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Home > Encyclopedia > 1-(Phenylazo)-2-naphthol

1-(Phenylazo)-2-naphthol

1-(Phenylazo)-2-naphthol structure

1-(Phenylazo)-2-naphthol 

structure
  • CAS No:

    842-07-9

  • Formula:

    C16H12N2O

  • Chemical Name:

    1-(Phenylazo)-2-naphthol

  • Synonyms:

    2-Naphthalenol,1-(2-phenyldiazenyl)-;C.I. Solvent Yellow 14;2-Naphthalenol,1-(phenylazo)-;Sudan Yellow;2-Naphthol,1-phenylazo-;1-(2-Phenyldiazenyl)-2-naphthalenol;C.I. 12055;Brasilazina Oil Orange;Calcogas Orange NC;Ceres Orange R;Dispersol Yellow PP;Enial Orange I;Fast Oil Orange I;Fast Orange;Fat Orange G;Fat Orange I;Fat Orange R;Fat Orange 4A;Fat Orange RS;Grasal Orange;Grasan Orange R;Hidaco Oil Orange;Lacquer Orange VG;Oil Orange;Oil Orange E;Oil Orange R;Oil Orange Z-7078;Oil Orange 2B;Oil Orange 31;Oil Orange 2311;Oil Orange 7078-V;Oil Orange PEL;Oleal Orange R;Orange R Fat Soluble;Orange 3RA Soluble in Grease;Organol Orange;Orient Oil Orange PS;Petrol Orange Y;Plastoresin Orange F 4A;Resinol Orange R;Silotras Orange TR;Solvent Yellow 14;Somalia Orange I;Stearix Orange;Sudan 1;Sudan Orange R;Sudan Orange RA New;Tertrogras Orange SV;Toyo Oil Orange;Waxoline Yellow I;Waxoline Yellow IM;Waxoline Yellow IP;Waxoline Yellow IS;Sudan I;1-(Phenylazo)-2-naphthol;Orange Pel;1-Benzeneazo-2-naphthol;Benzeneazo-β-naphthol;1-Phenylazo-β-naphthol;Sudan Orange RA;Fat Soluble Orange;Oil Soluble Orange;2-Hydroxynaphthyl-1-azobenzene;2-Hydroxy-1-(phenylazo)naphthalene;α-Phenylazo-β-naphthol;Morton Orange Y;1-(Phenylazo)-2-hydroxynaphthalene;1-(2-Hydroxynaphthyl)azobenzene;Oil orange PS;1-Phenylazo-2-naphthalenol;Waxoline Orange EP-FW;Sudan Orange 220;C.I. Disperse Yellow 97;104407-03-6;1846566-64-0

  • Categories:

    Dyes and Pigments  >  Dye

Description

Sudan I is an organic compound, typically classified as an azo dye.


C.i. solvent yellow 14 appears as dark reddish-yellow leaflets or orange powder. Slight odor. (NTP, 1992)


C.i. solvent yellow 14 appears as dark reddish-yellow leaflets or orange powder. Slight odor. (NTP, 1992)|Sudan I is an azo compound. It has a role as a dye. It derives from a 2-naphthol.

1-(Phenylazo)-2-naphthol Basic Attributes

248.28

248.28

212-668-2

48I7IBB68J

51524|11227

DTXSID4021135

BRICK-RED CRYSTALS (LEAFLETS FROM ETHANOL)

2928000090

Characteristics

44.95000

4.24

Orange to red or brown Powder

1.1055 g/cm3 @ Temp: 17.2 °C

134 °C

443.7±28.0 °C at 760 mmHg

290.2±13.3 °C

1.634

H2O: 0.5 g/L (30 ºC)

Amber Vial, Refrigerator, Under Inert Atmosphere

mmo-sat 300 ng/plate SCIEAS 236,933,87

Thermal decomposition to emit toxic nitrogen oxide fumes

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

Azo, Diazo, Azido, Hydrazine, and Azide Compounds

Explosive

C.I. SOLVENT YELLOW 14 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

68-53-43-40-36/37/38

61-46-36/37-22-36-26

QL4900000

Xn,Xi

Warehouse ventilated, low temperature and dry

Incompatible with strong oxidizing agents.

