Resorcinol 1.3- benzenediol

Kluge C, A Tschech, G Fuchs (1990) Anaerobic metabolism of resorcylic acids (m-dihydroxybenzoates) and resorcinol (1,3-benzenediol) in a fermenting and in a denitrifying bacterium. Arch Microbiol 155 68-74. 

CAS 102-29-4 EINECS/ELINCS 203-022-0 Synonyms 3-Acetoxyphenol m-Acetoxyphenol Acetyl resorcinol 1,3-Benzenediol, monoacetate 3-Hydroxyphenyl acetate m-Hydroxyphenyl acetate Resorcin acetate Resorcin monoacetate Resorcinol monoacetate Resorcitate Definition Monoester of resorcinol and acetic acid Empirical CsHsOs Formula C6H4OHOCOCH3 Properties Yel. vise, liq. m.w. 152.15 sp.gr. 

Polyhydric phenols with more than two hydroxy groups (ie, the three positional isomers of benzenetriol, the three isomeric benzenetetrols, benzenepentol [4270-96-6] and benzenehexol [608-80-0]) are discussed in this article. The benzenediols are catechol, resorcinol, and hydroquinone (see Hydroquinone, RESORCINOL, AND CATECHOL). 

The close electrochemical relationship of the simple quinones, (2) and (3), with hydroquinone (1,4-benzenediol) (4) and catechol (1,2-benzenediol) (5), respectively, has proven useful in ways extending beyond their offering an attractive synthetic route. Photographic developers and dye syntheses often involve (4) or its derivatives (10). Biochemists have found much interest in the interaction of mercaptans and amino acids with various compounds related to (3). The reversible redox couple formed in many such examples and the frequendy observed quinonoid chemistry make it difficult to avoid a discussion of the aromatic reduction products of quinones (see Hydroquinone, resorcinol, and catechol). 

Benzenedisulfonic acid [831-59-4] (disodium salt), produced by the neutralization of the disulfonic acid with sodium sulfite [7757-83-7] is used in the manufacture of resorcinol [108-46-3] (1,3-benzenediol) (2), a chemical component found in mbber products and wood adhesives (72). The disodium salt is fused with sodium hydroxide, dissolved in water, and acidified to produce resorcinol, which is isolated via extraction (73). 

Flickinger CW. 1976. The benzenediols Catechol, resorcinol and hydroquinone - A review of the industrial toxicology and current industrial exposure limits. Am Ind Hyg Assoc J 37 596-606. 

Flickenger CW The benzenediols Catechol, resorcinol and hydroquinone—Review of the... 

Very recently, MacGillivray et al. succeeded in the supramolecular construction of molecular ladders in the solid state using a linear template approach [48]. They designed the cocrystals 1,3-benzenediol (resorcinol) or a derivative with an all-trans-bis(4-pyridyl)butadiene or hexatriene, in which two resorcinol molecules preorganize two polyene molecules through two hydrogen bond interactions, for [2-1-2] photoaddition (Scheme 5). In this design, two polyenes would... 

Chem. Abstr. Serv. Reg.No.. 108-46-3 Chem. Abstr. Name. 1,3-Benzenediol lUPAC Systematic Name. Resorcinol Synonyms. meto-Benzenediol resorcin... 

Exercise 26-3 Treatment of 1,3-benzenediol (resorcinol) with an ammonia-ammonium chloride solution under pressure at 200° (no sulfite) gives 3-amino-benzenol. Write a reasonable mechanism for this transformation. Would you expect benzenol itself to react similarly Why ... 

Exercise 26-7 1,3-Benzenediol (resorcinol) can be converted to a carboxylic acid with carbon dioxide and alkali. Would you expect 1,3-benzenediol to react more, or less, readily than benzenol Why Which is the most likely point of monosubstitution Explain. 

Raney cobalt alloy, see Aluminium—cobalt alloy, 0049 Raney nickel alloys, see Aluminium—nickel alloys, 0055 Resorcinol diacetate, see 1,3-Diacetoxybenzene, 3285 Resorcinol, see 1,3-Benzenediol, 2325 Rhenium hexafluoride, 4367 Rhenium hexamethoxide, 2599 Rhenium nitride tetrafluoride, 4338 Rhenium, 4884... 

