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Disperse Yellow 3

Disperse Yellow 3 structure

Disperse Yellow 3 

structure
  • CAS No:

    2832-40-8

  • Formula:

    C15H15N3O2

  • Chemical Name:

    Disperse Yellow 3

  • Synonyms:

    Acetamide,N-[4-[2-(2-hydroxy-5-methylphenyl)diazenyl]phenyl]-;C.I. Disperse Yellow 3;Acetamide,N-[4-[(2-hydroxy-5-methylphenyl)azo]phenyl]-;Acetanilide,4′-(6-hydroxy-m-tolylazo)-;N-[4-[2-(2-Hydroxy-5-methylphenyl)diazenyl]phenyl]acetamide;C.I. 11855;Acetamine Yellow CG;Acetate Fast Yellow G;Acetoquinone Light Yellow 4JLZ;Amacel Yellow G;Artisil Yellow 2GN;Atrisil Direct Yellow G;Calcosyn Yellow GC;Celliton Discharge Yellow GL;Celliton Fast Yellow G;Celliton Fast Yellow GA-CF;Celutate Yellow GH;Cibacete Yellow GBA;Cibacet Yellow 2GC;Cibacet Yellow GBA;Cilla Fast Yellow G;Diacelliton Fast Yellow G;Disperse Yellow G;Disperse Yellow 3;Dispersol Fast Yellow G;Dispersol Printing Yellow G;Durgacet Yellow G;Eastone Yellow GN;Esteroquinone Light Yellow 4JL;Fenacet Fast Yellow G;Interchem Acetate Yellow G;Interchem Hisperse Yellow GH;Kayalon Fast Yellow G;KCA Acetate Fast Yellow G;Microsetile Yellow GR;Miketon Fast Yellow G;Nacelan Fast Yellow CG;Novalon Yellow 2GN;Nyloquinone Yellow 4J;Palanil Yellow G;Perliton Yellow G;Reliton Yellow C;Safaritone yellow G;Serinyl Hosiery Yellow GD;Serisol Fast Yellow GD;Setacyl Yellow G;Setacyl Yellow 2GN;Silotras Yellow TSG;Supracet Fast Yellow G;Terasil Yellow 2GC;Terasil Yellow GBA Extra;Vonteryl Yellow G;Yellow Reliton G;Yellow Z;Disperse Yellow Z;Setacyl Yellow P 2GL;Synten Yellow 2G;4′-[(2-Hydroxy-5-methylphenyl)azo]acetanilide;12227-01-9;12238-70-9;66057-65-6

  • Categories:

    Dyes and Pigments  >  Dye

Description

ChEBI: An azo dye with a structure consisting of acetanilide substituted on the 4-position of the phenyl group with a 6-hydroxy-m-tolylazo group.


C.i. disperse yellow 3 is a brownish-yellow powder. (NTP, 1992)


C.i. disperse yellow 3 is a brownish-yellow powder. (NTP, 1992)|4-(2-hydroxy-5-methylphenylazo)acetanilide is an azo dye with a structure consisting of acetanilide substituted on the 4-position of the phenyl group with a 6-hydroxy-m-tolylazo group. It has a role as a dye and an allergen. It is a monocarboxylic acid amide and a member of azobenzenes. It derives from an azobenzene.

Disperse Yellow 3 Basic Attributes

269.3

269.30

220-600-8

0890872E2E

DTXSID6021450

2927000090

Characteristics

74.05000

4.14740

C.i. disperse yellow 3 is a brownish-yellow powder. (NTP, 1992)

1.2 g/cm3

195 °C

533.9ºC at 760 mmHg

1.604

32.32ug/L(25 ºC)

Keep in a cool, dry, dark location in a tightly sealed container or cylinder. Keep away from incompatible materials, ignition sources and untrained individuals. Secure and label area. Protect containers/cylinders from physical damage.

