68189-32-2

Basic information

• Product Name: 6-acetamidonaphthalene-2-sulphonic acid
• Synonyms: 6-acetamidonaphthalene-2-sulphonic acid;6-Acetamido-2-naphthalenesulfonic acid;6-Acetylamino-2-naphthalenesulfonicacid;6-ACETYLAMINONAPHTHALENE-2-SULFONIC ACID
• CAS NO: 68189-32-2
• Molecular Formula: C₁₂H₁₁NO₄S
• Molecular Weight: 265.28504
• EINECS: 269-189-7
• Mol File: 68189-32-2.mol
• Article Data: 3

Chemical Properties

• Appearance: /
• Density: 1.478 g/cm³
• Refractive Index: 1.678
• PKA: 0.27±0.40(Predicted)
• CAS DataBase Reference: 6-acetamidonaphthalene-2-sulphonic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 6-acetamidonaphthalene-2-sulphonic acid(68189-32-2)
• EPA Substance Registry System: 6-acetamidonaphthalene-2-sulphonic acid(68189-32-2)

Safety Data

• Hazardous Substances Data: 68189-32-2(Hazardous Substances Data)

Usage

General Description

6-acetamidonaphthalene-2-sulphonic acid is a chemical compound that contains a naphthalene core with an acetamide and a sulfonic acid group attached to it. It is often used as an intermediate in the synthesis of various pharmaceutical compounds and dyes. The acetamide group provides a site for potential biological activity, making it useful in medicinal chemistry research. The sulfonic acid group gives the compound water solubility, making it suitable for use in aqueous solutions. Overall, 6-acetamidonaphthalene-2-sulphonic acid has potential applications in both the pharmaceutical and dyestuff industries.

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 articles and documents

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.

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.