118736-08-6

Basic information

• Product Name: 2-METHOXY-2-(2-NAPHTHYL)ACETONITRILE
• Synonyms: α-methoxy-2-naphthaleneacetonitrile;2-Methoxy-2-(2-naphthyl)ethanenitrile
• CAS NO: 118736-08-6
• Molecular Formula: C₁₃H₁₁NO
• Molecular Weight: 0
• Mol File: 118736-08-6.mol

Chemical Properties

• Boiling Point: 333.5°C at 760 mmHg
• Flash Point: 93.3°C
• Appearance: /
• Density: 1.06g/cm³
• Vapor Pressure: 0.000136mmHg at 25°C
• Refractive Index: 1.57
• CAS DataBase Reference: 2-METHOXY-2-(2-NAPHTHYL)ACETONITRILE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-METHOXY-2-(2-NAPHTHYL)ACETONITRILE(118736-08-6)
• EPA Substance Registry System: 2-METHOXY-2-(2-NAPHTHYL)ACETONITRILE(118736-08-6)

Safety Data

• Hazard Codes: N
• Statements: 50
• Safety Statements: 61
• RIDADR: UN 3077 9/PG 3
• WGK Germany: 2
• Hazardous Substances Data: 118736-08-6(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
2-METHOXY-2-(2-NAPHTHYL)ACETONITRILE is used as a synthetic intermediate for the production of various organic compounds. Its application in organic synthesis is due to its ability to undergo a range of chemical reactions, such as substitution, addition, and condensation, which can lead to the formation of diverse chemical products.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 2-METHOXY-2-(2-NAPHTHYL)ACETONITRILE is used as a key building block for the development of novel drug candidates. Its unique structure allows for the creation of new molecules with potential therapeutic properties, contributing to the discovery of innovative treatments for various diseases.
Used in Chemical Research:
2-METHOXY-2-(2-NAPHTHYL)ACETONITRILE is also utilized in chemical research as a model compound for studying various reaction mechanisms and exploring new synthetic routes. Its reactivity and structural features make it an ideal candidate for understanding the fundamental principles of organic chemistry and developing new methodologies for chemical synthesis.
Used in Material Science:
In the field of material science, 2-METHOXY-2-(2-NAPHTHYL)ACETONITRILE can be employed as a precursor for the development of advanced materials with specific properties, such as optoelectronic materials, polymers, and coatings. Its incorporation into these materials can lead to enhanced performance and novel applications in various industries.

InChI:InChI=1/C13H11NO/c1-10(14-9-15)12-8-4-6-11-5-2-3-7-13(11)12/h2-8,10H,1H3/t10-/m0/s1

Upstream product

• 7677-24-9 trimethylsilyl cyanide 
• 77196-31-7 2-(dimethoxymethyl)naphthalene 
• 20862-03-7 2-naphthyl cyanohydrin 
• 126644-23-3 α-acetoxy-2-naphthylacetonitrile 
• 475582-26-4 (R)-α-hydroxy-2-naphthylacetamide 
• 126567-33-7 (R)-(-)-1-cyano-1-(2-naphthyl)methyl acetate 
• 66-99-9 β-naphthaldehyde 

Downstream Products

• 156942-67-5 (R)-α-methoxynaphthalen-2-ylacetic acid 
• 43210-73-7 (R)-2-hydroxy-2-(2-naphthyl)acetic acid 
• 66-99-9 β-naphthaldehyde 

Relevant articles and documents

Design, synthesis and evaluation of novel P450 fluorescent probes bearing α-cyanoether

Four α-cyano-containing ethers based on 2-alkoxy-2-naphthylacetonitriles have been designed as a novel structural class of cytochrome P450 fluorescent probes. Their syntheses, fluorescence properties and evaluation in the fluorogenic assay of cytochrome P

Copper-mediated conversion of alkynes into nitriles via iodotriazoles

We disclose our studies on a copper-mediated reaction of alkynes with trimethylsilyl azide to afford nitriles, and proposed a reaction mechanism, which involves an iodoalkyne and an iodotriazole as intermediates.

A Sterically Congested α-Cyanoamine as a Cyanating Reagent: Cyanation of Acetals and Orthoesters

The cyanation of acetals and orthoesters by using a sterically congested α-cyanoamine as a cyanating reagent was investigated. The α-cyanoamine effectively facilitated cyanation in the presence of trichlorosilyl triflate to produce a variety of cyanated adducts in excellent yields. Analysis of the reaction mixture by 1H NMR spectroscopy revealed that trichlorosilyl triflate produced an oxocarbenium cation species as an intermediate.

Chemo-enzymatic synthesis of enantiomerically pure (R)-2-naphthylmethoxyacetic acid

Enantiomerically pure (R)-2-naphthylmethoxyacetic acid (2-NMA) was synthesized from 2-naphthaldehyde via an integrated chemo-enzymatic procedure. The one-pot, successive use of SnBr2-TMSCN and AcBr worked effectively to give a racemic cyanohydrin acetate. Lipase from Burkholderia cepacia then mediated the highly enantioselective hydrolysis of the (S)-enantiomer of the racemate, leaving the (R)-acetate with an e.e. of >99.9%. The resulting product of this enzyme-catalyzed hydrolysis, an (S)-cyanohydrin, spontaneously decomposed into naphthaldehyde, the starting material of this synthetic route, which could be recycled. The hydration of nitrile to amide as well as the hydrolysis of the acetate was performed with a microorganism, Rhodococcus rhodochrous, under very mild conditions without any loss of the enantiomeric purity. The amide group was hydrolyzed with nitrosylsulfuric acid, and the product was isolated as an α-hydroxy ester. The α-hydroxyl group was methylated with diazomethane-silica gel and the final task, hydrolysis of the ester, was accomplished under conditions as mild as neutral pH with an esterase from Krebsiella oxytoca to give enantiomerically pure 2-NMA.