67886-70-8

Basic information

• Product Name: 2-CYANO-6-METHOXYNAPHTHALENE
• Synonyms: 2-CYANO-6-METHOXYNAPHTHALENE;6-METHOXY-2-CYANONAPHTHALENE;6-METHOXY-2-NAPHTHONITRILE;6-Methoxy-2-naphthalenecarbonitrile;6-Methoxynaphthalene-2-carbonitrile;2-Naphthalenecarbonitrile, 6-Methoxy-;Naproxen Nitrile IMpurity;6-Methoxy-2-naphthonitrile 98%
• CAS NO: 67886-70-8
• Molecular Formula: C₁₂H₉NO
• Molecular Weight: 183.21
• Mol File: 67886-70-8.mol
• Article Data: 21

Chemical Properties

• Melting Point: 106-107 °C(lit.)
• Boiling Point: 205-208 °C14 mm Hg(lit.)
• Flash Point: 146.9 °C
• Appearance: White to yellow/Crystalline Powder
• Density: 1.1261 (rough estimate)
• Vapor Pressure: 5.11E-05mmHg at 25°C
• Refractive Index: 1.5880 (estimate)
• CAS DataBase Reference: 2-CYANO-6-METHOXYNAPHTHALENE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-CYANO-6-METHOXYNAPHTHALENE(67886-70-8)
• EPA Substance Registry System: 2-CYANO-6-METHOXYNAPHTHALENE(67886-70-8)

Safety Data

• Hazard Codes: Xn,T
• Statements: 20/21/22-36/37/38
• Safety Statements: 26-37/39
• WGK Germany: 3
• HazardClass: TOXIC
• Hazardous Substances Data: 67886-70-8(Hazardous Substances Data)

Usage

Uses

6-Methoxy-2-naphthonitrile (2-cyano-6-methoxynaphthalene) was used in the synthesis of 2-cyano-1-(1,3-diarylpropyl)-6-methoxynaphthalenes.

Synthesis Reference(s)

The Journal of Organic Chemistry, 49, p. 4995, 1984 DOI: 10.1021/jo00199a048

InChI:InChI=1/C12H9NO/c1-14-12-5-4-10-6-9(8-13)2-3-11(10)7-12/h2-7H,1H3

Upstream product

• 5111-65-9 2-Bromo-6-methoxynaphthalene 
• 31892-41-8 N-cyano-benzimidazole 
• 55305-43-6 N-cyano-N-phenyl-p-toluenesulfonamide 
• 105-56-6 ethyl 2-cyanoacetate 
• 129113-00-4 2-ethynyl-6-methoxynaphthalene 
• 5807-02-3 4-morpholinoacetonitrile 
• 55090-57-8 phenyl 6-methoxy-2-naphthoate 
• 82408-29-5 phenyl naphthalene-2-carboxylate 
• 874-77-1 2-(4-methylpiperazin-1-yl)acetonitrile 
• 77287-34-4 formamide 
• 557-21-1 zinc(II) cyanide 
• 79215-28-4 6-methoxy-3,4-dihydronaphthalene-2-carbonitrile 
• 34093-07-7 6-methoxy-1-oxo-1,2,3,4-tetrahydronaphthalene-2-carbonitrile 
• 606494-99-9 1-hydroxy-2-cyano-6-methoxy-1,2,3,4-tetrahydronaphthalene 

Downstream Products

• 127660-84-8 1-(6-methoxynaphthalen-2-yl)-2-phenylethanone 
• 84255-35-6 (6-methoxynaphthalen-2-yl)(phenyl)methanone 
• 2471-70-7 2-methoxy-6-naphthoic acid 
• 16712-64-4 6-Hydroxy-2-naphthoic acid 
• 60201-22-1 (6-methoxy-2-naphthyl)methanol 
• 59115-50-3 2-methoxy-6-(4-methylphenyl)naphthalene 
• 93-04-9 2-Methoxynaphthalene 
• 1398119-47-5 C₂₇H₁₇NO₃ 
• 1019477-32-7 N-((6-methoxynaphthalen-2-yl)methyl)propan-2-amine 
• 1402577-15-4 (6-methoxynaphthalen-2-yl)diphenylphosphine oxide 
• 791-28-6 Triphenylphosphine oxide 
• 190434-38-9 6-benzyl-2-naphthalenol 
• 2471-69-4 6-methoxy-1,2,3,4-tetrahydronaphthalene-2-carboxylic acid 
• 58601-32-4 6-methoxy-2-naphthoyl chloride 

Relevant articles and documents

Decarbonylative Synthesis of Aryl Nitriles from Aromatic Esters and Organocyanides by a Nickel Catalyst

A decarbonylative cyanation of aromatic esters with aminoacetonitriles in the presence of a nickel catalyst was developed. The key to this reaction was the use of a thiophene-based diphosphine ligand, dcypt, permitting the synthesis of aryl nitrile without the generation of stoichiometric metal- or halogen-containing chemical wastes. A wide range of aromatic esters, including hetarenes and pharmaceutical molecules, can be converted into aryl nitriles.

Nickel-Catalyzed Transformation of Alkene-Tethered Oxime Ethers to Nitriles by a Traceless Directing Group Strategy

Nickel-catalyzed transformation of alkene-tethered oxime ethers to nitriles using a traceless directing group strategy has been developed. A series of alkene-tethered oxime ethers derived from benzaldehyde and cinnamyl aldehyde derivatives were converted into the corresponding benzonitriles and cinnamonitriles in 46-98% yields using the nickel catalyst system. Control experiments showed that the alkene group tethered to an oxygen atom on the oximes via one methylene unit plays a key role as a traceless directing group during the catalysis.

Ni-Mediated Generation of "cN" Unit from Formamide and Its Catalysis in the Cyanation Reactions

The in situ generation of a "cyano" unit from readily available organic precursors is of high interest in synthetic chemistry. Herein, we report the first example of Ni-mediated dehydration of formamide to form "CN" and its subsequent catalytic applications in the hydrocyanation of alkynes and cyanation of aryl halides. Formamide can serve as a convenient source for the nitrile unit, in that it releases water as the only byproduct.