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Cas Database

135-19-3

135-19-3

Identification

  • Product Name:2-Naphthol

  • CAS Number: 135-19-3

  • EINECS:205-182-7

  • Molecular Weight:144.173

  • Molecular Formula: C10H8O

  • HS Code:2907151000

  • Mol File:135-19-3.mol

Synonyms:2-Naphthol(8CI);2-Hydroxynaphthalene;Azogen Developer A;Betanaphthol;C.I. 37500;C.I. Developer 5;Developer AMS;Developer BN;Isonaphthol;NSC 2044;Naphthol B;b-Hydroxynaphthalene;b-Naphthol;b-Naphthyl alcohol;

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Safety information and MSDS view more

  • Pictogram(s):HarmfulXn,DangerousN

  • Hazard Codes: Xn:Harmful;

  • Signal Word:Warning

  • Hazard Statement:H302 Harmful if swallowedH332 Harmful if inhaled H400 Very toxic to aquatic life

  • First-aid measures: General adviceConsult a physician. Show this safety data sheet to the doctor in attendance.If inhaled Fresh air, rest. In case of skin contact Rinse and then wash skin with water and soap. In case of eye contact First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention. If swallowed Rinse mouth. Give one or two glasses of water to drink. Refer for medical attention . Immediate first aid: Ensure that adequate decontamination has been carried out. If patient is not breathing, start artificial respiration, preferably with a demand-valve resuscitator, bag-valve-mask device, or pocket mask, as trained. Perform CPR as necessary. Immediately flush contaminated eyes with gently flowing water. Do not induce vomiting. If vomiting occurs, lean patient forward or place on left side (head-down position, if possible) to maintain an open airway and prevent aspiration. Keep patient quiet and maintain normal body temperature. Obtain medical attention. /Phenols and related compounds/

  • Fire-fighting measures: Suitable extinguishing media Suitable extinguishing media: Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide. Wear self-contained breathing apparatus for firefighting if necessary.

  • Accidental release measures: Use personal protective equipment. Avoid dust formation. Avoid breathing vapours, mist or gas. Ensure adequate ventilation. Evacuate personnel to safe areas. Avoid breathing dust. For personal protection see section 8. Personal protection: particulate filter respirator adapted to the airborne concentration of the substance. Sweep spilled substance into covered containers. If appropriate, moisten first to prevent dusting. Do NOT let this chemical enter the environment. Accidental Release Measures. Personal precautions, protective equipment and emergency procedures: Use personal protective equipment. Avoid dust formation. Avoid breathing vapours, mist or gas. Ensure adequate ventilation. Evacuate personnel to safe areas. Avoid breathing dust. Environmental precautions: Prevent further leakage or spillage if safe to do so. Do not let product enter drains. Discharge into the environment must be avoided. Methods and materials for containment and cleaning up: Pick up and arrange disposal without creating dust. Sweep up and shovel. Keep in suitable, closed containers for disposal.

  • Handling and storage: Avoid contact with skin and eyes. Avoid formation of dust and aerosols. Avoid exposure - obtain special instructions before use.Provide appropriate exhaust ventilation at places where dust is formed. For precautions see section 2.2. Store in an area without drain or sewer access.Conditions for safe storage, including any incompatibilities: Keep container tightly closed in a dry and well-ventilated place. Light sensitive.

  • Exposure controls/personal protection:Occupational Exposure limit valuesBiological limit values Handle in accordance with good industrial hygiene and safety practice. Wash hands before breaks and at the end of workday. Eye/face protection Safety glasses with side-shields conforming to EN166. Use equipment for eye protection tested and approved under appropriate government standards such as NIOSH (US) or EN 166(EU). Skin protection Wear impervious clothing. The type of protective equipment must be selected according to the concentration and amount of the dangerous substance at the specific workplace. Handle with gloves. Gloves must be inspected prior to use. Use proper glove removal technique(without touching glove's outer surface) to avoid skin contact with this product. Dispose of contaminated gloves after use in accordance with applicable laws and good laboratory practices. Wash and dry hands. The selected protective gloves have to satisfy the specifications of EU Directive 89/686/EEC and the standard EN 374 derived from it. Respiratory protection Wear dust mask when handling large quantities. Thermal hazards

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Relevant articles and documentsAll total 441 Articles be found

-

Maikopar

, (1869)

-

2,4-dinitrophenyl ether-containing chemodosimeters for the selective and sensitive in vitro and in vivo detection of hydrogen sulfide

El Sayed, Sameh,De La Torre, Cristina,Santos-Figueroa, Luis E.,Martinez-Manez, Ramon,Sancenon, Felix,Orzaez, Mar,Costero, Ana M.,Parra, Margarita,Gil, Salvador

, p. 244 - 254 (2015)

Four probes (i.e. D1-D4) for the selective and sensitive fluorogenic detection of HS- have been prepared and characterised. HEPES (10 mM, pH 7.4)-DMSO 99:1 v/v solutions of D1-D4 are essentially non-fluorescent. Changes in the emission using D1-D4 in the presence of anions (F-, Cl-, Br-, I-,N-3, CN-, SCN-, AcO-,CO2-3 ,PO2-4,SO2-4, HS- and OH-), biothiols (GSH, Cys, Hcy, Me-Cys and lipoic acid), reducing agents (SO2-3 and S2O2-3) and oxidants (H2O2) demonstrated that only HS- is able to induce the appearance of intense emission bands in the 400-520 nm range in the four probes. The selectivity observed was ascribed to a unique hydrogen sulfide-induced hydrolysis of the 2,4-dinitrophenyl ether moiety that yielded the corresponding free highly fluorescent alcohols. The potential detection of intracellular HS- was also studied.

Effect of cyclodextrin complexation on photo-fries rearrangement of naphthyl esters

Banu, Habeeb Shayira,Pitchumani, Kasi,Srinivasan, Chockalingam

, p. 9601 - 9610 (1999)

Photolysis of β-cyclodextrin inclusion complexes of 1- and 2-naphthyl esters (acetates and benzoates) in aqueous medium, results in rearrangement to give one isomer of acylnaphthol in excess, whereas the solid state irradiation of the cyclodextrin complexes yields selectively one isomer. In addition, formation of cleavage product is totally suppressed. This remarkable selectivity is attributed to specific modes of the complexation of the esters into the β-CD cavity.

