Production Method 1

619-72-7

91949-95-0

Reaction Conditions

1.1 Reagents: Sodium hydroxide Solvents: Dimethylformamide ;  20 min, 25 °C

Reference

Light-emitting diode light-enabled denitrative etherification of 4-nitrobenzonitrile under catalyst-free conditions at room temperature

Soltani, Roghaye; Abdollahi, Fatemeh; Ghaderi, Arash, Journal of Chemical Research, 2021, 45(1-2), 56-59

Production Method 2

874-90-8

91949-95-0

Reaction Conditions

1.1 Reagents: Potassium tert-butoxide Solvents: 1,4-Dioxane ;  rt → 80 °C; 16 h, 80 °C

Reference

Metal-Free Etherification of Aryl Methyl Ether Derivatives by C-OMe Bond Cleavage

Wang, Xueqiang ; Li, Chenchen ; Wang, Xia; Wang, Qingli; Dong, Xiu-Qin; et al, Organic Letters, 2018, 20(14), 4267-4272

Production Method 3

767-00-0

91949-95-0

Reaction Conditions

1.1 Reagents: Potassium carbonate Solvents: Acetone ;  5 h, reflux

Reference

N-[4-(Methylsulfonylamino)benzyl]thiourea analogues as vanilloid receptor antagonists: analysis of structure-activity relationships for the 'C-Region'

Lee, Jeewoo; Kang, Sang-Uk; Lim, Ju-Ok; Choi, Hyun-Kyung; Jin, Mi-kyung; et al, Bioorganic & Medicinal Chemistry, 2004, 12(2), 371-385

Production Method 4

874-90-8

91949-95-0

Reaction Conditions

1.1 Catalysts: N′′′-(1,1-Dimethylethyl)-N,N′,N′′-tris[tris(dimethylamino)phosphoranylidene]phos… Solvents: Tetrahydrofuran ,  Hexane ;  18 h, 50 °C

Reference

Phosphazene Base tBu-P4 Catalyzed Methoxy-Alkoxy Exchange Reaction on (Hetero)Arenes

Shigeno, Masanori ; Hayashi, Kazutoshi; Nozawa-Kumada, Kanako; Kondo, Yoshinori, Chemistry - A European Journal, 2019, 25(24), 6077-6081

Production Method 5

623-00-7

91949-95-0

Reaction Conditions

1.1 Reagents: Sodium hydride Solvents: Toluene
1.2 Catalysts: Tris(dibenzylideneacetone)dipalladium ,  1,1′-(1R)-[1,1′-Binaphthalene]-2,2′-diylbis[bis(4-methylphenyl)phosphine Solvents: Toluene
1.3 Reagents: Water Solvents: Diethyl ether

Reference

Preparation of aryl ethers

, World Intellectual Property Organization, , ,

Production Method 6

623-00-7

91949-95-0

Reaction Conditions

1.1 Reagents: Sodium hydride Solvents: Toluene
1.2 Catalysts: Tris(dibenzylideneacetone)dipalladium ,  1,1′-(1S)-[1,1′-Binaphthalene]-2,2′-diylbis[1,1-bis(4-methylphenyl)phosphine Solvents: Toluene
1.3 Reagents: Water Solvents: Diethyl ether

Reference

Palladium-Catalyzed Intermolecular Carbon-Oxygen Bond Formation: A New Synthesis of Aryl Ethers

Palucki, Michael; Wolfe, John P.; Buchwald, Stephen L., Journal of the American Chemical Society, 1997, 119(14), 3395-3396

Production Method 7

37181-39-8

51570-75-3

91949-95-0

Reaction Conditions

1.1 Reagents: Potassium tert-butoxide Solvents: Dimethylformamide ,  Tetrahydrofuran ;  10 min, 25 °C
1.2 3 h, 25 °C

Reference

From Anilines to Aryl Ethers: A Facile, Efficient, and Versatile Synthetic Method Employing Mild Conditions

Wang, Dong-Yu; Yang, Ze-Kun; Wang, Chao; Zhang, Ao; Uchiyama, Masanobu, Angewandte Chemie, 2018, 57(14), 3641-3645

Production Method 8

86164-70-7

6967-88-0

91949-95-0

Reaction Conditions

1.1 Reagents: Zinc Catalysts: Nickel, (2,2′-bipyridine-κN1,κN1′)dibromo-, (SP-4-2)- Solvents: Dimethylacetamide ;  2 min, rt; 16 h, 80 °C; 80 °C → rt
1.2 Reagents: Sodium bicarbonate Solvents: Water ;  rt

Reference

Ni-Catalyzed Reductive Cyanation of Aryl Halides and Phenol Derivatives via Transnitrilation

Mills, L. Reginald; Graham, Joshua M.; Patel, Purvish; Rousseaux, Sophie A. L., Journal of the American Chemical Society, 2019, 141(49), 19257-19262

