39528-57-9

Basic information

• Product Name: 1-NAPHTHOYLACETONITRILE
• Synonyms: 1-NAPHTHOYLACETONITRILE;3-(1-NAPHTHYL)-3-OXOPROPANENITRILE;3-(naphthalen-1-yl)-3-oxopropanenitrile
• CAS NO: 39528-57-9
• Molecular Formula: C₁₃H₉NO
• Molecular Weight: 195.22
• Mol File: 39528-57-9.mol
• Article Data: 10

Chemical Properties

• Melting Point: 90-97 °C
• Boiling Point: 405.014 °C at 760 mmHg
• Flash Point: 198.746 °C
• Appearance: /
• Density: 1.183 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.63
• PKA: 7.78±0.30(Predicted)
• CAS DataBase Reference: 1-NAPHTHOYLACETONITRILE(CAS DataBase Reference)
• NIST Chemistry Reference: 1-NAPHTHOYLACETONITRILE(39528-57-9)
• EPA Substance Registry System: 1-NAPHTHOYLACETONITRILE(39528-57-9)

Safety Data

• Hazardous Substances Data: 39528-57-9(Hazardous Substances Data)

Usage

General Description

1-Naphthoylacetonitrile is a chemical compound with the molecular formula C12H9NO. It is a white to light yellow crystalline powder that is soluble in organic solvents but insoluble in water. 1-NAPHTHOYLACETONITRILE is used in the synthesis of various pharmaceuticals and agrochemicals. It can also be used as an intermediate in the production of dyes, pigments, and other organic compounds. 1-Naphthoylacetonitrile has potential applications in the field of organic chemistry and is often used as a reagent in various chemical reactions, such as the formation of heterocycles and the synthesis of complex organic molecules. Additionally, it is important to handle this compound with care, as it may pose hazards if not used properly.

InChI:InChI=1/C13H9NO/c14-9-8-13(15)12-7-3-5-10-4-1-2-6-11(10)12/h1-7H,8H2

Upstream product

• 143-33-9 sodium cyanide 
• 13686-51-6 2-bromoaceto-1-naphthone 
• 13922-41-3 1-Naphthylboronic acid 
• 109-77-3 malononitrile 
• 3007-97-4 ethyl 1-naphthoate 
• 75-05-8 acetonitrile 
• 2459-24-7 methyl 1-naphthoate 
• 14271-86-4 1-naphthoyl cyanide 
• 590-17-0 cyanomethyl bromide 

Downstream Products

• 33656-65-4 ethyl 2-(1-naphthyl)-2-oxoacetate 
• 1401052-74-1 4-hydroxy-1,2-diphenylphenanthrene-3-carbonitrile 

Relevant articles and documents

Deadly KCN and pricey metal free track for accessing β-ketonitriles employing mild reaction conditions

A one pot synthesis of β-ketonitriles from readily accessible 3-chloropropenals using economically benign iodine, aqueous ammonia and sodium hydroxide solution, employing mild reaction conditions have been described. This report presents a convenient, inexpensive, highly toxic-matter-free and eco-friendly approach for β-ketonitriles.

Asymmetric Hydroacylation Involving Alkene Isomerization for the Construction of C3-Chirogenic Center

A new transformation pattern for enantioselective intramolecular hydroacylation has been developed involving an alkene isomerization strategy. Proceeding through a five-membered rhodacycle intermediate, 3-enals were converted to C3- or C3,C5-chirogenic cyclopentanones with satisfactory yields, diastereoselectivities, and enantioselectivities. A catalytic cycle has been theoretically calculated and the origin of the stereoselection is rationally explained.

Substrate-controlled switchable asymmetric annulations to access polyheterocyclic skeletons

An unexpected domino process from Morita-Baylis-Hillman carbonates of isatins and acrylate and α-cyano-α,β-unsaturated ketones to deliver highly enantioenriched tetrahydrofuro[2′,3′:4,5]pyrano[2,3-b]indoles catalysed by cinchona-derived tertiary amines, involving α-regioselective cyclopropanation, ring-opening, and ring-closure cascade reactions, was disclosed. In contrast, spirooxindoles incorporating a cyclopentene motif were produced through [3+2] annulations by employing Morita-Baylis-Hillman carbonates from isatins and acrylonitrile under similar catalytic conditions. Density functional theory calculations were conducted to elucidate the novel domino process and the switchable annulation reactions.