An efficient approach for the synthesis and antimicrobial evaluation of some new benzocoumarins and related compounds

Hekal, Mohamed H.,Abu El-Azm, Fatma S. M.,Samir, Sandy S.

, p. 2175 - 2186 (2021)

A convenient synthetic approach for pharmaceutically important benzocoumarin-based heterocyclic compounds has been studied. β-enaminonitrile has been used for the synthesis of a broad diversity of new benzocoumarins and related compounds over different reaction steps. Various synthetic approaches were used in this research for synthesis of heterocyclic systems such as acid-catalyzed hydrolysis, decarboxylation, deamination, ring opening and ring closure. The molecular structures of the newly synthesized derivatives were established by elemental analyses and spectral data (IR, 1H-NMR, and 13C-NMR). Some of the newly synthesized compounds were explored for their antimicrobial activities.

Regio- and stereochemistry of Na-mediated reductive cleavage of alkyl aryl ethers

Azzena, Ugo,Carraro, Massimo,Meloni, Claudia,Murgia, Irene,Pisano, Luisa,Pittalis, Mario,Luisi, Renzo,Musio, Biagia,Degennaro, Leonardo

, p. 1550 - 1554 (2014)

We have investigated the regio-and stereochemistry of the reductive dealkoxylation of alkyl aryl ethers. Chiral non-racemic secondary alcohols were converted into the corresponding m-terphenyl or 2-biphenyl ethers either via inversion of configuration under Mitsunobu reaction conditions or with retention of configuration under SNAr conditions. The successive cleavage of the aromatic C-O bond occurred in the presence of a stoichiometric amount of Na metal in dry tetrahydrofuran at rt with retention of configuration, thus highlighting that the overall inversion or retention of configuration for the whole two-step procedure is dictated by the stereochemistry of the first synthetic step.

MILD CLEAVAGE OF METHOXYMETHYL (MOM) ESTERS WITH TRIMETHYLSILYLBROMIDE

Hanessian, Stephen,Delorme, Daniel,Dufresne, Yves

, p. 2515 - 2518 (1984)

Trimethylsilyl bromide is an effective reagent for the deprotection of methoxymethyl ethers under mild conditions.

Synthesis, structures and inclusion properties of tetranaphthalides: New macrocyclic clathrate hosts

Tanaka, Koichi,Hori, Kyosuke,Masumoto, Asuka,Arakawa, Ryuichi,Caira, Mino R.

, p. 2911 - 2915 (2011)

Novel tetranaphthalide host compounds 3 and 4 bearing isomeric naphthalene moieties have been synthesized and their inclusion properties were investigated. These host compounds enclathrated several kinds of ketones, cyclic ethers, amides, sulfoxides and aromatic compounds. The structures of two representative inclusion compounds containing different host molecules and a common guest (dimethyl sulfoxide) were investigated by X-ray diffraction to determine the nature of guest inclusion and to rationalize their distinctly different thermal decomposition profiles.

Hydrolytic enzymes conjugated to quantum dots mostly retain whole catalytic activity

Iyer, Aditya,Chandra, Anil,Swaminathan, Rajaram

, p. 2935 - 2943 (2014)

Background Tagging a luminescent quantum dot (QD) with a biological like enzyme (Enz) creates value-added entities like quantum dot-enzyme bioconjugates (QDEnzBio) that find utility as sensors to detect glucose or beacons to track enzymes in vivo. For such applications, it is imperative that the enzyme remains catalytically active while the quantum dot is luminescent in the bioconjugate. A critical feature that dictates this is the quantum dot-enzyme linkage chemistry. Previously such linkages have put constraints on polypeptide chain dynamics or hindered substrate diffusion to active site, seriously undermining enzyme catalytic activity. In this work we address this issue using avidin-biotin linkage chemistry together with a flexible spacer to conjugate enzyme to quantum dot. Methods The catalytic activity of three biotinylated hydrolytic enzymes, namely, hen egg white lysozyme (HEWL), alkaline phosphatase (ALP) and acetylcholinesterase (AChE) was investigated post-conjugation to streptavidin linked quantum dot for multiple substrate concentrations and varying degrees of biotinylation. Results We demonstrate that all enzymes retain full catalytic activity in the quantum dot-enzyme bioconjugates in comparison to biotinylated enzyme alone. However, unlike alkaline phosphatase and acetylcholinesterase, the catalytic activity of hen egg white lysozyme was observed to be increasingly susceptible to ionic strength of medium with rising level of biotinylation. This susceptibility was attributed to arise from depletion of positive charge from lysine amino groups after biotinylation. Conclusions We reasoned that avidin-biotin linkage in the presence of a flexible seven atom spacer between biotin and enzyme poses no constraints to enzyme structure/dynamics enabling retention of full enzyme activity. General significance Overall our results demonstrate for the first time that streptavidin-biotin chemistry can yield quantum dot enzyme bioconjugates that retain full catalytic activity as native enzyme.

Decarbethoxylative Arylation Employing Arynes: A Metal-Free Pathway to Arylfluoroamides

Gupta, Ekta,Kant, Ruchir,Mohanan, Kishor

, p. 6016 - 6019 (2017)

An efficient, metal-free decarbethoxylative arylation protocol for the synthesis of α-aryl-α-fluoroamides from fluoromalonamates, under ambient reaction conditions using aryne as an electrophilic arylating agent, is reported. This decarbethoxylative arylation proceeds under mild conditions and provides a practical and effective entry to a wide range of α-aryl-α-fluoroacetamides. Interestingly, the use of the tert-butyl ester of fluoromalonamate prevented the otherwise rapid decarboxylation step, affording the arylated fluoromalonamate in moderate yield.

Nucleophilic Hydroxylation in Water Media Promoted by a Hexa-Ethylene Glycol-Bridged Dicationic Ionic Liquid

Jadhav, Vinod H.,Kim, Jin Gwan,Jeong, Hyeon Jin,Kim, Dong Wook

, p. 7275 - 7280 (2015)

Hexaethylene glycol bis(3-hexaethylene glycol imidazolium) dimesylate ionic liquid (hexaEG-DHIM) was designed and prepared as a highly efficient promoter for the nucleophilic hydroxylation of alkyl halides to the corresponding alcohol products in neat water media. It was observed that hexaEG-DHIM promoter enhanced the nucleophilicity of water significantly in the reaction. In addition, the hexaEG-DHIM could be reused several times without loss of activity. Moreover, the hydroxylation reactions of base-sensitive and/or polar alkyl halide substrates proceeded highly chemoselectively in excellent yields.

