Category: 72016-73-0

Shen, Yan-Ming; Song, Lin-Lin; Qian, Xu-Hong; Yang, You-Jun published an article on January 31 ,2013. The article was titled 《A scalable synthesis of 1-amino-5-cyanonaphthalene, a precursor for a nitric oxide probe (NO550) designed via the dye assembly principle》, and you may find the article in Chinese Chemical Letters.Application of 72016-73-0 The information in the text is summarized as follows:

A convenient and scalable synthesis of 1-amino-5-cyanonaphthalene was described. In the experimental materials used by the author, we found 5-Amino-1-naphthonitrile(cas: 72016-73-0Application of 72016-73-0)

5-Amino-1-naphthonitrile(cas: 72016-73-0) belongs to anime.Typically the presence of an amine functional group is deduced by a combination of techniques, including mass spectrometry as well as NMR and IR spectroscopies. 1H NMR signals for amines disappear upon treatment of the sample with D2O. In their infrared spectrum primary amines exhibit two N-H bands, whereas secondary amines exhibit only one.Application of 72016-73-0

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

In 1954,Journal of the Chemical Society included an article by Gray, G. W.; Jones, Brynmor. Safety of 5-Amino-1-naphthonitrile. The article was titled 《The preparation of 4- and 5-n-alkoxy-1-naphthoic and 6-and 7-n-alkoxy-2-naphthoic acids》. The information in the text is summarized as follows:

