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

• 73481-53-5 Ethyl 2--4-(2-methyl-1,3-dioxolan-2-yl)cyclohexane-1-carboxylate 
• 22126-67-6 naphazoline 
• 94678-31-6 (4-dimethylamino-phenylimino)-[2]naphthyl-acetonitrile 
• 422564-76-9 N-hydroxy-2-(naphthalen-2-yl)acetamidine 
• 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 
• 1390632-66-2 N-(2-cyclohexyl-2-(naphthalen-2-yl)ethyl)benzimidamide 
• 1390632-72-0 2-cyclohexyl-2-(naphthalen-2-yl)acetonitrile 

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).

METHOD FOR MANUFACTURING AROMATIC NITRILE COMPOUND

The present invention provides a method for industrially producing a highly pure aromatic nitrile compound and a highly pure aromatic carboxylic acid compound safely and highly efficiently at low costs. Compound (2) is subjected to Willgerodt reaction in the presence of an additive as necessary, and the obtained amide compound (3) is hydrolyzed and neutralized to give carboxylic acid compound (4). Carboxylic acid compound (4) is reacted with a halogenating agent in the presence of a catalyst as necessary in an organic solvent, and further reacted with an amidating agent, and the obtained amide compound (5) or (6) is reacted with a dehydrating agent to give nitrile compound (1). Alternatively, carboxylic acid compound (4) is reacted with a halogenating agent and a compound represented by the formula R6SO2R7 in the presence of a catalyst as necessary in an organic solvent to give nitrile compound (1). Np is a naphthyl group optionally having substituent(s), R5 is an alkylene group having 1-3 carbon atoms, and other symbols are as described in the DESCRIPTION.

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.

Divergent synthesis of isonitriles and nitriles by palladium- catalyzed benzylic substitution with TMSCN

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.

New [4]helicene derivatives: Synthesis, characterization and photophysical properties

The design and synthesis of new [4]helicene derivatives were carried out by incorporating well-defined electron donor and acceptor groups at selected positions of the aromatic nuclei, aiming to use them in optical applications. Helicenes have been obtained in good overall yields through a five-step sequence involving mild experimental conditions and easy purification. Photophysical properties of these tetracyclic systems have been evaluated by UV–visible absorption and fluorescence spectroscopies and an emission in the visible region was observed.

Copper-Catalyzed Cyanation of N-Tosylhydrazones with Thiocyanate Salt as the "cN" Source

A novel protocol for the synthesis of α-aryl nitriles has been successfully achieved via a copper-catalyzed cyanation of N-tosylhydrazones employing thiocyanate as the source of cyanide. The features of this method include a convenient operation, readily available substrates, low-toxicity thiocyanate salts, and a broad substrate scope.

One-Pot Preparation of C1-Homologated Aliphatic Nitriles from Aldehydes through a Wittig Reaction under Metal-Cyanide-Free Conditions

A one-pot protocol to obtain C1-homologated aliphatic nitriles was achieved by treating aromatic and aliphatic aldehydes with the (methoxymethyl)triphenylphosphonium ylide followed by hydrolysis of the resulting methyl vinyl ethers with pTsOH (Ts = para-toluenesulfonyl) and treatment with molecular iodine and aqueous ammonia under metal cyanide free conditions. Neopentyl-type nitriles, which could not be obtained by conventional methods that involved conversion of the neopentyl alcohol into a tosylate and treatment with metal cyanide, were successfully obtained by using the present method.

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

N-Acyloxy-N-alkoxyamides are direct-acting mutagens in S. typhimurium TA100 with a linear dependence upon log P that maximises at log P0 = 6.4. Eight N-acyloxy-N-alkoxyamides (2-9) bearing a naphthalene group on any of the three side-chains and with log P0 6.4 have been demonstrated to be significantly and uniformly more mutagenic towards S. typhimurium TA100 than 50 mutagens without naphthalene. The activity enhancement of 2-9 is likely due to intercalative binding of naphthalene to bacterial DNA as a number are also active in TA98, a frame-shift strain of S. typhimurium, which is modified by intercalators. DNA damage profiles for naphthalene-bearing mutagens confirm enhanced reactivity with DNA when naphthalene is incorporated and a different binding mode when compared to mutagens without naphthalene. The effect is independent of whether the naphthalene is attached to an electron-donating alkyl or electron-withdrawing acyl group, alkyl tether length or, in the case of 6 and 7, the point of attachment to naphthalene. A new quantitative structure activity relationship has been constructed for all 58 congeners incorporating log P and an indicator variable, I, for the presence (I = 1) or absence (I = 0) of naphthalene and from which the activity enhancing effect of a naphthalene has been quantified at between three and four log P units. Contrary to conventional views, simple naphthalene groups could target molecules to DNA through intercalation.