Cationic reverse micelles create water with super hydrogen-bond-donor capacity for enzymatic catalysis: Hydrolysis of 2-naphthyl acetate by α-Chymotrypsin

Moyano, Fernando,Falcone, R. Falcone,Mejuto,Silber, Juana J.,Correa, N. Mariano

, p. 8887 - 8893 (2010)

Reverse micelles (RMs) are very good nanoreactors because they can create a unique microenvironment for carrying out a variety of chemical and biochemical reactions. The aim of the present work is to determine the influence of different RM interfaces on the hydrolysis of 2-naphthyl acetate (2NA) by α-chymotrypsin (α-CT). The reaction was studied in water/benzyl-nhexadecyldimethylammonium chloride (BHDC)/benzene RMs and, its efficiency compared with that observed in pure water and in sodium 1,4-bis-2-ethylhexylsulfosuccinate (AOT) RMs. Thus, the hydrolysis rates of 2-NA catalyzed by α-CT were determined by spectroscopic measurements. In addition, the method used allows the joint evaluation of the substrate partition constant Kp between the organic and the micellar pseudophase and the kinetic parameters: catalytic rate constant kcat, and the Michaelis constant KM of the enzymatic reaction. The effect of the surfactant concentration on the kinetics parameters was determined at constant W 0= [H2O]/[surfactant], and the variation of W0 with surfactant constant concentration was investigated. The results show that the classical Michaelis-Menten mechanism is valid for α-CT in all of the RMs systerns studied and that the reaction takes place at both RM interfaces. Moreover, the catalytic efficiency values kcat/KM obtained in the RMs systems are higher than that reported in water. Furthermore, there is a remarkable increase in α-CT efficiency in the cationic RMs in comparison with the anionic system, presumably due to the unique water properties found in these confined media. The results show that in cationic RMs the hydrogen-bond donor capacity of water is enhanced due to its interaction with the cationic interface. Hence, entrapped water can be converted into "super-water" for the enzymatic reaction studied in this work.

HCl/DMF for enhanced chemoselectivity in catalytic hydrogenolysis reactions

Ochocinska, Agata,Siegbahn, Anna,Ellervik, Ulf

, p. 5200 - 5202 (2010)

An improved, chemoselective hydrogenolysis method has been developed. By employing a solvent-acid combination (i.e., DMF-aq HCl) we were able to favor debenzylation rather than aromatic hydrogenation and acid-mediated bond cleavage which are the two main drawbacks of these reactions. The generality of the method, which was primarily developed as a solution to a carbohydrate problem, is shown by the successful hydrogenolysis of 1,8-naphthalide, a previously unsolved problem.

A novel application of Hβ-zeolite in catalytic dehalogenation of halophenols

Adimurthy, Subbarayappa,Ramachandraiah, Gadde,Bedekar, Ashutosh V.

, p. 6391 - 6392 (2003)

A new application of Hβ-zeolite for debromination of bromophenols and deiodination of iodophenols is presented in this note. The heterogeneous catalyst can be recovered and recycled effectively for subsequent reactions. The catalyst was found ineffective for similar action on chlorophenols.

Functional Analyses of House Fly Carboxylesterases Involved in Insecticide Resistance

Feng, Xuechun,Liu, Nannan

, (2020)

Carboxylesterase-mediated metabolism is one of major mechanisms involved in insecticide resistance. Our previous study has identified multiple carboxylesterase genes with their expression levels were significantly upregulated in pyrethroid resistant house flies. To further explore their metabolic functions, we used insect Spodoptera frugiperda (Sf9) cells to express these carboxylesterases in vitro and measure their hydrolytic activities toward esterase substrates. Our results indicated that these carboxylesterases can efficiently hydrolyze α-naphthyl acetate rather than β- naphthyl acetate. A cell based MTT cytotoxicity assay indicated that carboxylesterase-expressing cells show enhanced tolerance to permethrin, suggesting important roles of these carboxylesterases in metabolizing permethrin and thereby protecting cells from permethrin treatments. The metabolic functions of carboxylesterases were further verified by conducting in vitro metabolism studies toward permethrin and its potential metabolites 3-phenoxybenzyl alcohol and 3-phenoxybenzaldehyde, which not only suggested the potential metabolic pathway of permethrin in insects, but also important roles of these candidate carboxylesterases in metabolizing permethrin and conferring resistance in house flies. Homology modeling and docking were finally conducted to reflect interactions between permethrin ligand and carboxylesterase proteins, visually confirming the metabolic functions of carboxylesterases to insecticides in house flies.

Pharmacokinetics of 2-naphthol following intrapericardial administration, and formation of 2-naphthyl-β-D-glucoside and 2-naphthyl sulphate in the American lobster, Homarus americanus

Li,James

, p. 609 - 626 (1997)

1. Following a 0.25-mg/kg intrapericardial dose of the phenolic compound, 2-naphthol, to the American lobster, Homarus americanus, a two-compartment model best described the disposition of parent [14C]-2-naphthol in the haemolymph. Male and female lobsters had similar α-phase half lives of 26 ± 19 min (mean ± SD, n = 4) and 29 ± 15 min respectively. The β-phase half lives were significantly longer in males, 63.9 ± 30.9 h, than in females, 30.6 ± 6.8 h (P -1 x kg-1 and was higher than that of males, 11.1 ± 5.9 ml x h-1 x kg-1 (p 99% bound to haemolymph proteins at 1 min find > 90% bound at 1 day after the dose, indicating that both 2-naphthol and 2-naphthyl-β-D-glucoside were highly protein bound. 4. 2-Naphthyl-β-D-glucoside was slowly eliminated from haemolymph in both males and females, with elimination half lives of 34-78 h. 2-Naphthyl-β-D-glucoside was the major metabolite in urine samples collected at 5 days after the dose. Hepatopancreas and antennal gland contained glucosidase activities, and the long half life of 2-naphthyl-β-D-glucoside could be explained by conjugation-deconjugation cycling. 5. 2-Naphthyl sulphate was eliminated from haemolymph with a half-life 10 h and was excreted in urine.

