Production Method 1

6971-51-3

824-98-6

Reaction Conditions

1.1 Reagents: Triethylamine ,  Thionyl chloride Solvents: Dichloromethane ;  rt; 1 h, rt

Reference

Discovery, Structure-Activity Relationships, and In Vivo Activity of Dihydropyridone Agonists of the Bile Acid Receptor TGR5

Picon, Sylvain; et al, Journal of Medicinal Chemistry, 2023, 66(17), 11732-11760

Production Method 2

591-31-1

824-98-6

Reaction Conditions

1.1 Reagents: Sodium borohydride Solvents: Tetrahydrofuran ;  0 °C; overnight, rt
1.2 Solvents: Water ;  rt
1.3 Reagents: Thionyl chloride Solvents: Dichloromethane ;  0 °C; overnight, rt

Reference

Palladium-catalyzed carboxylative coupling of benzyl chlorides with allyltributylstannane: remarkable effect of palladium nanoparticles

Feng, Xiujuan; et al, Organic Letters, 2013, 15(1), 108-111

Production Method 3

151-10-0

824-98-6

Reaction Conditions

1.1 Reagents: Zinc

Reference

Zinc-Promoted Selective Cleavage of Ethers in Presence of Acyl Chloride

Bhar, Sanjay; et al, Journal of Organic Chemistry, 1995, 60(3), 745-7

Production Method 4

6971-51-3

824-98-6

Reaction Conditions

1.1 Reagents: Hydrochloric acid Solvents: Water ;  20 min, 10 bar, 120 °C

Reference

Hydrogen Chloride Gas in Solvent-Free Continuous Conversion of Alcohols to Chlorides in Microflow

Borukhova, Svetlana; et al, Organic Process Research & Development, 2016, 20(2), 568-573

Production Method 5

59276-28-7

824-98-6

Reaction Conditions

1.1 Reagents: Acetyl chloride ,  Triethylsilane Catalysts: Stannous chloride Solvents: Dichloromethane

Reference

Halogenative allylation and reduction of aromatic acetals by double substitution of alkoxyl groups in acetal

Oriyama, Takeshi; et al, Bulletin of the Chemical Society of Japan, 1991, 64(4), 1410-12

Production Method 6

591-31-1

824-98-6

Reaction Conditions

1.1 Reagents: Sodium borohydride Solvents: Tetrahydrofuran ;  0 °C; overnight, rt
1.2 Reagents: Water ;  rt
1.3 Reagents: Thionyl chloride

Reference

Regio- and chemoselective palladium-catalyzed benzylallylation of activated olefins: the remarkable effect of palladium nanoparticles

Zhang, Xuan; et al, Organic & Biomolecular Chemistry, 2013, 11(24), 4016-4024

Production Method 7

34192-19-3

824-98-6

Reaction Conditions

1.1 Reagents: Magnesium Solvents: Diethyl ether
2.1 Reagents: Thionyl chloride Solvents: Toluene

Reference

Intramolecular alkylations of aromatic compounds. XVI. Syntheses of 4-methyl- and 2,4-dimethyl-5-benzyl-5,6,7,8-tetrahydroquinolines

Reimann, Eberhard; et al, Archiv der Pharmazie (Weinheim, 1985, 318(12), 1105-15

Production Method 8

100-83-4

824-98-6

Reaction Conditions

1.1 Reagents: Sodium hydroxide Solvents: Water ;  25 - 30 °C; pH 8 - 9, 30 - 35 °C; 3 h, 30 - 35 °C
2.1 Reagents: Potassium borohydride Solvents: Water ;  0 °C; 2 - 3 h, 30 - 35 °C
2.2 Reagents: Hydrochloric acid Solvents: Water ;  pH 6
3.1 Reagents: Thionyl chloride Catalysts: Pyridine Solvents: Benzene ;  rt → 10 °C; 10 °C; 2 h, 35 - 45 °C

Reference

Synthesis of 3-methoxybenzyl chloride

Shen, Xin-an; et al, Huaxue Shiji, 2015, 37(10), 948-950

1-(chloromethyl)-3-methoxybenzene Raw materials

• 3-Hydroxybenzaldehyde
• 2,4-dimethyl-5,6,7,8-tetrahydroquinolin-5-one
• 1-(Dimethoxymethyl)-3-methoxybenzene
• 3-Methoxybenzenemethanol
• 1,3-Dimethoxybenzene
• 3-Methoxybenzaldehyde

1-(chloromethyl)-3-methoxybenzene Preparation Products

• 1-(chloromethyl)-3-methoxybenzene (824-98-6)

