A-Hydroxynaphthalene

SYNS BASF URSOL ERN C.I. 76605 C.I. OXIDATION BASE 33 DURAFUR DEVELOPER D FOURANENE ERN FOURRINE 99 FOURRINE ERN FURRO ER a-HYDROXYNAPHTHALENE 1-HYDROXYNAPHTHALENE NAKO TRB 1-NAPHTHALENOL O-NAPHTHOL TERTRAL ERN URSOL ERN ZOBA ERN... 

Hydroxymethyl) undecane. See Butyloctanol 1-Hydroxynaphthalene a-Hydroxynaphthalene. See 1 -Naphthol 12-Hydroxyoctadecanoic acid. See Hydroxystearic acid Hydroxyoctadecanoic acid, 2-hydroxyethyl ester. See Glycol hydroxy-... 

Hydroxynaphthalene. See P-Naphthol a-Hydroxynaphthalene. See 1-Naphthol P-Hydroxynaphthalene. See P-Naphthol 2-Hydroxy-1,4-naphthalenedione. See Lawsone... 

CAS 90-15-3 EINECS/ELINCS 201-969-4 Synonyms Cl 76605 1-Hydroxynaphthalene a-Hydroxynaphthalene 1-Naphthalenol a-Naphthol... 

Colombo and Moreau (1967) studied Raman line widths in solids as a function of temperature and Korshunov, Shabanov, and Rusetskii (1967) carried out similar studies for solid a hydroxynaphthalene. 

Naphthalenol. 1-Naphthol, a-naphthol, or l-hydroxynaphthalene/P(9-/j5 -iJ forms colorless needles, mp 96°C, bp 288°C, which tend to become colored on exposure to air or light. It is almost insoluble in water, but readily soluble in alcohol, ether, and benzene. 1-Naphthol and 2-naphthol are found in coal tar (56). 

Naphthalenol. 2-Naphthol or p-naphthol or 2-hydroxynaphthalene/7i3 -/5 -i7 melts at 122°C and boils at 295°C, and forms colorless crystals of characteristic, phenoHc odor which darken on exposure to air or light. 2-Naphthol [135-19-3] is manufactured by fusion of sodium 2-naphthalenesulfonate with sodium hydroxide at ca 325°C, acidification of the drowned fusion mass which is quenched ia water, isolation and water-washing of the 2-naphthalenol, and vacuum distillation and flaking of the product. A continuous process of this type has been patented (69). The high sulfate content ia the primary effluent from 2-naphthol production is greatiy reduced ia modem production plants by the recovery of sodium sulfate. 

Naphthalenediol. This diol is prepared by the alkah fusion of 2-hydroxynaphthalene-6-sulfonic acid (Schaffer acid) at 290—295°C. Schaffer acid is usually produced by sulfonation of 2-naphthol with the addition of sodium sulfate at 85—105°C. This acid is also used as a coupling component in the production of a2o dyes such as Acid Black 26. 2,6-Naphthalenediol is used as a component in the manufacture of aromatic polyesters which, as is also tme of the corresponding amides, display Hquid crystal characteristics (52). 

Benzoxepins require drastic conditions for the thermal rearrangement to naphthols. When 3-benzoxepin-2,4-dicarboxylic acid is heated to 300 C, a decarboxylation reaction takes place and 3-hydroxynaphthalene-2-carboxylic acid (10) is formed in 44% yield.91... 

Modified PAN fibres containing aldehyde groups can be used to obtain chemically stained fibres. The chemical addition of dyes can be conducted following two schemes A) The fibres of the above composition are treated with aromatic amines, e.g., l-amino-8-hydroxynaphthalene-3,6-disulfonic acid ( H-acid ), and then azocoupling is carried out with a diazonium salt ... 

This comprises a heterogeneons gronp of enzymes that is used for the degradation of snbstrates including gentisate, salicylate, and l-hydroxynaphthalene-2-carboxylate by pathways that do not involve catechols ... 

Partial reduction of polyarenes has been reported. Use of boron trifluoride hydrate (BF3 OH2) as the acid in conjunction with triethylsilane causes the reduction of certain activated aromatic systems 217,262 Thus, treatment of anthracene with a 4-6 molar excess of BE3 OH2 and a 30% molar excess of triethylsilane gives 9,10-dihydroanthracene in 89% yield after 1 hour at room temperature (Eq. 120). Naphthacene gives the analogously reduced product in 88% yield under the same conditions. These conditions also result in the formation of tetralin from 1-hydroxynaphthalene (52%, 4 hours), 2-hydroxy naphthalene (37%, 7 hours), 1-methoxynaphthalene (37%, 10 hours), 2-methoxynaphthalene (26%, 10 hours), and 1-naphthalenethiol (13%, 6 hours). Naphthalene, phenanthrene, 1-methylnaphthalene, 2-naphthalenethiol, phenol, anisole, toluene, and benzene all resist reduction under these conditions.217 Use of deuterated triethylsilane to reduce 1-methoxynaphthalene gives tetralin-l,l,3-yielding information on the mechanism of these reductions.262 2-Mercaptonaphthalenes are reduced to 2,3,4,5-tetrahydronaphthalenes in poor to modest yields.217 263... 

