4537-00-2

Basic information

• Product Name: 8-chloronaphthalene-1-carboxylic acid
• CAS NO: 4537-00-2
• Molecular Formula: C₁₁H₇ClO₂
• Molecular Weight: 206.6251
• Mol File: 4537-00-2.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 400.6°C at 760 mmHg
• Flash Point: 196.1°C
• Density: 1.395g/cm³
• Vapor Pressure: 3.89E-07mmHg at 25°C
• Refractive Index: 1.679
• CAS DataBase Reference: 8-chloronaphthalene-1-carboxylic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 8-chloronaphthalene-1-carboxylic acid(4537-00-2)
• EPA Substance Registry System: 8-chloronaphthalene-1-carboxylic acid(4537-00-2)

Safety Data

• Hazardous Substances Data: 4537-00-2(Hazardous Substances Data)

Upstream product

• 86-55-5 1-naphthalenecarboxylic acid 
• 40490-13-9 8-chloro-[1]naphthoic acid methyl ester 
• 81-84-5 1,8-Naphthalic anhydride 
• 2216-13-9 8-nitro-1-naphthalenecarboxylic acid 
• 7553-56-2 iodine 
• 7782-50-5 chlorine 
• 64-19-7 acetic acid 
• 7719-09-7 thionyl chloride 
• 71-43-2 benzene 
• 129-02-2 8-amino-[1]naphthoic acid 

Downstream Products

• 1366067-88-0 (8-chloronaphthalen-1-yl)(1-pentyl-1H-indol-3-yl)methanone 
• 1366067-92-6 JWH-462 
• 22743-02-8 1-benzyl-1H-benzo[cd]indol-2-one 
• 1830-56-4 1-ethylbenzo[cd]indole-2(1H)-one 

Relevant articles and documents

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.

Transmission of Polar Effects. Part 16. Ionisation of 8-Substituted 1-Naphthoic Acids and the Alkaline Hydrolysis of their Methyl Esters

Kirkwood-Westheimer calculations were carried out for the ionisation of three 8-substituted 1-naphthoic acids in 80percent (w/w) 2-methoxyethanol-water at 25 deg C.The reversed substituent polar effects are accounted for qualitatively and quantitatively for the 8-chloro and 8-bromo acids.For the 8-nitro acid the critical nature of the assumptions regarding the geometry is discussed.The rate coeeficients for the alkaline hydrolysis of six methyl 8-substituted 1-naphthoates have been determined in 70percent (v/v) dimethyl sulphoxide-water at 83.3 deg C.All 8-substituents show very large steric 'bulk' retardations and their significance is discussed.