5.00e-11 mmHg

Abdominal-rat LD50: 8190mg/kg; Abdominal-mouse LD50: 8080 mg/kg

Flammable; decomposes by heating to release toxic nitrogen oxide fumes

Azo dyes can be explosive when suspended in air at certain concentrations. Insoluble in water.

Amides and Imides

Explosive

C.I. DISPERSE YELLOW 3 is an azo compound. Azo, diazo, azido compounds can detonate. This applies in particular to organic azides that have been sensitized by the addition of metal salts or strong acids. Toxic gases are formed by mixing materials of this class with acids, aldehydes, amides, carbamates, cyanides, inorganic fluorides, halogenated organics, isocyanates, ketones, metals, nitrides, peroxides, phenols, epoxides, acyl halides, and strong oxidizing or reducing agents. Flammable gases are formed by mixing materials in this group with alkali metals. Explosive combination can occur with strong oxidizing agents, metal salts, peroxides, and sulfides. This chemical is incompatible with strong oxidizing agents and strong acids (NTP, 1992).

Safety Information

NONH for all modes of transport

2

40-43

22-36/37-46

AC3662000

Xn

Warehouse ventilated, low temperature and dry

Allergic effect

P280

H317-H351

Feinman SE, Doyle EA; Sensitization to Dyes in Textiles and Other Consumer Products; J of Toxicol 7 (3): 195-222 (1988).|DHHS/NTP; Carcinogenesis Studies of C.I. Disperse Yellow 3 in F344/N Rats and B6C3F1 Mice (Feed Study) Technical Report Series No. 222 (1982) NIH Publication No. 82-1778

Flash point data for this chemical are not available; however, it is probably combustible. (NTP, 1992)

|Warning|H317: May cause an allergic skin reaction [Warning Sensitization, Skin]|P201, P202, P261, P272, P280, P281, P302+P352, P308+P313, P321, P333+P313, P363, P405, and P501|H317 (100%): May cause an allergic skin reaction [Warning Sensitization, Skin]|Aggregated GHS information provided by 155 companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|P261, P272, P280, P302+P352, P321, P333+P313, P363, and P501

Fires involving this material can be controlled with a dry chemical, carbon dioxide or Halon extinguisher. (NTP, 1992)

SMALL SPILLS AND LEAKAGE: Should a spill occur while you are handling this chemical, FIRST REMOVE ALL SOURCES OF IGNITION, then you should dampen the solid spill material with 60-70% ethanol and transfer the dampened material to a suitable container. Use absorbent paper dampened with 60-70% ethanol to pick up any remaining material. Seal the absorbent paper, and any of your clothes, which may be contaminated, in a vapor-tight plastic bag for eventual disposal. Solvent wash all contaminated surfaces with 60-70% ethanol followed by washing with a soap and water solution. Do not reenter the contaminated area until the Safety Officer (or other responsible person) has verified that the area has been properly cleaned. STORAGE PRECAUTIONS: You should store this material at ambient temperatures. (NTP, 1992)

RECOMMENDED RESPIRATOR: Where the neat test chemical is weighed and diluted, wear a NIOSH-approved half face respirator equipped with a combination filter cartridge, i.e. organic vapor/acid gas/HEPA (specific for organic vapors, HCl, acid gas, SO2 and a high efficiency particulate filter). (NTP, 1992)

COLOR FROM DISPERSE YELLOW 3 WAS REMOVED BY COAGULATION WITH CATIONIC POLYMERS, EG NALCO 603, NALCO 7132, & CAT-FLOC. POLYMER REQUIREMENTS FOR DISPERSE DYES ARE DETERMINED BY CONCN OF DISPERSING AGENT, EG REAX 85A.|CATIONIC POLYMERS & ALUM EFFECTIVELY DESTABILIZED DISPERSE YELLOW 3 OVER BROAD PH RANGE. RELATION BETWEEN OPTIMUM DOSAGE OF EACH CATIONIC POLYMER & DISPERSANT CONCN WAS DIRECT OR STOICHIOMETRIC.

