Naphthalenedisulfonic acid

Naphthalenedisulfonic acid refers to organic compounds with the formula C10H6(SO3H)2. They are derivatives of naphthalene. Twelve isomers are possible, but only a few have been examined in some depth, often as precursors to azo dyes or to various drugs.[1] They are colorless solids with high solubility in water. Some derivatives are prepared by sulfonation of naphthalene or its monosulfonic acids. A few are produced by indirect routes.

Hydroxynaphthalenesulfonic acids
nameRegistry numberm.p., °CprepPrecursor to
1,3-Naphthalenedisulfonic acid6094-26-4250deamination 2-aminonaphthalene-6,8-disulfonic acidobscure
1,5-Naphthalenedisulfonic acid, Armstrong acid81-04-9240-245sulfonation of naphthalene with oleum (together with 1,6-isomer)1-hydroxynaphthalene-5-sulfonic acid, 1,5-dihydroxynaphthalene, 1,3,5-naphthalenetrisulfonic acid
1,6-Naphthalenedisulfonic acid525-37-1125sulfonation of naphthalene with oleum (together with 1,5-isomer)1,6-dihydroxynaphthalene, 1,3,6-naphthalenetrisulfonic acid
1,7-Naphthalenedisulfonic acid5724-16-3?low T sulfonation of naphthalene-2-sulfonic acid in low yieldsobscure
2,6-Naphthalenedisulfonic acid581-75-9?high T sulfonation of naphthalene2-hydroxynaphthalene-6-sulfonic acid and 2,6-dihydroxynaphthalene
2,7-Naphthalenedisulfonic acid92-41-12?high T sulfonation of naphthalene2-hydroxynaphthalene-7-sulfonic acid, 2,7-dihydroxynaphthalene-
1-Aminonaphthalene-8-hydroxy-2,4-disulfonic acid (Chicago acid)82-47-3?base hydrolysis of naphthosultam-2,4-disulfonic acidprecursor to C.I. Direct Blue 1 199, Direct Blue 22, Direct Blue 76[2]

In addition to these compounds, several naphthalenetrisulfonic acids are known as well as several hydroxy derivatives.

References

  1. ↑ Booth, Gerald (2000). "Naphthalene Derivatives". Ullmann's Encyclopedia of Industrial Chemistry. doi:10.1002/14356007.a17_009. ISBN 978-3-527-30385-4.
  2. ↑ Hartwell, J. L.; Fieser, Louis F. (1936). "Coupling of o-Tolidine and Chicago Acid". Organic Syntheses. 16: 12. doi:10.15227/orgsyn.016.0012.