1-Naphthol was alkylated with NaOEt and the n-alkyl bromide or iodide by boiling 8 h. in EtOH. Distillation under reduced pressure gives the following ethers in 65-70% yield (b. p./mm. given): Me 134°/13, Et 152°/17 (m. 5°), Pr 143°/3, Bu 160°/4 (m. 19.5°), pentyl 173°/6 (m. 29.5°), hexyl 166°/4 (m. -3°), heptyl 171°/5, octyl 189°/5, nonyl 185°/4, decyl 212°/4, dodecyl 227°/3, hexadecyl 258°/1 (m. 31°), octadecyl 236°/10-2 (m. 50.5°). The 1-n-alkoxynaphthalenes were brominated with IBr in CHCl3 at 10-20°. The CHCl3 is removed and the 4-Br ethers are distilled under reduced pressure, being obtained in 65-75% yields (b. p./mm. given): Me 159°/4, Et 158°/3 (m. 48.5°), Pr 188°/8 (m. 31°), Bu 199°/5 (m. 25°), pentyl 181°/3 (m. 47.5°), hexyl 206°/5 (m. 45°). 1-n-Alkoxynaphthalenes in CS2 containing AlCl3 are treated with BrCN to form 4-n-alkoxy-1-naphthonitriles (I) in 80% yield (m. p. given): Et 88°, pentyl 60°, hexyl 62°, heptyl 54°, octyl 61°, nonyl 53°, decyl 64°, dodecyl 67°, hexadecyl 69°, octadecyl 71°. 4-n-Alkoxy-1-naphthoic acids are made from 1 g.-atom Mg turnings and 2 g. of the 1-bromonaphthalene in 25 mL. ether by refluxing 5 min. A total of 0.1 mol of the 1-bromonaphthalene in 75 mL. ether is added dropwise in 30 min. and reflux is continued 10 h. The mixture is added to ether saturated with Dry Ice. The excess CO2 is evaporated and the solution stirred with 50 mL. 17% HCl. The ether is removed and the acid washed free of MgCl2. The acids are recrystallized from glacial HOAc in 80-5% yield. Another method of forming the acids is to reflux 0.1 mol of the nitrile with 250 mL. of a solution of MeOH saturated with KOH for 15-25 h. The diluted mixture is acidified, redissolved in NaOH, and reacidified to give the following 1-carboxy analogs of I in 95-7% yields (m. p. given): Me 248°, Et 220°, Pr 203°, Bu 213.5°, pentyl 207°, hexyl 212°, heptyl 189°, octyl 183.5°, nonyl 161°, decyl 174.5°, dodecyl 147.5°, hexadecyl 136°, octadecyl 137.5°. Na 5-aminonaphthalene-1-sulfonate (70 g.) and 14 g. KCN are ground together and dry-distilled in an all-glass retort at 500-600°, the distillate is dissolved in 1.3 l. boiling 0.3N HCl, the solution is cooled and filtered, and the filtrate is neutralized with concentrated NH3 to give 22-6% 5-amino-1-naphthonitrile (II), m. 140°, b2-3 187-93°. II (0.03 mol) is dissolved in 60 mL. glacial HOAc at 80°, 60 mL. 40% H2SO4 is added with stirring, the solution is cooled to 0°, 0.06 mol NaNO2 in 30 mL. H2O is added, the solution is stirred at 0-5° until it clears, urea is used to destroy the excess NO2-, the solution is immediately added dropwise with stirring to a boiling solution of 180 mL. 40% H2SO4 in 30 min. refluxing is continued 1 h., the mixture is cooled, 300 mL. H2O is added, the solution is extracted with ether, the ether is extracted with N NaOH, and the basic extract is acidified to give 67% 5-hydroxy-1-naphthonitrile (III), m. 204-6°. After 8.4 g. III is refluxed with 50 g. KOH in 100 mL. H2O for 4-5 h., acidification gives 90% 5-hydroxy-1-naphthoic acid (IV), m. 238°; acetyl derivative, m. 204-5°. IV is methylated with Me sulfate at 40-50° in basic solution (the ester, which is a byproduct, is removed by refluxing with MeOH-KOH). The product is 5-methoxy-1-naphthoic acid (V), m. 232.5°. The following homologs of V are similarly prepared (alkyl and m. p. given): Et 201°, Pr 189°, Bu 172°, pentyl 143°, hexyl 154°, heptyl 135.5°, octyl 142.5°, nonyl 143°, decyl 137°, dodecyl 125°, hexadecyl 117.5°, octadecyl 122°. 2-Naphthol (1 mol) in 400 mL. glacial HOAc is brominated at room temperature and the resulting 1,6-dibromo-2-naphthol is reduced with mossy Sn at reflux to give 90-100% 6-bromo-2-naphthol (VI), m. 123-7°. The VI is treated with Me sulfate in alkali to give 60-70% 2-bromo-6-methoxynaphthalene (VII), m. 106-7°, b. 189-99°/20 mm. 6-Methoxy-2-naphthoic acid is formed from VII by the method of Fries and Schimmelschmidt (C.A. 20, 1616), m. 206° in 50-5% yield. AcCl treated with VII in the presence of AlCl3 in PhNO2 and distillation gives 5% 2-acetyl-6-methoxynaphthalene (VIII), m. 104-5°, b. 165-70°/3-4 mm. VIII (50 g.) in 350 mL. dioxane, is treated with NaOBr (from 140 g. NaOH, 600 mL. H2O, and 50 mL. Br) dropwise for 30 min. at 35-40° (reaching 50-5° at the end), excess Br is destroyed, 2 l. H2O is added, dioxane and CHBr3 are removed by steam distillation, and the solution is filtered and acidified with concentrated HCl to give 70-5% 6-methoxy-2-naphthoic acid (IX), m. 205-6°. IX (8 g.) is heated 2.5 h. with 35 mL. AcOH, 35 mL. 48% HBr, and 20 mL. glacial HOAc to give 6-hydroxy-2-naphthoic acid (X), m. 250° (Bz derivative, m. 257°; Ac derivative, m. 228°; phenylsulfonyl derivative, m. 228.5°). X was alkylated in 85-90% yield. The following 6-alkoxy analog of X were prepared (alkyl and m. p. given): Me 206°, Et 213°, Pr 208°, Bu 198°, pentyl 179.5°, hexyl 147°, heptyl 163°, octyl 161.5°, nonyl 147.5°, decyl 139°, dodecyl 119°, hexadecyl 107°, octadecyl 114.6°, isopentylnaphthoic acid 194.6°, 3,5,5-trimethylhexyl 170°. 7-Amino-2-naphthonitrile m. 197°. 7-Hydroxy-2-naphthonitrile, m. 186.5°. 7-Hydroxy-2-naphthoicacid m. 269-70°. 7-n-Octyloxy-2-naphthoic acid m. 142.5°, sublimes 170°/2-3 mm. 7-n-Hexadecyloxy-2-naphthoic acid m. 138°. The results came from multiple reactions, including the reaction of 5-Amino-1-naphthonitrile(cas: 72016-73-0Safety of 5-Amino-1-naphthonitrile)