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Warren,Smiles

, p. 2207,2210 (1931)

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The reduction of graphene oxide with hydrazine: elucidating its reductive capability based on a reaction-model approach

Chua, Chun Kiang,Pumera, Martin

, p. 72 - 75 (2016)

We have performed an experimental investigation on the effects of hydrazine treatment on graphene oxide via a reaction-model approach. Hydrazine was reacted with small conjugated aromatic compounds containing various oxygen functional groups to mimic the structure of graphene oxide. The hydroxyl and carboxylic groups were not readily removed while carbonyl groups reacted with hydrazine to form the corresponding hydrazone complexes. In the presence of adjacent hydroxyl groups, carboxyl groups underwent thermal decarboxylation.

PHOTOCHEMICAL REACTIONS OF NAPHTHYL-VINYL NON-CONJUGATED BICHROMOPHORIC SYSTEMS

Kashoulis, Annoula,Gilbert, Andrew,Ellis-Davies, Graham

, p. 2905 - 2908 (1984)

2-(1-Naphthyl)ethyl vinyl ether undergoes intramolecular 1,2-photocycloaddition whereas the 2-naphthyl isomer yields a product reflecting dimerisation and loss of the elements of acetylene: consistent with such diverse photochemistry, the addition of 2,3-dihydropyran to naphthalene produces only the 1,2-, 1',2'-regioisomer.

-

Soffer et al.

, p. 1556 (1952)

-

-

Wessely,Grill

, p. 282,286 (1947)

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Mechanistic Insights into Hydrogen Evolution by Photocatalytic Reforming of Naphthalene

Al-Madanat, Osama,Alsalka, Yamen,Bahnemann, Detlef W.,Curti, Mariano,Dillert, Ralf

, p. 7398 - 7412 (2020)

Heterogeneous photocatalysis has been widely considered, among other applications, for environmental remediation and hydrogen production. While these applications have been traditionally seen as well-separated areas, recent examples have highlighted the possibility of coupling them. Here, we demonstrate the simultaneous production of H2 and naphthalene removal from aqueous solutions with (unoptimized) photonic efficiencies of 0.97 and 0.33percent, respectively, over Pt-TiO2 under simulated sunlight. Photocatalytic and spin-trapping experiments in the presence of a hydroxyl radical and hole scavengers evinced that only the photogenerated holes play a significant role in the oxidation of naphthalene. Isotopic labeling analyses showed that the evolved H2 isotopologues match those of the solvent and that deuterated water (but not deuterated naphthalene) decreases the reaction rate, suggesting its involvement in the rate-determining step. Moreover, the use of Ti18O2 does not lead to the significant formation of 18O-enriched CO2, suggesting that water is the source of the oxygen atoms. Ultimately, by considering the stable and transient reaction intermediates, we propose a plausible reaction pathway. Our work illustrates that environmental remediation can be effectively coupled to solar fuel production, providing a double purpose to photocatalytic reactions, while the mechanistic insights will be of use for the further development of this strategy.

Conversion of 1-tetralone over HY zeolite: An indicator of the extent of hydrogen transfer

Prasomsri, Teerawit,Galiasso Tailleur, Roberto E.,Alvarez, Walter E.,Sooknoi, Tawan,Resasco, Daniel E.

, p. 140 - 146 (2010)

The conversion of pure 1-tetralone and its mixtures with n-decane, decalin, tetralin, or 1,5-dimethyl tetralin (DMT) has been investigated over HY zeolite. The dominant reactions undergone by 1-tetralone are the dehydrogenation to 1-naphthol and the subsequent isomerization to 2-naphthol. In the presence of hydrocarbons, the hydrogen transfer/dehydration of naphthols is accelerated, and naphthalene is formed in different amounts, depending on the nature of the co-fed hydrocarbon. In this contribution, it is demonstrated how the product distribution from the tetralone conversion can be used as an indicator of the hydrogen transfer ability of a particular hydrocarbon, or mixture of hydrocarbons. The relative order of hydrogen transfer ability of the various hydrogen donating compounds, as inferred from the naphthalene-to-naphthol product ratio, is DMT > tetralin ≈ decalin > n-decane. This trend agrees well with the hydride dissociation energy of individual donors calculated by DFT.

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Linstead,Michaelis

, p. 1134,1138 (1940)

-

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Hodgkinson,Limpach

, p. 1096 (1891)

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Formation of naphthalene hydrates in the enzymatic conversion of 1,2-dihydronaphthalene by two fungal peroxygenases and subsequent naphthalene formation

Kluge, Martin,Ullrich, Rene,Scheibner, Katrin,Hofrichter, Martin

, p. 56 - 60 (2014)

The formation of naphthalene hydrates (i.e. 1- and 2-hydroxy-1,2- dihydronaphthalene) displays a new activity (besides epoxidation) in the enzymatic transformation of 1,2-dihydronaphthalene by two fungal unspecific peroxygenases (UPOs) accounting for 16-19% of the overall turnover. These arene hydrates decayed into naphthalene that in turn was converted by UPOs into naphthols. The oxygen transferred during hydroxylation was shown to derive from hydrogen peroxide proving a true peroxygenation reaction.

