17075-39-7

Usage

Synthesis Reference(s)

Tetrahedron, 52, p. 8863, 1996 DOI: 10.1016/0040-4020(96)00433-4

InChI:InChI=1/C11H9Cl/c1-8-6-7-11(12)10-5-3-2-4-9(8)10/h2-7H,1H3

Upstream product

• 4523-45-9 1-amino-4-methylnaphthalene 
• 97585-94-9 (4-Chloro-naphthalen-1-ylmethyl)-triphenyl-phosphonium; chloride 
• 7791-25-5 sulfuryl dichloride 
• 90-12-0 1-Methylnaphthalene 
• 1034050-52-6 4-chloronaphthalen-1-yl trifluoromethanesulfonate 
• 934-56-5 trimethyl(phenyl)stannane 
• 6627-78-7 1-bromo-4-methylnaphthalene 
• 86-57-7 1-Nitronaphthalene 
• 676-58-4 methylmagnesium chloride 

Downstream Products

• 5471-26-1 4-chloronaphthalenecarbaldehyde 
• 22531-51-7 ethyl 2-(2-methoxy-1-naphthyl)-2-oxoacetate 
• 101093-81-6 ethyl 4-methyl-1-naphthyloxoacetate 
• 4488-40-8 4-Methyl-1-naphthoic acid 
• 79996-98-8 1-bromomethyl-4-chloronaphthalene 
• 136613-48-4 4-chloro-2-naphthonitrile 
• 109297-22-5 4--1-naphthonitrile 

Relevant academic research and scientific papers

SURFACE PHOTOCHEMISTRY: THE PHOTO-CHLORINATION OF AROMATIC HYDROCARBONS WITH FERRIC CHLORIDE ON ALUMINA

Irradiation of a number of aromatic hydrocarbons adsorbed on alumina in the presence of ferric chloride leads to monochlorination.

Solvent coordination to palladium can invert the selectivity of oxidative addition

Reaction solvent was previously shown to influence the selectivity of Pd/PtBu3-catalyzed Suzuki-Miyaura cross-couplings of chloroaryl triflates. The role of solvents has been hypothesized to relate to their polarity, whereby polar solvents stabilize anionic transition states involving [Pd(PtBu3)(X)]- (X = anionic ligand) and nonpolar solvents do not. However, here we report detailed studies that reveal a more complicated mechanistic picture. In particular, these results suggest that the selectivity change observed in certain solvents is primarily due to solvent coordination to palladium. Polar coordinating and polar noncoordinating solvents lead to dramatically different selectivity. In coordinating solvents, preferential reaction at triflate is likely catalyzed by Pd(PtBu3)(solv), whereas noncoordinating solvents lead to reaction at chloride through monoligated Pd(PtBu3). The role of solvent coordination is supported by stoichiometric oxidative addition experiments, density functional theory (DFT) calculations, and catalytic cross-coupling studies. Additional results suggest that anionic [Pd(PtBu3)(X)]- is also relevant to triflate selectivity in certain scenarios, particularly when halide anions are available in high concentrations.

Cobalt-Catalyzed Enantioselective C–H Arylation of Indoles

Atropoisomeric (hetero)biaryls are scaffolds with increasing importance in the pharmaceutical and agrochemical industries. Although it is the most obvious disconnection to construct such compounds, the direct enantioselective C–H arylation through the concomitant induction of the chiral information remains extremely challenging and uncommon. Herein, the unprecedented earth-abundant 3d-metal-catalyzed atroposelective direct arylation is reported, furnishing rare atropoisomeric C2-arylated indoles. Kinetic studies and DFT computation revealed an uncommon mechanism for this asymmetric transformation, with the oxidative addition being the rate- and enantio-determining step. Excellent stereoselectivities were reached (up to 96% ee), while using an unusual N-heterocyclic carbene ligand bearing an essential remote substituent. Attractive dispersion interactions along with positive C–H-π interactions exerted by the ligand were identified as key factors to guarantee the excellent enantioselection.

GLYCOLATE OXIDASE INHIBITORS FOR THE TREATMENT OF DISEASE

Described herein are compounds, methods of making such compounds, pharmaceutical compositions and medicaments containing such compounds, and methods of using such compounds to treat or prevent diseases or disorders associated with a defect in glyoxylate metabolism, for example a disease or disorder associated with the enzyme glycolate oxidase (GO) or alterations in oxalate metabolism. Such diseases or disorders include, for example, disorders of glyoxylate metabolism, including primary hyperoxaluria, that are associated with production of excessive amounts of oxalate.

GLYCOLATE OXIDASE INHIBITORS FOR THE TREATMENT OF DISEASE

Described herein are compounds, methods of making such compounds, pharmaceutical compositions and medicaments containing such compounds, and methods of using such compounds to treat or prevent diseases or disorders associated with the enzyme glycolate oxidase (GO). Such diseases or disorders include, for example, disorders of glyoxylate metabolism, including primary hyperoxaluria, that are associated with production of excessive amounts of oxalate.

Microwave assisted solid additive effects in simple dry chlorination reactions with n-chlorosuccinimide

Solid additives participate in the dry microwave assisted chlorination reaction of N-chlorosuccinimide with the xylenes affecting both yields and chemoselectivities. Total yields can be increased up to nine times for simple alkylaromatics and chemoselectivities can be altered according to the desired ring or α-side chlorination product by choosing the appropriate additive. We believe that in these reactions the solid additives play a very important role by increasing yields and affecting chemoselectivities, as well as behaving as microwave energy absorbers that consequently aid the transfer of heat to the active reagents.

Mild chlorination of aromatic compounds with tin(IV) chloride and lead tetraacetate

SnCl4/Pb(OAc)4 acts as a safe source of Cl2 for the chlorination of aromatic compounds. A variety of aromatic compounds are effectively chlorinated with SnCl4/Pb(OAc)4 under mild conditions. The mixture is a selective chlorinating agent, particularly with polyalkylbenzenes, polycyclic aromatic compounds and anisoles.

Halogenation Using Quaternary Ammonium Polyhalides. XIX. Aromatic Chlorination of Arenes with Benzyltrimethylammonium Tetrachloroiodate

The reaction of arenes with a calculated amount of benzyltrimethylammonium tetrachloroiodate in acetic acid at room temperature or at 70 deg C gave nuclear chloro-substituted arenes in fairly good yields.

INTRODUCTION OF METHYL GROUPS INTO POLYCYCLIC COMPOUNDS THROUGH THE PHOSPHONIUM SALTS OF METHYLNAPHTHALENE AND 9-METHYLPHENANTHRENE

Chloromethyl derivatives synthesized by the chloromethylation of naphthalene and methylnaphthalenes were converted into the corresponding triphenylphosphonium salts.Alkaline hydrolysis of the latter gave 1-methylnaphthalene and some di-, tri-, and tetramethylnaphthalenes. 9-Methylphenanthrene was obtained similarly from phenanthrene.The corresponding diarylethenes were synthesized from the phosphonium salts by the Wittig reaction.