Production Method 1

32721-21-4

93-04-9

947-62-6

Reaction Conditions

1.1 Reagents: Carbon dioxide ,  Triphenylphosphine ,  Tetraethylammonium p-toluenesulfonate Catalysts: Dichlorobis(triphenylphosphine)palladium Solvents: Dimethylformamide

Reference

Palladium(0)-catalyzed electroreductive carboxylation of aryl halides, β-bromostyrene, and allyl acetates with carbon dioxide

Torii, Sigeru; Tanaka, Hideo; Hamatani, Takeshi; Morisaki, Kazuo; Jutand, Anny; et al, Chemistry Letters, 1986, (2), 169-72

Production Method 2

3401-47-6

93-04-9

Reaction Conditions

1.1 Reagents: Tripotassium phosphate Catalysts: Palladium diacetate ,  Dicyclohexyl[4-methoxy-3-(2-methoxyphenyl)-2-naphthalenyl]phosphine Solvents: Methanol ,  Benzene ;  16 h, 40 °C

Reference

A mixed naphthyl-phenyl phosphine ligand motif for Suzuki, Heck, and hydrodehalogenation reactions

Demchuk, Oleg M.; Yoruk, Bilge; Blackburn, Tom; Snieckus, Victor, Synlett, 2006, (18), 2908-2913

Production Method 3

135-19-3

93-04-9

Reaction Conditions

1.1 Catalysts: 1-Ethyl-3-methylimidazolium bromide ;  rt; rt → 120 °C; 2.8 h, 120 °C

Reference

Catalytic O-methylation of phenols with dimethyl carbonate to aryl methyl ethers using [BMIm]Cl

Shen, Zhen Lu; Jiang, Xuan Zhen; Mo, Wei Min; Hu, Bao Xiang; Sun, Nan, Green Chemistry, 2005, 7(2), 97-99

Production Method 4

135-19-3

93-04-9

Reaction Conditions

1.1 Catalysts: Dimanganese decacarbonyl ;  1 h, 180 °C

Reference

Methylation of phenol and its derivatives with dimethyl carbonate in the presence of Mn2(CO)10, W(CO)6, and Co2(CO)8

Khusnutdinov, R. I.; Shchadneva, N. A.; Mayakova, Yu. Yu., Russian Journal of Organic Chemistry, 2015, 51(3), 330-334

Production Method 5

135-19-3

93-04-9

Reaction Conditions

1.1 Catalysts: Dimethyl sulfide Solvents: Dimethyl carbonate ;  4 h, rt → 220 °C

Reference

Methylation with Dimethyl Carbonate/Dimethyl Sulfide Mixtures: An Integrated Process without Addition of Acid/Base and Formation of Residual Salts

Lui, Yuen Wai; Chan, Bun ; Lui, Matthew Y., ChemSusChem, 2022, 15(3),

Production Method 6

135-19-3

93-04-9

Reaction Conditions

1.1 Reagents: Potassium carbonate Solvents: Dimethylformamide ;  rt; 2 h, rt
1.2 Reagents: Hydrochloric acid Solvents: Water ;  rt

Reference

C-H Nickelation of Naphthyl Phosphinites: Electronic and Steric Limitations, Regioselectivity, and Tandem C-P Functionalization

Mangin, Loic P.; Zargarian, Davit, Organometallics, 2019, 38(24), 4687-4700

Production Method 7

135-19-3

93-04-9

Reaction Conditions

1.1 0.15 MPa, 290 °C

Reference

Process for continuously preparing β-naphthyl methyl ether

, China, , ,

Production Method 8

104116-17-8

93-04-9

Reaction Conditions

1.1 Reagents: Potassium tert-butoxide Catalysts: [1,3-Bis[2,6-bis(1-methylethyl)phenyl]-2-imidazolidinylidene]chloro(η5-2,4-cyclo… Solvents: Isopropanol ;  24 h, 25 °C

Reference

Highly active, well-defined (cyclopentadiene)(N-heterocyclic carbene)palladium chloride complexes for room-temperature Suzuki-Miyaura and Buchwald-Hartwig cross-coupling reactions of aryl chlorides and deboronation homocoupling of arylboronic acids

