Primuline

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Primuline
Primuline.svg
Primuline-3D-balls.png
Names
IUPAC name
sodium;2-[2-(4-aminophenyl)-1,3-benzothiazol-6-yl]-6-methyl-1,3-benzothiazole-7-sulfonate
Other names
Direct yellow 59
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.030.698 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 233-781-3
PubChem CID
Properties
C21H15N3O3S3 (free acid)
Molar mass 453.557 g/mol (free acid)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Primuline is a dye containing the benzothiazole ring system. Primuline itself is also known as Direct yellow 7, Carnotine, or C.I. 49010.

The primulines are considered derivatives of dehydrothiotoluidine (aminobenzenyltoluylmercaptan), which is obtained when para-toluidine is heated with sulfur for eighteen hours at 180–190 °C and then for a further six hours at 200–220 °C [1] Dehydrothiotoluidine is not itself a dye-stuff, but if the heating is carried out at a higher temperature in the presence of more sulfur, then a base is formed, which gives primuline yellow upon sulfonation. [2]

Primuline yellow is a mixture of sodium salts and probably contains at least three thiazole rings in combination. It is a substantive cotton dye of rather fugitive shade, but can be diazotized on the fibre and then developed with other components, yielding a series of ingrain colors. [3]

Primuline is usually available as a sodium salt. Primuline is fluorescent.

Thioflavin T is obtained by the methylation of dehydrothiotoluidine with methanol in the presence of hydrochloric acid. Thioflavin S results from the methylation of dehydrothiotoluidine with sulfonic acid. This sulfonic acid on oxidation with bleaching powder or with lead peroxide, in alkaline solution yields chloramine yellow, which dyes cotton a beautiful yellow. [3]

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Naphthalene is an organic compound with formula C
10
H
8
. It is the simplest polycyclic aromatic hydrocarbon, and is a white crystalline solid with a characteristic odor that is detectable at concentrations as low as 0.08 ppm by mass. As an aromatic hydrocarbon, naphthalene's structure consists of a fused pair of benzene rings. It is best known as the main ingredient of traditional mothballs.

Aniline Chemical compound

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. It is an industrially significant commodity chemical, as well as a versatile starting material for fine chemical synthesis. Its main use is in the manufacture of precursors to polyurethane, dyes, 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.

Quinoline

Quinoline is a heterocyclic aromatic organic compound with the chemical formula C9H7N. It is a colorless hygroscopic liquid with a strong odor. Aged samples, especially if exposed to light, become yellow and later brown. Quinoline is only slightly soluble in cold water but dissolves readily in hot water and most organic solvents. Quinoline itself has few applications, but many of its derivatives are useful in diverse applications. A prominent example is quinine, an alkaloid found in plants. Over 200 biologically active quinoline and quinazoline alkaloids are identified. 4-Hydroxy-2-alkylquinolines (HAQs) are involved in antibiotic resistance.

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Resorcinol

Resorcinol (or resorcin) is an organic compound with the formula C6H4(OH)2. It is one of three isomeric benzenediols, the 1,3-isomer (or meta-isomer). It is a white, water-soluble solid.

Thiazole, or 1,3-thiazole, is a heterocyclic compound that contains both sulfur and nitrogen; the term 'thiazole' also refers to a large family of derivatives. Thiazole itself is a pale yellow liquid with a pyridine-like odor and the molecular formula C3H3NS. The thiazole ring is notable as a component of the vitamin thiamine (B1).

Sulfonic acid

A sulfonic acid (or sulphonic acid) refers to a member of the class of organosulfur compounds with the general formula R−S(=O)2−OH, where R is an organic alkyl or aryl group and the S(=O)2(OH) group a sulfonyl hydroxide. As a substituent, it is known as a sulfo group. A sulfonic acid can be thought of as sulfuric acid with one hydroxyl group replaced by an organic substituent. The parent compound (with the organic substituent replaced by hydrogen) is the parent sulfonic acid, HS(=O)2(OH), a tautomer of sulfurous acid, S(=O)(OH)2. Salts or esters of sulfonic acids are called sulfonates.

Safranin

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.

