Tobias acid

Last updated
Tobias acid
Tobias acid structure.svg
Names
Preferred IUPAC name
2-Aminonaphthalene-1-sulfonic acid
Other names
2-Naphthylamine-1-sulfonic acid
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.001.211 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 201-331-5
PubChem CID
UNII
  • InChI=1S/C10H9NO3S/c11-9-6-5-7-3-1-2-4-8(7)10(9)15(12,13)14/h1-6H,11H2,(H,12,13,14)
    Key: GWIAAIUASRVOIA-UHFFFAOYSA-N
  • C1=CC=C2C(=C1)C=CC(=C2S(=O)(=O)O)N
Properties
C10H9NO3S
Molar mass 223.25 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Tobias acid (2-amino-1-naphthalenesulfonic acid) is an organic compound with the formula C10H6(SO3H)(NH2). It is named after the German chemist Georg Tobias. [1] It is one of several aminonaphthalenesulfonic acids, which are derivatives of naphthalene containing both amine and sulfonic acid functional groups. It is a white solid, although commercial samples can appear otherwise. [2] It is used in the synthesis of azo dyes such as C.I. Acid Yellow 19 and C.I. Pigment Red 49. It is prepared via the Bucherer reaction of 2-hydroxynaphthalene-1-sulfonic acid with ammonia and ammonium sulfite. [3]

Related Research Articles

Naphthalene Chemical compound

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.

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 different 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 there are many derivatives and applications.

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.

The Mannich reaction is a three-component organic reaction that involves the amino alkylation of an acidic proton next to a carbonyl functional group by formaldehyde and a primary or secondary amine or ammonia. The final product is a β-amino-carbonyl compound also known as a Mannich base. Reactions between aldimines and α-methylene carbonyls are also considered Mannich reactions because these imines form between amines and aldehydes. The reaction is named after Carl Mannich.

The Sandmeyer reaction is a chemical reaction used to synthesize aryl halides from aryl diazonium salts using copper salts as reagents or catalysts. It is an example of a radical-nucleophilic aromatic substitution. The Sandmeyer reaction provides a method through which one can perform unique transformations on benzene, such as halogenation, cyanation, trifluoromethylation, and hydroxylation.

Aromatic sulfonation is an organic reaction in which a hydrogen atom on an arene is replaced by a sulfonic acid functional group in an electrophilic aromatic substitution. Aryl sulfonic acids are used as detergents, dye, and drugs.

Isatin Chemical compound

Isatin, also known as tribulin, is an organic compound derived from indole with formula C8H5NO2. The compound was first obtained by Otto Linné Erdman and Auguste Laurent in 1840 as a product from the oxidation of indigo dye by nitric acid and chromic acids.

2-Naphthylamine Chemical compound

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.

The Bucherer reaction in organic chemistry is the reversible conversion of a naphthol to a naphthylamine in the presence of ammonia and sodium bisulfite. The reaction is widely used in the synthesis of dye precursors aminonaphthalenesulfonic acids.

1-Naphthylamine Chemical compound

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.

The Schiemann reaction is a chemical reaction in which a primary aromatic amine is transformed to an aryl fluoride via a diazonium tetrafluoroborate intermediate. This reaction is a traditional route to fluorobenzene and some related derivatives, including 4-fluorobenzoic acid.

Armstrongs acid Chemical compound

Armstrong's acid (naphthalene-1,5-disulfonic acid) is a fluorescent organic compound with the formula C10H6(SO3H)2. It is one of several isomers of naphthalenedisulfonic acid. It a colorless solid, typically obtained as the tetrahydrate. Like other sulfonic acids, it is a strong acid. It is named for British chemist Henry Edward Armstrong.

2-Naphthol Chemical compound

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.

Naphthionic acid Chemical compound

Naphthionic acid is an organic compound with the formula C10H6(SO3H)(NH2). It is one of several aminonaphthalenesulfonic acids, derivatives of naphthalene containing both amine and sulfonic acid functional groups. It is a white solid, although commercial samples can appear gray. It is used in the synthesis of azo dyes such as Rocceline (a. k. a. Solid Red A), during which the amino group of the acid (in the form of a salt) is diazotated and then coupled with, in the case mentioned, β-naphthol. It is prepared by treating 1-aminonaphthalene with sulfuric acid.

Aminonaphthalenesulfonic acids are compounds with the composition C10H6(NH2)(SO3H), being derived from naphthalene (C10H8) substituted by an amino and sulfonic acid groups. These compounds are colorless solids. They are useful precursors to dyes.

In organic chemistry, peri-naphthalenes are particular derivatives of naphthalene with the formula C10H6-1,8-X2. Owing to the rigidity of the naphthalene skeleton, these substituents on the 1- and 8-positions are constrained to be relatively close 2.5 Å, which is within the van der Waals radius for many atoms. In contrast, ortho-substituents pendant from a benzene ring are separated by about 3.3 Å.

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

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.

1-Naphthalenethiol Chemical compound

1-Naphthalenethiol is an organosulfur compound with the formula C10H7SH. It is a white solid. It is one of two monothiols of naphthalene, the other being 2-naphthalenethiol.

Naphthalene-1-sulfonic acid Organic chemical compound

Naphthalene-1-sulfonic acid is an organic compound with the formula C10H7SO3H. A colorless, water-soluble solid, it is often available as the dihydrate C10H7SO3H.2H2O. It is one of two monosulfonic acids of naphthalene, the other being the more stable naphthalene-2-sulfonic acid. The compound is mainly used in the production of dyes.

Naphthalene-2-sulfonic acid Chemical compound

Naphthalene-2-sulfonic acid is an organic compound with the formula C10H7SO3H. A colorless, water-soluble solid, it is often available as the mono- and trihydrates C10H7SO3H.2H2O. It is one of two monosulfonic acids of naphthalene, the other being naphthalene-1-sulfonic acid. The compound is mainly used in the production of dyes via nitration en route to aminonaphthalenesulfonic acids. The compound is prepared by sulfonation of naphthalene with sulfuric acid, however under equilibrating conditions that allow the 1-sulfonic acid isomer to convert to the more stable 2-sulfonic acid.

References

  1. Tobias, Georg (January 1890). "Zur Anwendung der Sandmeyer' schen Reaction auf Diazosulfosäuren und über die Zersetzung dieser Verbindungen bei Gegenwart von Kupfer oder Kupferoxydul" [On the application of Sandmeyer's reaction to diazosulfonic acids and the decomposition of these compounds in the presence of copper or copper oxide]. Berichte der deutschen chemischen Gesellschaft (in German). 23 (1): 1628–1634. doi:10.1002/cber.189002301270.
  2. CID 6670 from PubChem
  3. Gerald Booth "Naphthalene Derivatives" in Ullmann's Encyclopedia of Industrial Chemistry, 2005, Wiley-VCH, Weinheim. doi : 10.1002/14356007.a17_009.