Toxicity

practically nontoxic

A carcinogenesis bioassay of C. I. Disperse Yellow 3 (87.6% dye), a textile dye, was conducted by feeding diets containing 5,000 or 10,000 ppm of the test substance to groups of 50 F344 rats of either sex for 103 weeks. Similar groups of 50 B6C3F1 mice received diets containing 2,500 or 5,000 ppm of the test substance for 103 weeks. Groups of 50 untreated rats and mice of each sex served as controls. Throughout the bioassay, mean body weights of dosed rats and mice of either sex were lower than those of the controls. Survival of dosed rats of either sex was significantly greater than that of the corresponding controls. No other compound-related clinical signs or effects on survival were observed. Under the conditions of this bioassay, C. I. Disperse Yellow 3 was considered carcinogenic for male F344 rats, causing an increased incidence of neoplastic nodules of the liver; this dye was not carcinogenic for female F344 rats. In addition, the stomach tumors found in the male rats may have been induced by the administration of the test chemical. C. I. Disperse Yellow 3 was carcinogenic for female B6C3F1 mice, as evidenced by the increased incidence of hepatocellular adenomas; C. I. Disperse Yellow 3 was not carcinogenic for male B6C3F1 mice. Also, the increased incidence of lymphoma in female mice may have been associated with the administration of C. I. Disperse Yellow 3.

Beauticians exposed to paraphenylenediamine derivatives in hair dyes, workers dyeing texitle resins, and photographic film developers exposed to color developing solutions not infrequently become sensitized to azo dyes. /Organic dyes/

Drug Information

Chemicals and substances that impart color including soluble dyes and insoluble pigments. They are used in INKS; PAINTS; and as INDICATORS AND REAGENTS. (See all compounds classified as Coloring Agents.)

SYMPTOMS: Exposure to this compound may cause allergic, contact-type dermatitis. It may also cause irritation. ACUTE/CHRONIC HAZARDS: When heated to decomposition this compound emits toxic fumes of nitrogen oxides, carbon dioxide and carbon monoxide. (NTP, 1992)

EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop. SKIN: IMMEDIATELY flood affected skin with water while removing and isolating all contaminated clothing. Gently wash all affected skin areas thoroughly with soap and water. If symptoms such as redness or irritation develop, IMMEDIATELY call a physician and be prepared to transport the victim to a hospital for treatment. INHALATION: IMMEDIATELY leave the contaminated area; take deep breaths of fresh air. IMMEDIATELY call a physician and be prepared to transport the victim to a hospital even if no symptoms (such as wheezing, coughing, shortness of breath, or burning in the mouth, throat, or chest) develop. Provide proper respiratory protection to rescuers entering an unknown atmosphere. Whenever possible, Self-Contained Breathing Apparatus (SCBA) should be used; if not available, use a level of protection greater than or equal to that advised under Protective Clothing. INGESTION: DO NOT INDUCE VOMITING. If the victim is conscious and not convulsing, give 1 or 2 glasses of water to dilute the chemical and IMMEDIATELY call a hospital or poison control center. Be prepared to transport the victim to a hospital if advised by a physician. If the victim is convulsing or unconscious, do not give anything by mouth, ensure that the victim's airway is open and lay the victim on his/her side with the head lower than the body. DO NOT INDUCE VOMITING. IMMEDIATELY transport the victim to a hospital. OTHER: Since this chemical is a known or suspected carcinogen you should contact a physician for advice regarding the possible long term health effects and potential recommendation for medical monitoring. Recommendations from the physician will depend upon the specific compound, its chemical, physical and toxicity properties, the exposure level, length of exposure, and the route of exposure. (NTP, 1992)