Benzothiazole Chemical compound

Benzothiazole is an aromatic heterocyclic compound with the chemical formula C
7
H
5
NS
. It is colorless, slightly viscous liquid. Although the parent compound, benzothiazole is not widely used, many of its derivatives are found in commercial products or in nature. Firefly luciferin can be considered a derivative of benzothiazole.

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Sodium sulfide

Sodium sulfide is the chemical compound with the formula Na2S, or more commonly its hydrate Na2S·9H2O. Both the anhydrous and the hydrated salts are colorless solids. They are water-soluble, giving strongly alkaline solutions. When exposed to moist air, Na2S and its hydrates emit hydrogen sulfide, which smells like rotten eggs. Some commercial samples are specified as Na2xH2O, where a weight percentage of Na2S is specified. Commonly available grades have around 60% Na2S by weight, which means that x is around 3. Such technical grades of sodium sulfide have a yellow appearance owing to the presence of polysulfides. These grades of sodium sulfide are marketed as 'sodium sulfide flakes'.

Thiophenol

Thiophenol is an organosulfur compound with the formula C6H5SH, sometimes abbreviated as PhSH. This foul-smelling colorless liquid is the simplest aromatic thiol. The chemical structures of thiophenol and its derivatives are analogous to phenols except the oxygen atom in the hydroxyl group (-OH) bonded to the aromatic ring is replaced by a sulfur atom. The prefix thio- implies a sulfur-containing compound and when used before a root word name for a compound which would normally contain an oxygen atom, in the case of 'thiol' that the alcohol oxygen atom is replaced by a sulfur atom.

Phenazine

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.

Thioflavin

Thioflavins are fluorescent dyes that are available as at least two compounds, namely Thioflavin T and Thioflavin S. Both are used for histology staining and biophysical studies of protein aggregation. In particular, these dyes have been used since 1989 to investigate amyloid formation. They are also used in biophysical studies of the electrophysiology of bacteria. Thioflavins are corrosive, irritants, and are acutely toxic, causing serious eye damage. Thioflavin T has been used in research into Alzheimer's disease and other neurodegenerative diseases.

1-Naphthylamine

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.

2-Naphthol

2-Naphthol, or β-naphthol, is a fluorescent colorless (or occasionally yellow) crystalline solid with the formula C10H7OH. It is an isomer of 1-naphthol, differing by the location of the hydroxyl group on the naphthalene ring. The naphthols are naphthalene homologues of phenol, but more reactive. Both isomers are soluble in simple alcohols, ethers, and chloroform. 2-Naphthol is a widely used intermediate for the production of dyes and other compounds.

Anthraquinone dyes

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Hydroxylamine-<i>O</i>-sulfonic acid

Hydroxylamine-O-sulfonic acid ("HOSA") is the inorganic compound with molecular formula H3NO4S that is formed by the sulfonation of hydroxylamine with oleum. It is a white, water-soluble and hygroscopic, solid, commonly represented by the condensed structural formula H2NOSO3H, though it actually exists as a zwitterion and thus is more accurately represented as +H3NOSO3. It is used as a reagent for the introduction of amine groups (–NH2), for the conversion of aldehydes into nitriles and alicyclic ketones into lactams (cyclic amides), and for the synthesis of variety of nitrogen-containing heterocycles.

N-Oleoylsarcosine is an amphiphilic oleic acid derivative having a sarcosine head group (N-methylglycine) which is used as a water-in-oil emulsifier and corrosion inhibitor.

1,4-butane sultone is a six-membered δ-sultone and the cyclic ester of 4-hydroxybutanesulfonic acid. As a sulfo-alkylating agent, 1,4-butanesultone is used to introduce the sulfobutyl group (–(CH2)4–SO3) into hydrophobic compounds possessing nucleophilic functional groups, for example hydroxy groups (as in the case of β-cyclodextrin) or amino groups (as in the case of polymethine dyes). In such, the sulfobutyl group is present as neutral sodium salt and considerably increases the water solubility of the derivatives.

References

  1. P. Jacobson (1889). "N/A". Ber. 22: 333.
    L. Gatterrnann, ibid. p. 1084
  2. A. G. Green (1888). "N/A". J. Soc. Chem. Ind. 1: 194.
  3. 1 2 Chisholm, Hugh, ed. (1911). "Primuline"  . Encyclopædia Britannica . 22 (11th ed.). Cambridge University Press. p. 342.