405196-36-3

Basic information

• Product Name: 6,7-difluoronaphthalene-1-carboxylic acid
• Synonyms: 6,7-difluoronaphthalene-1-carboxylic acid
• CAS NO: 405196-36-3
• Molecular Formula: C11H6F2O2
• Molecular Weight: 208.1609464
• Mol File: 405196-36-3.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 6,7-difluoronaphthalene-1-carboxylic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 6,7-difluoronaphthalene-1-carboxylic acid(405196-36-3)
• EPA Substance Registry System: 6,7-difluoronaphthalene-1-carboxylic acid(405196-36-3)

Safety Data

• Hazardous Substances Data: 405196-36-3(Hazardous Substances Data)

Upstream product

• 88-14-2 2-furanoic acid 
• 367-11-3 ortho-difluorobenzene 
• 100-42-5 styrene 
• 2993-71-7 2,3-difluoronaphthalene 
• 405196-49-8 2-(3,4-difluorophenyl)pentanedioic acid 5-(1,1-dimethylethyl)-1-ethyl ester 
• 405196-51-2 6,7-difluoro-4-hydroxy-1,2,3,4-tetrahydro-naphthalene-1-carboxylic acid ethyl ester 
• 405196-50-1 6,7-difluoro-1,2,3,4-tetrahydro-4-oxo-1-naphthalenecarboxylic acid ethyl ester 
• 504386-90-7 2-(3,4-difluoro-phenyl)-pentanedioic acid 1-ethyl ester 
• 405196-52-3 6,7-difluoro-1,2-dihydro-1-naphthalenecarboxylic acid ethyl ester 
• 129409-55-8 ethyl 2-(3,4-difluorophenyl)acetate 
• 405196-61-4 ethyl 6,7-difluoro-1-naphthoate 

Relevant articles and documents

Synthesis of functionalized difluoronaphthalenes by regioselective C—H functionalization of 2,3-difluoronaphthalene

2,3-Difluoronaphthalene (1) was selectively converted into 1-methyl-, 1,4-dimethyl-, 1-acetyl-, 1-acetyl-4-methyl-, 1-formyl-, and 1-carboxyl-substituted 2,3-difluoronaphthalenes using lithiation with BuLi as a key step. Nitration and bromination of compound 1 predominantly gave 6,7-difluoro-1-nitronaphthalene and 1-bromo-6,7-difluoronaphthalene, respectively. Regioselectivity of acylation of compound 1 and 2,3-difluoro-1,4-dimethylnaphthalene with AcCl in the presence of AlCl3 dramatically depended on the order of mixing and addition of the reagents. Under the optimized conditions, the yields of 1-(6,7-difluoronaphthalen-1-yl) ethanones and 1-(6,7-difluoronaphthalen-2-yl)ethanones reached 68–93%.

A simple route to 6- and 7-fluoro-substituted naphthalene-1-carboxylic acids

A simple one-pot method for the synthesis of 6-fluoro- and 6,7-difluoro-1-naphthoic acid is described. 6-Fluoro-1-naphthoic acid can be converted into 7-fluoro-1-naphthoic acid in three straightforward steps.

DIHYDROIMIDAZOTHIAZOLE DERIVATIVES

Compounds of formula (I): or pharmaceutically acceptable salts thereof, exhibit 5-HT1A agonism in addition to noradrenaline reuptake inhibition and optionally also 5-HT reuptake inhibition are useful for the treatment of obesity.

Synthesis of mono- and difluoronaphthoic acids

Aryl carboxamides are useful structural units found in several biologically active compounds. Unlike their benzoic acid counterparts, fluorinated versions of naphthoic acids are relatively unknown. In connection with a recent project, we needed viable syntheses of several mono- and difluorinated naphthoic acids. Herein we describe the synthesis of 5-, 6-, 7-, and 8-fluoro-1-naphthalenecarboxylic acids and 5,7-, 5,8-, 6,7-, and 4,5-difluoro-1-naphthalenecarboxylic acids. The 5-fluoro derivative 1 was obtained from the corresponding 5-bromo compound via electrophilic fluorination of the lithio-intermediate. The rest of the monofluoro (2, 3, and 4) and the difluoro acids (5, 6, and 7) were prepared by a new, general route which entailed the elaboration of commercial fluorinated phenylacetic acids to 2-(fluoroaryl)glutaric acids with differential ester groups; selective hydrolysis to a mono acid, intramolecular Friedel-Crafts cyclization, and aromatization furnished the target structures. An alternative process to assemble a naphthalene skeleton is also presented for the difluoro acids 5 and 6. Finally, 4,5-difluoro-1-naphthalenecarboxylic acid (8) was prepared expeditiously from 1,8-diaminonaphthalene by adapting classical reactions.