119-15-3

Basic information

• Product Name: 4-(2,4-DINITROANILINO)PHENOL
• Synonyms: acetoquinonelightyellow2rz;Amacel Yellow RR;amacelyellowrr;C.I. 10345;C.I. Disperse Yellow 1;C.I. Solvent yellow 52;c.i.10345;c.i.disperseyellow1
• CAS NO: 119-15-3
• Molecular Formula: C₁₂H₉N₃O₅
• Molecular Weight: 275.22
• EINECS: 204-300-4
• Mol File: 119-15-3.mol
• Article Data: 5

Chemical Properties

• Melting Point: 191 °C (dec.)(lit.)
• Boiling Point: 418.17°C (rough estimate)
• Flash Point: 222.2°C
• Appearance: /
• Density: 1.3877 (rough estimate)
• Vapor Pressure: 1.72E-08mmHg at 25°C
• Refractive Index: 1.5700 (estimate)
• PKA: 10.20±0.26(Predicted)
• Water Solubility: 2.477mg/L(25 oC)
• CAS DataBase Reference: 4-(2,4-DINITROANILINO)PHENOL(CAS DataBase Reference)
• NIST Chemistry Reference: 4-(2,4-DINITROANILINO)PHENOL(119-15-3)
• EPA Substance Registry System: 4-(2,4-DINITROANILINO)PHENOL(119-15-3)

Safety Data

• Hazard Codes: F,Xi
• Statements: 11-36/37/38
• Safety Statements: 16-26-33-36/37/39
• RIDADR: UN 1325 4.1/PG 2
• WGK Germany: 2
• RTECS: SL3070000
• HazardClass: 4.1
• PackingGroup: III
• Hazardous Substances Data: 119-15-3(Hazardous Substances Data)

Usage

Uses

Disperse Yellow 1 is an azo disperse dye which is water insoluble. Disperse Yellow 1 can be used to dye polyester and acetate fibers. Dyes and metabolites, Environmental Testing.

Preparation

4-Aminophenol and 1-Chloro-2,4-dinitrobenzene??condensation

General Description

Reddish-brown solid.

Air & Water Reactions

Insoluble in water.

Reactivity Profile

4-(2,4-DINITROANILINO)PHENOL is an organonitrate/phenol. Organonitrate compounds range from slight to strong oxidizing agents. If mixed with reducing agents, including hydrides, sulfides and nitrides, they may begin a vigorous reaction that culminates in a detonation. The aromatic nitro compounds may explode in the presence of a base such as sodium hydroxide or potassium hydroxide even in the presence of water or organic solvents. The explosive tendencies of aromatic nitro compounds are increased by the presence of multiple nitro groups. Phenols do not behave as organic alcohols, as one might guess from the presence of a hydroxyl (-OH) group in their structure. Instead, they react as weak organic acids. Phenols and cresols are much weaker as acids than common carboxylic acids (phenol has Ka = 1.3 x 10^[-10]). These materials are incompatible with strong reducing substances such as hydrides, nitrides, alkali metals, and sulfides. Flammable gas (H2) is often generated, and the heat of the reaction may ignite the gas. Heat is also generated by the acid-base reaction between phenols and bases.

Fire Hazard

Flash point data for 4-(2,4-DINITROANILINO)PHENOL are not available, however, 4-(2,4-DINITROANILINO)PHENOL is probably combustible.

Properties and Applications

yellow. Insoluble in water, slightly soluble in alcohol. In concentrated sulfuric acid for claybank, dilution after yellow. Used for cellulose ester, polystyrene and other thermoplastic resin paint color.

InChI:InChI=1/C12H9N3O5/c16-10-4-1-8(2-5-10)13-11-6-3-9(14(17)18)7-12(11)15(19)20/h1-7,13,16H

Upstream product

• 37051-70-0 4-methyl-N-(4-oxocyclohexa-2,5-dien-1-ylidene)benzenesulfonamide 
• 85290-52-4 Benzyl-((E)-1-methyl-2-nitro-vinyl)-amine 
• 123-30-8 4-amino-phenol 
• 70-34-8 2,4-Dinitrofluorobenzene 
• 97-00-7 1-chloro-2,4-dinitro-benzene 
• 2363-30-6 4-amino-2',4'-dinitrodiphenyl ether 
• 109-89-7 diethylamine 

Downstream Products

• 36942-33-3 2,6-dichloro-[1,4]benzoquinone-4-(2,4-dinitro-phenylimine) 
• 36942-32-2 2,6-dichloro-4-(2,4-dinitro-anilino)-phenol 
• 7475-04-9 2.4-diamino-4'-oxy-diphenylamine 
• 77806-34-9 amino-2 nitro-4 hydroxy-4' diphenylamine 
• 6731-01-7 [4-(2,4-dinitro-phenoxy)-phenyl]-(2,4-dinitro-phenyl)-amine 
• 36942-29-7 4-(2,4-dinitrophenylimino)cyclohexa-2,5-dien-1-one 
• 967-35-1 N-(4-methoxyphenyl)-2,4-dinitrobenzenamine 
• 6364-21-2 8-amino-phenazin-2-ol 
• 861797-56-0 N-(2,4-dinitro-phenyl)-N-(4-hydroxy-phenyl)-acetamide 

Relevant articles and documents

Deep eutectic solvent as an operative media on structure-reactivity relationships

Deep eutectic solvents seem to be environmentally friendly solvents, particularly because they are prepared easily and have very low-vapor pressures under ambient conditions. They are suitable candidates as green solvents for reaction media with special properties. To present this behavior, substitution reactions of some para- and meta-substituted anilines with 1-fluoro-2,4-dinitrobenzene have been spectrophotometrically investigated in varying mole fractions of ethaline as a deep eutectic solvent in dimethyl sulfoxide (DMSO). The measured rate coefficients of the reaction demonstrated a noticeable variation with the increasing mole fraction of ethaline in ethaline-DMSO mixtures. The linear free energy relationship (LFER) of second-order rate coefficients based on Hammett's substituent constants demonstrates a reasonably linear straight line with a negative slope in different mole fractions of ethaline-DMSO mixtures. Another LFER investigation based on the polarity parameters of the media showed a good agreement with hydrogen bond donor and acceptor abilities of the solvent. Non-LFER assay according to the preferential solvation model confirmed differences between the microsphere solvation of the solute molecules and the bulk composition of the solvents.

Quinoneimines in the Nenitzescu reaction

The Nenitzescu reaction involving quinoneimines was studied; new 5-aminoindole, 5-aminobenzofuran, and 9-aminochromenopyridine derivatives were synthesized.

ACCES AUX DINITRO-2,4 DIARYLAMINES PAR SUBSTITUTION NUCLEOPHILE SNAr-LIMITES DE LA REACTION ET APPLICATION A LA SYNTHESE DE CYANOCARBAZOLES

3-Cyanocarbazoles, key-intermediates in the total synthesis of pyrido carbazoles, have been obtained starting from easily available materials and involving the cyclization of diarylamines.The first step of the preparation consists in a SNAr reaction between a para substituted aniline and a chloro- (or bromo)-dinitrobenzene.This nucleophilic substitution has been found to be hindered by the steric effect of a methyl group, explained in terms of inhibition of resonance and confirmed by X-ray determination.