7498-57-9

Basic information

• Product Name: 2-Naphthylacetonitrile
• Synonyms: 2-NAPHTHYLACETONITRILE;2-NAPHTHALENEACETONITRILE;beta-Naphthyleneacetonitrile;2-Naphthtyl acetonitrile;2-Naphthylacetonitrile, tech., 90-95%;2-(NAPHTHALEN-2-YL)ACETONITRILE;(b-Naphthyl)acetonitrile;2-(Cyanomethyl)naphthalene
• CAS NO: 7498-57-9
• Molecular Formula: C₁₂H₉N
• Molecular Weight: 167.21
• EINECS: 231-352-5
• Product Categories: Naphthalene derivatives;Aromatic Nitriles
• Mol File: 7498-57-9.mol

Chemical Properties

• Melting Point: 82-84 °C(lit.)
• Boiling Point: 303 °C(lit.)
• Flash Point: 303°C
• Appearance: white to light yellow powder
• Density: 1.092 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.000956mmHg at 25°C
• Refractive Index: 1.5785 (estimate)
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: Chloroform (Slightly), Ethyl Acetate (Slightly)
• Water Solubility: Insoluble in water.
• BRN: 1862879
• CAS DataBase Reference: 2-Naphthylacetonitrile(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Naphthylacetonitrile(7498-57-9)
• EPA Substance Registry System: 2-Naphthylacetonitrile(7498-57-9)

Safety Data

• Hazard Codes: Xn,C,F
• Statements: 20/21/22-34-11
• Safety Statements: 36-24/25-45-36/37/39-26-16
• RIDADR: 3276
• WGK Germany: 3
• HazardClass: 6.1
• PackingGroup: III
• Hazardous Substances Data: 7498-57-9(Hazardous Substances Data)

Usage

Uses

Used in Chemical Synthesis:
2-Naphthylacetonitrile is used as a starting reagent for the synthesis of 2-(1-cyano-1-(2-naphthyl))methylidene-3-phenyl-thiazolidine-4,5-dione, a compound with potential applications in various fields.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 2-Naphthylacetonitrile is used as a key intermediate in the synthesis of various drugs and pharmaceutical compounds. Its chemical properties make it a versatile building block for the development of new medications.
Used in Organic Chemistry Research:
2-Naphthylacetonitrile is also used in organic chemistry research as a reagent for the synthesis of various organic compounds, including coumarins. It undergoes three-component coupling with benzyne and DMF to yield these compounds, which have a wide range of applications in the chemical and pharmaceutical industries.
Overall, 2-Naphthylacetonitrile is a valuable compound in the fields of chemical synthesis, pharmaceuticals, and organic chemistry research due to its versatility and reactivity.

Synthesis Reference(s)

Synthetic Communications, 23, p. 1061, 1993 DOI: 10.1080/00397919308018582

InChI:InChI=1/C12H9N/c13-8-7-10-5-6-11-3-1-2-4-12(11)9-10/h1-6,9H,7H2

Upstream product

• 143-33-9 sodium cyanide 
• 939-26-4 2-bromomethylnaphthyl bromide 
• 151-50-8 potassium cyanide 
• 91-20-3 naphthalene 
• 107-14-2 chloroacetonitrile 
• 139109-58-3 3-(2-Naphtholyl)-2-hydroxyiminopropionic acid 
• 37859-25-9 2-naphthylacetyl chloride 
• 959842-57-0 carbonic acid, cyano(2-naphthyl)methyl ethyl ester 
• 66-99-9 β-naphthaldehyde 
• 1592-38-7 2-Naphthalenemethanol 
• 581-96-4 2-naphthylacetic acid 
• 91-57-6 2-Methylnaphthalene 
• 7677-24-9 trimethylsilyl cyanide 
• 928664-98-6 4-isoxazoleboronic acid pinacol ester 

Downstream Products

• 5681-33-4 2-(naphthalen-2-yl)-3-phenylpropanenitrile 
• 22126-67-6 naphazoline 
• 81250-60-4 1-(4'-aminophenyl)-1,4-dihydro-3(2H)-benzoisoquinolinone 
• 81250-67-1 1-(4'-chloroacetylamino)phenyl-1,4-dihydro-3(2H)-benzoisoquinolinone 
• 81250-68-2 1-<4'-(ethylaminoacetyl)aminophenyl>-1,4-dihydro-3(2H)-benzoisoquinolinone 
• 552326-71-3 naphthalen-2-yl-(3-pyridin-4-yl-1H-pyrazolo[3,4-b]pyridin-6-yl)-acetonitrile 
• 882182-35-6 2-methyl-2-(((1S)-1-phenylethyl)amino)propanenitrile 
• 1145685-84-2 C₂₁H₂₀N₂ 
• 2086-62-6 2-(2-bromoethyl)naphthalene 
• 1485-07-0 naphthalen-2-ethanol 

Relevant articles and documents

Metal-Free Deoxygenation of Chiral Nitroalkanes: An Easy Entry to α-Substituted Enantiomerically Enriched Nitriles

A metal-free, mild and chemodivergent transformation involving nitroalkanes has been developed. Under optimized reaction conditions, in the presence of trichlorosilane and a tertiary amine, aliphatic nitroalkanes were selectively converted into amines or nitriles. Furthermore, when chiral β-substituted nitro compounds were reacted, the stereochemical integrity of the stereocenter was maintained and α-functionalized nitriles were obtained with no loss of enantiomeric excess. The methodology was successfully applied to the synthesis of chiral β-cyano esters, α-aryl alkylnitriles, and TBS-protected cyanohydrins, including direct precursors of four active pharmaceutical ingredients (ibuprofen, tembamide, aegeline and denopamine).

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Assembly of α-(Hetero)aryl Nitriles via Copper-Catalyzed Coupling Reactions with (Hetero)aryl Chlorides and Bromides

α-(Hetero)aryl nitriles are important structural motifs for pharmaceutical design. The known methods for direct synthesis of these compounds via coupling with (hetero)aryl halides suffer from narrow reaction scope. Herein, we report that the combination of copper salts and oxalic diamides enables the coupling of a variety of (hetero)aryl halides (Cl, Br) and ethyl cyanoacetate under mild conditions, affording α-(hetero)arylacetonitriles via one-pot decarboxylation. Additionally, the CuBr/oxalic diamide catalyzed coupling of (hetero)aryl bromides with α-alkyl-substituted ethyl cyanoacetates proceeds smoothly at 60 °C, leading to the formation of α-alkyl (hetero)arylacetonitriles after decarboxylation. The method features a general substrate scope and is compatible with various functionalities and heteroaryls.

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Ligand-controlled palladium-catalyzed divergent synthesis of isonitriles and nitriles from benzylic carbonates and TMSCN has been developed. The BINAP- or DPEphos-ligated palladium catalyst selectively provides the corresponding benzylic isonitriles, wher

Nickel-Catalyzed Cyanation of Benzylic and Allylic Pivalate Esters

A nickel-catalyzed cyanation reaction of benzylic and allylic pivalate esters is reported using an air-stable Ni(II) precatalyst and substoichiometric quantities of Zn(CN)2. Alkene additives were found to inhibit catalysis, suggesting that avoiding β-hydride elimination side reactions is essential for productive catalysis. An enantioenriched allylic ester undergoes enantiospecific cross-coupling to produce an enantioenriched allylic nitrile. This method was applied to an efficient synthesis of (±)-naproxen from commercially available starting materials.

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Mutagenicity of N-acyloxy-N-alkoxyamides as an indicator of DNA intercalation part 1: Evidence for naphthalene as a DNA intercalator

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