P280

H317-H341-H351-H413

DHHS/NTP; Toxicology & Carcinogenesis Studies of C.I. Solvent Yellow 14 in F344/N Rats and B6C3F1 Mice (Feed Study) Technical Report Series No. 226 (1982) NIH Publication No. 82-1782

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, P273, 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 2771 companies from 6 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|H341: Suspected of causing genetic defects [Warning Germ cell mutagenicity]|P201, P202, P260, P281, P308+P313, P314, P405, and P501

Fires involving this material can be controlled with a dry chemical, carbon dioxide or Halon extinguisher. A water spray may also be used. (NTP, 1992)

SMALL SPILLS AND LEAKAGE: If a spill of this chemical occurs, FIRST REMOVE ALL SOURCES OF IGNITION, then you should dampen the solid spill material with acetone and transfer the dampened material to a suitable container. Use absorbent paper dampened with acetone to pick up any remaining material. Seal your contaminated clothing and the adsorbent paper in a vapor-tight plastic bag for eventual disposal. Solvent wash all contaminated surfaces with acetone 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 protect this material from exposure to light. Keep it away from oxidizing materials and store it 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)

Toxicity

A carcinogenesis bioassay of C.I. solvent Yellow 14 (94.1% pure), a widely used monoazo dye, was conducted by feeding diets containing 250 or 500 ppm of C.I. Solvent Yellow 14 to groups of 50 F344 rats of either sex for 103 weeks. Similar groups of 50 B6C3F1 mice received diets containing 500 or 1,000 ppm of C.I. Solvent Yellow 14 for 103 weeks. Groups of 50 untreated rats and mice of either sex served as controls. Throughout the bioassay, mean body weights of dosed rats and mice were slightly lower than those of controls. No compound-related clinical signs or effects on survival were observed. Increases in nonneoplastic lesions included cardiac valve fibrosis for male and female rats, lymphoid hyperplasia of the lung for male rats, and for female rats, bile duct hyperplasia, focal atrophy of the pancreatic acinus, and nephropathy. None of these effects were observed in mice. Under the conditions of this bioassay, C.I. Solvent Yellow 14 was carcinogenic in male and female F344/N rats, as evidenced by increaed incidences of neoplastic nodules of the liver. C.I. Solvent Yellow 14 was not carcinogenic for B6C3F1 mice of either sex.

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

Drug Information

Substances that increase the risk of NEOPLASMS in humans or animals. Both genotoxic chemicals, which affect DNA directly, and nongenotoxic chemicals, which induce neoplasms by other mechanism, are included. (See all compounds classified as Carcinogens.)|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.)

ADMIN ORALLY TO RABBITS, THIS DYESTUFF ... UNDERGOES REDUCTIVE SCISSION, BUT IS ALSO METABOLIZED BY HYDROXYLATION OF BENZENE RING.|YIELDS 2,6-DIHYDROXY-1-PHENYLAZONAPHTHALENE, 2-HYDROXY -1-(PARA-HYDROXYPHENYLAZO)NAPHTHALENE, & 1-PHENYLHYDRAZO-2-NAPHTHOL IN RABBITS & RATS. /FROM TABLE/|... ORAL ADMIN IN RABBITS, 1.2% ... UNCHANGED, 1.5% AS 1-PARA-HYDROXYPHENYLAZO-2-NAPHTHOL, 44% AS FREE & CONJUGATED PARA-AMINOPHENOL, 24% AS PARA-AMINOPHENYLGLUCURONIDE, 0.5% AS ORTHO-AMINOPHENOL & 1.1% AS ANILINE; PARA-ACETAMIDOPHENYL GLUCURONIDE, 1-PARA-HYDROXYPHENYLAZO-2-NAPHTHOL GLUCURONIDE & 1-AMINO-2-NAPHTHOL ... .|... GLUCURONIDES OF 4',6-DIHYDROXY-1-PHENYLAZO-2-NAPHTHOL & 4'- & 6-HYDROXY-1-PHENYLAZO-2-NAPHTHOL WERE PRESENT IN ... BILE & URINE OF RABBITS. URINE ALSO CONTAINED 1-AMINO-2-NAPHTHYL HYDROGEN SULFATE, 1-AMINO-2-NAPHTHYL GLUCURONIDE & N-GLUCURONIDES OF 1-PHENYLHYDRAZO-2-NAPHTHOL & OF 4'-HYDROXY-1-PHENYLHYDRAZO-2-NAPHTHOL ... .|For more Metabolism/Metabolites (Complete) data for C.I. SOLVENT YELLOW 14 (6 total), please visit the HSDB record page.|Sudan I has known human metabolites that include 1-Amino-2-naphthol and aniline.

