Yellow No. 2
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Yellow No. 2
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CAS No:
85-84-7
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Formula:
C16H13N3
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Chemical Name:
Yellow No. 2
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Synonyms:
2-Naphthalenamine,1-(2-phenyldiazenyl)-;C.I. Solvent Yellow 5;2-Naphthalenamine,1-(phenylazo)-;2-Naphthylamine,1-phenylazo-;1-(2-Phenyldiazenyl)-2-naphthalenamine;C.I. 11380;1-Benzeneazo-β-naphthylamine;Cerisol Yellow AB;Dolkwal Yellow AB;Ext. D and C Yellow No. 9;FD and C Yellow No. 3;Grasal Yellow;Oil Yellow A;Oil Yellow AB;Oil Yellow AB Pure;Yellow AB;A.F. Yellow No. 2;Yellow No. 2;C.I. Food Yellow 10;1-Benzeneazo-2-naphthylamine;1-(Phenylazo)-2-naphthylamine;2-Amino-1-phenylazonaphthalene;1-Phenylazo-2-aminonaphthalene;Solvent Yellow 5;NSC 11228;Japan Yellow 404;Yellow No. 404;Japan Yellow No. 404;1-Phenyldiazenylnaphthalen-2-amine;167973-57-1
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CAS No:
Description
Orange or red platelets. Insoluble in water; soluble in alcohol and oils.
Yellow AB is a member of azobenzenes.
Yellow No. 2 Basic Attributes
247.29500
247.29
201-636-3
3VSI4D701X
11228
DTXSID0058932
Red platelets from absolute alcohol|Orange or red platelets|Orange crystals
2927000090
Characteristics
50.74000
5.41860
1.173g/cm3
102-104 °C
458.035ºC at 760 mmHg
230.811ºC
1.647
0.3mg/L(37 ºC)
6.51X10-7 mm Hg at 25 deg C (est)
LDLo oral in mouse: 1gm/kg
Henry's Law constant = 4.35X10-10 atm-cu m/mol at 25 °C (est)
Alcoholic solution becomes redder with hydrochloric acid addition, and is unaltered by sodium hydroxide addition|Turns blue in concentration sulfurid acid|Hydroxyl radical reaction rate constant = 4.9X10-11 cu cm/molec-sec at 25 °C (est)
Safety Information
SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational harm/injury/toxicity or environmental contamination. Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in soil or water; effects on animal and plant life; and conformance with environmental and public health regulations.
...DELISTED FOR INTERNAL USE IN 1959: FED REG 24, 883 (1959), CA 53; 12505A. DELISTED ALSO FOR EXTERNAL USE IN 1960.
Toxicity
C.I. Food Yellow 10's production and use as a biological stain(1) may result in its release to the environment through various waste streams(SRC).
TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 6.6X10+4(SRC), determined from a structure estimation method(2), indicates that C.I. Food Yellow 10 is expected to be immobile in soil(SRC). Volatilization of C.I. Food Yellow 10 from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 5.1X10-10 atm-cu m/mole(SRC), using a fragment constant estimation method(3). C.I. Food Yellow 10 is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 6.5X10-7 mm Hg at 25 °C(SRC), determined from a fragment constant method(4). Biodegradation data in soil were not available(SRC,2011).|AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 6.6X10+4(SRC), determined from a structure estimation method(2), indicates that C.I. Food Yellow 10 is expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(3) based upon an estimated Henry's Law constant of 5.1Z10-10 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). According to a classification scheme(5), an estimated BCF of 10(SRC), from an estimated log Kow of 4.77(6) and a regression-derived equation(7), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Biodegradation data in water were not available(SRC,2011). However, azo dyes are hydrophobic compounds, suggesting they will partition strongly to bottom sediments where reductive cleavage of the azo linkage may occur. This transformation process could result in the release of potentially hazardous aromatic amines to the water column(8), in this case, aniline and 1,2 naphthylamine(SRC).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), C.I. Food Yellow 10, which has an estimated vapor pressure of 6.5X10-7 mm Hg at 25 °C(SRC), determined from a fragment constant method(2) will exist in both the vapor and particulate phases in the ambient atmosphere. Vapor-phase C.I. Food Yellow 10 is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC); the half-life for this reaction in air is estimated to be 3 hours(SRC), calculated from its rate constant of 4.9X10-11 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). Particulate-phase C.I. Food Yellow 10 may be removed from the air by wet or dry deposition(SRC). C.I. Food Yellow 10 contains chromophores that absorb at wavelengths >290 nm(4), and therefore may be susceptible to direct photolysis by sunlight(SRC).
The rate constant for the vapor-phase reaction of C.I. Food Yellow 10 with photochemically-produced hydroxyl radicals has been estimated as 4.9X10-11 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 3 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). C.I. Food Yellow 10 is expected to undergo hydrolysis in the environment due to the presence of functional groups that hydrolyze under environmental conditions(2). C.I. Food Yellow 10 does contains chromophores that absorb at wavelengths >290 nm(2), and therefore may be susceptible to direct photolysis by sunlight(SRC).
