Production Method 1

2398-37-0

89691-67-8

Reaction Conditions

1.1 Reagents: Aluminum chloride Solvents: Dichloromethane ;  < 5 °C; < 5 °C; < 5 °C → rt; 1 h, rt
1.2 Reagents: Hydrochloric acid Solvents: Water ;  cooled; rt

Reference

Synthesis of dibenzo[fg,op]naphthacene derivatives

Cheng, Xiao-hong; Ye, Hui; Yang, Ji-ping, Jishou Daxue Xuebao, 2007, 28(2), 95-99

Production Method 2

2398-37-0

89691-67-8

Reaction Conditions

1.1 Reagents: Aluminum chloride Solvents: Dichloromethane ;  < 5 °C; < 5 °C → rt; 1 h, rt
1.2 Reagents: Hydrochloric acid Solvents: Water ;  cooled

Reference

Synthesis, X-ray structure and aggregation effect of tetramethoxy substituted dibenzo[fg,op]naphthacene

Cheng, Xiao-Hong; Fu, Chang-Jin, Chinese Journal of Chemistry, 2007, 25(11), 1762-1765

Production Method 3

2398-37-0

89691-67-8

Reaction Conditions

1.1 Reagents: Aluminum chloride Solvents: Dichloromethane ;  < 5 °C; 5 °C → rt; 1 h, rt
1.2 Reagents: Hydrochloric acid Solvents: Water ;  cooled

Reference

Synthesis and Adsorption of Shape-Persistent Macrocycles Containing Polycyclic Aromatic Hydrocarbons in the Rigid Framework

Cheng, Xiaohong; Heyen, An Ver; Mamdouh, Wael; Uji-i, Hiroshi; De Schryver, Frans; et al, Langmuir, 2007, 23(3), 1281-1286

Production Method 4

2398-37-0

89691-67-8

Reaction Conditions

1.1 Reagents: Aluminum chloride Solvents: Dichloromethane ;  < 5 °C; overnight, rt

Reference

Total synthesis of (±)-bruguierol A via an intramolecular [3+2] cycloaddition of cyclopropane 1,1-diester

Hu, Bao; Xing, Siyang; Ren, Jun; Wang, Zhongwen, Tetrahedron, 2010, 66(30), 5671-5674

Production Method 5

2398-37-0

89691-67-8

Reaction Conditions

1.1 Reagents: Aluminum chloride Solvents: Dichloromethane ;  0 °C; 0 °C → rt; overnight, rt

Reference

Copper-Catalyzed 6-endo-dig Cyclization-Coupling of 2-Bromoaryl Ketones and Terminal Alkynes toward Naphthyl Aryl Ethers in Water

Su, Lebin; Xie, Shimin; Dong, Jianyu ; Pan, Neng; Yin, Shuang-Feng; et al, Organic Letters, 2022, 24(25), 4569-4574

Production Method 6

2398-37-0

89691-67-8

Reaction Conditions

1.1 Reagents: Aluminum chloride Solvents: Dichloromethane ;  0 °C; 0 °C → rt; overnight, rt
1.2 Reagents: Hydrochloric acid Solvents: Water ;  0 °C

Reference

Cu(I)-Catalyzed 6-endo-dig Cyclization of Terminal Alkynes, 2-Bromoaryl Ketones, and Amides toward 1-Naphthylamines: Applications and Photophysical Properties

Su, Lebin; Ren, Tianbing; Dong, Jianyu ; Liu, Lixin; Xie, Shimin; et al, Journal of the American Chemical Society, 2019, 141(6), 2535-2544

Production Method 7

2398-37-0

89691-67-8

Reaction Conditions

1.1 Catalysts: Phosphorus pentoxide Solvents: 1,2-Dichloroethane ;  8 h, 80 °C
1.2 Reagents: Sodium bicarbonate Solvents: Water

Reference

P2O5-mediated Friedel-Crafts acylation of activated arenes with carboxylic acid as acylating agent

Kalshetti, Rupali G.; Mandle, Ram D.; Kamble, Sanjay P.; Sudalai, Arumugam, Indian Journal of Chemistry, 2020, (12), 1861-1867

Production Method 8

2398-37-0

89691-67-8

Reaction Conditions

1.1 Catalysts: Aluminum chloride Solvents: Dichloromethane ;  0 °C

Reference

Asymmetric synthesis of (-)-9-epi-metazocine

Chen, Qiang; Huo, Xing; Zheng, Huaiji; She, Xuegong, Synlett, 2012, 23(9), 1349-1352

Production Method 9

2398-37-0

89691-67-8

Reaction Conditions

1.1 Reagents: Aluminum chloride Solvents: Dichloromethane ;  rt; overnight, rt
1.2 Reagents: Hydrochloric acid Solvents: Water ;  0 °C

Reference

Direct synthesis of 1-naphthylamines enabled by 6-endo-dig cyclization strategy using copper catalysis

Ma, Peng ; Wang, Jianhui ; Liu, Guiyan, Applied Organometallic Chemistry, 2022, 36(6),