Enzymatic Reaction in Water-in-Oil Microemulsions. Part 2. - Rate of Hydrolysis of a Hydrophobic Substrate, 2-Naphthyl Acetate

Miyake, Yoshikazu,Owari, Takuya,Ishiga, Fumio,Teramoto, Masaaki

, p. 979 - 986 (1994)

The catalytic hydrolysis rates of a hydrophobic substrate, 2-naphthyl acetate (NA), have been measured both in aqueous solution and in water-in-oil microemulsions (ME) formed by di(2-ethylhexyl)sodium sulfosuccinate (AOT) in heptane.The catalysts used were lipase, α-chymotrypsin and imidazole.The dependence of WO = OV/OV at a constant OV and of OV at a constant WO on the overall rate constants were discussed in terms of a reaction model.The reaction model includes three parameters, the distribution constants of NA and the catalysts and the rate constant of the local reaction field.The distribution constant of NA was evaluated by measurements of the distribution of NA between the ME in the Winsor II region and the aqueous phase, but that of catalysts was treated as a fitting parameter.It is suggested that the reactions with these catalysts proceeds at the interfacial region of ME.For the imidazole-catalysed reaction, if the imidazole exists preferentially at the interface, the rate constant is independent of WO, but the values was 0.2 times that in the aqueous phase.Superactivity of lipase was observed, that is the turnover number in ME was greater than that in the aqueous phase.However, as the Michaelis constant was also large, the rate constant (kCAT/km) in ME was smaller than that in the aqueous phase.The rate constant increased as WO increased.The dependence was caused by the conformation change of lipase due to the interaction of AOT molecules.The rate constants for both imidazole and lipase decreased with increase in at constant WO, which might be caused by the change in the structure of ME.The turnover number for α-chymotrypsin at the interface was lower than that in the aqueous phase and approached the values in the aqueous phase as WO and increased.However, the Michaelis constant decreased with increase in WO and approached a constant value, which was 25 times that in the aqueous phase.

Novel spectral manipulations for determinations of Tolnaftate along with related toxic compounds: Drug profiling and a comparative study

Emam, Raghda A.,Abdelrahman, Maha M.,Abdelaleem, Eglal A.,Ali, Nouruddin W.

, (2019)

A comparative study using novel quadruple divisor and mean centering of ratio spectra spectrophotometric methods was developed for resolution of five- component mixture of Tolnaftate, β-naphthol (Tolnaftate alkaline degradation product and its toxic impurity), methyl(m-tolyl)carbamic acid (Tolnaftate alkaline degradation product), N-methyl-m-toluidine (Tolnaftate toxic impurity) and methyl paraben (as a preservative). For the novel quadruple divisor method, each component in the quinary mixture was determined by dividing the quinary mixture spectrum by a sum of standard spectrum of equal concentration of the other four components as a quadruple divisor. First derivative of each ratio spectra was then obtained which allowed selective determination of each component without interference from other components in the mixture. The second method was mean centering of ratio spectra that depended on utilizing the mean centered ratio spectra in four successive steps leading to enhancement of the signal to noise ratio. The absorption spectra of the five studied components were recorded in the wavelength range of 210–350 nm. The mean centered fourth ratio spectra amplitudes for each component were used for its determination. The developed methods were successfully applied for determination of laboratory prepared quinary mixtures to ensure method's specificity, then, were further applied on Tinea Cure cream where no interference from excipients. For the first time, Tolnaftate was determined along with its toxic impurity; β-naphthol, that could be absorbed by the skin, causing systemic toxic effects, unlike Tolnaftate that poorly absorbed, indicating the significance of this work. The proposed methods were statistically compared with each other and with the reference method. Furthermore, ICH guidelines were followed for their validation.

Oxyfunctionalization of Hydrocarbons. 17. Acid-Dependent High Regioselectivity Hydroxylation of Naphthalene with Hydrogen Peroxide Giving 1- or 2-Naphthol

Olah, George A.,Keumi, Takashi,Lecoq, Jean Claud,Fung, Alexander P.,Olah, Judith A.

, p. 6148 - 6151 (1991)

The acid-catalyzed hydroxylation of naphthalene with 90percent hydrogen peroxide was investigated.Regioselectivity of the reaction depends on the acidity of the system and the solvent used.In anhydrous hydrogen fluoride or 70percent HF-30percent pyridine solution at -10 to +20 deg C 1-naphthol is the product formed in > 98percent selectivity.In contrast, 2-naphthol is obtained in hydroxylation in superacid (HF-BF3, HF-SbF5, HF-TaF5, FSO3H-SbF5) solution at -60 to -78 deg C in > 98percent selectivity.When 1-naphthol reacted under the latter conditions 1,5- and 1,7-dihydroxynaphthalene were obtained, while 2-naphthol gave 1,6-dihydroxynaphthalene (along with only minor amounts of 1,7-dihydroxynapthtalene).The mechanism of the reactions is discussed, contrasting electrophilic hydroxylation of naphthalene, giving predominantly 1-substitution, with reaction of protonated naphthalenes (i.e., naphthtalenium ions) with hydrogen peroxide.

Mechanistic imperatives for catalysis of aldol addition reactions: Partitioning of the enolate intermediate between reaction with bronsted acids and the carbonyl group

Richard, John P.,Nagorski

, p. 4763 - 4770 (1999)

The lyoxide ion catalyzed intramolecular aldol addition reaction of 2- (2-oxopropyl)benzaldehyde (1) to give the aldol adduct 3 proceeds via essentially irreversible formation of the acetone-like enolate intermediate 2, because reprotonation of 2 by a solvent of H2O or D2O (k(HOH) or k(DOD)) is much slower than intramolecular addition of the enolate to the carbonyl group (k(c)). The aldol addition reaction of 1 catalyzed by high concentrations of 3-substituted quinuclidine buffers proceeds via reversible deprotonation of 1 to give the enolate 2, and rate-determining addition of the enolate to the carbonyl group. A rate constant ratio of k(c)/k(HOH) = 35 was determined for partitioning of the enolate 2 between intramolecular addition to the carbonyl group and protonation by solvent water. The corresponding ratios k(BH)/k(c) (M-1) for the protonation of 2 by Bronsted buffer acids and intramolecular aldol addition increase from 7 to 450 as the acidity of the buffer acid is increased from pK(BH) = 11.5 to 7.5. The data show that the electrophilic reactivity of the benzaldehyde carbonyl group toward intramolecular addition of the enolate 2 is the same as that of a hypothetical tertiary ammonium cation of pK(BH) = 13.3. The Marcus intrinsic barrier for addition of the enolate 2 to the carbonyl group is unexpectedly small, which suggests that the transition state for this reaction is stabilized by interactions between the soft-soft acid-base pair. The relevance of this work to chemical and enzymatic catalysis of aldol condensation reactions is discussed.

Selective Reductive Cleavage of Arenocrown Ethers by Alkali Metals in THF

Sokol, Maria,Kowalczuk, Marek,Grobelny, Zbigniew,Janeczek, Henryk,Jedlinski, Zbigniew,et al.