In the photometric determination of copper, a coupling product formed between the diazonium salt from 2-amino-pyridine and resorcinol, or 4-(2-pyridinylazo)-l,3-benzenediol 21, has been used. Here the formed copper complex under acetate buffer exhibits an absorption peak at 520 nm, which is measured photometrically <2003KPU28>. Similarly for photometric determination of iron(ll), a coupling product formed between the diazonium salt of 2-amino-4,6-dihydroxypyrimidine and 8-hydroxyquinoline, or 6-hydroxy-2-(8-hydroxy-7-quinolinyl)azo-4(l//)-pyrimidinone 22, has been used. This reagent forms a blue complex with iron(n) ions with an absorption maximum at 625 nm that does not interfere with the presence of other metals <2003KD95>. 

SYNS 1,3-BENZENEDIOL, 2,4,6-TRINITRO-, BARIUM SALT, HYDRATE (2 1 1) RESORCINOL, 2,4,6-TRINITRO-, BARIUM SALT, HYDRATE (2 1 1)... 

Phenols may have more than one hydroxy group attached to the same benzene ring - for example, the three isomeric dihydroxybenzenes catechol (ortho-dihydroxy-benzene or 1,2-benzenediol), resorcinol (meta-dihydroxy-benzene or 1,3-benzenediol) and hydroquinone (para-dihydroxybenzene or 1,4-benzenediol) see Figure 25.3. 

The three monohydroxy derivatives of phenol are all well-known componnds, the o-, m- and p-species with the long-established, trivial names catechol, resorcinol and hydro-quinone. These compounds are all benzenediols and, as snch, they and their snbstimted derivatives will be discussed later in this text. 

Although there are ten isomeric naphthalenediols, there are enthalpy of formation data for only five of them. The enthalpy of formation data for the 1,4-isomer from two sources are disparate, as are the data from the two sources for the 2,3-isomer. The 1,3-naphthalenediol is more stable than either the 1,2- or the 1,4-diols for the same reason that the m-benzenediol, resorcinol, is more stable than its isomers more stable resonance structures for 1,3-dihydroxy substitution on an aromatic ring. From the appropriate OH/H increment exchange energies and the enthalpy of formation of naphthalene, we would have predicted a value of —329 kJ moE and —208 kJ mol for any solid and gaseous naphthalenediol, respectively. Only for 1,3- and 2,7-naphthalenediol is the expectation confirmed the others with their less stable ortho- and para-type substitution are less negative. 

H.24) 1,3-Benzenediol, resorcinol, resorcin, 1,3-dihydroxybenzene, m-hydroquinone 1108-46-3] FEMA 3589... 

Styphnic Acid. 2,4,6-Trinilro-l,3-benzenediol 2,4,6-trinitroresorcinol 2,4 -dihydrixy -1,3,5 -trinitrobenzene, C(H,N,Ot mo] wt 245.11. C 29.40fv, H 1.23%, N 17.14%, O 52.22%. May be prepd from natural sources, such as Pernambuco wood extract or quebracho extract by the action of nitric acid Einbeck, Jablonski, Ber. 54, 1086 (1921). Prepd industrially by first sulfonating, then nitrating resorcinol Merz, Zetter, Ber. 12, 681, 2037 (1879) Datta, Varma, J. Am. Chem. Soe. 41, 2043 (1919). Prepd by nitrating 2,4-di. nitroresorcinol Kametani, Ogasawara, Chem. Pharm. Bull IS, 893 (1967). 

Beilstein Handbook Reference) 1,3-Benzenediol, monobenzoate Benzoic acid, m-hydroxyphenyl ester BRN 1873897 Eastman Inhibitor RMB EINECS 205-241-7 3-Hydroxyphenyl benzoate NSC 4807 Resorcinol monobenzoate. Industrial grade UV absorber/stabilizer for cellulosic plastics and PVC formulations. White crystalline solid mp = 133-135" insoluble in H2O, CeHe, soluble in EtOH, MezCO LDso (rat orl) = 1600 mg/kg. Eastman Chem. Co Monomer -Polymer Dajac. 

The discoveries of the isomeric dihydric phenols were as old as that of phenol itself. Catechol,(1,2-benzenediol, 1,2-dihydroxybenzene, o-dihydroxybenzene) was first obtained in 1839 essentially from the dry distillation of tannin. Resorcinol (1,3-dihydroxybenzene), was isolated in 1864 from the alkaline fusion of galbanum, and of asafoetida, resins, repectively from Iranian species of Ferula and Narthex asafoetida. In 1820 hydroquinone was recovered from the dry distillation of quinic acid although it was not investigated structurally until 1844 by Wohler. 

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