68189-32-2

Usage

Uses

Used in Pharmaceutical Industry:
6-acetamidonaphthalene-2-sulphonic acid is used as an intermediate in the synthesis of various pharmaceutical compounds for its potential biological activity. The acetamide group allows for the attachment of different functional groups, enhancing the compound's therapeutic properties.
Used in Dye Industry:
6-acetamidonaphthalene-2-sulphonic acid is used as an intermediate in the synthesis of dyes due to its water solubility and chemical stability. The sulfonic acid group provides a platform for the attachment of different chromophores, resulting in a wide range of color variations.
Used in Medicinal Chemistry Research:
6-acetamidonaphthalene-2-sulphonic acid is used as a research compound in medicinal chemistry for its potential to be modified and optimized for specific biological targets. The acetamide group offers a site for chemical modifications, enabling the development of novel therapeutic agents.

InChI:InChI=1/C12H11NO4S/c1-8(14)13-11-4-2-10-7-12(18(15,16)17)5-3-9(10)6-11/h2-7H,1H3,(H,13,14)(H,15,16,17)

Synthetic route

acetic anhydride (108-24-7) + 2-amino-naphthalene-sulfonic acid-(6) → 6-acetylamino-naphthalene-2-sulfonic acid (68189-32-2)

Conditions	Yield
With pyridine

acetic anhydride (108-24-7) + Bronner acid (93-00-5) → 6-acetylamino-naphthalene-2-sulfonic acid (68189-32-2)

Conditions	Yield
In water at 25℃;	144.5 g

6-acetylamino-naphthalene-2-sulfonic acid (68189-32-2) → C35H23N5O11S5 (1221150-08-8)

Conditions	Yield
Multi-step reaction with 4 steps 1.1: chlorosulfonic acid / 1 h / 20 °C 2.1: sodium carbonate / water; acetone / 10 - 13 °C / pH 7 - 8 3.1: hydrogenchloride / water / 2.5 h / 80 °C 4.1: hydrogenchloride; sodium nitrite / water / 1 h / 0 - 10 °C 4.2: 20 - 25 °C View Scheme

6-acetylamino-naphthalene-2-sulfonic acid (68189-32-2) → C54H36N10O17S7

Conditions	Yield
Multi-step reaction with 5 steps 1.1: chlorosulfonic acid / 1 h / 20 °C 2.1: sodium carbonate / water; acetone / 10 - 13 °C / pH 7 - 8 3.1: hydrogenchloride / water / 2.5 h / 80 °C 4.1: hydrogenchloride; sodium nitrite / water / 1 h / 0 - 10 °C 4.2: 20 - 25 °C 5.1: isopentyl nitrite / water / 2.5 h / 45 °C View Scheme

6-acetylamino-naphthalene-2-sulfonic acid (68189-32-2) → 6-Acetylamino-2-naphthalenesulfonyl chloride (28131-80-8)

Conditions	Yield
With chlorosulfonic acid at 20℃; for 1h;	49.1 g

6-acetylamino-naphthalene-2-sulfonic acid (68189-32-2) → C22H18N2O12S4 (1221150-06-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: chlorosulfonic acid / 1 h / 20 °C 2: sodium carbonate / water; acetone / 10 - 13 °C / pH 7 - 8 View Scheme

6-acetylamino-naphthalene-2-sulfonic acid (68189-32-2) → C20H16N2O11S4 (1221150-07-7)

Conditions	Yield
Multi-step reaction with 3 steps 1: chlorosulfonic acid / 1 h / 20 °C 2: sodium carbonate / water; acetone / 10 - 13 °C / pH 7 - 8 3: hydrogenchloride / water / 2.5 h / 80 °C View Scheme

Upstream product

• 108-24-7 acetic anhydride 
• 93-00-5 Bronner acid 

Downstream Products

• 28131-80-8 6-Acetylamino-2-naphthalenesulfonyl chloride 

Relevant academic research and scientific papers

DISAZO COMPOUNDS AND THEIR USE IN INK-JET PRINTING

A compound of Formula (1) or a salt thereof: wherein: X is N or C(CN); Z is optionally substituted naphthyl; Ar is an aryl group carrying at least one substituent selected from the group consisting of an acetyl group, an acetate ester group, an amide group, a sulfonamide group, a sulfoxide group, a sulfone group, a phosphonate group, a nitrile group, an isonitrile group, a quaternary amine, a carbonyl group (other than a carboxylic acid), a polyhaloalkyl group or a halogen atom; and Ar may optionally be substituted with one or more further substituents. Also compositions, inks, printing processes, printed material and ink-jet cartridges.

Single-vessel process for preparing 2-acetaminonaphthalene-6-sulfonic acid of high purity

A single-vessel process for preparing 2-acetaminonaphthalene-6-sulfonic acid of high purity by sulfonating 2-hydroxynaphthalene with concentrated sulfuric acid, converting the 2-hydroxynaphthalenesulfonic acid formed with ammonia in the presence of ammonium hydrogensulfite into 2-amino-naphthalene-6-sulfonic acid (Bucherer reaction) and N-acetylating the latter to give 2-acetaminonaphthalene-6-sulfonic acid, which comprises, after diluting the sulfonating melt with water, substantially removing any impurities still present in the resulting aqueous solution of 2-hydroxynaphthalene-6-sulfonic acid, in particular 2-hydroxynaphthalene, by extraction with toluene or xylene and/or clarification using active carbon.

Process for the preparation of N-acetylaminoarylsulfonic acids in sulfuric acid as solvent

The invention relates to salt-free N-acetylaminoarylsulfonic acids, their preparation by acetylation with acetic anhydride or acetyl chloride, sulfuric acid, which can also contain a small amount of water and/or dimethylformamide and/or N-methylpyrrolidone, serving as the solvent, and the use of the N-acetylaminoarylsulfonic acids for the preparation of their acid chlorides.