Naphthalene-1-sulfonic acid

Last updated
Naphthalene-1-sulfonic acid
1-naphthalenesulfonic acid.svg
Names
Preferred IUPAC name
Naphthalene-1-sulfonic acid
Other names
1-naphthalenesulfonic acid
Identifiers
3D model (JSmol)
2099069
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.001.464 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 246-676-2
366290
KEGG
PubChem CID
UNII
  • InChI=1S/C10H8O3S/c11-14(12,13)10-7-3-5-8-4-1-2-6-9(8)10/h1-7H,(H,11,12,13)
    Key: PSZYNBSKGUBXEH-UHFFFAOYSA-N
  • C1=CC=C2C(=C1)C=CC=C2S(=O)(=O)O
Properties
C10H8O3S
Molar mass 208.23 g·mol−1
Appearancewhite solid
Melting point 139–140 °C (282–284 °F; 412–413 K)
good
Hazards
GHS labelling:
GHS-pictogram-acid.svg GHS-pictogram-exclam.svg GHS-pictogram-silhouette.svg GHS-pictogram-pollu.svg
Danger
H302, H314, H351, H411
P201, P202, P260, P264, P270, P273, P280, P281, P301+P312, P301+P330+P331, P303+P361+P353, P304+P340, P305+P351+P338, P308+P313, P310, P321, P330, P363, P391, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

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. [1]

Naphthalene-1-sulfonic acid undergoes many reactions, some of which are or were of commercial interest. Upon heating with dilute aqueous acid, it reverts to naphthalene. Fusion with sodium hydroxide followed by acidification gives 1-naphthol. Further sulfonation gives 1,5-naphthalene-disulfonic acid. Reduction with triphenylphosphine gives 1-naphthalenethiol.

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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 the main ingredient of traditional mothballs.

<span class="mw-page-title-main">Phthalic acid</span> Chemical compound

Phthalic acid is an aromatic dicarboxylic acid, with formula C6H4(CO2H)2. Although phthalic acid is of modest commercial importance, the closely related derivative phthalic anhydride is a commodity chemical produced on a large scale. Phthalic acid is one of three isomers of benzenedicarboxylic acid, the others being isophthalic acid and terephthalic acid.

<span class="mw-page-title-main">Phthalic anhydride</span> Chemical compound

Phthalic anhydride is the organic compound with the formula C6H4(CO)2O. It is the anhydride of phthalic acid. Phthalic anhydride is a principal commercial form of phthalic acid. It was the first anhydride of a dicarboxylic acid to be used commercially. This white solid is an important industrial chemical, especially for the large-scale production of plasticizers for plastics. In 2000, the worldwide production volume was estimated to be about 3 million tonnes per year.

<span class="mw-page-title-main">Sulfonic acid</span> Organic compounds with the structure R−S(=O)2−OH

In organic chemistry, sulfonic 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 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.

<span class="mw-page-title-main">Naphthalenesulfonate</span>

Naphthalenesulfonates are derivatives of sulfonic acid which contain a naphthalene functional unit. A related family of compounds are the aminonaphthalenesulfonic acids. Of commercial importance are the alkylnaphthalene sulfonates, which are used as superplasticizers in concrete. They are produced on a large scale by condensation of naphthalenesulfonate or alkylnaphthalenesulfonates with formaldehyde.

<span class="mw-page-title-main">2-Naphthylamine</span> 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.

<span class="mw-page-title-main">1-Naphthylamine</span> 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.

<span class="mw-page-title-main">Armstrong's acid</span> Chemical compound

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Dinonylnaphthylsulfonic acid (DINNSA) is an organic chemical, an aryl sulfonic acid. Its melting point is 259.5 °C and its boiling point is 600.4 °C. It has very low water solubility. It is a moderate skin irritant and a strong eye irritant. It has low volatility and vapor pressure and is stable above 100 °C.

Dodecylbenzene is an organic compound with the formula C
12
H
25
C
6
H
5
. Dodecylbenzene is a colorless liquid with a weak oily odor that floats on water.

<span class="mw-page-title-main">2-Naphthol</span> 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.

<span class="mw-page-title-main">EDANS</span> Chemical compound

EDANS is a donor for FRET-based nucleic acid probes and protease substrates. EDANS is often paired with DABCYL or DABSYL. The combination can be used in enzyme assays. When the two compounds are in close proximity, most of the energy emitted from EDANS will be quenched by DABCYL. However, if the compounds are separated EDANS will fluoresce, giving an indication of enzyme presence.

<span class="mw-page-title-main">Naphthionic acid</span> 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.

<span class="mw-page-title-main">Tobias acid</span> Chemical compound

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. 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. 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.

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.

<span class="mw-page-title-main">1-Naphthalenethiol</span> 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.

<span class="mw-page-title-main">Naphthalene-2-sulfonic acid</span> 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.

The molecular formula C10H8O3S (molar mass: 208.234 g/mol, exact mass: 208.0194 u) may refer to:

References

  1. Gerald Booth (2005). "Naphthalene Derivatives". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a17_009. ISBN   3-527-30673-0.