85-83-6

Basic information

• Product Name: Solvent Red 24
• Synonyms: 1-((2-Methyl-4-((2-methylphenyl)azo)phenyl)azo)-2-naphthalenol;1-((4-(o-tolylazo)-o-tolyl)azo)-2-naphtho;1-((E)-(2-Methyl-4-[(E)-(2-methylphenyl)diazenyl]phenyl)diazenyl)-2-naphth;1-(4-(o-Tolylazo)-o-tolylazo)-2-naphthol;1-(4-o-tolylazo-o-tolylazo)-2-naphthol;1-[[2-methyl-4-[(2-methylphenyl)azo]phenyl]azo]-2-naphthaleno;2',3-Dimethyl-4-(2-hydroxynaphthylazo)azobenzene;2’,3-dimethyl-4-(2-hydroxynaphthylazo)azobenzene
• CAS NO: 85-83-6
• Molecular Formula: C₂₄H₂₀N₄O
• Molecular Weight: 380.44
• EINECS: 201-635-8
• Product Categories: Organics;Solvent Dyestuff;Aromatics;Intermediates & Fine Chemicals;Pharmaceuticals;Solvents and Intermediates;Azo
• Mol File: 85-83-6.mol
• Article Data: 2

Chemical Properties

• Melting Point: 199 °C (dec.)(lit.)
• Boiling Point: 260°C
• Flash Point: 424.4 °C
• Appearance: Red Brown/Powder/Solid
• Density: 1.1946 (rough estimate)
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.6000 (estimate)
• Storage Temp.: Flammables area
• Solubility: Insoluble in water; soluble in benzene, methanol, acetone, isopr
• PKA: 13.52±0.50(Predicted)
• Water Solubility: 23μg/L at 25℃
• Stability: Stable. Incompatible with strong oxidizing agents.
• Merck: 14,8393
• BRN: 709018
• CAS DataBase Reference: Solvent Red 24(CAS DataBase Reference)
• NIST Chemistry Reference: Solvent Red 24(85-83-6)
• EPA Substance Registry System: Solvent Red 24(85-83-6)

Safety Data

• Hazard Codes: Xi,T
• Statements: 36/38-45
• Safety Statements: 26-36-53-45
• WGK Germany: 3
• RTECS: QL5775000
• TSCA: Yes
• HazardClass: IRRITANT
• Hazardous Substances Data: 85-83-6(Hazardous Substances Data)

Usage

Chemical Properties

dark red to brown crystals or powder

Uses

Different sources of media describe the Uses of 85-83-6 differently. You can refer to the following data:
1. Solvent Red 24 has been used to promote wound healing and biological stain.
2. Fat stain.
3. It has been used to promote wound healing. Biological stain. Dyes and metabolites, Environmental Testing.

Definition

ChEBI: A bis(azo) compound that is 2-naphthol substituted at position 1 by a {2-methyl-4-[(2-methylphenyl)diazenyl]phenyl}diazenyl group. A fat-soluble dye predominantly used for demonstrating triglycerides in frozen sections, but which may also stain some protei bound lipids in paraffin sections.

General Description

Sudan IV is a hydrophobic azo dye. It stains triglycerides and imparts an intense red color. The dye does not stain lipid droplets or phospholipids.

Flammability and Explosibility

Notclassified

Safety Profile

Questionable carcinogen with experimental tumorigenic data. Mutation data reported. When heated to decomposition it emits toxic fumes of NOx.

Properties and Applications

red to blue light red. Red powder, resistance to 5% of hydrochloric acid and sodium carbonate solution. Insoluble in water, soluble in ethanol and acetone, soluble in benzene. In concentrated sulfuric acid to blue light green, dilution have red precipitation. Mainly used in acetate fiber, organic glass, ABS resin, rigid polyvinyl chloride (PVC) and so on the many kinds of plastic coloring, and can also be used to paint and ballpoint ink color, also can be used for polyester fiber colouring. Standard Light Fastness Heat-resistant(℃) water Sodium Carbonate(5%) Hydrochloric acid(5%) Melting point Stable ISO Good 184-185 120 Insoluble No change No change

Standard

Light Fastness

Melting point

Stable

ISO

Good

Purification Methods

Crystallise the dye from EtOH/water or acetone/water. [Beilstein 16 IV 249.]

InChI:InChI=1/C24H20N4O/c1-16-7-3-6-10-21(16)26-25-19-12-13-22(17(2)15-19)27-28-24-20-9-5-4-8-18(20)11-14-23(24)29/h3-15,29H,1-2H3/b26-25+,28-27+

Synthetic route

β-naphthol (135-19-3) + o-aminoazotoluene (97-56-3) → Sudan-IV (85-83-6)

Conditions	Yield
Stage #1: o-aminoazotoluene With hydrogenchloride In water at 20℃; for 0.5h; Stage #2: With sodium nitrate In water at 3℃; for 4h; Stage #3: β-naphthol In water for 3h; Temperature;	97.23%

β-naphthol (135-19-3) + diazotized 4'-amino-2.3'-dimethyl-azobenzene → Sudan-IV (85-83-6)

thallium (I) ethoxide (20398-06-5) + Sudan-IV (85-83-6) → Tl(1+)*C10H6ON2C6H3CH3N2C6H4CH3(1-)=TlC10H6ON2C6H3CH3N2C6H4CH3

Conditions	Yield
In tetrahydrofuran (Ar), to soln. of ligand in dry THF added dropwise soln. of TlOEt at room temp., stirred for 2 h; filtered;	99%

4-(dimethylsilyl)benzoic acid (27628-29-1) + Sudan-IV (85-83-6) → C33H30N4O2Si

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 24h; Inert atmosphere; Schlenk technique;	62%

Sudan-IV (85-83-6) + tin dichloride → 1-amino-2-naphthol (2834-92-6) + o-toluidine (95-53-4) + 2-methyl-p-phenylenediamine (95-70-5)

3-(Dimethylamino)propyl chloride (109-54-6) + Sudan-IV (85-83-6) → C29H31N5O (1353278-96-2)

Conditions	Yield
Stage #1: Sudan-IV With potassium hydroxide In 5,5-dimethyl-1,3-cyclohexadiene; water Reflux; Stage #2: 3-(Dimethylamino)propyl chloride In 5,5-dimethyl-1,3-cyclohexadiene; water at 70℃; for 48h; Reflux;

Upstream product

• 135-19-3 β-naphthol 
• 97-56-3 o-aminoazotoluene 

Downstream Products

• 2834-92-6 1-amino-2-naphthol 
• 95-53-4 o-toluidine 
• 95-70-5 2-methyl-p-phenylenediamine 
• 1353278-96-2 C₂₉H₃₁N₅O 

Relevant articles and documents

A CONTINUOUS PROCESS FOR THE SYNTHESIS OF AZO DYES INVOLVING IN-SITU GENERATION OF DIAZONIUM SALTS

The present disclosure provides a continuous process for the synthesis coupled compounds of diazonium salts including azo dyes involving in-situ generation of diazonium salts. It further discloses a set up to carry out the process for the synthesis of coupled compounds of diazonium salts.