492-80-8

Basic information

• Product Name: Yellow pyoctanine
• Synonyms: 4,4'-(Imidocarbonyl)bis(N,N-Dimethylaniline);Blauramine;C.I. 41000B;C.I. Basic Yellow 2, Free Base;C.I. Solvent Yellow 34;Carbonoimidoylbis(N,N-dimethylbenzenamine);Waxoline yellow D;Yellow pyoctanine
• CAS NO: 492-80-8
• Molecular Formula: C₁₇H₂₁N₃
• Molecular Weight: 267.36874
• EINECS: 207-762-5
• Product Categories: Dyes and Pigments;Auramine;Solvent Dyestuff
• Mol File: 492-80-8.mol
• Article Data: 3

Chemical Properties

• Melting Point: 138℃
• Boiling Point: 400.55°C (rough estimate)
• Flash Point: 199.4 °C
• Appearance: yellow powder
• Density: 1.01
• Refractive Index: 1.6360 (estimate)
• PKA: 10.12±0.50(Predicted)
• BRN: 2215338
• CAS DataBase Reference: Yellow pyoctanine(CAS DataBase Reference)
• NIST Chemistry Reference: Yellow pyoctanine(492-80-8)
• EPA Substance Registry System: Yellow pyoctanine(492-80-8)

Safety Data

• Hazard Codes: Xn,N
• Statements: 22-36-40-51/53
• Safety Statements: 36/37-61
• RIDADR: UN 3077 9 / PGIII
• WGK Germany: 3
• RTECS: BY3500000
• Hazardous Substances Data: 492-80-8(Hazardous Substances Data)

Usage

Description

Yellow pyoctanine, also known as Auramine, is a member of the class of imines that is benzophenone imine carrying two dimethylamino substituents at positions 4 and 4'. It is a yellow crystalline powder or yellow needles, and its hydrochloride salt is the biological stain 'auramine O'. It is soluble in cold water, soluble in hot water for brilliant yellow, and soluble in ethanol for yellow. In concentrated sulfuric acid, it turns colorless, but upon dilution, it turns buff. It has a stable melting point and exhibits poor light fastness and heat resistance.

Uses

Used in Textile Industry:
Yellow pyoctanine is used as a dye for coloring textiles, providing a brilliant green-yellow hue to the fabric.
Used in Paper Industry:
It is used as a dye for paper, imparting a vibrant yellow color to the material.
Used in Leather Industry:
Yellow pyoctanine is used as a dye for leather, giving it a bright yellow appearance.
Used in Pharmaceutical Industry:
It is used as an antiseptic, particularly in ear and nose surgery and in the treatment of gonorrhea, due to its powerful antiseptic properties.
Used in Chemical Industry:
Yellow pyoctanine is used as a dye intermediate for the production of other dyes and colorants.
Used in Oil Industry:
It is used as a dye for oil, providing a distinctive color for identification and safety purposes.
Used in Paraffin Wax Industry:
Yellow pyoctanine is used as a dye for paraffin wax, enhancing its appearance and making it more visually appealing.
Used in Paint Industry:
It is used as a dye for alcohol-soluble paint, providing a bright yellow color to the paint.
Used in Printing Industry:
Yellow pyoctanine is used as a dye for printing inks, offering a vibrant yellow color for various printing applications.

Preparation

(a) will Sulphur dissolved in 4-(4-(Dimethylamino)benzyl)-N,N-dimethylbenzenamine?methane. Add in ammonia and sodium chloride, ammonia in 175 ℃ heat the mixture, with hot water extraction dye and salting out (GP53614); (b) Bis (4 – (dimethylamino) phenyl) methanone and ammonia and Zinc chloride in a total of 150 ~ 160 ℃ heat (GP 29060). Free base is to add the same amount of naoh aqueous solution hydrochloride, sodium carbonate and ammonia and have to.

Reactivity Profile

Yellow pyoctanine neutralizes acids in exothermic reactions to form salts plus water. May be incompatible with isocyanates, halogenated organics, peroxides, phenols (acidic), epoxides, anhydrides, and acid halides. May generate hydrogen, a flammable gas, in combination with strong reducing agents such as hydrides.

Hazard

Confirmed carcinogen.

Health Hazard

Inhalation of material may be harmful. Contact may cause burns to skin and eyes. Inhalation of Asbestos dust may have a damaging effect on the lungs. Fire may produce irritating, corrosive and/or toxic gases. Some liquids produce vapors that may cause dizziness or suffocation. Runoff from fire control may cause pollution.

Fire Hazard

Some may burn but none ignite readily. Containers may explode when heated. Some may be transported hot.

Trade name

WAXOLINE YELLOW O?

