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HomeProduct name list1-Aminonaphthalene-6-sulfonic acid

1-Aminonaphthalene-6-sulfonic acid

  • CAS NO.:119-79-9
  • Empirical Formula: C10H9NO3S
  • Molecular Weight: 223.25
  • MDL number: MFCD00004030
  • EINECS: 204-351-2
  • SAFETY DATA SHEET (SDS)
  • Update Date: 2024-06-06 16:20:44
1-Aminonaphthalene-6-sulfonic acid Structural

What is 1-Aminonaphthalene-6-sulfonic acid?

Chemical properties

Purple Solid. 1-Aminonaphthalene-6-sulfonic acid [119- 79-9]. (5-aminonaphthalene-2-sulfonic acid), 1,6-Cleve’s acid, C10H9NO3S, Mr 223.24, crystallizes from boiling water as plates of the dihydrate. Its sodium, potassium, and calcium salts are all readily soluble in water, but the barium salt is only sparingly soluble. Sulfonation with 10 % oleum yields 1-aminonaphthalene-4,6-disulfonic acid. Caustic fusion gives 5- amino-2-hydroxynaphthalene, and Bucherertype hydrolysis gives 1-hydroxynaphthalene-6- sulfonic acid.

The Uses of 1-Aminonaphthalene-6-sulfonic acid

Intermediate of dyestuff

The Uses of 1-Aminonaphthalene-6-sulfonic acid

Fluorescent reagent.

The Uses of 1-Aminonaphthalene-6-sulfonic acid

5-Amino-2-naphthalenesulfonic acid (1,6-Cleve′s acid) was used in the synthesis of nitrate reductase and detection of nitrate reduction by anaerobic bacteria.

Definition

ChEBI: 5-aminonaphthalene-2-sulfonic acid is an aminonaphthalenesulfonic acid.

Production Methods

Sulfonation of 1-naphthylamine with concentrated sulfuric acid at 130℃ gives mainly 1-aminonaphthalene-6-sulfonic acid. However, the latter is always made, together with the 1,7-isomer, by nitration of naphthalene-2-sulfonic acid to give the mixed 5- and 8- nitronaphthalene-2-sulfonic acids follwed by reduction to ‘‘mixed Cleve’s acids.’’ A b-sulfonation mass is diluted with sulfuric acid, then 67.5 % nitric acid is added slowly at 34℃. After being quenched and neutralized with calcium carbonate, the filtered liquor is reduced by boiling with iron powder, slight acidity being maintained with sulfuric acid. After basification with magnesia the iron residues are filtered off and the filtrate is evaporated until the magnesium salt of the product crystallizes on cooling. Filtration followed by washing with magnesium sulfate gives a 34 % yield of the magnesium salt of 1,6-Cleve’s acid. Purification by dissolution in hot water, acidification, and filtration of the free acid while hot reduce the yield to 25 % based on naphthalene.

General Description

The crystal structure of 5-amino-2-naphthalenesulfonic acid (1,6-Cleve′s acid) depicted the presence of a sulfonate-aminium group zwitterion.

Properties of 1-Aminonaphthalene-6-sulfonic acid

Melting point: >300°C
Density  1.3588 (rough estimate)
vapor pressure  0Pa at 25℃
refractive index  1.6500 (estimate)
storage temp.  Refrigerator
solubility  soluble100mg/mL, clear, brown (1N NH4OH)
form  Solid
pka pK1: 3.80 (25°C)
color  Purple
Water Solubility  1g/L(16 ºC)
Merck  14,2350
BRN  1819887
CAS DataBase Reference 119-79-9(CAS DataBase Reference)
NIST Chemistry Reference 1-Naphthylamine-6-sulfonic acid(119-79-9)
EPA Substance Registry System 2-Naphthalenesulfonic acid, 5-amino- (119-79-9)

Safety information for 1-Aminonaphthalene-6-sulfonic acid

Signal word Warning
Pictogram(s)
ghs
Exclamation Mark
Irritant
GHS07
GHS Hazard Statements H315:Skin corrosion/irritation
H319:Serious eye damage/eye irritation
Precautionary Statement Codes P264:Wash hands thoroughly after handling.
P264:Wash skin thouroughly after handling.
P280:Wear protective gloves/protective clothing/eye protection/face protection.

Computed Descriptors for 1-Aminonaphthalene-6-sulfonic acid

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