Jin, Zhong; Guo, Su-Xian; Gu, Xiao-Peng; Qiu, Ling-Ling; Song, Hai-Bing; et al, Advanced Synthesis & Catalysis, 2009, 351(10), 1575-1585

Production Method 9

135-19-3

93-04-9

Reaction Conditions

1.1 Reagents: Sodium carbonate
1.2 Reagents: Polyethylene glycol

Reference

Etherification of phenols catalyzed by solid-liquid phase transfer catalyst PEG-400 without solvent

Cao, Yu-Qing; Pei, Ben-Gao, Synthetic Communications, 2000, 30(10), 1759-1766

Production Method 10

135-19-3

93-04-9

Reaction Conditions

1.1 Reagents: Sodium hydroxide Solvents: Dimethylformamide ;  25 °C
1.2 2 h, 25 °C

Reference

Synthesis of 6-propyl-2-naphthol

Li, Yan-yan; Liu, Qian-feng, Yingyong Huagong, 2014, 43(5), 901-904

Production Method 11

80-48-8

135-19-3

93-04-9

Reaction Conditions

1.1 Reagents: Sodium hydroxide ,  1-Pentanaminium, N-(carboxymethyl)-N,N-dipentyl-, inner salt Solvents: Water ;  8 h, 80 °C

Reference

Aqueous reaction solvent containing carboxybetains used for organic chemistry

, Japan, , ,

Production Method 12

135-19-3

93-04-9

Reaction Conditions

1.1 Reagents: Sodium hydroxide Solvents: 1,2-Dichloroethane ,  Water ;  0.5 h, 50 - 60 °C; 3 - 5 h, 60 °C → 40 °C

Reference

Preparation of DL-naproxen

, China, , ,

Production Method 13

5111-65-9

93-04-9

Reaction Conditions

1.1 Reagents: Tetrabutylammonium bromide Catalysts: Nickel alloy, base, Ni 95,Ag 5 Solvents: Water ;  24 h, 80 °C

Reference

Preparation of a cost-effective Ni-Ag bimetallic catalyst for hydrodehalogenation of aryl halides under mild conditions

Deng, Jiazhu; Xue, Teng; Wu, Haihong; Wu, Peng, New Journal of Chemistry, 2022, 46(25), 12169-12176

Production Method 14

55090-57-8

93-04-9

Reaction Conditions

1.1 Reagents: Poly(methylhydrosiloxane) Catalysts: Nickel acetate tetrahydrate ,  1,2-Bis(dicyclohexylphosphino)ethane Solvents: Toluene ;  24 h, 170 °C

Reference

Selective Reductive Removal of Ester and Amide Groups from Arenes and Heteroarenes through Nickel-Catalyzed C-O and C-N Bond Activation

Yue, Huifeng; Guo, Lin; Lee, Shao-Chi; Liu, Xiangqian; Rueping, Magnus, Angewandte Chemie, 2017, 56(14), 3972-3976

Production Method 15

3401-47-6

93-04-9

Reaction Conditions

1.1 Reagents: 1,8-Diazabicyclo[5.4.0]undec-7-ene Catalysts: 9-Hydroxy-1H-phenalen-1-one Solvents: Dimethyl sulfoxide ;  12 h, rt

Reference

Transforming Non-innocent Phenalenyl to a Potent Photoreductant: Captivating Reductive Functionalization of Aryl Halides through Visible-Light-Induced Electron Transfer Processes

Pathania, Vishali ; Roy, Vishal Jyoti; Roy, Sudipta Raha, Journal of Organic Chemistry, 2022, 87(24), 16550-16566

Production Method 16

5111-65-9

93-04-9

Reaction Conditions

1.1 Reagents: 4-Methylmorpholine ,  Diboronic acid Catalysts: Palladium Solvents: 1,2-Dichloroethane ;  3 h, 50 °C

Reference

Catalytic Reductions Without External Hydrogen Gas: Broad Scope Hydrogenations with Tetrahydroxydiboron and a Tertiary Amine

Korvinson, Kirill A.; Akula, Hari K.; Malinchak, Casina T.; Sebastian, Dellamol; Wei, Wei; et al, Advanced Synthesis & Catalysis, 2020, 362(1), 166-176