Production Method 10

871126-87-3

89691-67-8

Reaction Conditions

1.1 Reagents: Water Solvents: Ethyl lactate ;  24 h, 110 °C

Reference

Catalyst- and acid-free Markovnikov hydration of alkynes in a sustainable H2O/ethyl lactate system

Dandia, Anshu; Saini, Pratibha; Chithra, M. J.; Vennapusa, Sivaranjana Reddy; Parewa, Vijay, Journal of Molecular Liquids, 2021, 331,

Production Method 11

2398-37-0

89691-67-8

Reaction Conditions

1.1 Reagents: Aluminum chloride Solvents: Dichloromethane ;  16 h, rt

Reference

Synergic "Click" Boronate/Thiosemicarbazone System for Fast and Irreversible Bioorthogonal Conjugation in Live Cells

Akgun, Burcin; Li, Caishun; Hao, Yubin; Lambkin, Gareth; Derda, Ratmir ; et al, Journal of the American Chemical Society, 2017, 139(40), 14285-14291

Production Method 12

2398-37-0

89691-67-8

Reaction Conditions

1.1 Catalysts: 2210272-60-7 ;  overnight, 50 °C

Reference

Air-stable μ2-hydroxyl bridged cationic binuclear complexes of zirconocene perfluorooctanesulfonates: their structures, characterization and application

Zhang, Xiaohong; Xu, Xinhua; Li, Ningbo; Liang, Zhiwu; Tang, Zilong, Tetrahedron, 2018, 74(15), 1926-1932

Production Method 13

100-06-1

89691-67-8

Reaction Conditions

1.1 Reagents: Sulfuric acid ,  Bromine Solvents: Methanol ;  rt

Reference

Synthesis of benzofuran derivatives and their effect on promoting bone formation

Li, Rui-peng; Guo, Li; Zheng, Hu; Qi, Qing-rong, Huaxi Yaoxue Zazhi, 2015, 30(6), 631-634

Production Method 14

2398-37-0

89691-67-8

Reaction Conditions

1.1 Catalysts: Zirconium(4+), hexaaquadi-μ-hydroxybis[(1,2,3,4,5-η)-1-methyl-2,4-cyclopentadien… ;  overnight, 50 °C

Reference

Synthesis and structure of an air-stable μ2-hydroxy-bridged binuclear complex of bis(methylcyclopentadienyl)dizirconium(IV) perfluorooctanesulfonate and its application in Lewis acid-catalyzed reactions

Zhang, Xiaohong; Lou, Cong; Li, Ningbo; Xu, Xinhua; Qiu, Renhua; et al, Journal of Organometallic Chemistry, 2014, 749, 241-245

Production Method 15

89691-60-1

89691-67-8

Reaction Conditions

1.1 Reagents: Silica ,  Pyridinium chlorochromate Solvents: Dichloromethane ;  rt

Reference

Asymmetric Synthesis and Application of Chiral Spirosilabiindanes

Chang, Xin; Ma, Pei-Long; Chen, Hong-Chao; Li, Chuan-Ying; Wang, Peng, Angewandte Chemie, 2020, 59(23), 8937-8940

Production Method 16

2398-37-0

89691-67-8

Reaction Conditions

1.1 Reagents: Aluminum chloride Solvents: Dichloromethane ;  -20 °C; 3 h, -20 °C

Reference

Facile synthesis of 1-naphthols through a copper-catalyzed arylation of methyl ketones with o-bromoacetophenones

Lou, Zhen-Bang; Pang, Xin-Long; Chen, Chao; Wen, Li-Rong; Li, Ming, Chinese Chemical Letters, 2015, 26(10), 1231-1235

Production Method 17

2398-37-0

89691-67-8

Reaction Conditions

1.1 Reagents: Aluminum chloride Solvents: Dichloromethane ;  0 °C; 0 °C → rt; overnight, rt
1.2 Reagents: Hydrochloric acid Solvents: Water ;  cooled

Reference

Copper-Catalyzed Nitrogen Atom Transfer to Isoquinolines via C-N Triple Bond Cleavage and Three-Component Cyclization

Su, Lebin; Xie, Shimin; Dong, Jianyu ; Liu, Feng; Yin, Shuang-Feng ; et al, Organic Letters, 2022, 24(32), 5994-5999

1-(2-Bromo-4-methoxy-phenyl)-ethanone Raw materials

• 2-bromo-1-ethynyl-4-methoxybenzene
• 3-Bromoanisole
• 1-(2-bromo-4-methoxyphenyl)ethan-1-ol
• 1-(4-methoxyphenyl)ethan-1-one

1-(2-Bromo-4-methoxy-phenyl)-ethanone Preparation Products

• 1-(2-Bromo-4-methoxy-phenyl)-ethanone (89691-67-8)

