84-86-6

Basic information

• Product Name: Naphthionic acid
• Synonyms: 4-AMINO-1-NAPHTHALENESULPHONICACID;1-Naphthylamine-4-sulfonic acid, Naphthionic acid;4-Amino-1-naphthalenesulfonic acid,98%;Naphthionic Acid 1-Naphthylamine-4-sulfonic Acid;4-Aminonaphthalene-1-sulfonic acid for synthesis;1,4-Naphthionic acid;1,4-naphthionicacid;1-Aminonaphthalene-4-sulfonic acid
• CAS NO: 84-86-6
• Molecular Formula: C₁₀H₉NO₃S
• Molecular Weight: 223.25
• EINECS: 201-567-9
• Product Categories: Intermediates of Dyes and Pigments;Building Blocks;Chemical Synthesis;Organic Building Blocks;Sulfonic/Sulfinic Acids;Sulfur Compounds
• Mol File: 84-86-6.mol

Chemical Properties

• Melting Point: ≥300 °C(lit.)
• Boiling Point: 220°C (rough estimate)
• Appearance: Slightly greyish to beige powder and granule
• Density: 1.67
• Refractive Index: 1.5250 (estimate)
• Storage Temp.: Store below +30°C.
• Solubility: Sparingly soluble in dichloromethane. Soluble in aqueous base.
• PKA: pK1: 2.81 (25°C)
• Water Solubility: 309.9mg/L(20 oC)
• Merck: 14,6403
• BRN: 1971299
• CAS DataBase Reference: Naphthionic acid(CAS DataBase Reference)
• NIST Chemistry Reference: Naphthionic acid(84-86-6)
• EPA Substance Registry System: Naphthionic acid(84-86-6)

Safety Data

• Hazard Codes: C
• Statements: 34-22
• Safety Statements: 26-36/37/39-45-25
• RIDADR: UN 2585 8/PG 3
• WGK Germany: 3
• RTECS: QK1270000
• TSCA: Yes
• HazardClass: 8
• PackingGroup: III
• Hazardous Substances Data: 84-86-6(Hazardous Substances Data)

Usage

Uses

Used in Dye Industry:
Naphthionic acid is used as an intermediate for azo dyes, such as Congo red. It plays a crucial role in the synthesis of these dyes, which are widely used in various applications, including textiles, plastics, and printing inks.
Used in Pharmaceutical Industry:
Naphthionic acid is used in the synthesis of 4-amino-1-naphthalenesulfonic acid, which has potent therapeutic applications. Its sodium salt has been used as a non-toxic hemostatic agent, helping to control bleeding in various medical conditions. Additionally, 4-amino-1-naphthalenesulfonic acid is a metabolite of azo dyes, which can have potential applications in the treatment of certain diseases.

Purification Methods

It crystallises from H2O as needles of the 0.5 hydrate. Salt solutions fluoresce strongly blue. The S-benzylisothiuronium salt has m 195o (from aqueous EtOH). [Beilstein 14 IV 2793.]

InChI:InChI=1/C10H9NO3S/c11-9-5-6-10(15(12,13)14)8-4-2-1-3-7(8)9/h1-6H,11H2,(H,12,13,14)

Upstream product

• 86-57-7 1-Nitronaphthalene 
• 21711-65-9 1-naphthylnitrosobenzene 
• 575-36-0 1-acetamidonaphthalene 
• 162109-20-8 1-bromo-4-naphthalenesulfonic acid 
• 607-30-7 hydroxynaphthylamine 
• 117-55-5 4-aminonaphthalene-1,5-disulfonic acid 
• 134-32-7 1-amino-naphthalene 
• 612-52-2 2-naphthylamine hydrochloride 
• 82-75-7 8-anilino-1-naphthalenesulfonate 
• 915-67-3 amaranth 
• 193887-78-4 citraconimide of 1-naphthylamine 
• 7664-93-9 sulfuric acid 
• 7790-94-5 chlorosulfonic acid 
• 5329-14-6 aminosulfonic acid 

Downstream Products

• 7355-16-0 4-amino-3-(2-phenyl-1-diazenyl)-1-naphthalenesulfonic acid 
• 188066-01-5 4-amino-3-(4-sulfo-phenylazo)-naphthalene-1-sulfonic acid 
• 571-60-8 1,4-Dihydroxynaphthalene 
• 90-15-3 α-naphthol 
• 84-87-7 1-hydroxy-4-naphthalenesulfonate 
• 117-80-6 2,3-Dichloro-1,4-naphthoquinone 
• 116-63-2 1-amino-2-naphthol-4-sulfonic acid 
• 4684-12-2 1-amino-4-chloronaphthalene 
• 2298-07-9 4-Bromo-1-naphthylamine 
• 20191-76-8 2,4-dibromo-1-naphthylamine 
• 85-74-5 4-amino-1,7-naphthalenedisulphonic acid 
• 85-75-6 4-aminonaphthalene-1,6-disulfonic acid 
• 88-99-3 benzene-1,2-dicarboxylic acid 
• 130-15-4 [1,4]naphthoquinone 

Relevant articles and documents

Sulfonation of aromatic amines under conditions of microwave heating

The possibility of intensifying solid-phase organic reactions by microwave heating is examined with sulfonation of aniline and α-naphthylamine as example. 1997 MAHK Hayka/Interperiodica Publishing.

