1013-04-3

Basic information

• Product Name: 4-chloro-1-naphthalenecarboxylic acid
• Synonyms: 4-chloro-1-naphthalenecarboxylic acid;4-Chloro-1-naphthoic acid, 98%;4-Chloro-1-napthalenecarboxylic Acid;4-chloro-1-phthalenecarboxylic acid
• CAS NO: 1013-04-3
• Molecular Formula: C₁₁H₇ClO₂
• Molecular Weight: 206.62508
• Mol File: 1013-04-3.mol

Chemical Properties

• Melting Point: 223-224 °C
• Boiling Point: 398.5±15.0 °C(Predicted)
• Appearance: /
• Density: 1.395±0.06 g/cm3(Predicted)
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: DMSO (Slightly), Methanol (Slightly, Heated)
• PKA: 3.48±0.10(Predicted)
• CAS DataBase Reference: 4-chloro-1-naphthalenecarboxylic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 4-chloro-1-naphthalenecarboxylic acid(1013-04-3)
• EPA Substance Registry System: 4-chloro-1-naphthalenecarboxylic acid(1013-04-3)

Safety Data

• Hazardous Substances Data: 1013-04-3(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
4-Chloro-1-naphthalenecarboxylic acid is used as a key intermediate in the synthesis of naphthoyl-indoles, which are CB1 and CB2 receptor inhibitors. These inhibitors play a crucial role in modulating the endocannabinoid system, which is involved in various physiological processes, including pain, appetite, and mood regulation. The development of CB1 and CB2 receptor inhibitors has significant potential in the treatment of various disorders, such as obesity, pain management, and neurodegenerative diseases.
Additionally, 4-chloro-1-naphthalenecarboxylic acid may also be utilized in the synthesis of other bioactive compounds and pharmaceutical agents, further expanding its applications in the pharmaceutical industry. Its unique structure and functional groups make it a valuable building block for the development of novel therapeutic agents and drug candidates.

InChI:InChI=1S/C11H7ClO2/c12-10-6-5-9(11(13)14)7-3-1-2-4-8(7)10/h1-6H,(H,13,14)

Upstream product

• 22531-53-9 1-acetyl-4-chloronaphthalene 
• 53220-82-9 1-bromo-4-chloronaphthalene 
• 16726-68-4 methyl 4-chloro-1-naphthoate 
• 90-13-1 1-Chloronaphthalene 
• 129667-52-3 4-acetylamino-[1]naphthonitrile 
• 58728-64-6 4-amino-1-naphthonitrile 
• 4053-08-1 p-chloro-1,8-naphthalicanhydride 
• 860539-19-1 1-(4-chloro-[1]naphthyl)-2-phenyl-ethanone 
• 64-19-7 acetic acid 
• 15719-64-9 methylammonium carbonate 
• 32018-87-4 4-Amino-1-naphthoic acid 
• 50265-01-5 4-chloro-1-chloromethylnaphthalene 
• 16243-44-0 4-chloro-[1]naphthonitrile 

Downstream Products

• 1292765-18-4 JWH-398 
• 1366067-50-6 JWH-397 
• 79996-98-8 1-bromomethyl-4-chloronaphthalene 
• 6948-43-2 4-chlor-1-naphthamid 
• 5471-26-1 4-chloronaphthalenecarbaldehyde 

Relevant articles and documents

Acid-base properties of substituted naphthoic acids in nonaqueous media

Thirteen substituted 1-naphthoic acids have been prepared and their dissociation constants, along with those of twenty-five substituted 2-naphthoic acids, have been measured potentiometrically in methanol, N,N-dimethylformamide, pyridine, and acetonitrile. The pKHA values obtained have been treated by linear regression using four sets of substituent constants. The experimental data have also been interpreted by statistical methods using latent variables. The first latent variable calculated by these methods can be used as a new set of substituent constants for describing substituent effects in naphthalene skeleton.

Naphthalene-based poly(aryl ether)s. II. Synthesis and characterization of poly(ether ketone)s containing two 1,4-naphthylene moieties in the repeat unit

Two new monomers, 4-chloro-1-(4′-fluoro-1-naphthoyl)naphthalene and 1,4-bis(4′-fluoro-1′-naphthoyl)benzene, have been synthesized and polymerized with four different bisphenols to give two series of the naphthalene-based poly(ether ketone)s that are analogous to commercial PEEK and PEEKK. The effect of the introduction of one or two 1,4-naphthylene moieties, in the backbone of the repeat unit, on the glass transition temperatures has been studied. The glass transition temperatures usually increased by 20-45°C upon replacing one 1,4-phenylene with one 1,4-naphthylene moiety. All new poly(ether ketone)s prepared in tetramethylene sulfone were amorphous, with the glass transition temperatures in a range of 212-273°C. The polymer produced from 1,4-bis(4′-fluoro-1′-naphthoyl)benzene and 1,4-hydroquinone in phenyl sulfone as a solvent at 300°C showed semicrystalline properties with a melting temperature of 310°C.