Diazotization of 3-(4-aminophenyl)sydnones followed by reaction with 1- or 2-hydroxynaphthalene provides azo dyestuff materials <1998MI209>. A new type of reaction between 4-acetyl-3-arylsydnones and hydrazine yields substituted pyrrolidinones by a cycloaddition process involving loss of nitric oxide (Equation 20) <1999H(51)95, 2001AHC73>. 

Hydroxy-3-naphthoic acid ( BONA or BON ) is prepared by heating the sodium salt of 2-hydroxynaphthalene with carbon dioxide in a pressure chamber at 240 to 250°C at a pressure of 15 bar (Kolbe synthesis). The reaction mixture is continuously agitated. Remaining 2-naphthol is separated and recycled ... 

Cultures of Bacillus sp. oxidized naphthalene to (-r)-fran5-l,2-dihydro-l,2-dihydroxy-naphthalene. In the presence of reduced nicotinamide adeninedinucleotide phosphate (NADPH2) and ferrous ions, a cell extract oxidized naphthalene to fra/ 5-naphthalenediol (Gibson, 1968). Hydroxylation by pure microbial cultures yielded an unidentified phenol, 1- and 2-hydroxynaphthalene (Smith and Rosazza, 1974). 

The effect of solution chemistry on the speciation of the organic contaminant 1-naphtol (1-hydroxynaphthalene) and its complexatiom with humic acid is reported by Karthikeyan and Chorover (2000). The complexation of 1-naphtol with humic acid (HA) was studied during seven days of contact, as a function of pH (4 to 11), ionic strength (0.001 and 0.1 M LiCl), and dissolved concentration (DO of 0 and 8 mg L ) using fluorescence, UV absorbance, and equilibrium dialysis techniques. In a LiCl solution, even in the absence of HA, oxidative transformation of 1-naphtol mediated by was observed. In addition, the presence of humic acid in solution, in the absence of DO, was found to promote 1-naphtol oxidation. These reactions are affected by the solution chemistry (pH, ionic strength, and cation composition). 

Lower-sulfonated subsidiary colors of sunset yellow, among them 5-(phenylazo)-6-hydroxy-naphthalene-2-sulfonic acid (ANSC) and 4-[(2-hydroxynaphthalene-l-yl)azo]benzenesulfonic acid (BNSC), were determined by reverse-phase HPLC using Novapak Cl 8 and gradient elution with a water-tetrahydrofuran solvent system buffered with ammonium acetate (192). 

A particularly important class of coupling components are the aminohydroxy-naphthalenesulfonic acids. Appropriate variation of the disazo component permits the development of shades ranging from orange to black. Orange and scarlet are achieved with I-acid (6-amino-l-hydroxy-naphthalene-3-sulfonic acid) and y-acid (7-amino-1-hydroxynaphthaIcne-3-sulfonic acid), whereas H-acid (8-amino-l-hydroxynaphthalene-3,6-disulfonic acid) and K-acid (8-amino-l-hydroxy-naphthalene-3,5-disulfonic acid) derivatives are useful for red to bluish-red hues. Extremely lightfast red shades are also accessible with disazo dyes ( brown dyes ). For chemical structures see Section 3.1.5). 

The synthesis of the 1 1 complex 8 is an example of [10] demethylative chroma-tion. It is prepared by diazotization of 5-amino-2-chlorohydroquinone dimethyl ether and coupling onto 1-hydroxynaphthalene-5-sulfonic acid. The reaction product and Cr203 in formic acid are heated in an autoclave at 130 °C. The chromium complex 8 [80004-31-5] is obtained as a black powder that gives grayish blue dyeings on wool and leather. 

As an example of 1 2-chromation by the dichromate-glucose method [20], the azo dye obtained by coupling of diazotized l-amino-2-hydroxy-5-nitrobenzene with l-methylsulfonylamino-7-hydroxynaphthalene is dissolved in dilute NaOH and boiled after addition of K2Cr20r2H20 and glucose. Chromation is complete after a few minutes. The resulting 1 2 chromium complex 12 [83748-22-5] is precipitated with NaCl to give a black powder that imparts bluish olive dyeings on wool in a weakly acidic dyebath. 

In the stepwise synthesis of the unsymmetrical complex dye 13 [ 70236-60-1] [10], the azo dye made from diazotized l-amino-2-hydroxy-5-nitrobenzene and 1-phenyl-3-methyl-5-pyrazolone and the 1 1 chromium complex obtained from 6-nitro-l-diazo-2-hydroxynaphthalene-4-sulfonic acid and 2-naphthol are heated together at 80 °C for 5 h. The adduct is salted out with NaCl. A black powder is obtained that dyes wool and leather in dark brown shades. The resulting colors are fast, particularly on shrink-resistant wool. 

The synthesis of photochromic compounds from a diarylpropargyl alcohol and a di-P -hydroxynaphthalene (2,3- or 2,6- or 2,7-) yields a dipyran.35 Scheme 9 shows the preparation of a dipyran (21) from 2,6-dihydroxynaphthalene (20). The photochromic properties of these compounds are quite similar to those of a 3,3-diary 1-3/ -naphtho[2,l-A]pyran with an oxy-containing heterocycle fused to the naphtho... 

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