Sudan I activated by pre-incubation with microsomal enzymes of rat livers covalently binds to DNA from calf thymus. Benzenediazonium ion formed from Sudan I by activation with microsomal enzymes is the principal active metabolite, which binds to DNA. Enzymatic hydrolysis of modified 14(C)-labelled DNA, followed by separation of deoxynucleosides on a Sephadex G-10 column revealed that deoxyguanosine is the principal target for the binding of activated Sudan I.

SYMPTOMS: Exposure to this compound may result in irritation. ACUTE/CHRONIC HAZARDS: This compound may cause irritation and is harmful if swallowed. It is also harmful if inhaled. When heated to decomposition it emits toxic fumes of carbon monoxide, carbon dioxide and nitrogen oxides. (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)

SKIN SENSITIVITY OF RED 225 & ITS IMPURITIES DETERMINED BY PATCH TEST. COMMERCIAL PREPN SHOWED POSITIVE REACTIONS IN ALL 6 SUBJECTS. SUDAN I ISOLATED & IDENTIFIED. SUDAN I ALSO SHOWED POSITIVE REACTIONS IN ALL 6 SUBJECTS.|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/|"Kumkums" are colored cosmetics frequently applied to the center of the forehead by Hindu women. Pigmented allergic contact dermatitis to "kumkum" was reported recently. It was associated with Brilliant Lake Red R and Sudan I allergy. These might be the causitive allergens. Three of 7 brands of red "kumkums" analyzed by gas chromatography-mass spectrophotometry were found to contain various concentrations of Sudan I. They ranged from 2.789 mg/g to 8.694 mg/g. Sudan I is probably the cause of pigmented allergic contact dermatitis in red "kumkum".

1-phenylazo-2-hydroxynaphthalene

1-(Phenylazo)-2-naphthol Use and Manufacturing

Methods of Manufacturing

Using aniline and 2-naphthol as raw materials, the former is first diazotized and then coupled with the latter to obtain the product. After filtering, drying and crushing, the finished product can be obtained. .

Uses

A food azo-dye, a liver and urinary bladder carcinogen for rodents and a potent contact allergen and sensitizer for humans.

Production

(1977) PROBABLY GREATER THAN 1.59X10+7 GRAMS|(1979) 1.59X10+8 GRAMS

ESSENTIALLY 100% AS A DYE

2-Naphthalenol, 1-(2-phenyldiazenyl)-: ACTIVE|ACCORDING TO USA INDUST SOURCES, WHEN SUDAN I IS NOT USED IN DRUGS OR COSMETICS, ITS MFR & TESTING DO NOT CONFORM TO RIGID CHEM SPECIFICATIONS, & ITS COMPOSITION MAY VARY IN ORDER TO MEET CUSTOMER SHADE & INTENSITY REQUIREMENTS.

DETERMINATION BY HIGH PERFORMANCE LIQUID CHROMATOGRAPHY, THIN LAYER CHROMATOGRAPHY.|Standard soln of Sudan I were prepared by dissolving 0.025 g of the dye in 50 ml of acetone, and then diluting with methanol. After distillation of 500 ml water containing Sudan I, residual dye in the condenser and other apparatus were washed with up to 100 ml acetone, which also improved formation of emulsion. Recovery of Sudan I was 88.5 to 93.9% in the pH range 1 to 11. Sudan I was then extracted by modified mixing extraction using hexane as solvent. Constant recoveries of 92.5 to 93.3% were obtained if the volume of distillate was in the range 400 to 450 ml. Recovery of Sudan I was also constant when the pH of the initial water varied from 1 to 13 (92.8 to 98.8%). Mean recovery of 2 ug Sudan I added to river water and to sea water was 96.4%. Detection of Sudan I was possible by high performance liquid chromatography (HPLC) with a methanol/water ratio of 90:10. The detection limit for a 500 ml water sample was 0.2 ug/l.|The identification of lipid soluble colors is usually carried out by chromatographic methods. ... 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. /Lipid soluble cmpd/

Computed Properties

Molecular Weight:248.28
XLogP3:4.1
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:2
Exact Mass:248.094963011
Monoisotopic Mass:248.094963011
Topological Polar Surface Area:45
Heavy Atom Count:19
Complexity:312
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

Material

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