Synthesis and pharmacology of 1-alkyl-3-(1-naphthoyl)indoles: Steric and electronic effects of 4- and 8-halogenated naphthoyl substituents

To develop SAR at both the cannabinoid CB1 and CB2 receptors for 3-(1-naphthoyl)indoles bearing moderately electron withdrawing substituents at C-4 of the naphthoyl moiety, 1-propyl and 1-pentyl-3-(4-fluoro, chloro, bromo and iodo-1-naphthoyl) derivatives were prepared. To study the steric and electronic effects of substituents at the 8-position of the naphthoyl group, the 3-(4-chloro, bromo and iodo-1-naphthoyl)indoles were also synthesized. The affinities of both groups of compounds for the CB1 and CB2 receptors were determined and several of them were evaluated in vivo in the mouse. The effects of these substituents on receptor affinities and in vivo activity are discussed and structure-activity relationships are presented. Although many of these compounds are selective for the CB2 receptor, only three JWH-423, 1-propyl-3-(4-iodo-1-naphthoyl)indole, JWH-422, 2-methyl-1-propyl-3-(4-iodo-1-naphthoyl)indole, the 2-methyl analog of JWH-423 and JWH-417, 1-pentyl-3-(8-iodo-1-naphthoyl)indole, possess the desirable combination of low CB1 affinity and good CB2 affinity.

The mercury-mediated decarboxylation (Pesci reaction) of naphthoic anhydrides investigated by microwave synthesis

The mercury-mediated decarboxylation (Pesci reaction) of several substituted naphthoic anhydrides has been investigated by microwave synthesis. A laboratory microwave reactor was found to be ideal for small-scale preparations of this slow reaction, reducing reaction times from typically four days to less than 1 h for the three-step process. The ionic reaction medium rapidly heated to high temperatures under microwave heating and could be efficiently maintained by low microwave power settings. Generation of stoichiometric CO2 was safely contained within the reaction tubes. A simplified reaction procedure has been developed. For substituted naphthoic anhydrides, 1H NMR analysis of the naphthoate ester derivatives indicated no change in the regioisomer ratio compared to previously reported thermal values.

AMINOETHANOL DERIVATIVES

The present invention provides a pharmaceutical agent having cholesteryl ester transfer protein inhibitory action and useful as a blood lipid lowering agent and the like. The present invention relates to a compound represented by the formula wherein Ar1 is an aromatic ring group optionally having substituents, Ar2 is an aromatic ring group having substituents, OR'' is an optionally protected hydroxyl group, R is an acyl group, R' is a hydrogen atom or a hydrocarbon group optionally having substituents, or a salt thereof, and a pharmaceutical composition containing a compound of the formula (I) or a salt thereof or a prodrug thereof.

Triazole derivative and pharmaceutical use thereof

An agent for the prophylaxis and treatment of immune-related diseases, in particular, immunosuppressant, an agent for the prophylaxis and treatment of allergic diseases, an agent for the prophylaxis and treatment of eosinophil-related diseases and an eosinophilia inhibitor, comprising, as an active ingredient, a series of triazole derivatives of the following formula (I) STR1 or the following formula (III) STR2 wherein each symbol is as defined in the specification, or a pharmaceutically acceptable salt thereof. A novel monocyclic or bicyclic triazole derivative. The agent for the prophylaxis and treatment of immune-related diseases, in particular, immunosuppressant, the agent for the prophylaxis and treatment of allergic diseases, the agent for the prophylaxis and treatment of eosinophil-related diseases, the eosinophilia inhibitor and the novel triazole derivative of the present invention all, have superior eosinophilia-inhibitory action and lymphocyte activation-inhibitory action. They are low toxic and persistent in action. They are particularly effective in the treatment of accumulation and activation of eosinophil and lymphocytes, inflammatory respiratory tract diseases, eosinophil-related diseases such as eosinophilia, and immune-related diseases.

Preparation of a series of substituted fluoromethylnaphthalenes

A series of 22 3- and 4-substituted 1-fluoromethylnaphthalenes have been synthesized.Details of practical procedures for the preparation of all intermediates are described, and physical properties for all of the substituted naphthalenes synthesized, and spectral parameters for 51 previously unknown compounds, are given.

Kinetics of Base-catalysed Iodination of Substituted Acetonaphthones

Kinetics of iodination of 6-substituted 2-acetonaphthones and of 4-substituted 1-acetonaphthones in 20percent pyridine-20percent methanol-60percent water (v/v) have been followed at three temperatures.The Hammett equation applies very well to these reactions.The rate constants for various heterocyclic base-catalysed iodination of acetophenone and of 1- and 2-acetonaphthones in 60percent (v/v) methanol-water solvent have been correlated with pKa values of the conjugate acids of the heterocyclic bases via the Broensted equation giving β values of 0.88, 1.01 and 0.92 for acetophenone, 1-acetonaphthone and 2-acetonaphthone respectively.The influence of solvent on the rates of pyridine-catalysed iodination of acetophenone and of 1- and 2-acetonaphthones has also been studied.