Grundinformationen
- Standard-SMILES
CC(=O)C(N=Nc1ccc(-c2ccc(N=NC(C(C)=O)C(=O)Nc3ccccc3)c(Cl)c2)cc1Cl)C(=O)Nc1ccccc1- InChIKey
GNCOVOVCHIHPHP-UHFFFAOYSA-N- Summenformel
- C32H26Cl2N6O4
- Durchschnittliche Molmasse
- 629,5 g/mol
- Monoisotopische Masse
- 628,1392587
Namen und Bezeichner
- Bevorzugter Name
- Pigment Yellow 12
- IUPAC
- 2-[[4-[4-[(1-anilino-1,3-dioxobutan-2-yl)diazenyl]-3-chlorophenyl]-2-chlorophenyl]diazenyl]-3-oxo-N-phenylbutanamide
- Englischer Name
- Pigment Yellow 12
- Summenformel
- C32H26Cl2N6O4
- Molmasse
- 629.49
Namen und Synonyme
Weitere Namen anzeigen
Datenbank-Bezeichner
- CAS
6358-85-6、86349-57-7- PubChem CID
- 186342
- DTXSID
DTXSID1021451- UNII
- N52TUS5TRY
- EC Number
- 228-787-8
- Nikkaji
- J81.914J
Eigenschaften
Berechnete Struktureigenschaften
- XLogP
- 8,1
- Polarare Oberfläche (TPSA)
- 142 Ų
- H-Brücken-Donoren
- 2
- H-Brücken-Akzeptoren
- 8
- Frei drehbare Bindungen
- 11
- Schwere Atome
- 44
- Formalladung
- 0
- Komplexität
- 979
Experimentelle und physikochemische Eigenschaften
Melting Point
593 to 608 °F (decomposes) (NTP, 1992)
320 °C
Physical Description
Diarylanilide yellow is an odorless fine yellow powder. (NTP, 1992)
Liquid; CBI; Dry Powder; Wet Solid
Yellow odorless solid; [CAMEO] Yellow powder; [MSDSonline]
Physikochemische Eigenschaften
- Schmelzpunkt
- 312 · 312-320 ºC
- Siedepunkt
- 805.4 · 805.4±65.0 °C(Predicted)
- Dichte
- 1.4735 · 1.4735 (rough estimate)
- Brechungsindex
- 1.735 · 1.7350 (estimate)
- pka
- 8.33 · 8.33±0.59(Predicted)
- Aggregatzustand
- Solid:nanomaterial
- Wasserlöslichkeit
- 0.1 G/100 · <0.1 G/100 ML AT 22 ºC
- Kosmetik-Inhaltsstoffe Funktionen
- HAIR DYEING
- InChIKey
- GNCOVOVCHIHPHP-UHFFFAOYSA-N
- SMILES
- ClC1=C(C=CC(C2C=CC(=C(C=2)Cl)N=NC(C(=O)C)C(=O)NC2C=CC=CC=2)=C1)N=NC(C(=O)C)C(=O)NC1C=CC=CC=1
- LogP
- 2.1 at · 2.1 at 23℃ and pH7
- CAS Datenbank
- 6358 · 6358-85-6(CAS DataBase Reference)
- EPA chemische Informationen
- 12 · C.I. Pigment Yellow 12 (6358-85-6)
Sicherheit und Regulatorisches
GHS-Klassifizierung
GHS Classification
This chemical does not meet GHS hazard criteria for 99.7% (360 of 361) of all reports.
Not Classified;Reported as not meeting GHS hazard criteria by 360 of 361 companies (only 0.3% companies provided GHS information). For more detailed information, please visit ECHA C&L website.
Aggregated GHS information provided per 361 reports by companies from 3 notifications to the ECHA C&L Inventory.;Reported as not meeting GHS hazard criteria per 360 of 361 reports by companies.;There is 1 notification provided by 1 of 361 reports by companies with hazard statement code(s).;Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website.