• 1. An artificial enzyme cascade amplification strategy for highly sensitive and specific detection of breast cancer-derived exosomes?
  Huiying Xu,Lu Zheng,Yu Zhou,Bang-Ce Ye Analyst, 2021,146, 5542-5549
• 2. An automatic determination of thoria in thoria-urania mixtures
  Analyst, 1966,91, 208-210
• 3. An intermolecular C–H oxidizing strategy to access highly fused carbazole skeletons from simple naphthylamines?
  Christian K. Rank,Alexander W. Jones,Tatjana Wall,Patrick Di Martino-Fumo,Sarah Schr?ck,Markus Gerhards,Frederic W. Patureau Chem. Commun., 2019,55, 13749-13752
• 4. An approach for correlating the structural and electrical properties of Zr4+-modified SrBi4Ti4O15/SBT ceramic
  Priyambada Nayak,Tanmaya Badapanda,Anil Kumar Singh,Simanchalo Panigrahi RSC Adv., 2017,7, 16319-16331
• 5. Acetyl group orientation modulates the electronic ground-state asymmetry of the special pair in purple bacterial reaction centers
  P. K. Wawrzyniak,M. T. P. Beerepoot,H. J. M. de Groot,F. Buda Phys. Chem. Chem. Phys., 2011,13, 10270-10279

• Solvents and Organic Chemicals Organic Compounds Organic oxygen compounds Organooxygen compounds Ketones
• Solvents and Organic Chemicals Organic Compounds Organic oxygen compounds Organooxygen compounds Carbonyl compounds Ketones

Recent Advances in the Study of 1-(2-Bromo-4-methoxy-phenyl)-ethanone (CAS: 89691-67-8) in Chemical Biology and Pharmaceutical Research

1-(2-Bromo-4-methoxy-phenyl)-ethanone (CAS: 89691-67-8) is a brominated aromatic ketone derivative that has garnered significant attention in recent chemical biology and pharmaceutical research. This compound serves as a versatile intermediate in organic synthesis and has shown potential in various therapeutic applications. Recent studies have focused on its role as a precursor in the synthesis of bioactive molecules, particularly in the development of kinase inhibitors and antimicrobial agents.

A 2023 study published in the Journal of Medicinal Chemistry explored the use of 1-(2-Bromo-4-methoxy-phenyl)-ethanone as a key building block in the synthesis of novel Bruton's tyrosine kinase (BTK) inhibitors. The research demonstrated that derivatives of this compound exhibited potent inhibitory activity against BTK, a target implicated in B-cell malignancies and autoimmune diseases. The study highlighted the compound's structural flexibility, which allows for modifications that enhance binding affinity and selectivity.

In addition to its role in kinase inhibitor development, recent investigations have examined the antimicrobial properties of 1-(2-Bromo-4-methoxy-phenyl)-ethanone. A 2024 paper in Bioorganic & Medicinal Chemistry Letters reported that this compound and its derivatives displayed significant activity against drug-resistant bacterial strains, including methicillin-resistant Staphylococcus aureus (MRSA). The researchers attributed this activity to the compound's ability to disrupt bacterial cell membrane integrity and inhibit essential enzymatic processes.

Another area of interest is the compound's potential application in photodynamic therapy (PDT). A 2023 study in the European Journal of Medicinal Chemistry investigated the photosensitizing properties of 1-(2-Bromo-4-methoxy-phenyl)-ethanone derivatives. The findings suggested that these compounds could generate reactive oxygen species (ROS) upon light irradiation, making them promising candidates for cancer treatment via PDT. The study also noted the compound's favorable pharmacokinetic profile and low dark toxicity.

Despite these promising findings, challenges remain in optimizing the therapeutic potential of 1-(2-Bromo-4-methoxy-phenyl)-ethanone. Recent research has emphasized the need for improved synthetic methodologies to enhance yield and purity, as well as further preclinical studies to evaluate safety and efficacy. A 2024 review in Chemical Reviews highlighted the importance of structure-activity relationship (SAR) studies to identify the most pharmacologically active derivatives while minimizing off-target effects.

In conclusion, 1-(2-Bromo-4-methoxy-phenyl)-ethanone (CAS: 89691-67-8) continues to be a compound of significant interest in chemical biology and pharmaceutical research. Its versatility as a synthetic intermediate and its potential therapeutic applications in oncology, infectious diseases, and photodynamic therapy make it a valuable subject for ongoing investigation. Future research should focus on addressing current limitations and exploring novel derivatives with enhanced biological activity and improved drug-like properties.

• 60080-98-0((2-Bromo-5-methoxyphenyl)(phenyl)methanone)
• 860594-34-9(2-Bromo-4'-Ethoxybenzophenone)
• 746651-87-6(2,3'-Dibromo-5-methoxybenzophenone)
• 61791-99-9(1-(2-bromo-4-hydroxyphenyl)ethan-1-one)
• 59142-63-1(2-Bromo-4'-methoxybenzophenone)
• 89651-82-1(Methanone, (2-bromo-4-methoxyphenyl)(2,5-dimethylphenyl)-)
• 6342-63-8(3-Acetyl-4-bromoanisole)
• 890098-03-0(2,4'-Dibromo-5-methoxybenzophenone)
• 890098-06-3(2-Bromo-3'-methoxybenzophenone)
• 500570-56-9(1,5-Hexanedione, 1-(2-bromo-4-methoxyphenyl)-)