticles and their applications as carbon–carbon coupling catalysts.  RSC Advances,  4  (58): (30914-30922).  [PMID:] [10.1039/C4RA05186F]

9. Liang Ren, Fan Yang, Yongfeng Li, Ting Liu, Liqiang Zhang, Guoqing Ning, Zhichang Liu, Jinsen Gao, Chunming Xu.  (2014)  Plasma synthesis of nitrogen-doped porous graphene supporting Pd nanoparticles as a new catalyst for C–C coupling reactions.  RSC Advances,  4  (51): (26804-26809).  [PMID:] [10.1039/C4RA01685H]