5-Amino-1-naphthonitrile(cas: 72016-73-0) belongs to anime. Primary amines having a tertiary alkyl group (R3CNH2) are difficult to prepare with most methods but are made industrially by the Ritter reaction. In this method a tertiary alcohol reacts with hydrogen cyanide (HCN) in the presence of a concentrated strong acid; a formamide, RNH―CHO, is formed first, which then undergoes hydrolysis.Safety of 5-Amino-1-naphthonitrile

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Application of 72016-73-0On November 30, 1979 ,《Chlorine as an activating group in an electrophilic substitution. The Friedel-Crafts acetylation of 1-chloronaphthalene》 appeared in Journal of the Chemical Society. The author of the article were Gore, Peter H.; Khan, Iqtidar M.. The article conveys some information:

The activating effect of chlorine in the Friedel-Crafts acetylation of 1-chloronaphthalene is reported. Compared to naphthalene, the chloro-substituent activated the 4-position by a factor of 5.1 in CHCl3, all other positions being deactivated. In nitromethane, the 2-, 4-, 6- and 7-positions are activated by factors of 4.5, 13, 1.5, and 1.5, resp., all other positions being deactivated. The experimental process involved the reaction of 5-Amino-1-naphthonitrile(cas: 72016-73-0Application of 72016-73-0)

5-Amino-1-naphthonitrile(cas: 72016-73-0) belongs to anime. Amines have a free lone pair with which they can coordinate to metal centers. Amine–metal bonds are weaker because amines are incapable of backbonding, but they are still important for sensing applications.While stronger than hydrogen bonds, amine–metal bonds are still weaker than both covalent and ionic bonds.Application of 72016-73-0

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

In 1980,Journal of Organic Chemistry included an article by Schuster, Ingeborg I.; Roberts, John D.. Category: nitriles-buliding-blocks. The article was titled 《Proximity effects on nitrogen-15 chemical shifts of 8-substituted 1-nitronaphthalenes and 1-naphthylamines》. The information in the text is summarized as follows:

The 15N chem. shifts of several title naphthalenes were determined and, except for high-field shifts observed for 8-cyano- or 8-nitro-1-naphthylamine (I), the substituent effects are unexpectedly small. The high-field shifts of the amine nitrogens of I may indicate complexing between the amino group of the proximate substituents of the type suggested by J. D. Dunitz, (1978). The smallness of the other substituent effects may be the result of mutual cancellation of opposing larger effects. The experimental part of the paper was very detailed, including the reaction process of 5-Amino-1-naphthonitrile(cas: 72016-73-0Category: nitriles-buliding-blocks)

5-Amino-1-naphthonitrile(cas: 72016-73-0) belongs to anime. Large quantities of aliphatic amines are made synthetically. The most widely used industrial method is the reaction of alcohols with ammonia at a high temperature, catalyzed by metals or metal oxide catalysts (e.g., nickel or copper). Mixtures of primary, secondary, and tertiary amines are thereby produced.Category: nitriles-buliding-blocks

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

The author of 《Convenient method for the preparation of hydroxynaphthoic acids》 were Cason, James. And the article was published in Journal of the American Chemical Society in 1941. Recommanded Product: 72016-73-0 The author mentioned the following in the article:

