16650-55-8

Basic information

• Product Name: 4-BROMO-1-NAPHTALENECARBOXYLIC ACID
• Synonyms: 4-BROMONAPHTHALENE-1-CARBOXYLIC ACID;4-BROMO-1-NAPHTALENECARBOXYLIC ACID;4-BROMO-1-NAPHTHOIC ACID;4-Bromo-1-naphthoic acid 98%;4-Bromo-1-naphthalenecarboxylic acid;4-Bromonaphthalene-1-carboxylic acid, 1-Bromo-4-carboxynaphthalene;1-Naphthalenecarboxylicacid, 4-bromo-;1-Naphthalenecarboxylicacid, 4-bromo-, methyl ester
• CAS NO: 16650-55-8
• Molecular Formula: C₁₁H₇BrO₂
• Molecular Weight: 251.07608
• Product Categories: blocks;Bromides;Carboxes
• Mol File: 16650-55-8.mol
• Article Data: 16

Chemical Properties

• Melting Point: 198-200
• Boiling Point: 408.8°Cat760mmHg
• Flash Point: 201°C
• Appearance: /Solid
• Density: 1.648g/cm³
• Vapor Pressure: 2.05E-07mmHg at 25°C
• Refractive Index: 1.697
• Storage Temp.: Keep Cold
• PKA: 3.48±0.10(Predicted)
• Water Solubility: Slightly soluble in water.
• CAS DataBase Reference: 4-BROMO-1-NAPHTALENECARBOXYLIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 4-BROMO-1-NAPHTALENECARBOXYLIC ACID(16650-55-8)
• EPA Substance Registry System: 4-BROMO-1-NAPHTALENECARBOXYLIC ACID(16650-55-8)

Safety Data

• Hazard Codes: Xi,N,Xn
• Statements: 22-36-50/53
• Safety Statements: 26-60-61
• Hazardous Substances Data: 16650-55-8(Hazardous Substances Data)

Usage

Uses

It is an important raw material and intermediate used in organic synthesis, pharmaceuticals, agrochemicals and dyestuffs.

InChI:InChI=1/C11H7BrO2/c12-10-6-5-9(11(13)14)7-3-1-2-4-8(7)10/h1-6H,(H,13,14)

Upstream product

• 46258-62-2 1-(4-bromonaphthalen-1-yl)ethanone 
• 83-53-4 1,4-dibromonaphthalene 
• 90-12-0 1-Methylnaphthalene 
• 90-11-9 1-Bromonaphthalene 
• 35615-97-5 4-bromo-naphthalene-1-carboxylic acid methyl ester 
• 50672-84-9 4-bromo-1-naphthaldehyde 
• 79996-99-9 1-bromo-4-bromomethyl-naphthalene 
• 2298-07-9 4-Bromo-1-naphthylamine 
• 124-38-9 carbon dioxide 
• 56052-26-7 (4-bromonaphthalen-1-yl)methanol 
• 81-86-7 4-bromo-1,8-naphthalenedicarboxylic anhydride 
• 7553-56-2 iodine 
• 6627-78-7 1-bromo-4-methylnaphthalene 
• 7697-37-2 nitric acid 

Downstream Products

• 35615-97-5 4-bromo-naphthalene-1-carboxylic acid methyl ester 
• 41014-20-4 4-bromomethyl-1-naphthonitrile 
• 79996-99-9 1-bromo-4-bromomethyl-naphthalene 
• 1366067-59-5 (4-bromo-1-naphthalenyl)(1-pentyl-1H-indol-3-yl)methanone 
• 1366067-63-1 JWH-394 
• 51934-43-1 ethyl 4-Bromo-1-naphthoate 
• 123524-53-8 1,1'-binaphthyl-4,4'-dicarboxylic acid 
• 643094-08-0 methyl 4-(4,4’,5,5’-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-naphthoate 
• 3839-19-8 4-cyano-1-naphthoic acid 
• 87700-65-0 4-bromo-1-naphthoic acid chloride 
• 56052-26-7 (4-bromonaphthalen-1-yl)methanol 
• 1093861-60-9 4-[5-[3-chloro-5-(trifluoromethyl)phenyl]-4,5-dihydro-5-(trifluoromethyl)-3-isoxazolyl]-N-[2-oxo-2-[(2,2,2-trifluoroethyl)amino]ethyl]-1-naphthalenecarboxamide 
• 1352794-90-1 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)naphthalene-1-carbonitrile 
• 664364-43-6 (4-cyanonaphthalen-1-yl)boronic acid 

Relevant articles and documents

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Discovery of novel, orally active dual NK1/NK2 antagonists

Exploration of the SAR around selective NK2 antagonists, SR48968 and ZD7944, led to the discovery that naphth-1-amide analogues provide potent dual NK1 and NK2 antagonists. ZD6021 inhibited binding of [3H]-NKA or [3H]-SP to human NK1 and NK2 receptors, with high-affinity (Ki=0.12 and 0.62 nM, respectively). In functional assays ZD6021 had, at 10-7 M, in human pulmonary artery pKB=8.9 and in human bronchus pKB=7.3, for NK1 and NK2, respectively. Oral administration of ZD6021 to guinea pigs dose-dependently attenuated ASMSP induced extravasation of plasma proteins, ED50=0.5 mg/kg, and NK2 mediated bronchoconstriction, ED50=13 mg/kg.

Preparation method of 1,4-naphthalic acid

The invention relates to a preparation method of 1,4-naphthalic acid, which is characterized by comprising the steps of performing Friedel-Crafts reaction on 1-naphthalene bromide serving as an initial raw material and acetyl chloride to generate 4-bromo-1-acetyl naphthalene; then carrying out oxidation by using pypocholoride to obtain 4-bromo-1-naphthoic acid; reacting 4-bromine-1-naphthoic acid with cuprous cyanide in a polar aprotic solvent in the presence of potassium iodide and copper sulfate in catalytic doses to generate a 4-cyano naphthoic acid copper salt complex; and carrying out alkaline hydrolysis on the 4-cyano naphthoic acid copper salt complex to obtain the 1,4-naphthalic acid. According to the preparation method of the naphthalene-1,4-dicarboxylic acid, the raw materials are easy to obtain, and the product does not contain color impurities, is high in purity and good in quality, and can be directly used as an intermediate of a dye, an ultraviolet light absorber, a scintillator and an optical whitening agent for further synthesis.

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.