Shipping

UN2811 Toxic solids, organic, n.o.s., Hazard Class: 6.1; Labels: 6.1-Poisonous materials, Technical Name Required. UN3143 Dyes, solid, toxic, n.o.s. or Dye intermediates, solid, toxic, n.o.s., Hazard Class: 6.1; Labels: 6.1-Poisonous materials, Technical Name Required.

Standard

Light Fastness

Melting point

Stable

ISO

Poor

Incompatibilities

Incompatible with oxidizers (chlorates, nitrates, peroxides, permanganates, perchlorates, chlorine, bromine, fluorine, etc.); contact may cause fires or explosions. Keep away from alkaline materials, strong bases, strong acids, oxoacids, epoxides.

Upstream product

• 586-77-6 4-bromo-N,N-dimethylaniline 
• 64-17-5 ethanol 
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• 345921-89-3 bis-(4-dimethylamino-phenyl)-methanethiol 
• 7664-41-7 ammonia 
• 106-51-4 p-benzoquinone 
• 98-95-3 nitrobenzene 
• 118-75-2 chloranil 
• 6083-47-2 4-(dimethylamino)benzamide 
• 5435-44-9 (E)-3-Ureido-but-2-enoic acid ethyl ester 
• 121-69-7 N,N-dimethyl-aniline 
• 101-61-1 4,4'-methylene-bis(N,N-dimethylaniline) 
• 90-94-8 bis(p-dimethylaminophenyl)methanone 

Downstream Products

• 1226-46-6 thiomichlersketone 
• 4593-77-5 4-(4,4'-bis-dimethylamino-benzhydrylidene)-5-methyl-2-phenyl-2,4-dihydro-pyrazol-3-one 
• 21497-95-0 N-(4,4'-bis-dimethylamino-benzhydrylidene)-2,4,6-trinitro-aniline 
• 87892-64-6 1,1-bis<4-(dimethylamino)phenyl>-2-nitroethylene 
• 747349-73-1 N-(4,4'-bis-dimethylamino-benzhydryliden)-acetamide 
• 25642-41-5 N-(4,4'-bis-dimethylamino-benzhydrylidene)-benzenesulfonamide 
• 25642-42-6 N-allyl-N'-(4,4'-bis-dimethylamino-benzhydrylidene)-thiourea 
• 2123-34-4 4,4'-(aminomethylene)bis(N,N-dimethylaniline) 
• 26514-42-1 N-methylene>aniline 
• 603-48-5 tris[4-(dimethylamino)phenyl]methane 

Relevant articles and documents

Molecular recognition studies on supramolecular systems. 32. Molecular recognition of dyes by organoselenium-bridged bis(β-cyclodextrin)s

A series of novel bis(β-cyclodextrin)s tethered with organoselenium linkers, i.e., 6,6′-(o-phenylenediseleno)-bridged bis(β-cyclodextrin) (2), 6,6′-[2,2′-diselenobis(benzoyloxy)]-bridged bis(β-cyclodextrin) (3), and 6,6′-[2,2′-diselenobis[2-(benzoylamino)ethylamino]]-bridged bis(β-cyclodextrin) (4), were synthesized from β-cyclodextrin (1). The inclusion complexation behavior of 1-4 with some dyes, such as 8-anilinonaphthalenesulfonate (ANS), Brilliant Green, Crystal Violet, Tropaeolin OO, Auramine O, and Methyl Orange, was investigated in aqueous phosphate buffer solution (pH 7.20) at 25 °C by UV-vis, fluorescence, and circular dichroism spectrometry, as well as fluorescence lifetime measurements. The complex stability constants (KS) and Gibbs free energy changes (δG°) for the stoichiometric 1:1 inclusion complexation of 1-4 with the dyes were obtained by the spectrophotometric or spectropolarimetric titrations. The bis(β-cyclodextrin)s 2-4 showed much higher affinities toward these guest dyes than native β-cyclodextrin I with fairly good molecular selectivities. The cooperative binding abilities of these bis(β-cyclodextrin)s are discussed from the viewpoints of size/shape-fit interaction, induced-fit concept, and multiple recognition mechanism.

Anhydrous bases and salts of dyestuffs of the auramine series, process for their preparation and their use

Process for the preparation of an anhydrous base or salt of a dyestuff of the Auramine series, which comprises isolating the base or salt in acetone, methylethylketone or diethylketone; products prepared by such a process; the hydrofluoride of the base of Auramine O; the phosphate of the base of Auramine O; the hydrobromide of the base of ethylauramine; the phosphate of the base of ethylauramine; the hydrofluoride and phosphate of the base of Auramine G and paper, inks, textile fibers, leather or plastics materials colored by the hydrofluoride of the base of Auramine O; the phosphate of the base of Auramine O; the hydrobromide of the base of ethylauramine; the phosphate of the base of ethylauramine.