The procedure of Butler and Royle (C. A. 17, 3182) for the synthesis of 4,2-C10H6(CO2H)OH gave very poor yields; various modifications produced the acid in satisfactory yields by way of the same intermediates. 4,2,5-C10H5(NH2)(CO2H)2(345 g.), 390 g. NaOH, 135 g. Zn and 900 cc. H2O, refluxed for 22 h., give 81-7% of 4,2-C10H6(NH2)SO3Na; distillation with KCN at about 500° gives 10-13% of 4,2-C10H6(NH2)CN, m. 125.5-6° (all m. ps. corrected); K4Fe(CN)6 (used by B. and R.) gives only 1-4%; CuCN could not be used because of foaming; a mixture of KCN with NaCN or K4Fe(CN)6 did not give better yields; hydrolysis with a mixture of 10 cc. AcOH and 2.5 cc. 70% H2SO4 gives 86% of 4,2-C10H6(NH2)CO2H, m. 215-16°; the diazo reaction did not give a good yield of 4,2-C10H6(OH)CO2H (I) but heating 4.5 g. of amine and 45 cc. 10% H2SO4 at 195-200° for 4 h. gives 90.5% of I, m. 225-6° (B. and R. give 182-3°); the Ac derivative (II) m. 211.5-12.5° (44° above reported value). II and PCl5, heated at 100° for 25 min., give 88% of 4-acetoxy-2-naphthoyl chloride (III), m. 96-8° and remelting at 99-9.5°; catalytic reduction in boiling xylene (Rosenmund’s method) gives 50-75% of 4-acetoxy-2-naphthaldehyde, m. 113.2-14.2°; semicarbazone (III), m. 230° (decomposition). Hydrolysis with N H2SO4 for 1 h. gives 63% of 2-hydroxy-2-naphthaldehyde (IV), buff, m. 169.5-70°. No definite product could be obtained on Wolff-Kishner reduction of III. Catalytic reduction (Cu-Cr catalyst) of IV gives 4,2-C10H6(OH)Me, m. 90-1°. The Na salt of 1,6-Cleve’s acid yields 9.5-10% of 5,2-C10H6(NH2)CN, m. 143.5-4°; hydrolysis gives 83.5% of 5,2-C10H6(NH2)-CO2H, m. 291-2°; 10% H2SO4 at 220-5° for 4 h. gives 67% of 5,2-C10H6(OH)CO2H, m. 215-16° (Ac derivative, m. 215-16°). 6-Amino-2-naphthonitrile, pale greenish yellow, iridescent plates, m. 199-9.5° (1.5% yield); with K4Fe-(CN)6 the yield is only 0.2%. 6,2-C10H6(OH)CO2H, m. 243-4°, 53.5% (Ac derivative, m. 223-4°). 5,1-C10H6(NH2)CN, m. 139.5-40°, results in 20% yield and 5,1-C10H6(OH)CO2H is formed in 53-7% yield. In the experiment, the researchers used 5-Amino-1-naphthonitrile(cas: 72016-73-0Recommanded Product: 72016-73-0)

5-Amino-1-naphthonitrile(cas: 72016-73-0) belongs to anime. Hydrogen peroxide (H2O2) and peroxy acids generally add an oxygen atom to the nitrogen of amines. With primary amines, this step is normally followed by further oxidation, leading to nitroso compounds, RNO, or nitro compounds, RNO2. Secondary amines are converted to hydroxylamines, R2NOH, and tertiary amines to amine oxides, R3NO.Recommanded Product: 72016-73-0

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Formula: C11H8N2On September 29, 2010 ,《A Highly Selective Low-Background Fluorescent Imaging Agent for Nitric Oxide》 was published in Journal of the American Chemical Society. The article was written by Yang, Youjun; Seidlits, Stephanie K.; Adams, Michelle M.; Lynch, Vincent M.; Schmidt, Christine E.; Anslyn, Eric V.; Shear, Jason B.. The article contains the following contents:

The authors introduce a novel sensing mechanism for nitric oxide (NO) detection with a particular easily synthesized embodiment (NO550), which displays a rapid and linear response to NO with a red shifted 1500-fold turn-on signal from a dark background. Excellent selectivity was observed against other reactive oxygen/nitrogen species, pH, and various substances that interfere with existing probes. NO550 crosses cell membranes but not nuclear membranes and is suitable for both intra- and extracellular NO quantifications. Good cytocompatibility was found during in vitro studies with two different cell lines. The high specificity, dark background, facile synthesis, and low pH dependence make NO550 a superior probe for NO detection when used as an imaging agent. In the part of experimental materials, we found many familiar compounds, such as 5-Amino-1-naphthonitrile(cas: 72016-73-0Formula: C11H8N2)

5-Amino-1-naphthonitrile(cas: 72016-73-0) belongs to anime. Left-handed and right-handed forms (mirror-image configurations, known as optical isomers or enantiomers) are possible when all the substituents on the central nitrogen atom are different (i.e., the nitrogen is chiral). With amines, there is extremely rapid inversion in which the two configurations are interconverted.Formula: C11H8N2