, p. 2365 - 2367 (1995)

Alkali metal solutions in tetrahydrofuran containing the arenocrown ethers naphtho-15-crown-5, benzo-15-crown-5, and benzo-18-crown-6 were investigated using 39K NMR, ESR, and GC-MS techniques.The cleavage of carbon-oxygen bonds in the crown ethers studied is discussed.

UEBER DIE REAKTION VON α- UND β-TETRALON MIT KALIUMSUPEROXID

Lissel, Manfred

, p. 2213 - 2214 (1984)

The reaction of α- and β-tetralone with potassium superoxide is described.In addition to 2-hydroxy-1,4-naphthoquinone α-naphthol is formed from α-tetralone and β-naphthol and 2-carboxy-benzenepropionic acid from β-tetralone.

Two channels of electron transfer observed for the reaction of n-butyl chloride parent radical cations with naphthols and hydroxybiphenyls

Mohan,Hermann,Naumov,Mittal,Brede

, p. 5754 - 5762 (1998)

Pulse radiolysis of naphthols (NpOH) and hydroxybiphenyls (ByOH) in n-butyl chloride (BuCl) at room temperature exhibits electron transfer at a bimolecular rate constant of (1.0-2.8) × 1010 dm3 mol-1 s-1. The experiments reveal the direct formation of two types of transients: phenol type radical cations (NpOH?+, ByOH?+) and phenoxyl type radicals (NpO?, ByO?). This is explained by a mechanism involving two different electron-transfer channels. The solute radical cations exhibit two optical absorption bands in the 570-650 and 360-460 nm regions and undergo electron transfer with triethylamine and proton transfer with ethanol with bimolecular rate constants of (4-12) × 109 and (3-6) × 108 dm3 mol-1 s-1, respectively. NpO? and ByO? have relatively long lifetimes and show absorption bands in the 340-400 and 470-540 nm regions. By way of comparison, these phenoxyl type radicals are separately generated by pulse radiolysis in aqueous alkaline solution containing sodium azide, i.e., by oxidation of the solutes with N3? radicals. Under these conditions, the phenoxyl radicals decay by second-order kinetics with 2k = (1.2-4.5) × 108 dm3 mol-1 s-1. The various modes of formation and decay of the phenolic radical cations are analyzed over a wide range of dose rate and solute concentrations. In comparison to radical cations of one-ring phenols, the increased stability of NpOH?+ and ByOH?+ is explained by the delocalization of the positive charge over the whole aromatic system, a postulate supported by open-shell quantum chemical calulations.

Acid-Catalyzed Versus Thermally Induced C1-C1′ Bond Cleavage in 1,1′-Bi-2-naphthol: An Experimental and Theoretical Study

Genaev, Alexander M.,Shchegoleva, Lyudmila N.,Salnikov, George E.,Shernyukov, Andrey V.,Shundrin, Leonid A.,Shundrina, Inna K.,Zhu, Zhongwei,Koltunov, Konstantin Yu.

, p. 7238 - 7243 (2019)

Experiments show that 1,1′-bi-2-naphthol (BINOL) undergoes facile C1-C1′ bond cleavage under action of triflic acid at temperatures above 0 °C to give mainly 2-naphthol along with oligomeric material. CASSCF and MRMP//CASSCF computations have demonstrated unambiguously that this unusual mode of scission of the biaryl bond can occur in the C1,C1′-diprotonated form of BINOL via a mechanism involving homolytic cleavage prompted by the intramolecular electrostatic repulsion. These findings also provide insights into the mechanism of a comparatively easy thermal cleavage of BINOL, implying the intermediacy of its neutral diketo form.

-

Klamann

, p. 814,819 (1953)

-

-

Kotlarek

, p. 67 (1973)

-

-

May

, p. 650 (1922)

-

Coordination of manganese porphyrins on amino-functionalized MCM-41 for heterogeneous catalysis of naphthalene hydroxylation

Yang, Fu,Gao, Shuying,Xiong, Cuirong,Wang, Haiqing,Chen, Jin,Kong, Yan

, p. 1035 - 1041 (2015)

The different amounts of [5,10,15,20-tetrakis-(pentafluorophenyl)porphyrin] manganese chloride (TF20PPMnCl) were immobilized on amino-functionalized MCM-41 for catalysis of the hydroxylation of naphthalene. The samples were characterized by X-ray powder diffraction, N2 adsorption/desorption isotherms, Fourier transform infrared spectroscopy, X-ray photoelectron spectroscopy, scanning electron microscopy, diffuse reflectance ultraviolet-visible spectroscopy, thermogravimetric and differential scanning calorimetry, and inductively coupled plasma mass spectrometry. The results indicated that the manganese porphyrins were axially coordinated on amino-functionalized MCM-41. The prepared samples showed remarkable catalytic activity in the hydroxylation of naphthalene with meta-chloroperbenzoic acid as the oxidant. The catalyst could be reused several times without loss of its activity.

-

Land et al.

, p. 1885,1887 (1961)

-

Atropselective hydrolysis of chiral BiNoL-phosphate esters catalyzed by the phosphotriesterase from Sphingobium sp. TCM1

Xiang, Dao Feng,Narindoshvili, Tamari,Raushel, Frank M.

, p. 4463 - 4469 (2020)

The phosphotriesterase from Sphingobium sp. TCM1 (Sb-PTE) is notable for its ability to hydrolyze a broad spectrum of organophosphate triesters, including organophosphorus flame retardants and plasticizers such as triphenyl phosphate and tris(2-chloroethyl) phosphate that are not substrates for other enzymes. This enzyme is also capable of hydrolyzing any one of the three ester groups attached to the central phosphorus core. The enantiomeric isomers of 1,1′-bi-2-naphthol (BINOL) have become among the most widely used chiral auxiliaries for the chemical synthesis of chiral carbon centers. PTE was tested for its ability to hydrolyze a series of biaryl phosphate esters, including mono- and bis-phosphorylated BINOL derivatives and cyclic phosphate triesters. Sb-PTE was shown to be able to catalyze the hydrolysis of the chiral phosphate triesters with significant stereoselectivity. The catalytic efficiency, kcat/Km, of Sb-PTE toward the test phosphate triesters ranged from ~10 to 105 M?1 s?1. The product ratios and stereoselectivities were determined for four pairs of phosphorylated BINOL derivatives.