Production Method 9

767-00-0

91949-95-0

Reaction Conditions

1.1 Reagents: Potassium carbonate Solvents: Acetone ;  rt; 73 h, 60 °C
1.2 6 h

Reference

Photocatalytic Reductive C-O Bond Cleavage of Alkyl Aryl Ethers by Using Carbazole Catalysts with Cesium Carbonate

Yabuta, Tatsushi; Hayashi, Masahiko ; Matsubara, Ryosuke, Journal of Organic Chemistry, 2021, 86(3), 2545-2555

Production Method 10

767-00-0

91949-95-0

Reaction Conditions

1.1 Reagents: Sodium ethoxide Solvents: Ethanol

Reference

Antiarrhythmic agents related to procainamide. II. Synthesis and pharmacological study

Reynaud, Pierre; Brion, Jean Daniel; Nguyen Tri Xuong, Emmanuel; Davrinche, Catherine; Pieri, Francois; et al, European Journal of Medicinal Chemistry, 1989, 24(4), 427-34

Production Method 11

91342-00-6

91949-95-0

Reaction Conditions

1.1 Reagents: Triethylamine ,  4-Nitro-1-[(trifluoromethyl)sulfonyl]-1H-imidazole Solvents: Acetonitrile ;  10 min, rt

Reference

A convenient reagent for the conversion of aldoximes into nitriles and isonitriles

Zhang, Wei; Lin, Jin-Hong; Zhang, Pengfei; Xiao, Ji-Chang, Chemical Communications (Cambridge, 2020, 56(46), 6221-6224

Production Method 12

767-00-0

91949-95-0

Reaction Conditions

1.1 Reagents: Triphenylphosphine ,  1,2-Bis(2-tricyclo[3.3.1.13,7]dec-1-ylethyl) 1,2-diazenedicarboxylate Solvents: Tetrahydrofuran ;  overnight, rt

Reference

Separation tagging with cyclodextrin-binding groups: Mitsunobu reactions with bis(2-(1-adamantyl)ethyl) azodicarboxylate (BadEAD) and bis(1-adamantylmethyl) azodicarboxylate (BadMAD)

Dandapani, Sivaraman; Newsome, Jeffery J.; Curran, Dennis P., Tetrahedron Letters, 2004, 45(35), 6653-6656

Production Method 13

623-00-7

91949-95-0

Reaction Conditions

1.1 Reagents: Sodium tert-butoxide Solvents: Dimethyl sulfoxide ;  4 h, rt

Reference

Transition-metal-free arylation of alcohols with aryl bromides at room temperature

Zhu, Da-Liang; Li, Jie; Wu, Qi; Wang, Yanqing; Young, David J. ; et al, Synthesis, 2023, 55(4), 637-646

Production Method 14

623-03-0

91949-95-0

Reaction Conditions

1.1 Reagents: Diisopropylethylamine Catalysts: Nickel sulfate (NiSO4) ,  4,4′-Dimethoxy-2,2′-bipyridine ,  2767997-30-6 Solvents: Acetonitrile ;  24 h, rt
1.2 Reagents: Water ;  rt

Reference

Discovery and characterization of a novel perylenephotoreductant for the activation of aryl halides

Li, Min; Li, Jia; Guo, Baodang; Liu, Xuanzhong; Yuan, Zhenbo ; et al, Journal of Catalysis, 2021, 399, 111-120

Production Method 15

623-03-0

91949-95-0

Reaction Conditions

1.1 Reagents: Potassium tert-butoxide Solvents: Dimethylformamide ,  Tetrahydrofuran ;  5 min, 0 °C; 6 h, 25 °C
1.2 Reagents: Ammonium chloride Solvents: Water ;  0 °C

Reference

Aryl Ether Syntheses via Aromatic Substitution Proceeding under Mild Conditions

Ando, Shin ; Tsuzaki, Marina; Ishizuka, Tadao, Journal of Organic Chemistry, 2020, 85(17), 11181-11189

Production Method 16

767-00-0

91949-95-0

Reaction Conditions

1.1 Reagents: 2,4-Dihydro-2,4,5-triphenyl-3H-1,2,4-triazol-3-ylidene Solvents: Acetonitrile ;  > 1 min, rt
1.2 Reagents: 4-[3,5-Bis(1,1-dimethylethyl)-4-oxo-2,5-cyclohexadien-1-ylidene]-2,6-bis(1,1-dim… ;  8 h, 80 °C

Reference

N-Heterocyclic carbene-mediated redox condensation of alcohols

Kato, Terumasa; Matsuoka, Shin-ichi; Suzuki, Masato, Chemical Communications (Cambridge, 2016, 52(55), 8569-8572

Production Method 17

623-03-0

6831-82-9

91949-95-0

Reaction Conditions

1.1 Catalysts: Nickel (poly-imidazolidene and poly-benzimidazolidene supported) Solvents: Dimethylformamide ;  16 h, 100 °C

Reference

Poly-n-heterocyclic carbene transition metal complexes and n-heterocyclic carbene transition metal complexes for carbon-sulfur and carbon-oxygen coupling reactions

