1657-16-5

Basic information

• Product Name: 2-[(p-nitrophenyl)azo]acetoacetanilide
• Synonyms: 2-[(p-nitrophenyl)azo]acetoacetanilide;Butanamide, 2-(4-nitrophenyl)azo-3-oxo-N-phenyl-;CIPIGMENTYELLOW4;PIGMENTYELLOW4;Pigment yellow 4 (C.I. 11665);2-[(4-Nitrophenyl)azo]-3-oxo-N-phenylbutanamide;C.I.11665;Hansa Yellow 13G
• CAS NO: 1657-16-5
• Molecular Formula: C₁₆H₁₄N₄O₄
• Molecular Weight: 326.30676
• EINECS: 216-754-0
• Mol File: 1657-16-5.mol
• Article Data: 3

Chemical Properties

• Melting Point: 214-215 °C
• Boiling Point: 527.6°Cat760mmHg
• Flash Point: 272.9°C
• Appearance: /
• Density: 1.32g/cm³
• Vapor Pressure: 3.2E-11mmHg at 25°C
• Refractive Index: 1.628
• PKA: 8.81±0.59(Predicted)
• CAS DataBase Reference: 2-[(p-nitrophenyl)azo]acetoacetanilide(CAS DataBase Reference)
• NIST Chemistry Reference: 2-[(p-nitrophenyl)azo]acetoacetanilide(1657-16-5)
• EPA Substance Registry System: 2-[(p-nitrophenyl)azo]acetoacetanilide(1657-16-5)

Safety Data

• Hazardous Substances Data: 1657-16-5(Hazardous Substances Data)

Usage

General Description

2-[(p-nitrophenyl)azo]acetoacetanilide, also known as Sudan I, is a synthetic organic compound commonly used as a red-orange dye in the food industry. It is classified as an azo dye, meaning it contains a nitrogen-nitrogen double bond. Sudan I has been banned for use in food products in many countries due to its potential carcinogenic and mutagenic properties. Exposure to Sudan I has been linked to an increased risk of cancer, as well as other health issues. Therefore, its use in food products is strictly regulated to protect public health.

InChI:InChI=1/C16H14N4O4/c1-11(21)15(16(22)17-12-5-3-2-4-6-12)19-18-13-7-9-14(10-8-13)20(23)24/h2-10,15H,1H3,(H,17,22)/b19-18+

Upstream product

• 102-01-2 N-phenylacetoacetamide 
• 100-01-6 4-nitro-aniline 
• 100-05-0 4-nitrobenzenediazonium chloride 

Relevant articles and documents

A quantitative one-pot synthesis method for industrial azo pigments with recyclable wastewater

Most industrial azo pigments are synthesized by diazotization in one pot and then coupling in another. This two-pot process has been transformed into a one-pot method by adding granular PTFE (polytetrafluoroethylene) to a mechanically agitated aqueous mixture of NaNO2, HCl, a diazo component and a coupling component. This method avoids the step of using a base or a surfactant to dissolve the coupling component. The reactions were fast and quantitative. The granular PTFE, wastewater and excess HCl were then reused 11 times without deteriorating the reaction rate and product purity. Altogether, 22 industrial pigments and 3 azo compounds were synthesized and the reaction can produce up to 22.7 g of product in the laboratory. Some reactions require less than 2 equiv. of HCl and a mechanism explaining this is proposed. In addition, an o-nitro group effect is advanced to explain the differences in coupling reaction rates for o-, m- and p-nitroaniline.

Synthesis of some new 1-carbamoyl-3-aminophenyl- and 1-carbamoyl-3-amino-(2-chlorophenyl)-5-methyl-4-arylazopyrazoles as possible potential antidiabetics

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