Triphendioxazine dyestuffs

The novel triphendioxazine dyestuffs of the formula STR1 in which the substituents R, R', T1, T2, X, Y and n have the meanings given in the description are highly suitable for the dyeing and printing of cellulose-containing or amido-containing material.

Process for the preparation of aminoaryl-sulphonic acids

Aminoaryl-sulphonic acids can be prepared by reaction of arylamines and sulphuric acid at elevated temperature and under pressure, where water formed and, where appropriate, water present as water of dilution, is left in the reaction mixture until the end of the reaction.

Solid phase acylation of aminosulfonic acids

This invention is directed to the acylation of aminosulfonic acids in the solid phase. Two discrete, sequential chemical reactions occur, i.e. (1) the neutralization of the aminosulfonic acid, and (2) the subsequent amine acylation, to produce an improved neutralized acyl-aminosulfonic acid at a reduced cost. Aminosulfonic acids having the general formula HO3 S-A-NH2 are acylated to neutralized acyl-aminosulfonic acids having the general formula RCONH-A-SO3 M, where A is an unsubstituted or substituted aliphatic, aromatic or heteroaromatic group and M is a neutralizing agent moiety. The yield is virtually quantitative.

Bisazo brown reactive dye

A brown reactive dye represented by a free acid of the formula, STR1 wherein R is a hydrogen atom or a C1 to C4 alkyl group, X is --SO2 CH2 CH2 Cl, --SO2 CH=CH2, --SO2 CH2 CH2 OSO3 H or --SO2 CH2 CH2 OPO3 H2, rings A, B and C are each a benzene or naphthalene ring which may have other substituent, m is 0 to 3 and n is 0 to 1. This dye is suitable for dyeing cellulose fibers brown to afford dyeings superior in fastnesses, acid stability, build-up property and level dyeing property.

Fiber-reactive disazo brown dye having vinylsulfone-type reactive group

A compound, or a salt thereof, represented by the following formula, STR1 wherein A is a substituted or unsubstituted phenylene or naphthylene group, B is STR2 in which R3 is a hydrogen atom or a lower alkyl, lower alkoxy, acylamino or ureido group, and R4 is a hydrogen atom or a lower alkyl or lower alkoxy group, R1 and R3 are independently a hydrogen atom or a substituted or unsubstituted lower alkyl group, X is a substituted or unsubstituted amino, lower alkoxy, substituted phenoxy or sulfo group, Y is --SO2 CH=CH2 or --SO2 CH2 CH2 Z, in which Z is a group capable of being split by the action of an alkali, and m is 2 or 3, which is useful for dyeing hydroxyl group- or amide group-containing fiber materials to give dyed products of a brown color having excellent fastness properties with good build-up property.

Fibre-reactive dyes, containing both chloro and fluoro triazine radicals

Fibre-reactive dyes of the formula STR1 wherein D is the radical of a benzene or naphthalene azo dye which contains sulpho groups, each of R1, R2 and R3 is a hydrogen atom, B is an arylene group and A is an amino group.

Relationship between azo dye structure and rat hepatic azoreductase activity

The rate of reduction was determined for a variety of azo dyes using the rat hepatic azoreductase enzyme system. In decreasing order, the rates of reduction for the azo dyes expressed as nmol of arylamine product formed/min/0.25 g of liver were amaranth (33.2), azosulfamide (32.5), orange G (12.4), 1,2-dimethyl-4-p-(carboxyphenylazo)-5-hydroxybenzene (CPA) (9.27), brilliant crystal scarlet (8.00), sulfachrysoidine (7.27), and Sudan I (1.03). A comparison of the partition coefficient with its rate of reduction indicated that the water-soluble azo dyes were reduced more rapidly than the lipid-soluble ones. Furthermore, higher rates of reduction were observed for those dyes containing electron-withdrawing groups on the aromatic rings.

Process for the preparation of aromatic aminosulphonic acids

Aminoarylsulphonic acids which have a relatively high purity and a relatively low content of aminoaryldisulphonic acids can be obtained, if they are prepared, from the corresponding arylammonium hydrogen sulphates, by an improved version of the so-called baking process, wherein the reaction is carried out under pressure at a temperature of at least 140° C. and, at least partially, in the presence of water.