, World Intellectual Property Organization, , ,

Production Method 18

623-00-7

91949-95-0

Reaction Conditions

1.1 Reagents: Sodium tert-butoxide Catalysts: (SP-4-3)-Chloro[8-[2-(dicyclohexylphosphino-κP)phenyl]-1,3,5,7-tetramethyl-2,4,6… Solvents: Toluene ;  18 h, 110 °C

Reference

Exploiting Ancillary Ligation To Enable Nickel-Catalyzed C-O Cross-Couplings of Aryl Electrophiles with Aliphatic Alcohols

MacQueen, Preston M.; Tassone, Joseph P.; Diaz, Carlos; Stradiotto, Mark, Journal of the American Chemical Society, 2018, 140(15), 5023-5027

Production Method 19

21382-98-9

91949-95-0

Reaction Conditions

1.1 Reagents: Potassium tert-butoxide Solvents: 1,4-Dioxane ;  rt → 80 °C; 16 h, 80 °C

Reference

Nucleophilic Amination and Etherification of Aryl Alkyl Thioethers

Wang, Xia; Tang, Yue; Long, Cheng-Yu; Dong, Wen-Ke; Li, Chenchen ; et al, Organic Letters, 2018, 20(16), 4749-4753

Production Method 20

623-00-7

91949-95-0

Reaction Conditions

1.1 Reagents: Quinuclidine Catalysts: 2,2′-Bipyridine ,  Nickel dichloride ,  [1,1′:4′,1′′-Terphenyl]-4,4′′-dicarboxaldehyde, polymer with 5′-(4-aminophenyl)[… Solvents: Dimethylacetamide ;  10 h

Reference

Covalent organic frameworks editing for efficient metallaphotoredox catalytic carbon-oxygen cross coupling of aryl halides with alcohols

Meng, Di; Xue, Jing; Zhang, Yufan; Liu, Tianjiao; Chen, Chuncheng; et al, Catalysis Science & Technology, 2023, 13(5), 1518-1526

4-Isopropoxybenzonitrile Raw materials

• 4-Methoxybenzonitrile
• 4-Bromobenzonitrile
• 4-(methylsulfanyl)benzonitrile
• Propanedinitrile, methylphenyl-
• 4-Hydroxybenzonitrile
• 1-bromo-4-(propan-2-yloxy)benzene
• 4-Chlorobenzonitrile
• p-Nitrobenzonitrile
• Potassium isopropoxide
• Benzenaminium, 4-cyano-N,N,N-trimethyl-
• (E)-N-{[4-(propan-2-yloxy)phenyl]methylidene}hydroxylamine

4-Isopropoxybenzonitrile Preparation Products

• 4-Isopropoxybenzonitrile (91949-95-0)

• 1. An astrophysically-relevant mechanism for amino acid enantiomer enrichment
  Stephen P. Fletcher,Richard B. C. Jagt,Ben L. Feringa Chem. Commun., 2007, 2578-2580
• 2. Acenaphthenic hopanoids, a novel series of aromatised
  Teresita Carrillo-Hernández,Philippe Schaeffer,Pierre Albrecht Chem. Commun., 2001, 1976-1977
• 3. An intermolecular C–C coupling reaction of iridium complexes?
  Kathrin Kutlescha,Rhett Kempe New J. Chem., 2010,34, 1954-1960
• 4. An artificial CO-releasing metalloprotein built by histidine-selective metallation?
  Inês S. Albuquerque,Hélia F. Jeremias,Miguel Chaves-Ferreira,Dijana Matak-Vinkovic,Omar Boutureira,Carlos C. Rom?o Chem. Commun., 2015,51, 3993-3996
• 5. An integrated process of CO2 capture and in situ hydrogenation to formate using a tunable ethoxyl-functionalized amidine and Rh/bisphosphine system?
  Yu-Nong Li,Liang-Nian He,Xian-Dong Lang,Xiao-Fang Liu,Shuai Zhang RSC Adv., 2014,4, 49995-50002

• Solvents and Organic Chemicals Organic Compounds Benzenoids Phenol ethers Phenol ethers
• Solvents and Organic Chemicals Organic Compounds Benzenoids Phenol ethers

• 25117-74-2(Benzonitrile, 4-ethoxy-)
• 185259-36-3(4-tert-Butoxybenzonitrile)
• 80407-66-5(4-(2-methoxyethoxy)benzonitrile)
• 25117-75-3(3-Ethoxybenzonitrile)
• 86120-21-0(4-(butan-2-yloxy)benzonitrile)
• 610797-50-7(Benzonitrile, 3-methyl-4-(1-methylethoxy)- (9CI))
• 62677-57-0(1-Naphthalenecarbonitrile, 4-(1-methylethoxy)-)
• 18859-06-8( )
• 7476-06-4(4,4'-(1,3-Propanediylbisoxy)bisbenzonitrile)
• 60758-84-1(4-propoxybenzonitrile)