2050-76-2

Usage

Uses

Used in Spectrophotometric Analysis:
2,4-Dichloro-1-naphthol is used as a reagent for the spectrophotometric determination of arginine with previous modifications of the Sakaguchi reaction. This application is crucial in the field of analytical chemistry for accurate measurements and analysis of arginine levels.
Used in Medical Diagnostics:
In the medical field, 2,4-Dichloro-1-naphthol serves as an essential component in the guanidinoacetate and guanidinosuccinate assay of urine. This assay is an indicator of kidney dysfunction, helping healthcare professionals diagnose and monitor kidney-related health issues.
Used in Chemical Research:
2,4-Dichloro-1-naphthol is also utilized in chemical research for its unique properties and potential applications in the synthesis of various compounds. Researchers can leverage its characteristics to develop new materials and explore its interactions with other chemical substances.

Purification Methods

Crystallise the naphthol pKEst from MeOH. The 1-methyl ether has m 58o (from EtOH). [Beilstein 6 H 612, 6 I 308, 6 II 582, 6 III 2934, 6 IV 4233.]

InChI:InChI=1/C10H6Cl2O/c11-8-5-9(12)10(13)7-4-2-1-3-6(7)8/h1-5,13H

Upstream product

• 90-15-3 α-naphthol 
• 94688-65-0 4,4'-trisulfanediyl-di-[1]naphthol 
• 604-44-4 4-chloronaphthalen-1-ol 
• 91-20-3 naphthalene 
• 7782-50-5 chlorine 
• 64-19-7 acetic acid 
• 605-36-7 1,2,3,4-tetrahydro-1,2,3,4-tetrachloronaphthalene 
• 17735-08-9 2,2,4-trichloro-1(2H)-naphthalenone 

Downstream Products

• 129015-48-1 2-chloro-[1,4]naphthoquinone-4-(4-dimethylamino-phenylimine) 
• 5435-74-5 acetic acid-(2,4-dichloro-[1]naphthyl ester) 
• 5466-48-8 (2,4-dichloro-[1]naphthyloxy)-acetic acid 
• 1010-60-2 2-chloro-1,4-naphthoquinone 
• 91-20-3 naphthalene 
• 17539-31-0 ethyl α-naphthyl sulfide 
• 6655-90-9 4-chloronaphthalene-1,2-dione 
• 133546-45-9 N,N'-thiobis<3-chloro-1,4-naphthoquinone 1-imine> 
• 57234-84-1 5-Chloronaphtho<1,2-c><1,2,5>thiadiazole 
• 34910-56-0 naphtho<1,2-c:3,4-c'>bis<1,2,5>thiadiazole 
• 90-15-3 α-naphthol 
• 136613-48-4 4-chloro-2-naphthonitrile 
• 136613-50-8 4-chloro-2-(p-tolylsulphonylmethyl)-1-naphthonitrile 
• 136613-51-9 2-chloro-4-(p-tolylsulphonylmethyl)-1-naphthonitrile 

Relevant academic research and scientific papers

Regioselective Oxidative Chlorination of Arenols Using NaCl and Oxone

We developed a practical and environmentally benign method for the chlorinative dearomatization of arenols using transient electrophilic chlorinating species generated in situ from inexpensive sodium chloride and Oxone as a Cl source and oxidant, respectively, under mild conditions. Moreover, the regioselective chlorination or chlorinative dearomatization of 1-naphthols was also achieved by changing the reaction conditions.

Ammonium Salt-Catalyzed Highly Practical Ortho-Selective Monohalogenation and Phenylselenation of Phenols: Scope and Applications

An ortho-selective ammonium chloride salt-catalyzed direct C-H monohalogenation of phenols and 1,1′-bi-2-naphthol (BINOL) with 1,3-dichloro-5,5-dimethylhydantoin (DCDMH) as the chlorinating agent has been developed. The catalyst loading was low (down to 0.01 mol %) and the reaction conditions were very mild. A wide range of substrates including BINOLs were compatible with this catalytic protocol. Chlorinated BINOLs are useful synthons for the synthesis of a wide range of unsymmetrical 3-aryl BINOLs that are not easily accessible. In addition, the same catalytic system can facilitate the ortho-selective selenylation of phenols.