An estimated BCF of 10 was calculated in fish for C.I. Food Yellow 10(SRC), using an estimated log Kow of 4.77(1) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is low(SRC).
Using a structure estimation method based on molecular connectivity indices(1), the Koc of C.I. Food Yellow 10 can be estimated to be 6.6X10+4suggests that C.I. Food Yellow 10 is expected to be immobile in soil.
The Henry's Law constant for C.I. Food Yellow 10 is estimated as 5.1X10-10 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that C.I. Food Yellow 10 is expected to be essentially nonvolatile from water and moist soil surfaces(2). C.I. Food Yellow 10 is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 6.5X10-7 mm Hg(SRC), determined from a fragment constant method(3).
Occupational exposure to C.I. Food Yellow 10 may occur through inhalation and dermal contact with this compound at workplaces where C.I. Food Yellow 10 is produced or used. Use data indicate that the general population may have be exposed to C.I. Food Yellow 10 via ingestion and dermal contact with consumer products containing C.I. Food Yellow 10, which are no longer approved uses. (SRC)
Drug Information
The color accumulates in fatty tissues of the body after its sc injection and is eliminated slowly: thus, 250 mg/kg bw /yellow Ab/ administered to rabbits /was/ excreted 17 days later in urine.
/SRP:/ Immediate first aid: Ensure that adequate decontamination has been carried out. If patient is not breathing, start artificial respiration, preferably with a demand valve resuscitator, bag-valve-mask device, or pocket mask, as trained. Perform CPR if necessary. Immediately flush contaminated eyes with gently flowing water. Do not induce vomiting. If vomiting occurs, lean patient forward or place on the left side (head-down position, if possible) to maintain an open airway and prevent aspiration. Keep patient quiet and maintain normal body temperature. Obtain medical attention. /Poisons A and B/|/SRP:/ Basic treatment: Establish a patent airway (oropharyngeal or nasopharyngeal airway, if needed). Suction if necessary. Watch for signs of respiratory insufficiency and assist ventilations if needed. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Monitor for pulmonary edema and treat if necessary ... . Monitor for shock and treat if necessary ... . Anticipate seizures and treat if necessary ... . For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with 0.9% saline (NS) during transport ... . Do not use emetics. For ingestion, rinse mouth and administer 5 mL/kg up to 200 mL of water for dilution if the patient can swallow, has a strong gag reflex, and does not drool ... . Cover skin burns with dry sterile dressings after decontamination ... . /Poisons A and B/|/SRP:/ Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious, has severe pulmonary edema, or is in severe respiratory distress. Positive-pressure ventilation techniques with a bag valve mask device may be beneficial. Consider drug therapy for pulmonary edema ... . Consider administering a beta agonist such as albuterol for severe bronchospasm ... . Monitor cardiac rhythm and treat arrhythmias as necessary ... . Start IV administration of D5W /SRP: "To keep open", minimal flow rate/. Use 0.9% saline (NS) or lactated Ringer's if signs of hypovolemia are present. For hypotension with signs of hypovolemia, administer fluid cautiously. Watch for signs of fluid overload ... . Treat seizures with diazepam or lorazepam ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Poisons A and B/
1-phenylazo-2-naphthylamine
Yellow No. 2 Use and Manufacturing
Formerly by coupling of diazotized aniline with 2-naphthylamine|/Yellow AB/ can be synthesized by coupling diazotized aniline with 2-naphthylamine ...
Biological stain.
(1972) NO COMMERCIAL PRODN REPORTED SINCE 1960|(1975) NOT PRODUCED COMMERCIALLY
2-Naphthalenamine, 1-(2-phenyldiazenyl)-: ACTIVE|One set of specifications for Yellow AB require that product contain minimum of 99.9% pure color... It has been reported, however, that this color cannot be produced commercially with any assurance that it does not contain 2-naphthylamine, a known carcinogen...|Color additives were initially regulated in the United States under the U.S. Department of Agriculture's (USDA) Bureau of Chemistry. In 1906, the Food and Drugs Act was passed by Congress, which prohibited the use of poisonous or deleterious colors in confectionery and the coloring or staining of food to conceal damage or inferiority. In 1927, responsibility of the Food and Drugs Act was transferred to FDA. Increasing government oversight, the Federal Food, Drug, and Cosmetic Act (FFDCA) was passed in 1938 and established the three following categories for colors: FD&C: colors used in foods, drugs and cosmetics; D&C: colors used in drugs and cosmetics when in contact with mucous membranes or ingested; and Ext. D&C: colors used in products applied externally.|The FDA has declared this color unsafe due to the impurity beta-naphthylamine, a proven carcinogen.
CHROMATOGRAPHIC SEPARATION & SPECTROPHOTOMETRIC DETERMINATION.
Computed Properties
Molecular Weight:247.29
XLogP3:4.3
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:2
Exact Mass:247.110947427
Monoisotopic Mass:247.110947427
Topological Polar Surface Area:50.7
Heavy Atom Count:19
Complexity:309
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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