IT APPEARS TO BE RESPONSIBLE FOR ALLERGIC, CONTACT TYPE DERMATITIS INDUCED BY NYLON STOCKINGS TINTED BY THIS COLOR. CROSS HYPERSENSITIVITY WAS FOUND WITH PARA-PHENYLENEDIAMINE AMONGST 13 REPORTED CASES OF SENSITIVITY TO CI DISPERSE YELLOW 3.|CLOTHING CONTACT ALLERGY TO DISPERSE YELLOW 3 IS OBSERVED. LITERATURE INDICATES ALLERGY CONFINED TO FEMALES, CASES OBSERVED HAVE SHOWN THAT IT CAN ALSO AFFECT MALES. CHEMICAL INVESTIGATIONS (CHROMATOGRAPHY, IR & NMR SPECTRA) & ALLERGOLOGICAL INVESTIGATION SHOW THAT THE DYE ITSELF IS SENSITIZER, & NOT ANY IMPURITIES.|Most organic azo dyes are potential skin sensitizers, the most important of which are paraphenylenediamine and its analogs. Water soluble azo dyes are more likely to cause clinical sensitization than insoluble dyes. ... In addition to allergic eczematous contact dermatitis, color developing solutions have caused lichen planus like eruptions. /Organic dyes/|The prevalence of textile dye contact sensitization was studied in 145 patients suspected of having allergic contact dermatitis from textile chemicals and in 576 patients with various eczemas. In patch tests, 23 allergic contact dermatitis patients (15.9%) reacted to at least one dye. All showed strong reactions. The dyes producing the most reactions were Disperse Blue 124, Disperse Red 1, Disperse Orange 3, and Disperse Yellow 3. Patch testing of the eczematous patients with these four dyes and a standard series elicited reactions in 19 with eight patients reacting to dyes only. Disperse Blue 124 produced the most reactions in this group. In the standard series, para-phenylenediamine produced the most positive reactions. All para-phenylenediamine positive subjects also reacted to Disperse Orange 3; this was considered to be a cross reaction. It was suggested that contact sensitization to textile disperse dyes is not rare. Females appear to be more susceptible to developing a contact allergy to textile disperse dyes than males.

D Yellow 3

Disperse Yellow 3 Use and Manufacturing

Methods of Manufacturing

CONDENSATION OF DIAZOTIZED P-AMINOACETANILIDE WITH P-CRESOL

Uses

Used for dyeing polyester and its blended fabrics

Production

(1977) PROBABLY GREATER THAN 1.36X10+7 G|(1979) 1.46X10+9 G

ESSENTIALLY 100% AS A DYE

Acetamide, N-[4-[2-(2-hydroxy-5-methylphenyl)diazenyl]phenyl]-: ACTIVE|TRADEMARK FOR SERIES OF DISPERSE DYESTUFFS CHARACTERIZED BY GOOD FASTNESS TO LIGHT, WASHING, ETC. USED FOR DYEING & PRINTING ACETATE FIBERS. /CELLITON/

Today, paper chromatography has largely been displaced by TLC, which is more rapid, sensitive and reproducible. Separations have been carried out on a large variety of sorbents, including silica gel, alumina, Kieselgur, cellulose and polyamide, and mixtures of these, using various solvent systems. ... Isolation of water-soluble azo colors from the food matrix has been carried out by the so-called wool-thread method, by adsorption on alumina columns, by liquid-liquid extraction using quinoline, by quarternary ammonium compounds, and by liquid ion exchanges. It was claimed that polyamide is a relatively more selective adsorbent for water-soluble acidic dyes and carboxymethylcellulose for basic dyes.|Earlier methods relied on paper chromatography. ... More recent work involves thin-layer chromatography. A survey of separation characteristics of various sorbents, such as silica gel, alumina, 1:1 mixtures of silica gel and alumina, starch, cellulose and polyamide powder, used with a wide variety of solvents indicates the techniques capable of separating most lipid-soluble azo colors. ... A method was described for the isolation of lipid-soluble colors from fats and chocolate by liquid/liquid partition and adsorption chromatography followed by identification by thin-layer chromatography.

Computed Properties

Molecular Weight:269.30
XLogP3:2.9
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:3
Exact Mass:269.116426730
Monoisotopic Mass:269.116426730
Topological Polar Surface Area:74
Heavy Atom Count:20
Complexity:351
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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