56886-72-7

Usage

Molecular weight

211.62 g/mol

Appearance

White to pale yellow solid

Melting point

84-86°C

Boiling point

312-314°C

Solubility

Slightly soluble in water, soluble in organic solvents such as acetone, ethyl acetate, and toluene

Primary use

Production of pharmaceuticals and agrochemicals

Chemical structure

A naphthalene ring with a carbonyl chloride group (-COCl) attached to the first position (1-position) and a fluorine atom (-F) attached to the fourth position (4-position)

Reactivity

Highly reactive and potentially hazardous

Handling precautions

Handle with caution, follow proper safety procedures in a laboratory or industrial setting.

Upstream product

• 573-03-5 4-fluoro-1-naphthoic acid 

Downstream Products

• 1542224-30-5 4-(2-cyanophenoxy)-1-naphthoic acid 
• 1542224-29-2 methyl 4-(2-cyanophenoxy)-1-naphthoate 
• 1377999-40-0 C₂₇H₂₉N₃O₂ 
• 1364933-59-4 (4-fluoro-1-naphthalenyl)(1-pentyl-1H-indol-3-yl)methanone 
• 105826-31-1 4-fluoro-naphthalene-1-carboxylic acid phenyl ester 

Relevant academic research and scientific papers

Chiral Br?nsted acid-catalyzed dynamic kinetic resolution of atropisomeric: Ortho -formyl naphthamides

Despite the widespread use of naphthamide atropisomers in biologically active compounds and asymmetric catalysis, few catalytic methods have succeeded in the enantioselective synthesis of these compounds. Herein, a chiral Br?nsted acid (CBA) catalysis strategy was developed for readily scalable dynamic kinetic resolution of challenging ortho-formyl naphthamides with pyrrolylanilines. The chiral axis of the atropisomeric amide and a stereogenic center were simultaneously established for a new family of potential biologically active pyrrolopyrazine compounds with high enantio- and diastereoselectivities (up to >20 : 1 d.r. and 98 : 2 e.r.). Epimerization experiments of its derivatives reveal that the N-substitution of the nearby stereogenic center could affect the configurational stability of the axially chiral aromatic amides. These results might be useful for the construction of other kinds of novel axially chiral molecules with a low rotational barrier.

Palladium-catalyzed directing group-assisted C8-triflation of naphthalenes

The transition-metal-catalyzed direct triflation of naphthyl amides and naphthyl ketones has been accomplished for the first time. Benzophenone (BP) was found to be a suitable ligand for the cross-coupling reactions. Density functional theory (DFT) calculations revealed that excessive amounts of HOTf inhibit the reductive elimination of the C-F bond to realize the unusual reductive elimination of the C-OTf bond.

Discovery and optimization of tetramethylpiperidinyl benzamides as inhibitors of EZH2

The identification and development of a novel series of small molecule Enhancer of Zeste Homologue 2 (EZH2) inhibitors is described. A concise and modular synthesis enabled the rapid development of structure-activity relationships, which led to the identification of 44 as a potent, SAM-competitive inhibitor of EZH2 that dose-dependently decreased global H3K27me3 in KARPAS-422 lymphoma cells.

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.

SUBSTITUTED PHENOXY THIAZOLIDINEDIONES AS ESTROGEN RELATED RECEPTOR-ALPHA MODULATORS

The present invention relates to compounds of Formula (I): methods for preparing these compounds, compositions, intermediates and derivatives thereof and for treating a condition including but not limited to ankylosing spondylitis, artherosclerosis, arthritis (such as rheumatoid arthritis, infectious arthritis, childhood arthritis, psoriatic arthritis, reactive arthritis), bone-related diseases (including those related to bone formation), breast cancer (including those unresponsive to anti-estrogen therapy), cardiovascular disorders, cartilage-related disease (such as cartilage injury/loss, cartilage degeneration, and those related to cartilage formation), chondrodysplasia, chondrosarcoma, chronic back injury, chronic bronchitis, chronic inflammatory airway disease, chronic obstructive pulmonary disease, diabetes, disorders of energy homeostasis, gout, pseudogout, lipid disorders, metabolic syndrome, multiple myeloma, obesity, osteoarthritis, osteogenesis imperfecta, osteolytic bone metastasis, osteomalacia, osteoporosis, Paget's disease, periodontal disease, polymyalgia rheumatica, Reiter's syndrome, repetitive stress injury, hyperglycemia, elevated blood glucose level, and insulin resistance.

ISOINDOLE DERIVATIVES USEFUL FOR TREATING PAIN, GASTROINTESTINAL DISEASES AND CANCER

Compounds of formula I or pharmaceutically acceptable salts thereof: [Chemical formula should be inserted here. Please see paper copy] I wherein X, R1, R2, R3, m and n are as defined in the specification as well as salts and pharmaceutical compositions including the compounds are prepared. They are useful in therapy, in particular in the management of pain.

Synthesis and structure-activity relationship of a novel series of aminoalkylindoles with potential for imaging the neuronal cannabinoid receptor by positron emission tomography

A new series of CB1 ligands with high binding affinity (K i = 0.7-100 nM) and moderate lipophilicity (cLogD7.4) in the range of 2.1-4.5 has been synthesized. A structure-activity relationship study demonstrated that for the studied set of aminoalkylindoles, the molecular dipole of the ground state conformation within the series was inversely related to the affinity. The racemic ligand with highest affinity (0.7 nM), 3-(4-fluoronaphthoyl)-1-(N-methylpiperidin-2-ylmethyl)indole, was radiolabeled with 18F. This radioligand specifically labeled CB1 receptors in mouse brain and accumulated in regions of high versus low CB 1 receptor density in a ratio of 1.6. The displaceable radioactivity of one enantiomer in the brains of mice determined in a pretreatment study using the CB1 antagonist N-(piperidinyl)-5-(4-chlorophenyl)-1-(2,4- dichlorophenyl)-4-methyl-1H-pyrazole-3-carboxamide (SR141716) was nearly double that of the race-mate for the same determination; therefore, the active enantiomer is a candidate for PET studies in animals. A pretreatement study for the other enantiomer found no displaceable radioactivity in the same group of mice; this result suggested the enantiomer was inactive.