Naphthalene-2-sulfonic acid

Names
Preferred IUPAC name

Naphthalene-2-sulfonic acid

Other names

2-Naphthalenesulfonic acid, napsylate (salt), napsilate (salt)

Identifiers

CAS Number

* 120-18-3

3D model (JSmol)

* Interactive image

Beilstein Reference

| 1955756
ChEMBL |

* ChEMBL1234624

ChemSpider |

* 8113

EC Number |

* 204-375-3

PubChem CID

* 8420

UNII |

* O9S4K2S25E

InChI

* 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

SMILES

* C1=CC=C2C=C(C=CC2=C1)S(=O)(=O)O

Properties

Chemical formula

| C10H8O3S
Molar mass | 208.23 g·mol−1 (anhydrous)
Appearance  | White solid
Melting point |  124 °C (255 °F; 397 K) (monohydrate)

Solubility in water

| good
Hazards
GHS pictograms |
GHS Signal word | Danger

GHS hazard statements

| H302, H314

GHS precautionary statements

| P260, P264, P270, P280, P301+312, P301+330+331, P303+361+353, P304+340, P305+351+338, 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).

Infobox references

Tracking categories (test):

* SizeSet

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] they find use as low-grade superplasticizers in concrete.

Idealized structure of naphthalenesulfonate/formaldehyde polymer used as a superplasticizer

## References

1. ↑ 1.0 1.1 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.

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*[CID]: Compound ID
*[H302]: Harmful if swallowed
*[H314]: Causes severe skin burns and eye damage
*[P260]: Do not breathe dust/fume/gas/mist/vapours/spray
*[P264]: Wash … thoroughly after handling
*[P270]: Do not eat, drink or smoke when using this product
*[P280]: Wear protective gloves/protective clothing/eye protection/face protection
*[P301+312]: IF SWALLOWED: Call a POISON CENTER or doctor/physician if you feel unwell
*[P301+330+331]: IF SWALLOWED: Rinse mouth. Do NOT induce vomiting
*[P303+361+353]: IF ON SKIN (or hair): Remove/Take off immediately all contaminated clothing. Rinse skin with water/shower
*[P304+340]: IF INHALED: Remove victim to fresh air and keep at rest in a position comfortable for breathing
*[P305+351+338]: IF IN EYES: Rinse continuously with water for several minutes. Remove contact lenses if present and easy to do – continue rinsing
*[P310]: Immediately call a POISON CENTER or doctor/physician
*[P321]: Specific treatment (see … on this label)
*[P330]: Rinse mouth
*[P363]: Wash contaminated clothing before reuse
*[P405]: Store locked up
*[P501]: Dispose of contents/container to …