Naphthalene-2-sulfonic acid

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Naphthalene-2-sulfonic acid
2-naphthalenesulfonic acid.svg
Names
Preferred IUPAC name
Naphthalene-2-sulfonic acid
Other names
2-Naphthalenesulfonic acid
Identifiers
3D model (JSmol)
1955756
ChEMBL
ChemSpider
ECHA InfoCard 100.003.978 Edit this at Wikidata
EC Number
  • 204-375-3
UNII
  • InChI=1S/C10H8O3S/c11-14(12,13)10-6-5-8-3-1-2-4-9(8)7-10/h1-7H,(H,11,12,13)
    Key: KVBGVZZKJNLNJU-UHFFFAOYSA-N
  • C1=CC=C2C=C(C=CC2=C1)S(=O)(=O)O
Properties
C10H8O3S
Molar mass 208.23 g·mol−1 (anhydrous)
Appearance White solid
Melting point 124 °C (255 °F; 397 K) (monohydrate)
good
Hazards
GHS labelling:
GHS05: CorrosiveGHS07: Exclamation mark
Danger
H302, H314
P260, P264, P270, P280, P301+P312, P301+P330+P331, P303+P361+P353, P304+P340, P305+P351+P338, P310, P321, P330, P363, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

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.[1]

Naphthalene-2-sulfonic acid undergoes many reactions, some of which are or were of commercial interest. Fusion with sodium hydroxide followed by acidification gives 2-naphthol. It is an intermediate in the formation of 2,6-, 2,7- and 1,6-naphthalene disulfonic acids as well as 1,3,6-naphthalenetrisulfonic acid. Naphthalene-2-sulfonic acid condenses with formaldehyde to give polymeric sulfonic acids.[1]

References[edit]

  1. ^ a b Gerald Booth (2005). "Naphthalene Derivatives". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a17_009. ISBN 3527306730.{{cite encyclopedia}}: CS1 maint: uses authors parameter (link)