Warning
H335: May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]
Gefahrenhinweise
Regulatory Information
Chemical: Butanamide, 2,2'-[(3,3'-dichloro[1,1'-biphenyl]-4,4'-diyl)bis(azo)]bis[3-oxo-N-phenyl-
Chemical: Butanamide, 2,2'-[(3,3'-dichloro[1,1'-biphenyl]-4,4'-diyl)bis(azo)]bis[3-oxo-N-phenyl-, labeled with carbon-14
Butanamide, 2,2'-[(3,3'-dichloro[1,1'-biphenyl]-4,4'-diyl)bis(2,1-diazenediyl)]bis[3-oxo-N-phenyl- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Butanamide, 2,2'-[(3,3'-dichloro[1,1'-biphenyl]-4,4'-diyl)bis(2,1-diazenediyl)]bis[3-oxo-N-phenyl- 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)
Status: Active Update: 06-05-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/15824
Butanamide, 2,2'-[(3,3'-dichloro[1,1'-biphenyl]-4,4'-diyl)bis(azo)]bis[3-oxo-N-phenyl-: Does not have an individual approval but may be used under an appropriate group standard
Other Safety Information
IMAP assessments - Butanamide, 2,2'-[(3,3'-dichloro[1,1'-biphenyl]-4,4'-diyl)bis(azo)]bis[3-oxo-N-phenyl-, labeled with carbon-14: Human health tier I assessment;IMAP assessments - Butanamide, 2,2'-[(3,3'-dichloro[1,1'-biphenyl]-4,4'-diyl)bis(azo)]bis[3-oxo-N-phenyl-, labeled with carbon-14: Environment tier I assessment
IMAP assessments - Selected benzidine-congener-based pigments: Human health tier II assessment;IMAP assessments - Butanamide, 2,2'-[(3,3'-dichloro[1,1'-biphenyl]-4,4'-diyl)bis(azo)]bis[3-oxo-N-phenyl-: Environment tier I assessment
Special Reports
ITC/USEPA; Information Review #133A (Draft) Pigment Yellow 12 CI, 21090 (1/25/88).
Bioassay of Diarylanilide for Possible Carcinogenicity (1978) Technical Rpt Series No. 30 DHEW Pub No. (NIH) 78-830, U.S. Department of Health Education and Welfare, National Cancer Institute, Bethesda, MD 20014
Hazard Classes and Categories
Not Classified
Specific target organ toxicity - Single exposure - Category 3 (Respiratory tract irritation)
Sicherheit und Schutzausrüstung
First Aid
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. If symptoms (such as redness or irritation) develop, immediately transport the victim to a hospital.;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. If symptoms (such as wheezing, coughing, shortness of breath, or burning in the mouth, throat, or chest) develop, call a physician and be prepared to transport the victim to a hospital. 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. (NTP, 1992)
Nonfire Spill Response
SMALL SPILLS AND LEAKAGE: If you spill this chemical, you should dampen the solid spill material with water, then transfer the dampened material to a suitable container. Use absorbent paper dampened with water to pick up any remaining material. Seal your contaminated clothing and the absorbent paper in a vapor-tight plastic bag for eventual disposal. Wash all contaminated surfaces 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 chemical at ambient temperatures, and keep it away from oxidizing materials. (NTP, 1992)
Disposal Methods
SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.
Personal Protective Equipment (PPE)
RECOMMENDED RESPIRATOR: Where the neat test chemical is weighed and diluted, wear a NIOSH-approved half face respirator equipped with an organic vapor/acid gas cartridge (specific for organic vapors, HCl, acid gas and SO2) with a dust/mist filter. (NTP, 1992)
Toxikologische Informationen
Environmental Fate
TERRESTRIAL FATE: Based on a recommended classification scheme(1), an estimated Koc value of 68(SRC), determined from an estimated log Kow(2) and a recommended regression-derived equation(3), indicates that C.I. Pigment Yellow 12 will have high mobility in soil(SRC). As C.I. Pigment Yellow 12 may act as an ionic compound in the environment, volatilization of this compound will not be important from moist soil surfaces(4,SRC). Based on limited data, C.I. Pigment Yellow 12 is expected to be resistant to aerobic biodegradation in soil(SRC); in the MITI test this compound is resistant to biodegradation; 0 biodegradation occurred after a period of two weeks(5).
AQUATIC FATE: Based on a recommended classification scheme(1), an estimated Koc value of 68(SRC), determined from an estimated log Kow(2) and a recommended regression-derived equation(1), indicates that C.I. Pigment Yellow 12 will not adsorb to suspended solids and sediment in water(SRC). As C.I. Pigment Yellow 12 may act as an ionic compound, volatilization from water surfaces is not expected(3,SRC). According to a classification scheme(4), experimental BCF values ranging from 0.38 to 5.4(5,SRC), suggests that bioconcentration in aquatic organisms is low(SRC). Based on limited data, C.I. Pigment Yellow 12 is expected to be resistant to aerobic biodegradation in water(SRC). Using the MITI test, this compound is resistant to biodegradation; 0 biodegradation occurred after a period of two weeks(5).
ATMOSPHERIC FATE: The ionic nature of C.I. pigment Yellow 12 in the environment makes this compound essentially non-volatile(1,SRC).
Ongoing Test Status
The following link will take the user to the National Toxicology Program (NTP) Test Agent Search Results page, which tabulates all of the "Standard Toxicology & Carcinogenesis Studies", "Developmental Studies", and "Genetic Toxicity Studies" performed with this chemical. Clicking on the "Testing Status" link will take the user to the status (i.e., in review, in progress, in preparation, on test, completed, etc.) and results of all the studies that the NTP has done on this chemical. [http://ntp-apps.niehs.nih.gov/ntp_tox/index.cfm?fuseaction=ntpsearch.searchresults&searchterm=6358-85-6]
Soil Adsorption/Mobility
The Koc of C.I. Pigment Yellow 12 is estimated as approximately 67(SRC), using an estimated log Kow(1) and a regression-derived equation(2,SRC). According to a recommended classification scheme(3), this estimated Koc value suggests that C.I. Pigment Yellow 12 has high mobility in soil(SRC). However, the ionic nature of the pigment may slow down or prevent leaching(SRC).
TSCA Test Submissions
Acute oral toxicity was evaluated in 10 young adult Charles River-CD male rats administered single doses of C.I. pigment yellow 12 (2,2'-((3,3'-dichloro(1,1'-biphenyl)-4,4'-diyl)bis(azo))bis(3-oxo -N-phenylbutanamide)) as a suspension in peanut oil at a level of 11,000 mg/kg of body weight. Mortality was not observed in any animal; an LD50 value of greater then 11,000 mg/kg body weight was reported. Clinical observations included yellow feces for a few days after dosing. Gross necropsy findings were not reported.
Human Toxicity Excerpts
... An incr in color printed newspapers might be a new source of clinical allergy to azo dyes. Patch tests were performed in 32 patients with an established p-aminoazobenzene allergy using a series of important azo dyes used in offset printing ink (Pigment Yellow 12, Pigment Yellow 13, Pigment Red 53, Pigment Red 57), as well as with dye containing inks and specimens of color printed newspaper containing these azo dyes. In 25 out of the 32 patients (78%), positive patch tests were seen to textile azo dyes, in particular to Disperse Orange 3 (24 patients). In none of the 32 patients were reactions observed to the azo dyes used in printing ink, to the inks used or to the color printed paper specimens, indicating that these products were apparently not a cause of contact dermatitis in /this/ group of patients with azo dye sensitization.
Carcinogen Classification
Diarylanilide yellow
TR-030: Bioassay of Diarylanilide Yellow for Possible Carcinogenicity (CASRN 6358-85-6) (1978 )
09/26/77
No Evidence
No Evidence
No Evidence
Environmental Bioconcentration
When carp were exposed to 0.1 mg/l C.I. Pigment Yellow 12, the experimental BCF ranged from 0.38 to 3.2 over a period of 6 weeks. When carp were exposed to 0.01 mg/l C.I. Pigment Yellow 12, the experimental BCF ranged from 2.4 to 5.4 over a 6 week period(1). According to a classification scheme(2), these BCF values suggest that bioconcentration in aquatic organisms is low.
Non-Human Toxicity Excerpts
BRILLIANT YELLOW; ANIONIC; NOT DAMAGING IN RABBIT EYE TEST.
MICE & RATS TOLERATED CI PIGMENT YELLOW 12 UP TO DIETARY LEVEL OF 9000 PPM EQUIVALENT TO 1960 OR 630 MG/KG/DAY WITH NO SIGNS OF INTOXICATION.
Pigment yellow 12 was tested for mutagenicity in the Salmonella/microsome preincubation assay using a protocol approved by the National Toxicology Program. Yellow 12 was tested over a wide range of doses (0, 100, 333, 1000, 3333, and 10,000 ug/plate) in four Salmonella typhimurium strains (TA98, TA100, TA1535, and TA1537) in the presence and absence of Aroclor-induced rat or hamster liver S9. Yellow 12 was negative in these tests and all dose levels tested caused formation of a precipitate.
/SRP: Pigment yellow 12, carcinogenicity summary response, N (non-carcinogenic)
For more Non-Human Toxicity Excerpts (Complete) data for C.I. PIGMENT YELLOW 12 (7 total), please visit the HSDB record page.
Probable Routes of Human Exposure
Processes in which dried dye is handled have the greatest potential for employee exposure during the manufacture or repackaging of benzidine-based dyes. ... During use of benzidine-based dyes, the greatest potential for exposure would be expected to be among dye-weighers who handle dry powders. /Benzidine-based dyes/
NIOSH (NOES Survey 1981-1983) has statistically estimated that 63,185 workers (4,180 of these are female) are potentially exposed to C.I. Pigment Yellow 12 in the US(1). Occupational exposure may be through inhalation and dermal contact with this compound at workplaces where C.I. Pigment Yellow 12 is produced or used(SRC). The general population will be exposed to C.I. Pigment Yellow 12 via dermal contact with products containing this compound(SRC).
Regulatorische Informationen
Regulatory Information
Chemical: Butanamide, 2,2'-[(3,3'-dichloro[1,1'-biphenyl]-4,4'-diyl)bis(azo)]bis[3-oxo-N-phenyl-
Chemical: Butanamide, 2,2'-[(3,3'-dichloro[1,1'-biphenyl]-4,4'-diyl)bis(azo)]bis[3-oxo-N-phenyl-, labeled with carbon-14
Butanamide, 2,2'-[(3,3'-dichloro[1,1'-biphenyl]-4,4'-diyl)bis(2,1-diazenediyl)]bis[3-oxo-N-phenyl- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Butanamide, 2,2'-[(3,3'-dichloro[1,1'-biphenyl]-4,4'-diyl)bis(2,1-diazenediyl)]bis[3-oxo-N-phenyl- 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)
Status: Active Update: 06-05-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/15824
Butanamide, 2,2'-[(3,3'-dichloro[1,1'-biphenyl]-4,4'-diyl)bis(azo)]bis[3-oxo-N-phenyl-: Does not have an individual approval but may be used under an appropriate group standard
Sicherheitsdaten
- tsca
- TSCA listed
- Giftige Stoffe Daten
- 6358-85-6(Hazardous Substances Data)
Chemie und Industrie
Pharmakologische Informationen
Metabolism/Metabolites
Various bacteria and yeast normally found in the small and large intestine can reduce the azo bond in /some/ benzidine-based dyes and release benzidine. /Benzidine-based dyes/
Humans as well as other mammals can change (metabolize) /some/ benzidine-based dyes back to benzidine. The major organ in which /some/ benzidine-based dyes are metabolized to benzidine is the liver, but other organs also can do this to a greater or lesser degree. /Benzidine-based dyes/
Absorption, Distribution and Excretion
PIGMENTS /INCLUDING PIGMENT YELLOW 12/ WERE NOT ABSORBED AFTER CHRONIC ORAL INGESTION & DID NOT UNDERGO METABOLIC SPLITTING TO 3,3-DICHLOROBENZIDINE OR 3,3-DIMETHYLBENZIDINE /IN MICE OR RATS/.