• 1. Emulsion soft templating of carbide-derived carbon nanospheres with controllable porosity for capacitive electrochemical energy storage?
  M. Zeiger,N. J?ckel,P. Strubel,L. Borchardt,R. Reinhold,W. Nickel,J. Eckert,V. Presser,S. Kaskel J. Mater. Chem. A, 2015,3, 17983-17990
• 2. Establishment and implications of a characterization method for magnetic nanoparticle using cell tracking velocimetry and magnetic susceptibility modified solutions
  Huading Zhang,Lee R. Moore,Maciej Zborowski,P. Stephen Williams,Shlomo Margel,Jeffrey J. Chalmers Analyst, 2005,130, 514-527
• 3. Evidence of field induced slow magnetic relaxation in cis-[Co(hfac)2(H2O)2] exhibiting tri-axial anisotropy with a negative axial component?
  Denis V. Korchagin,Elena A. Yureva,Alexander V. Akimov,Eugenii Ya. Misochko,Gennady V. Shilov,Artem D. Talantsev,Roman B. Morgunov,Alexander A. Shakin,Sergey M. Aldoshin,Boris S. Tsukerblat Dalton Trans., 2017,46, 7540-7548
• 4. Enabling non-flammable Li-metal batteries via electrolyte functionalization and interface engineering?
  Jing Yu,Yu-Qi Lyu,Jiapeng Liu,Mohammed B. Effat,Junxiong Wu J. Mater. Chem. A, 2019,7, 17995-18002
• 5. Ester-directed orthogonal dual C–H activation and ortho aryl C–H alkenylation via distal weak coordination?
  Manickam Bakthadoss,Tadiparthi Thirupathi Reddy,Vishal Agarwal,Duddu S. Sharada Chem. Commun., 2022,58, 1406-1409

• Solvents and Organic Chemicals Organic Compounds Benzenoids Benzene and substituted derivatives Benzyl halides Benzyl chlorides
• Solvents and Organic Chemicals Organic Compounds Alcohol/Ether

Introduction to 1-(chloromethyl)-3-methoxybenzene (CAS No. 824-98-6)

1-(chloromethyl)-3-methoxybenzene, with the chemical formula C?H?ClO, is a significant intermediate in the field of organic synthesis and pharmaceutical development. This compound, identified by its CAS number 824-98-6, has garnered attention due to its versatile applications in the synthesis of various bioactive molecules. The presence of both a chloromethyl group and a methoxy substituent on the benzene ring imparts unique reactivity, making it a valuable building block for medicinal chemists and synthetic organic chemists alike.

The structural features of 1-(chloromethyl)-3-methoxybenzene enable it to participate in a wide range of chemical transformations, including nucleophilic addition reactions, alkylation, and condensation reactions. These properties have been leveraged in the development of novel therapeutic agents targeting diverse biological pathways. Recent advancements in synthetic methodologies have further enhanced the utility of this compound, allowing for more efficient and scalable production processes.

In the realm of pharmaceutical research, 1-(chloromethyl)-3-methoxybenzene has been utilized as a precursor in the synthesis of small molecule inhibitors and modulators. For instance, studies have demonstrated its role in the preparation of compounds that exhibit inhibitory activity against specific enzymes implicated in inflammatory and neurodegenerative diseases. The methoxy group provides a handle for further functionalization, enabling the creation of structurally diverse derivatives with tailored pharmacological properties.

One particularly noteworthy application of 1-(chloromethyl)-3-methoxybenzene is in the development of anticancer agents. Researchers have explored its potential as a scaffold for designing molecules that interfere with critical signaling pathways involved in tumor growth and progression. By modifying the chloromethyl moiety or introducing additional functional groups, novel analogs have been synthesized, some of which show promising preclinical activity against various cancer cell lines. These findings highlight the compound's significance as a pharmacophore in oncology research.

The synthetic chemistry surrounding 1-(chloromethyl)-3-methoxybenzene has also seen innovative approaches to improve yield and selectivity. Transition metal-catalyzed reactions, such as palladium-mediated cross-coupling reactions, have been employed to introduce additional substituents at specific positions on the benzene ring. These methods not only enhance the efficiency of synthesis but also open up new avenues for structural diversification. Such advancements are crucial for accelerating the discovery and development of new drugs.

Another area where 1-(chloromethyl)-3-methoxybenzene has found utility is in materials science. Its ability to undergo polymerization reactions has led to the exploration of its use in creating novel polymers with unique properties. These materials have potential applications in coatings, adhesives, and even electronic components due to their tailored chemical functionalities. The versatility of this compound underscores its importance beyond traditional pharmaceutical applications.

Recent studies have also delved into the computational modeling of 1-(chloromethyl)-3-methoxybenzene to better understand its reactivity and interactions with biological targets. Molecular docking simulations have been used to predict how this compound might bind to specific proteins or enzymes, providing insights into its mechanism of action. Such computational approaches are increasingly integral to drug discovery pipelines, complementing experimental efforts and reducing reliance on trial-and-error methodologies.

The environmental impact of synthesizing and using 1-(chloromethyl)-3-methoxybenzene is another consideration that has garnered attention. Efforts are being made to develop greener synthetic routes that minimize waste and reduce energy consumption. Catalytic processes that employ recyclable catalysts or solvent-free conditions are being explored as alternatives to traditional methods. These sustainable practices align with broader initiatives to promote environmentally responsible chemistry.

In conclusion, 1-(chloromethyl)-3-methoxybenzene (CAS No. 824-98-6) is a multifaceted compound with significant implications in pharmaceuticals, materials science, and organic synthesis. Its unique structural features enable diverse applications, from drug development to advanced material creation. As research continues to uncover new methodologies and applications, this compound will undoubtedly remain a cornerstone in scientific innovation.

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