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

《13C NMR investigated of electronic interactions in 5-substituted 1-naphthonitriles》 was written by Schuster, Ingeborg I.. Product Details of 72016-73-0 And the article was included in Magnetic Resonance in Chemistry on April 30 ,1996. The article conveys some information:

Carbon-13 NMR chem. shifts of 5-Z-substituted 1-naphthonitriles (1; Z = H, F, Cl, Br, NH2, NMe2, CN, NO2, OMe, CHO, CO2Me) in deuteriochloroform and in neat trifluoroacetic acid (TFA) are reported. The CN carbon shifts are found to correlate well with the dual substituent parameters (DSPs). Neg. values of the transmission coefficients in the DSP correlation give evidence of a reverse substituent electronic effect, which is associated with variations in π polarization of the CN multiple bond, due primarily to differences in the through-space field effects of the various Z. The effect diminishes for 1 in neat TFA because of the greater contribution of dipolar ArC+=N- to the resonance hybrid. Deviations of the aromatic carbon shifts from substituent chem. shift additives are small, yet show distinct patterns for many of the carbon resonances. The deviations of the C-1-CN ipso carbon shifts of 1 in neutral solvents and in TFA correlate roughly with the DSPs. They are attributable to changes in charge d. at C-1 that arise as a consequence of substituent- and increased mesomeric activity by electron-donating groups, Z, in response to the CN-induced charge depletion within the adjacent aromatic ring. From the location of data for 5-methoxy-1-naphthonitrile (1; Z = OMe) in the chem. shift correlations of 1 in neat TFA, one can conclude that the methoxy group of this compound, unlike that of 1-methoxynaphthalene itself, is not significantly hydrogen-bonded by TFA. The experimental part of the paper was very detailed, including the reaction process of 5-Amino-1-naphthonitrile(cas: 72016-73-0Product Details of 72016-73-0)

5-Amino-1-naphthonitrile(cas: 72016-73-0) belongs to anime. Examples of direct uses of amines and their salts are as corrosion inhibitors in boilers and in lubricating oils (morpholine), as antioxidants for rubber and roofing asphalt (diarylamines), as stabilizers for cellulose nitrate explosives (diphenylamine), as protectants against damage from gamma radiation (diarylamines), as developers in photography (aromatic diamines), as flotation agents in mining, as anticling and waterproofing agents for textiles, as fabric softeners, in paper coating, and for solubilizing herbicides.Product Details of 72016-73-0

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

The author of 《Dissociation of naphthoic acids in non-aqueous media. Comparison of benzene and naphthalene skeletons》 were Parik, Patrik; Wolfova, Jitka; Ludwig, Miroslav. And the article was published in Collection of Czechoslovak Chemical Communications in 2000. Application In Synthesis of 5-Amino-1-naphthonitrile The author mentioned the following in the article:

Seven monosubstituted 1-naphthoic acids were synthesized by new or modified procedures, and their dissociation constants were measured potentiometrically at 25° in MeOH, MeCN, DMF, and pyridine. Dissociation constants of these along with 13 substituted 1-naphthoic acids and twenty-five substituted 2-naphthoic acids previously studied were measured at 25° in EtOH and DMSO. The pKKA values of 3- and 4-substituted 1-naphthoic acids were treated by simple linear regression and principal component anal., and the results were used for comparison of model compounds and of corresponding 3- and 4-substituted benzoic acids with the aim of comparison of benzene and naphthalene skeletons. It was found, the 3 and 4 positions of the 1-naphthyl system can roughly be compared with the meta and para positions of benzene, resp. The experimental part of the paper was very detailed, including the reaction process of 5-Amino-1-naphthonitrile(cas: 72016-73-0Application In Synthesis of 5-Amino-1-naphthonitrile)

5-Amino-1-naphthonitrile(cas: 72016-73-0) belongs to anime. Halogenation, in which one or more hydrogen atoms of an amine is replaced by a halogen atom, occurs with chlorine, bromine, and iodine, as well as with some other reagents, notably hypochlorous acid (HClO). With primary amines the reaction proceeds in two stages, producing N-chloro- and N,N-dichloro-amines, RNHCl and RNCl2, respectively. With tertiary amines, an alkyl group may be displaced by a halogen.Application In Synthesis of 5-Amino-1-naphthonitrile

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts