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1-((2-Chloro-4-nitrophenyl)azo)-2-naphthol

HCID 17778
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Basic information

CAS
2814-77-9
Standard SMILES
O=[N+]([O-])c1ccc(N=Nc2c(O)ccc3ccccc23)c(Cl)c1
InChIKey
XLTMWFMRJZDFFD-UHFFFAOYSA-N
Molecular formula
C16H10ClN3O3
Average molar mass
327.72 g/mol
Monoisotopic mass
327.0410689

Names & identifiers

Preferred name
1-((2-Chloro-4-nitrophenyl)azo)-2-naphthol
IUPAC
1-[(2-chloro-4-nitrophenyl)diazenyl]naphthalen-2-ol
English name
Pigment Red 4
Molecular formula
C16H10ClN3O3
Molecular weight
327.72

Names & synonyms

1-((2-Chloro-4-nitrophenyl)azo)-2-naphthol1-[(2-Chloro-4-nitrophenyl)azo]-2-naphthol220-562-2RefChem:5725512814-77-9Flaming RedPermanent Red RCarnelio Red RFlame tonesD and C Red No. 36D&C Red No. 36CI 12085
Show more names
2-NaptholC.I. 12085AKA228RED 36Red 4812094redD&CRED36redno.228Red 12094HSDB 7720
OE8ZA0KN9Z2-Naphthalenol, 1-((2-chloro-4-nitrophenyl)azo)-1-[(2-chloro-4-nitrophenyl)diazenyl]naphthalen-2-olMFCD000590951-(2-Chloro-4-nitrophenyl)azo-2-naphtholPermansa RedTiger OrangeBlazing Red

Database identifiers

CAS
2814-77-9
PubChem CID
17778
DTXSID
DTXSID7044637
UNII
OE8ZA0KN9Z
EC Number
220-562-2
Nikkaji
J34.110J

Properties

Computed structural properties

XLogP
5
Topological polar surface area
90.8 Ų
Hydrogen bond donors
1
Hydrogen bond acceptors
5
Rotatable bonds
2
Heavy atoms
23
Formal charge
0
Complexity
456

Experimental & physicochemical properties

Polymers · 2 items

Plastics -> N.a.

Plastics -> Pigments agents

Cosmetics · 2 items

Cosmetics ingredient -> Colorant

Cosmetic colorant; Hair dyeing

Food AdditivesDrugs, Cosmetics -> FDA Regulatory Status of Color Additives
Color/FormIntense yellowish red
DecompositionWhen heated to decomposition it emits toxic fumes of Cl- and NOx.
Melting Point276 °C
Physical DescriptionCBI

Physicochemical properties

Boiling point
558.9 · 558.9±50.0 °C(Predicted)
Density
1.4414 · 1.4414 (rough estimate)
refractive index

Safety & regulation

Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.

GHS classification

GHS Classification · 5 items

This chemical does not meet GHS hazard criteria for 87.1% (270 of 310) of all reports.

Warning

H319 (12.9%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]

P264+P265, P273, P280, P305+P351+P338, P337+P317, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 310 reports by companies from 5 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Hazard information

Regulatory Information · 5 items

Chemical: 2-Naphthalenol, 1-[(2-chloro-4-nitrophenyl)azo]-

Hazard Traits - Bioaccumulation; Environmental Persistence

2-Naphthalenol, 1-[2-(2-chloro-4-nitrophenyl)diazenyl]- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 2-Naphthalenol, 1-[2-(2-chloro-4-nitrophenyl)diazenyl]- are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)

REACH registered substance: 1-[(2-chloro-4-nitrophenyl)azo]-2-naphthol (EC: 220-562-2)

2-Naphthalenol, 1-(2-chloro-4-nitrophenyl)azo-: Does not have an individual approval but may be used under an appropriate group standard

Other Safety InformationIMAP assessments - 2-Naphthalenol, 1-[(2-chloro-4-nitrophenyl)azo]-: Human health tier I assessment
FDA RequirementsAll batches of this color additive when used for drugs shall meet the specifications, uses and restrictions, and labeling regulations contained in 21 CFR Part 74 and be certified in accordance with regulations in 21 CFR Part 80.
Hazard Classes and CategoriesEye Irrit. 2 (12.9%)

Chemistry & industry

Uses & manufacturing

Uses · 3 items

Pigment in cosmetic lip products only 3% w/w max ; externally applied cosmetics only

Used in some inks and in low cost articles such as detergents, floor polishes, colored pencils

Pigment (printing inks, resins, paper, cosmetics)

U.S. Production · 2 items

2023: 50,000 - <250,000 lb

Production volumes for non-confidential chemicals reported under the Inventory Update Rule. [Table#7383]

Consumer UsesPigment
Industry UsesPigment
Methods of Manufacturing · 2 items

... Manufactured by diazotization of 2-chloro-4-nitrobenzenamine in acid medium and coupling with 2-naphthalenol in acid medium.

2-Chloro-4-nitroaniline + beta-napthol (diazotisation)

Household ProductsCosmetics product ingredient: 2-Naphthalenol, 1-[(2-chloro-4-nitrophenyl)azo]- (Red 36; Pigment red 4; CI 12085; Aka228)
Use Classification · 3 items

Plastics -> Pigments agents

Cosmetics -> Cosmetic colorant; Hair dyeing

Plastics -> Polymer Type -> N.a.

General Manufacturing Information · 5 items

Synthetic Dye and Pigment Manufacturing

2-Naphthalenol, 1-[2-(2-chloro-4-nitrophenyl)diazenyl]-: ACTIVE

The color additive D&C Red No. 36 /Pigment Red 4/ may be safely used for coloring ingested drugs, other than mouthwashes and dentifrices, in amounts not to exceed 1.7 mg/daily dose of the drug for drugs that are taken continuously only less than 1 year. For drugs taken continuously for longer than 1 year, the color additive shall not be used for amounts to exceed 1.0 mg/daily dose of the drug. /Pigment Red 4/ may be safely used for coloring externally applied drugs in amounts consistent with current good manufacturing practice.

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Compound notes

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On this pageBasic informationNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
1.647 · 1.6470 (estimate)
Colour Index
12085 · 12085
pka
13.5 · 13.50±0.50(Predicted)
form
powder to crystal
color
Orange to Brown
Henry's Law Constant
1.1 · 1.1×107 mol/(m3Pa) at 25℃, HSDB (2015)
Cosmetics Ingredients Functions
HAIR DYEINGCOLORANT
LogP
5.252 · 5.252 (est)
CAS DataBase Reference
2814 · 2814-77-9(CAS DataBase Reference)
FDA 21 CFR
74.1336 · 74.1336; 74.2336; 82.1336
EWG's Food Scores
2 · 2-5
FDA UNII
8 ZA0KN9Z · OE8ZA0KN9Z
EPA Substance Registry System
4 · C.I. Pigment Red 4 (2814-77-9)
Symbol(GHS)
7 · GHS07
Signal word
Warning
Hazard statements
315 · H315-H319
Precautionary statements
264 · P264-P280-P302+P352-P337+P313-P305+P351+P338-P362+P364-P332+P313
Hazard Codes
Xi
Risk Statements
36 · 36
Safety Statements
26 · 26
RTECS
3436000 · QL3436000
TSCA
TSCA listed
HS Code
3204.17 · 3204.17.0485
Hazardous Substances Data
2814 · 2814-77-9(Hazardous Substances Data)
REACH Registrations
Active

Safety & protection

Disposal Methods · 1 item

SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational exposure 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, aquatic, and plant life; and conformance with environmental and public health regulations.

Toxicology

Environmental Fate · 3 items

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 2.3X10+5(SRC), determined from a structure estimation method(2), indicates that C.I. Pigment Red 4 is expected to be immobile in soil(SRC). Volatilization of C.I. Pigment Red 4 from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 9.3X10-13 atm-cu m/mole(SRC), using a fragment constant estimation method(3). C.I. Pigment Red 4 is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 1.6X10-10 mm Hg(SRC), determined from a fragment constant method(4). Biodegradation data were not available(SRC, 2009).

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 2.3X10+5(SRC), determined from a structure estimation method(2), indicates that C.I. Pigment Red 4 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 9.3X10-13 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 6.6(6) and a regression-derived equation(7), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Biodegradation data were not available(SRC, 2009).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), C.I. Pigment Red 4, which has an estimated vapor pressure of 1.6X10-10 mm Hg at 25 °C(SRC), determined from a fragment constant method(2), is expected to exist solely in the particulate phase in the ambient atmosphere. Particulate-phase C.I. Pigment Red 4 may be removed from the air by wet or dry deposition(SRC). C.I. Pigment Red 4 contains functional groups that are typically chromophores which absorb at wavelengths >290 nm(3); therefore C.I. Pigment Red 4 may be susceptible to direct photolysis by sunlight(SRC).

Soil Adsorption/Mobility · 1 item

Using a structure estimation method based on molecular connectivity indices(1), the Koc of C.I. Pigment Red 4 can be estimated to be 2.3X10+5(SRC). According to a classification scheme(2), this estimated Koc value suggests that C.I. Pigment Red 4 is expected to be immobile in soil.

Artificial Pollution SourcesC.I. Pigment Red 4's production and use in cosmetic lip products(1), printing inks(2), and limited use as a drug colorant(3) may result in its release to the environment through various waste streams(SRC).
Environmental Bioconcentration · 1 item

An estimated BCF of 10 was calculated for C.I. Pigment Red 4(SRC), using an estimated log Kow of 6.6(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).

Volatilization from Water/Soil · 1 item

The Henry's Law constant for C.I. Pigment Red 4 is estimated as 9.3X10-13 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that pigment red 4 is expected to be essentially nonvolatile from water surfaces(2). The Henry's Law constant of C.I. Pigment Red 4 indicates that volatilization from moist soil surfaces is not expected(SRC). C.I. Pigment Red 4 is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 1.6X10-10 mm Hg(SRC), determined from a fragment constant method(3).

Non-Human Toxicity Excerpts · 3 items

/LABORATORY ANIMALS: Chronic Exposure or Carcinogenicity/ D&C Red No. 36, a drug and cosmetic dye commonly used for coloring lipsticks, was evaluated for its carcinogenic potential in male and female Wistar rats. ... In the present study, 50 male and 50 female rats in each group were given diets containing D&C Red No. 36 at 2 different concentrations, 1,000 ppm and 2,000 ppm, for 78 weeks and sacrificed at week 98. It was found that dye treatment had no significant effect on the survival of either male or female animals /nor on/ body weight gain in males. However, body weight gain of treated females was slightly lower than that of the control group. Histopathological assessment demonstrated a number of benign and malignant tumors to have developed in various organs of both dye treated and control groups. In male rats, benign liver tumors were found at incidences of 16.7% and 18.8% of the low (1,000 ppm) and high (2,000 ppm) dose groups, respectively, similar to the 20% for the control group. Malignant tumors of the thyroid gland were observed only in the low dose and control groups, at 4.2% and 2%, respectively. In the high dose group, the incidences of lung, liver, urinary bladder and soft tissue cancers were 4.2%, 2.1%, 2.1% and 2.1%, respectively, only one soft tissue cancer being observed in a control group animal. In females, benign tumors were observed in the liver and mammary glands. The incidences of liver tumors in the low and high dose groups were 12.8% and 16%, respectively, and 6% in the control group. Values for mammary gland tumors were 10.6%, 10%, and 18% respectively. Malignant tumors were also observed in various other organs, including the uterus, lung, kidney, thyroid, thymus and salivary gland, but the incidences were very low (about 2-4%) and in dye treated male and female rats were not statistically different from those in the control animals. The results of the present study thus demonstrated that D&C Red No. 36 at the concentrations of 1,000 ppm and 2,000 ppm in the diet is not carcinogenic either to male or female Wistar rats. While the occurrence of benign liver tumors in female rats may be related to dye treatment, the lack of any apparent dose-dependence or any statistically significant difference from the control group (P = 0.06) suggests that this is unlikely.

/GENOTOXICITY/ This dye has been shown to exhibit mutagenic activity towards Salmonella typhimurium TA 98 in the presence of S9 mix.

/GENOTOXICITY/ ... The Salmonella/mammalian microsome assay was used to test a number of colorants commonly used in drugs and cosmetics. These agents were mostly lakes, which are dye-alumina complexes, or insoluble salts from which the dyes were solubilized prior to mutagenicity testing. Agents causing mutations in Salmonella typhimurium were D & C Red No. 19, D & C Red No. 36 and D & C Orange No. 17. Rat liver microsomes were used.

Environmental Abiotic Degradation · 1 item

C.I. Pigment Red 4 is not expected to undergo hydrolysis in the environment due to the lack of functional groups that hydrolyze under environmental conditions(1). C.I. Pigment Red 4 contains functional groups which are typically chromophores that absorb at wavelengths >290 nm(1); therefore C.I. Pigment Red 4 may be susceptible to direct photolysis by sunlight(SRC).

Probable Routes of Human Exposure · 1 item

Occupational exposure to C.I. Pigment Red 4 may occur through inhalation of dust and dermal contact with this compound at workplaces where C.I. Pigment Red 4 is produced or used. Use data indicate that the general population may be exposed to C.I. Pigment Red 4 via dermal contact with consumer products and ingestion of limited drugs containing this compound. (SRC)

Environmental Fate/Exposure Summary · 1 item

C.I. Pigment Red 4's production and use in printing inks, resins, paper, cosmetic lip products, and limited use as a drug colorant may result in its release to the environment through various waste streams. If released to air, an estimated vapor pressure of 1.6X10-10 mm Hg at 25 °C indicates C.I. Pigment Red 4 will exist solely in the particulate phase in the atmosphere. Particulate-phase C.I. Pigment Red 4 will be removed from the atmosphere by wet or dry deposition C.I. Pigment Red 4 contains functional groups that are typically chromophores which absorb at wavelengths >290 nm; therefore C.I. Pigment Red 4 may be susceptible to direct photolysis by sunlight. If released to soil, C.I. Pigment Red 4 is expected to be immbobile based upon an estimated Koc of 2.3X10+5. Volatilization from moist soil surfaces is not expected to be an important fate process based upon an estimated Henry's Law constant of 9.3X10-13 atm-cu m/mole. C.I. Pigment Red 4 is not expected to volatilize from dry soil surfaces based upon its vapor pressure. Biodegradation data were not available. If released into water, C.I. Pigment Red 4 is expected to adsorb to suspended solids and sediment based upon the estimated Koc. Volatilization from water surfaces is not expected to be an important fate process based upon this compound's estimated Henry's Law constant. An estimated BCF of 10 suggests bioconcentration in aquatic organisms is low. Hydrolysis is not expected to be an important environmental fate process since this compound lacks functional groups that hydrolyze under environmental conditions. Occupational exposure to C.I. Pigment Red 4 may occur through inhalation of dust and dermal contact with this compound at workplaces where C.I. Pigment Red 4 is produced or used. Use data indicate that the general population may be exposed to C.I. Pigment Red 4 via dermal contact with consumer products and ingestion of limited drugs containing this compound. (SRC)

Antidote and Emergency Treatment · 3 items

/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/

Regulatory information

FDA RequirementsAll batches of this color additive when used for drugs shall meet the specifications, uses and restrictions, and labeling regulations contained in 21 CFR Part 74 and be certified in accordance with regulations in 21 CFR Part 80.

Safety data

tsca
TSCA listed
rtecs
QL3436000
hs_code
3204.17.0485
risk_code
36
Signal word
Warning
Symbol(GHS)
GHS07
hazard_code
Xi
safety_code
26
Hazard statements
H315-H319
REACH Registrations
Active
Precautionary statements
P264-P280-P302+P352-P337+P313-P305+P351+P338-P362+P364-P332+P313
Hazardous Substances Data
2814-77-9(Hazardous Substances Data)

Pigment is not used in foods as it is prohibited by the FDA.

... Show poor bleed and bake resistance and a tendency to bloom in enamels. use... has declined markedly as a result of greater quality demands by the coatings industry

Applications

UsesPigment Red 4 (cas# 2814-77-9) is a useful research chemical. Dyes and metabolites, Environmental Testing.Is used in process for treating keratin materials using Acrylic Anhydride polymer in oily dispersions and plasticizer and Amine.

Upstream & downstream products

Upstream raw materials

Urea2-Chloro-4-nitroanilineSodium nitriteHydrochloric acidSodium hydroxide2-Naphthol4-[(2-hydroxy-1-naphthyl)azo]benzenesulphonic acid