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Chemically 1-phenylazo-2-naphthol.

Chemical designation 1-[4-(Phenylazo)phenylazo]-2-naphthol.

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The reaction with naphthalen-2-ol

Melting Point
Diazo coupling of aniline and 2-naphthol
a.k.a Sudan I, Spirit Orange
Industrially used as colorant for waxes, polishes, oils, and solvents
Used as adulterant in food condiments such as in curry powder and chili powder

Aniline – dH2O as solvent
– concentrated HCl

2-naphthol – dH2O as solvent
– aq.

Chemical designation 2,3-Dihydro-2,2-dimethyl-6-[[4-(phenylazo)-1-naphthyl]azo]-1H-Perimidine.

Sudan I [1-(phenylazo)-2-hydroxynaphthalene, C.I. Solvent Yellow 14, CAS No: 842-07-9] is used as the compound employed in chemical industry and to color materials such as hydrocarbon solvents, oils, fats, waxes, plastics, printing inks, shoe and floor polishes and gasoline. Such a wide used could result in a considerable human exposure. Sudan I is known to cause developments of tumors in the liver or urinary bladder in rats, mice, and rabbits, and is considered a possible weak human carcinogen and mutagen. This carcinogen is also a potent contact allergen and sensitizer. Here, we compare the data concerning the Sudan I oxidative metabolism catalyzed by cytochrome P450 (CYP) and peroxidase enzymes, which has been investigated in our laboratory during the last two decades. These two types of enzymes are responsible both for Sudan I detoxication and activation. Among the Sudan I metabolites, C-hydroxylated derivatives and a dimer of Sudan I are suggested to be the detoxication metabolites formed by CYPs and peroxidases, respectively. Metabolic activation of Sudan I by both types of enzymes leads to formation of reactive species (the benzenediazonium ion by CYP and Sudan I radicals by peroxidase) that bind to DNA and RNA, generating covalent adducts in vitro and in vivo. Whereas the structure of the major adduct formed by the benzenediazonium ion in DNA has already been identified to be the 8-(phenylazo)guanine adduct, the structures of adducts formed by peroxidase, have not been characterized as yet. Biological significance of the DNA adducts of Sudan I activated with CYP and peroxidase enzymes and further aims of investigations in this field are discussed in this study.

2 (2,5-dimethoxyphenyl-azo-2-naphthol) and ext.

Some of the colorants have in common the 2-amino-1-naphthol structure.

We have surveyed the literature for genotoxic and cancer data on nine colorants, which are structurally related to 1-phenylazo-2-hydroxynaphthalene (C.I.

Azo dyes are a large group of chemically related compounds widely used for industrial purposes and as colorants of materials of daily use. Organic azo colorants are grouped into several types, depending on similarity in the chemical structure. One of such types is a group of azo compounds that are structurally similar to Sudan I [1-(phenylazo)-2-hydroxynaphthalene, C.I. Solvent Yellow 14, CAS No: 842-07-9, )].


deeper stain than Sudan III,Chemical designation 1-[[2-methyl-4-[(2-methylphenyl)azo]phenyl]azo]-2-Naphthalenol

Naphthalen-2-ol is also known as 2-naphthol or beta-naphthol. It contains an -OH group attached to a naphthalene molecule rather than to a simple benzene ring. Naphthalene has two benzene rings fused together.

The reaction is done under exactly the same conditions as with phenol. The naphthalen-2-ol is dissolved in sodium hydroxide solution to produce an ion just like the phenol one. This solution is cooled and mixed with the benzenediazonium chloride solution.

14 (1-xylylazo-2-naphthol)
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    The synthesis of Sudan I involves the reaction of phenyldiazonium salts with 2-naphthol

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Synthesis of 1-phenylazo-2-naphthol Anjelika Mae L

There are position isomers; alpha-naphthol (also called 1-naphthol) is 1-hydroxynaphthalene and beta-naphthol (also called 2-naphthol) is 2-hydroxynaphthalene.

1-phenylazo-2-naphthol - Brief Profile - ECHA

and and (2001)Synthesis, crystal structure and catalytic properties of (p-cymene)ruthenium(II) azophenol complexes: azophenyl to azophenol conversion by oxygen insertion to a ruthenium---carbon bond. In: Journal of Organometallic Chemistry, 633 (1-2). pp. 79-84.

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