Induline is a dye of blue, bluish-red or black shades. [1] Induline consists of a mixture of several intensely colored species, so the name is often indulines. It was one of the first synthetic dyes, discovered in 1863 by J. Dale and Heinrich Caro. The main components of induline are various substituted phenazines. Although induline no longer in use, the related dye nigrosin is still produced commercially. [2]
Induline is a derivative of the eurhodines (aminophenazines, aminonaphthophenazines). By means of their diazo derivatives can be de-amidated, yielding in this way azonium salts; consequently they may be considered as amidated azonium salts. The first reaction giving a clue to their constitution was the isolation of the intermediate azophenin by O. Witt, which was proved by Fischer and Hepp to be dianilidoquinone dianil, a similar intermediate compound being found shortly afterwards in the naphthalene series. Azophenin, C30H24N4, is prepared by warming quinone dianil with aniline, by melting together quinone, aniline and aniline hydrochloride, or by the action of aniline on para-nitrosophenol or para-nitrosodiphenylamine. The indulines are prepared as mentioned above from aminoazo compounds, or by condensing oxy- and amido-quinones with phenylated ortho-diamines. The indulines may be subdivided into the following groups: (1) benzindulines, derivatives of phenazine; (2) isorosindulines; and (3) rosindulines, both derived from naphthophenazine; and (4) naphthindulines, derived from naphthazine. [1]
The rosindulines and naphthindulines have a strongly basic character, and their salts possess a marked red color and fluorescence. Benzinduline (aposafranine), C18H13N3, is a strong base, but cannot be diazotized, unless it be dissolved in concentrated mineral acids. When warmed with aniline it yields anilido-aposafranine, which may also be obtained by the direct oxidation of ortho-aminodiphenylamine. Isorosinduline is obtained from quinone dichlorimide and phenyl-β-naphthylamine; rosinduline from benzene-azo-α-naphthylamine and aniline and naphthinduline from benzene-azo-α-naphthylamine and naphthylamine. [1]
In organic chemistry, amines (, UK also ) are compounds and functional groups that contain a basic nitrogen atom with a lone pair. Amines are formally derivatives of ammonia, wherein one or more hydrogen atoms have been replaced by a substituent such as an alkyl or aryl group (these may respectively be called alkylamines and arylamines; amines in which both types of substituent are attached to one nitrogen atom may be called alkylarylamines). Important amines include amino acids, biogenic amines, trimethylamine, and aniline; see Category:Amines for a list of amines. Inorganic derivatives of ammonia are also called amines, such as monochloramine (NClH2).
Acridine is an organic compound and a nitrogen heterocycle with the formula C13H9N. Acridines are substituted derivatives of the parent ring. It is a planar molecule that is structurally related to anthracene with one of the central CH groups replaced by nitrogen. Like the related molecule pyridine and quinoline, acridine is mildly basic. It is an almost colorless solid. There are no commercial applications of acridines but at one time acridine dyes were popular. It crystallizes in needles.
Aniline is an organic compound with the formula C6H5NH2. Consisting of a phenyl group attached to an amino group, aniline is the simplest aromatic amine. Its main use is in the manufacture of precursors to polyurethane and other industrial chemicals. Like most volatile amines, it has the odor of rotten fish. It ignites readily, burning with a smoky flame characteristic of aromatic compounds.
The quinones are a class of organic compounds that are formally "derived from aromatic compounds [such as benzene or naphthalene] by conversion of an even number of –CH= groups into –C(=O)– groups with any necessary rearrangement of double bonds", resulting in "a fully conjugated cyclic dione structure". The class includes some heterocyclic compounds.
In organic chemistry, an aryl halide is an aromatic compound in which one or more hydrogen atoms directly bonded to an aromatic ring are replaced by a halide. The haloarene are distinguished from haloalkanes because they exhibit many differences in methods of preparation and properties. The most important members are the aryl chlorides, but the class of compounds is so broad that many derivatives enjoy niche applications
Azo compounds are compounds bearing the functional group diazenyl R−N=N−R′, in which R and R′ can be either aryl or alkyl.
Safranin is a biological stain used in histology and cytology. Safranin is used as a counterstain in some staining protocols, colouring cell nuclei red. This is the classic counterstain in both Gram stains and endospore staining. It can also be used for the detection of cartilage, mucin and mast cell granules.
Azo dyes are organic compounds bearing the functional group R−N=N−R′, in which R and R′ are usually aryl. They are a commercially important family of azo compounds, i.e. compounds containing the linkage C-N=N-C. Azo dyes are widely used to treat textiles, leather articles, and some foods. Chemically related to azo dyes are azo pigments, which are insoluble in water and other solvents.
Diazonium compounds or diazonium salts are a group of organic compounds sharing a common functional group R−N+
2X−
where R can be any organic group, such as an alkyl or an aryl, and X is an inorganic or organic anion, such as a halogen.
An azo coupling is an organic reaction between a diazonium compound and another aromatic compound that produces an azo compound. In this electrophilic aromatic substitution reaction, the aryldiazonium cation is the electrophile and the activated arene is a nucleophile. In most cases, including the examples below, the diazonium compound is also aromatic.
Phenazine is an organic compound with the formula (C6H4)2N2. It is a dibenzo annulated pyrazine, and the parent substance of many dyestuffs, such as the toluylene red, indulines, and safranines (and the closely related eurhodines). Phenazine crystallizes in yellow needles, which are only sparingly soluble in alcohol. Sulfuric acid dissolves it, forming a deep-red solution.
The Herz reaction, named after the chemist Richard Herz, is the chemical conversion of an aniline-derivative (1) to a so-called Herz salt (2) with disulfur dichloride, followed by hydrolysis of this Herz salt (2) to the corresponding sodium thiolate (3):
Phenylhydrazine is the chemical compound with the formula C6H5NHNH2. It is often abbreviated as PhNHNH2.
2-Naphthylamine is one of two isomeric aminonaphthalenes, compounds with the formula C10H7NH2. It is a colorless solid, but samples take on a reddish color in air because of oxidation. It was formerly used to make azo dyes, but it is a known carcinogen and has largely been replaced by less toxic compounds.
1-Naphthylamine is an aromatic amine derived from naphthalene. It can cause bladder cancer. It crystallizes in colorless needles which melt at 50 °C. It possesses a disagreeable odor, sublimes readily, and turns brown on exposure to air. It is the precursor to a variety of dyes.
Phenol oxidation with hypervalent iodine reagents leads to the formation of quinone-type products or iodonium ylides, depending on the structure of the phenol. Trapping of either product is possible with a suitable reagent, and this method is often employed in tandem with a second process.
Electrophilic aromatic substitution is an organic reaction in which an atom that is attached to an aromatic system is replaced by an electrophile. Some of the most important electrophilic aromatic substitutions are aromatic nitration, aromatic halogenation, aromatic sulfonation, and alkylation and alkylating Friedel–Crafts reaction.
Acetoacetanilide is an organic compound with the formula CH3C(O)CH2C(O)NHC6H5. It is the acetoacetamide derivative of aniline. It is a white solid that is poorly soluble in water. It and many related compounds (prepared from various aniline derivatives) are used in the production of organic pigments called arylide yellows.
Ortho effect refers mainly to the set of steric effects and some bonding interactions along with polar effects caused by the various substituents which are in a given molecule altering its chemical properties and physical properties. In a general sense the ortho effect is associated with substitued benzene compounds.