Production Method 17

580-13-2

93-04-9

Reaction Conditions

1.1 Reagents: Triethylamine Catalysts: Cadmium sulfide ,  Nickel dichloride ,  4,4′-Bis(1,1-dimethylethyl)-2,2′-bipyridine Solvents: Dimethylacetamide ;  rt

Reference

Practical heterogeneous photoredox/nickel dual catalysis for C-N and C-O coupling reactions

Liu, Yi-Yin; Liang, Dong; Lu, Liang-Qiu; Xiao, Wen-Jing, Chemical Communications (Cambridge, 2019, 55(33), 4853-4856

Production Method 18

135-19-3

93-04-9

Reaction Conditions

1.1 Catalysts: Carbon ,  Sulfuric acid Solvents: Benzene ;  15 min, 80 °C

Reference

Synthesis of β-naphthyl methyl ether catalyzed by activated carbon modified by H2SO4 under ultrasonic irradiation

Xiao, Dongcai; Yang, Jinhui, Jingxi Huagong, 2010, 27(10), 1038-1040

Production Method 19

67886-70-8

93-04-9

Reaction Conditions

1.1 Reagents: Triisopropylsilane Catalysts: Tributyl phosphite ,  Di-μ-chlorobis[(1,2,5,6-η)-1,5-cyclooctadiene]dirhodium Solvents: Ethylcyclohexane ;  15 h, 130 °C

Reference

Rhodium-catalyzed carbon-cyano bond cleavage reactions using organosilicon reagents

Kita, Yusuke; Tobisu, Mamoru; Chatani, Naoto, Yuki Gosei Kagaku Kyokaishi, 2010, 68(11), 1112-1122

Production Method 20

67886-70-8

93-04-9

Reaction Conditions

1.1 Reagents: Triisopropylsilane Catalysts: Triisopropyl phosphite ,  Di-μ-chlorobis[(1,2,5,6-η)-1,5-cyclooctadiene]dirhodium Solvents: Ethylcyclohexane ;  15 h, 130 °C

Reference

Rhodium-catalyzed reductive decyanation of nitriles using hydrosilane as a reducing agent: scope, mechanism and synthetic application

Tobisu, Mamoru; Nakamura, Ryo; Kita, Yusuke; Chatani, Naoto, Bulletin of the Korean Chemical Society, 2010, 31(3), 582-587

Production Method 21

135-19-3

93-04-9

Reaction Conditions

1.1 Reagents: Sodium hydroxide Solvents: Acetone ;  10 min, 25 °C

Reference

Method for synthesizing aryl methyl ether

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2-Methoxynaphthalene Raw materials

• 1-Iodo-2-methoxynaphthalene
• 2-Bromo-6-methoxynaphthalene (Naproxen Impurity N)
• 6-Methoxy-2-cyanonaphthalene
• methyl 4-methylbenzene-1-sulfonate
• 2-Bromonaphthalene
• 6-Methoxy-2-naphthalenecarboxylic acid phenyl ester
• 1-Bromo-2-methoxy-naphthalene
• (2-Methoxynaphthalen-1-yl)boronic Acid
• naphthalen-2-ol

2-Methoxynaphthalene Preparation Products

• 2-Methoxy-1-naphthoic acid (947-62-6)
• 2-Methoxynaphthalene (93-04-9)

• 1. Essential effect of the electrolyte on the mechanical and chemical degradation of LiNi0.8Co0.15Al0.05O2 cathodes upon long-term cycling??
  Xiaoming Liu,Zachary D. Hood,Wangda Li,Donovan N. Leonard,Arumugam Manthiram,Miaofang Chi J. Mater. Chem. A, 2021,9, 2111-2119
• 2. Enabling high-throughput single-animal gene-expression studies with molecular and micro-scale technologies
  Jason Wan Lab Chip, 2020,20, 4528-4538
• 3. Dissociation of large gaseous serine clusters produces abundant protonated serine octamer
  Jacob S. Jordan,Evan R. Williams Analyst, 2021,146, 2617-2625
• 4. Excimer and exciplex formation in a pair of bright phosphorescent isomers constructed from Cu3(pyrazolate)3 and Cu3I3 coordination luminophores?
  Shun-Ze Zhan,Mian Li,Xiao-Ping Zhou,Dan Li,Seik Weng Ng RSC Adv., 2011,1, 1457-1459
• 5. Dissolved oxygen sensor based on fluorescence quenching of oxygen-sensitive ruthenium complexes immobilized in sol–gel-derived porous silica coatings
  Analyst, 1996,121, 785-788