The average environmental exposure levels of four of the workers /in a dye manufacturing facility/ were 4.3, 5.2, 11.7, and 17.4 mg total particulate/cu m. The corresponding urinary concentrations of benzidine average 52, 11, 10, and 112 ppb, respectively /SRP: from the precursor during manufacturing/. /Benzidine-based dyes/
The oral and dermal absorption and distribution of water insoluble (WI) 3,3'-dichlorobenzidine (DCB) based pigments were evaluated in Fischer 344 rats. Chlorodiane blue (CDB) and pigment yellow 12 (PY-12) ... were synthesized from DCB and labeled with (14)C. Rats were given oral doses of ... 1.11 mg/kg labeled WI PY-12 for absorption studies or 0.99 mg/kg for a 24 hour balance study. ... In an 8 hour oral study of CDB, blood samples taken from 10 min to 8 hr showed radioactivity at background levels. Dermal application resulted in background levels, as well. After the oral dose, all of the administered dose was accounted for in feces. For PY-12, radioactivity in blood at background levels after oral or dermal application. The entire dose was accounted for in feces after the oral dose. ...
Verwendung und Herstellung
Uses
Used in printing inks, lacquers, inks for wrappers, tinplate printing, wallpaper, rubber, PVC, other polymers, paper coloring, textile printing, and linoleum; [HSDB]
Pulp and Paper Processing [Category: Industry];Painting (Pigments, Binders, and Biocides) [Category: Paint];Textiles (Printing, Dyeing, or Finishing) [Category: Industry]
Printing inks and lacquers giving good heat resistance, high tinctorial strength and high transparency; stoving lacquers and inks for wrappers, tinplate printing and wallpaper. In rubber, PVC, U/F and P/F resins as fastness to rubber curing and to solvents is superior to that of CI Pigment Yellow 1. Paper, textile printing, linoleum.
Pigments (lacquers, printing inks, plastics, rubber).
Printing inks, lacquers resistant to heat and solvents, in rubber and resins, in paper coloring, textile printing.
Plastics -> Typical concentration range in plastic materials -> 2%
U.S. Imports
(1972) 4.50X10+7 GRAMS (PRINCPL CUSTMS DISTS)
(1975) 2.82X10+7 GRAMS (PRINCPL CUSTMS DISTS)
U.S. Production
2023: 10,000,000 - <25,000,000 lb;2022: 10,000,000 - <50,000,000 lb;2021: 10,000,000 - <25,000,000 lb;2020: 10,000,000 - <25,000,000 lb
(1972) 1.86X10+9 GRAMS
(1975) 1.77X10+9 GRAMS
(1984) 7.03X10+9 GRAMS
13,892X10+3 lb
1.066X10+7 kg (1993)
Methods of Manufacturing
3,3'-Dichlorobenzidene dihydrochloride + acetoactanilide (diazotisation/azo coupling).
Condensation of 3,3'-dichlorobenzidine di-diazotate with acetoacetanilide.
Use Classification
Plastics -> Polymer Type -> Polyolefin-I; PUR; Polyolefin-II; PVC (soft); ABS; PVC (rigid); PET; PMMA; PA; PC; (E)PS
Cosmetics -> Hair dyeing
Plastics -> Pigments agents
General Manufacturing Information
Paint and Coating Manufacturing;Printing Ink Manufacturing;Printing and Related Support Activities;Custom Compounding of Purchased Resins
Butanamide, 2,2'-[(3,3'-dichloro[1,1'-biphenyl]-4,4'-diyl)bis(2,1-diazenediyl)]bis[3-oxo-N-phenyl-: ACTIVE
Anwendungen
BeschreibungC.I. Pigment Yellow-12, 21090 [6358-85-6] is a very important diarylide pigment and one of the most important organic pigments.
VerwendenPigment Yellow 12 is an organic azo dye used in a variety of materials, including food packaging plastics. Pigment Yellow 12 has been used to prepare organic dye nanoparticles by laser ablation.
Vor- und nachgelagerte Produkte
Vorgelagerte Rohstoffe
Anbieter46 Anbieter
Zugehörige Reaktionen
Verknüpfte Notizen
Wird geladen…