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1-Aminonaphthalene-6-sulfonic acid

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1-Aminonaphthalene-6-sulfonic acid Basic information

Product Name:
1-Aminonaphthalene-6-sulfonic acid
Synonyms:
  • 1,6-CLEVES ACID
  • 1,6-CLEVE'S ACID
  • 1-amino-6-naphthalenesulfonic acid
  • 1-Naphthalene -6-sulfonic acid
  • 1-naphthylamine-6-sulfonic
  • 2-Naphthalenesulfonic acid, 5-amino-
  • 2-Naphthalenesulfonicacid,5-amino-
  • 5-amino-2-naphthalenesulfonicaci
CAS:
119-79-9
MF:
C10H9NO3S
MW:
223.25
EINECS:
204-351-2
Product Categories:
  • Organic Building Blocks
  • Sulfonic/Sulfinic Acids
  • Sulfur Compounds
  • Amines
  • Aromatics
  • Fluorescent Labels & Indicators
  • Intermediates of Dyes and Pigments
  • Organics
Mol File:
119-79-9.mol
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1-Aminonaphthalene-6-sulfonic acid Chemical Properties

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
Dissociation constant
0 at 39℃
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)
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Safety Information

Risk Statements 
36/37/38
Safety Statements 
26-36/37/39-24/25
RIDADR 
1759
WGK Germany 
1
RTECS 
QK1285000
TSCA 
Yes
HazardClass 
8
PackingGroup 
III
HS Code 
29309090

MSDS

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1-Aminonaphthalene-6-sulfonic acid Usage And Synthesis

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.

Uses

Fluorescent reagent.

Uses

Intermediate of dyestuff

Uses

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.

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