Bacterial Oxidation of Naphtharene to 1-Naphthol

Inoue, Masami,Inoue, Tomoni,Okami, Mituaki,Sayama, Michio,Hirai, Yoshiro

, p. 1315 - 1316 (1994)

The oxidation of naphtharene in a liquid culture was carried out in the presence of Bacillus cereus. 1-Naphthol was obtained in 11-20percent yield and the selectivity of 65-77percent at 28 deg C and pH 7.0 after 12-24 h.The ratio of 1-naphthol to 2-naphthol was 94:6.

Effect of Confinement on the Properties of Sequestered Mixed Polar Solvents: Enzymatic Catalysis in Nonaqueous 1,4-Bis-2-ethylhexylsulfosuccinate Reverse Micelles

Durantini, Andres M.,Falcone, R. Dario,Silber, Juana J.,Correa, N. Mariano

, p. 1678 - 1685 (2016)

The influence of different glycerol, N,N-dimethylformamide (DMF) and water mixtures encapsulated in 1,4-bis-2-ethylhexylsulfosuccinate (AOT)/n-heptane reverse micelles (RMs) on the enzymatic hydrolysis of 2-naphthyl acetate by α-chymotrypsin is demonstrated. In the case of the mixtures with DMF and protic solvents it has been previously shown, using absorption, emission and dynamic light-scattering techniques, that solvents are segregated inside the polar core of the RMs. Protic solvents anchor to the AOT, whereas DMF locates to the polar core of the aggregate. Thus, DMF not only helps to solubilize the hydrophobic substrate, increasing its effective concentrations but surprisingly, it does not affect the enzyme activity. The importance of ensuring the presence of RMs, encapsulation of the polar solvents and the corrections by substrate partitioning in order to obtain reliable conclusions is highlighted. Moreover, the effect of a constrained environment on solvent–solvent interactions in homogenous media and its impact on the use of RMs as nanoreactors is stressed.

-

Arzoumanidis,Rauch

, p. 4443,4444,4445 (1973)

-

-

Harrison

, p. 616 (1969)

-

A mild and practical method for deprotection of aryl methyl/benzyl/allyl ethers with HPPh2andtBuOK

Pan, Wenjing,Li, Chenchen,Zhu, Haoyin,Li, Fangfang,Li, Tao,Zhao, Wanxiang

, p. 7633 - 7640 (2021/09/22)

A general method for the demethylation, debenzylation, and deallylation of aryl ethers using HPPh2andtBuOK is reported. The reaction features mild and metal-free reaction conditions, broad substrate scope, good functional group compatibility, and high chemical selectivity towards aryl ethers over aliphatic structures. Notably, this approach is competent to selectively deprotect the allyl or benzyl group, making it a general and practical method in organic synthesis.

PREPARING METHODE FOR NAPHTHOL

-

Paragraph 0032-0048, (2021/01/28)

The present invention provides a method for producing naphthol by oxidizing naphthalene and an oxidizing agent in the presence of a catalyst. According to the present invention, naphthol can be produced in a single process of direct oxidation of naphthalene, and the yield and selectivity of naphthalene can be improved by controlling process variables such as the molar ratio of the oxidizing agent and naphthalene, catalyst input amount, and reaction time.

Mn(III) active site in hydrotalcite efficiently catalyzes the oxidation of alkylarenes with molecular oxygen

Wang, Anwei,Zhou, WeiYou,Sun, Zhonghua,Zhang, Zhong,Zhang, Zhihui,He, MingYang,Chen, Qun

, (2020/12/07)

Developing efficient heterogeneous catalytic systems based on easily available materials and molecular oxygen for the selective oxidation of alkylarenes is highly desirable. In the present research, NiMn hydrotalcite (Ni2Mn-LDH) has been found as an efficient catalyst in the oxidation of alkylarenes using molecular oxygen as the sole oxidant without any additive. Impressive catalytic performance, excellent stability and recyclability, broad applicable scope and practical potential for the catalytic system have been observed. Mn3+ species was proposed to be the efficient active site, and Ni2+ played an important role in stabilizing the Mn3+ species in the hydrotalcite structure. The kinetic study showed that the aerobic oxidation of diphenylmethane is a first-order reaction over Ni2Mn-LDH with the activation energy (Ea) and pre-exponential factor (A0) being 85.7 kJ mol?1 and 1.8 × 109 min?1, respectively. The Gibbs free energy (ΔG≠) was determined to be -10.4 kJ mol-1 K-1 for the oxidation based on Eyring-Polanyi equation, indicating the reaction is exergonic. The mechanism study indicated that the reaction proceeded through both radical and carbocation intermediates. The two species were then trapped by molecular oxygen and H2O or hydroxyl species, respectively, to yield the corresponding products. The present research might provide information for constructing highly efficient and stable active site for the catalytic aerobic oxidation based on available and economic material.

Ligand compound for copper catalyzed aryl halide coupling reaction, catalytic system and coupling reaction

-

Paragraph 0152-0159, (2021/05/29)

The invention provides a ligand compound capable of being used for copper catalyzed aryl halide coupling reaction, the ligand compound is a three-class compound containing a 2-(substituted or non-substituted) aminopyridine nitrogen-oxygen group, and the invention also provides a catalytic system for the aryl halide coupling reaction. Thecatalytic system comprises a copper catalyst, a compound containing a 2-(substituted or non-substituted) aminopyridine nitrogen-oxygen group adopted as a ligand, alkali and a solvent, and meanwhile, the invention also provides a system for the aryl halide coupling reaction adopting the catalyst system. The compound containing the 2-(substituted or non-substituted) aminopyridine nitrogen oxygen group can be used as the ligand for the copper catalyzed aryl chloride coupling reaction, and the ligand is stable under a strong alkaline condition and can well maintain catalytic activity when being used for the copper-catalyzed aryl chloride coupling reaction. In addition, the copper catalyst adopting the compound as the ligand can particularly effectively promote coupling of copper catalyzed aryl chloride and various nucleophilic reagents which are difficult to generate under conventional conditions, C-N, C-O and C-S bonds are generated, and numerous useful small molecule compounds are synthesized. Therefore, the aryl halide coupling reaction has a very good large-scale application prospect by adopting the copper catalysis system of the ligand.