• Solvents and Organic Chemicals Organic Compounds Benzenoids Naphthalenes Naphthalenes
• Solvents and Organic Chemicals Organic Compounds Benzenoids Naphthalenes
• Solvents and Organic Chemicals Organic Compounds Alcohol/Ether

Introduction to 2-Methoxynaphthalene (CAS No. 93-04-9)

2-Methoxynaphthalene, also known by its CAS number 93-04-9, is a significant organic compound widely utilized in the pharmaceutical and chemical industries. This compound, a derivative of naphthalene, features a methoxy group (-OCH?) attached to the second carbon atom of the naphthalene ring. Its unique structural and chemical properties make it a valuable intermediate in synthesizing various bioactive molecules.

The molecular structure of 2-Methoxynaphthalene consists of two fused benzene-like rings with an oxygen-methyl substituent on one of the rings. This arrangement imparts distinct reactivity and solubility characteristics, making it a versatile building block in organic synthesis. The presence of the methoxy group enhances its ability to participate in various chemical reactions, including nucleophilic substitution and electrophilic aromatic substitution, which are pivotal in drug development.

In recent years, 2-Methoxynaphthalene has garnered attention for its role in pharmaceutical research. Its derivatives have been explored as potential candidates for treating neurological disorders, cancer, and infectious diseases. For instance, studies have demonstrated its utility in synthesizing small-molecule inhibitors that target specific enzymes involved in disease pathways. The compound's ability to undergo selective functionalization allows researchers to tailor its properties for targeted therapeutic applications.

The pharmaceutical industry has leveraged 2-Methoxynaphthalene in the development of novel drug candidates due to its favorable pharmacokinetic properties. Researchers have incorporated it into molecules designed to enhance bioavailability and reduce toxicity. Additionally, its role in creating chiral centers has been investigated, as many therapeutic agents require specific stereochemical configurations for efficacy. This has opened up new avenues for designing enantiomerically pure drugs with improved therapeutic outcomes.

Beyond pharmaceuticals, 2-Methoxynaphthalene finds applications in the synthesis of dyes, pigments, and agrochemicals. Its aromatic structure and methoxy substituent contribute to its stability and colorfastness, making it suitable for industrial applications. Furthermore, its derivatives have been used in material science research, particularly in developing organic semiconductors and liquid crystals. These materials are crucial for electronic devices such as organic light-emitting diodes (OLEDs) and liquid crystal displays (LCDs).

The chemical reactivity of 2-Methoxynaphthalene allows for diverse modifications, enabling the creation of complex molecular architectures. Researchers have utilized palladium-catalyzed cross-coupling reactions to introduce various functional groups onto the naphthalene core. These reactions are essential for constructing biaryl compounds, which are prevalent in many biologically active molecules. Such synthetic strategies have facilitated the rapid discovery and development of new chemical entities with potential therapeutic value.

In conclusion, 2-Methoxynaphthalene (CAS No. 93-04-9) is a multifaceted compound with broad applications across multiple industries. Its unique structural features and reactivity make it an indispensable tool in pharmaceutical research, material science, and industrial chemistry. As scientific understanding advances, the potential uses of this compound are expected to expand further, driving innovation in drug discovery and material development.

• 2216-69-5(1-Methoxynaphthalene)
• 5486-55-5(2,6-Dimethoxynaphthalene)
• 3900-49-0(1,6-Dimethoxynaphthalene)
• 613-80-9(2,2'-Dinaphthyl Ether)
• 84-85-5(4-methoxynaphthalen-1-ol)
• 10075-63-5(1,5-Dimethoxynaphthalene)
• 10075-62-4(1,4-Dimethoxynaphthalene)
• 5111-66-0(6-Methoxy-2-naphthol)
• 3469-26-9(2,7-Dimethoxynaphthalene)
• 5309-18-2(1,7-Dimethoxynaphthalene)