N-Chloro-N-methoxybenzenesulfonamide: A Chlorinating Reagent

A structurally simple and reactive chlorinating reagent, N-chloro-N-methoxybenzenesulfonamide, was conveniently and economically prepared in high yield. 1,3-Diketones, β-keto esters, benzoyl trifluoroacetones, phenols, anisoles, heteroarenes, and aromatic amines were successfully chlorinated, and the products were obtained in good to high yields.

A succinct synthesis of the vaulted biaryl ligand vanol via a dienone-phenol rearrangement

Vanol is a member of the vaulted biaryl family of ligands and it has been proven to be very effective in a number of asymmetric catalytic reactions. The previous synthesis of vanol, while effective, is limited by the cost of reagents involved. The present work evaluates three different approaches to the synthesis of 3-phenyl-1-naphthol, a key intermediate in the synthesis of vanol. The first approach has its key step as the Michael addition of a benzyl Grignard to methyl cinnamate. In the second approach the key step is the first step, a Reformatsky reaction of ethyl bromoacetate and deoxybenzoin. The final and most-efficient approach involves a dienone-phenol rearrangement of a 4-aryl-1-tetralenone generated in-situ from the reaction of 4-chloro-1-naphthol with AlCl3 and benzene, and preliminary results are reported on the extension of this method to substituted vanol derivatives.

Imidazolylsulfonates: Electrophilic partners in cross-coupling reactions

Aryl imidazolylsulfonates participate as electrophilic coupling partners in palladium-mediated cross-coupling reactions. The aryl imidazolylsulfonates display good stability while maintaining good reactivity in a variety of palladium-catalyzed coupling reactions. Imidazolylsulfonates are a practical and economic alternative to triflates.

LEWIS ACID CATALYZED HALOGENATION OF ACTIVATED CARBON ATOMS

A practical and efficient method for halogenation of activated carbon atoms using readily available /V-haloimides and a Lewis acid catalyst has been disclosed. This methodology is applicable to a range of compounds and any halogen atom can be directly introduced to the substrate. The mild reaction conditions, easy workup procedure and simple operation make this method valuable from both an environmental and preparative point of view.

Lewis acid catalyzed highly selective halogenation of aromatic compounds

A simple and efficient procedure for the halogenation of aromatic compounds with NCS, NBS, NIS and NFSI in the presence of catalytic amount of ZrCl 4 is described. Chlorination, bromination, iodination and fluorination of various aromatic compounds are performed with high selectivity under mild reaction conditions. Georg Thieme Verlag Stuttgart.

HALOGENATION REGIOSELECTIVE EN SERIE AROMATIQUE-II CHLORATION DES NAPHTOLS ET LEURS ETHERS A L'AIDE DE REACTIFS METTANT EN JEU DES INTERACTIONS DU TYPE DONNEUR-ACCEPTEUR

The regispecific chlorination of naphtols by hexachlorocyclohexadienones as selective chlorinating reagents is described.The selectivity attained is better than that which we have obtained with phenol derivatives and confirms the importance of the donor-acceptor interaction between the reagent and the naphthol during the chlorination.

Spirans. Part 13. The Synthesis and Orientation of Spirans related to Abel's Ketone (Naphthofuran-2(1H)-spiro-1'(2'H)-naphthalen-2'-one)

The aryl substituents in the stereoisomers (2) and (3) of 1-phenylnaphthofuran-2(1H)-spiro-1'(2'H)-naphthalen-2'-one are subject to hindered rotation by an energy barrier of ca. 15 kcal mol-1.If the phenyl substituent carries an ortho substituent, however, rotation is prevented at temperatures up to 60 deg C (the highest examined): only one rotamer is obtainable (the other is too crowded) and it has the ortho-substituent cisoid with respect to the triarylmethine proton. The temperature-variable broadening of the signals from the protons of the aryl substituent serves to identify these in the 1H n.m.r. spectra.Some other resonances can be regularly identified by combinations of coupling constants, double-irradiation experiments, and shifts induced by using benzene instead of trichloromethane as sovent, but the only one of value for determining the configuration at the triarylmethine centre is that already known, i.e. the upfield shift in the resonance of the vinylic (3') proton caused by the aryl substituent when this lies immediately below it.A less precise but more general test of configuration is afforded by the mutual shielding of the aryl substituent and ring E when these are in adjacent planes. Methods of preparation are given for several related spirans, especially those containing the spiro-1'(4'H)-naphthalen-4'-one nucleus, and n.m.r. methods used to establish the configurations.