Well-defined Cp*Co(III)-catalyzed Hydrogenation of Carbonates and Polycarbonates

Dahiya, Pardeep,Gangwar, Manoj Kumar,Sundararaju, Basker

, p. 934 - 939 (2020/12/15)

We herein report the catalytic hydrogenation of carbonates and polycarbonates into their corresponding diols/alcohols using well-defined, air-stable, high-valent cobalt complexes. Several novel Cp*Co(III) complexes bearing N,O-chelation were isolated for the first time and structurally characterized by various spectroscopic techniques including single crystal X-ray crystallography. These novel Co(III) complexes have shown excellent catalytic activity to produce value added diols/alcohols from carbonate and polycarbonates through hydrogenation using molecular hydrogen as sole reductant or iPrOH as transfer hydrogenation source. To demonstrate the developed methodology's practical applicability, we have recycled the bisphenol A monomer from compact disc (CD) through hydrogenation under the established reaction conditions using phosphine-free, earth-abundant, air- and moisture-stable high-valent cobalt catalysts.

Process route upstream and downstream products

Process route

[1]naphthyl-nitro-amine
4323-69-7

[1]naphthyl-nitro-amine

water
7732-18-5

water

1-amino-naphthalene
134-32-7

1-amino-naphthalene

β-naphthol
135-19-3

β-naphthol

Conditions
Conditions Yield
titanium dioxide
13463-67-7

titanium dioxide

β-naphthol
135-19-3

β-naphthol

Conditions
Conditions Yield
86.5%
2-chloronaphthalene
91-58-7

2-chloronaphthalene

1-Pentyne
627-19-0

1-Pentyne

ethylbenzene
100-41-4,27536-89-6

ethylbenzene

β-naphthol
135-19-3

β-naphthol

Conditions
Conditions Yield
With water; titanium(IV) oxide; at 25 ℃; for 0.833333h; pH=3; Reagent/catalyst; Wavelength; pH-value; Concentration; Time; Kinetics; Mechanism; UV-irradiation;
2,3-dihydro-1,2,3-triphenyl-1H-naphth<1,2-e><1,3>oxazine
66311-81-7

2,3-dihydro-1,2,3-triphenyl-1H-naphth<1,2-e><1,3>oxazine

benzaldehyde
100-52-7

benzaldehyde

2,4-diphenyl-2'(1'H)-oxo-2,3-dihydrospiro<4H-benzo<f>chroman-3,1'-naphthalone>
82507-88-8

2,4-diphenyl-2'(1'H)-oxo-2,3-dihydrospiro<4H-benzochroman-3,1'-naphthalone>

β-naphthol
135-19-3

β-naphthol

Conditions
Conditions Yield
at 210 - 215 ℃; for 1.5h;
8%
5%
1-(α-aminobenzyl)-2-naphthol hydrochloride
219897-32-2

1-(α-aminobenzyl)-2-naphthol hydrochloride

benzaldehyde
100-52-7

benzaldehyde

β-naphthol
135-19-3

β-naphthol

Conditions
Conditions Yield
at 100 ℃;
ethanol
64-17-5

ethanol

1-(α-aminobenzyl)-2-naphthol hydrochloride
219897-32-2

1-(α-aminobenzyl)-2-naphthol hydrochloride

benzylidene-1,1'-bis(2-naphthol)
29114-24-7

benzylidene-1,1'-bis(2-naphthol)

14-phenyl-14H-dibenzo[a.j]xanthene
36441-29-9

14-phenyl-14H-dibenzo[a.j]xanthene

benzaldehyde
100-52-7

benzaldehyde

β-naphthol
135-19-3

β-naphthol

Conditions
Conditions Yield
hydrogenchloride
7647-01-0,15364-23-5

hydrogenchloride

benzylidene-1,1'-bis(2-naphthol)
29114-24-7

benzylidene-1,1'-bis(2-naphthol)

acetic acid
64-19-7,77671-22-8

acetic acid

14-phenyl-14H-dibenzo[a.j]xanthene
36441-29-9

14-phenyl-14H-dibenzo[a.j]xanthene

benzaldehyde
100-52-7

benzaldehyde

β-naphthol
135-19-3

β-naphthol

Conditions
Conditions Yield
anthranilic acid amide
28144-70-9,88-68-6

anthranilic acid amide

2-hydroxynaphthalene-1-carbaldehyde
708-06-5

2-hydroxynaphthalene-1-carbaldehyde

4-Hydroxyquinazoline
491-36-1

4-Hydroxyquinazoline

2-(2-hydroxynaphthalen-1-yl)-4(3H)-quinazolinone
106910-74-1

2-(2-hydroxynaphthalen-1-yl)-4(3H)-quinazolinone

β-naphthol
135-19-3

β-naphthol

Conditions
Conditions Yield
With sodium hydrogensulfide; In N,N-dimethyl acetamide; at 150 ℃; for 2h;
72%
19%
41%
2-(2-hydroxynaphthalene-1-yl)-2,3-dihydroquinazolin-4(1H)-one
106910-75-2

2-(2-hydroxynaphthalene-1-yl)-2,3-dihydroquinazolin-4(1H)-one

4-Hydroxyquinazoline
491-36-1

4-Hydroxyquinazoline

β-naphthol
135-19-3

β-naphthol

Conditions
Conditions Yield
In 1,2-dichloro-benzene; for 6h; Heating;
69%
56%
1,4-Dihydroxynaphthalene
571-60-8

1,4-Dihydroxynaphthalene

α-naphthol
90-15-3

α-naphthol

2,7-Dihydroxynaphthalene
582-17-2

2,7-Dihydroxynaphthalene

1,8-dihydroxynaphthalene
569-42-6

1,8-dihydroxynaphthalene

1,5-dihydroxynaphthalene
83-56-7

1,5-dihydroxynaphthalene

β-naphthol
135-19-3

β-naphthol

Conditions
Conditions Yield
With n-butyllithium; potassium tert-butylate; Product distribution; multistep reaction; isomer distribution as a function of the solvent and conditions (THF only monosubstitution), also after reaction with Me2SO4;

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