3839-18-7

Basic information

• Product Name: 1-Naphthalenecarboxylic acid, 3-cyano-
• CAS NO: 3839-18-7
• Molecular Formula: C12H7NO2
• Molecular Weight: 197.193
• Mol File: 3839-18-7.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: 1-Naphthalenecarboxylic acid, 3-cyano-(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Naphthalenecarboxylic acid, 3-cyano-(3839-18-7)
• EPA Substance Registry System: 1-Naphthalenecarboxylic acid, 3-cyano-(3839-18-7)

Safety Data

• Hazardous Substances Data: 3839-18-7(Hazardous Substances Data)

Usage

Parent compound

Naphthalene (a polycyclic aromatic hydrocarbon)

Functional groups

Carboxylic acid group (-COOH)
Cyano group (-CN)

Usage

Synthesis of pharmaceuticals and agrochemicals

Importance

Valuable intermediate in organic synthesis

Research potential

Studied for potential biological activities and pharmacological effects

Upstream product

• 496835-91-7 4-bromonaphthalene-2-carbonitrile 
• 109-72-8 n-butyllithium 
• 124-38-9 carbon dioxide 

Downstream Products

• 939972-59-5 3-cyano-naphthalene-1-carboxylic acid [(2S)-2-(3,4-dichloro-phenyl)-4-methylsulfonyl-butyl]-methyl-amide 
• 939972-38-0 3-cyano-N-[(2S)-2-(3,4-dichlorophenyl)-4-{4-[(1R,2S)-1-(2-furyl)-2,3-dihydroxypropyl]piperazin-1-yl}butyl]-N-methyl-1-naphthamide 
• 255050-49-8 3-cyano-naphthalene-1-carboxylic acid [(2S)-(3,4-dichloro-phenyl)-4-hydroxy-butyl]-methyl-amide 
• 255050-50-1 N-[2-(S)-(3,4-dichlorophenyl)-4-oxobutyl]-N-methyl-3-cyano-1-naphthamide 
• 255050-56-7 N-[2-(4-chlorophenyl)-4-hydroxybutyl]-N-methyl-3-cyano-1-naphthamide 
• 669068-30-8 1-N-methyl-4-(4-fluorophenyl)-4-(3-(3-cyanonaphth-1-yl)-(3-oxo-2-azaprop-1-yl))piperidine 

Relevant articles and documents

A new route for manufacture of 3-cyano-1-naphthalenecarboxylic acid

3-Cyano-1-naphthalenecarboxylic acid is an intermediate required for manufacture of tachykinin receptor antagonists. The 1,3-disubstitution pattern on the naphthalene skeleton complicates the synthesis of this cyano acid. Previous literature-based chemistry is unattractive for large-scale manufacture due to stoichiometric use of mercury salts, low yield, and other operational difficulties. An attractive new route has been developed by establishing the 1,3-substitution on the carbon atoms destined for only one-half of the naphthalene 2-ring system, via 3-bromocoumalate, and then building up the rest of the naphthalene ring system by Diels-Alder addition of 3-bromocoumalate to in situ-generated benzyne. The resulting 4-bromo-2-naphthoate was converted to the required cyanoacid by transformation of ester to nitrile followed by carbonylation of the bromo substituent. The new route has been scaled up successfully and offers significant advantages over previous literature chemistry in terms of improved process environmental implications, improved yield, lower cost, and improved robustness and ease of operation at larger scales of operation.