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C.I. Disperse Yellow 3

HCID 17811
NotesReactions
Basic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
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Basic information

CAS
2832-40-8
Standard SMILES
CC(=O)Nc1ccc(N=Nc2cc(C)ccc2O)cc1
InChIKey
PXOZAFXVEWKXED-UHFFFAOYSA-N
Molecular formula
C15H15N3O2
Average molar mass
269.3 g/mol
Monoisotopic mass
269.11642673

Overview

C.I. Disperse Yellow 3 can cause cancer according to an independent committee of scientific and health experts.

Names & identifiers

Preferred name
C.I. Disperse Yellow 3
IUPAC
N-[4-[(2-hydroxy-5-methylphenyl)diazenyl]phenyl]acetamide
English name
Disperse Yellow 3
Molecular formula
C15H15N3O2
Molecular weight
269.3

Names & synonyms

Disperse yellow 32832-40-8C.I. Disperse Yellow 3Disperse yellow GDisperse yellow ZAmacel Yellow GPalanil yellow GReliton yellow CArtisil Yellow GPerliton yellow GCelutate yellow ghCibacet yellow gba
Show more names
yellowzZlut diYellow ZCI 11855NCI-C53781c.i.3/11855C.I. 3/11855estoneyellowgnfenacetyellowg
Serisol fast yellow gdAcetate Fast Yellow GCibacet yellow 2gcCibacete yellow gbaNovalon yellow 2gnCalcosyn Yellow GCSafaritone yellow GAcetamine Yellow CG

Database identifiers

CAS
2832-40-8
PubChem CID
17811
DTXSID
DTXSID6021450
ChEMBL
CHEMBL1590721
ChEBI
CHEBI:53617
UNII
0890872E2E

Properties

Computed structural properties

XLogP
2.9
Topological polar surface area
74.1 Ų
Hydrogen bond donors
2
Hydrogen bond acceptors
4
Rotatable bonds
3
Heavy atoms
20
Formal charge
0
Complexity
351

Experimental & physicochemical properties

Chemical ClassesDyes -> Azo Dyes
CosmeticsCosmetic ingredients (Disperse Yellow 3) -> CIR (Cosmetic Ingredient Review)
LogP2.85
Solubility · 2 items

less than 0.1 mg/mL at 64 °F (NTP, 1992)

SOL IN ACETONE, ETHANOL & BENZENE

Melting Point514 to 518 °F (NTP, 1992)
Physical Description · 2 items

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

Brownish-yellow powder; [CAMEO]

Collision Cross Section167.8 Ų [M+H]+ [CCS Type: DT; Buffer gas: N2; Ionization: APCI+; Dataset: TOXCAST; Source Identifier: DTXSID6021450]

Physicochemical properties

Melting point
268 · 268-270 °C(lit.)

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 · 6 items

Warning

H317: May cause an allergic skin reaction [Warning Sensitization, Skin]

P203, P261, P272, P280, P302+P352, P318, P321, P333+P317, P362+P364, P405, and P501 (click each P-code to see the statement)

Warning

H317 (100%): May cause an allergic skin reaction [Warning Sensitization, Skin]

P203, P261, P272, P280, P302+P352, P318, P321, P333+P317, P362+P364, P405, and P501 (click each P-code to see the statement)

Hazard information

Regulatory Information · 3 items

Chemical: Acetamide, N-[4-[(2-hydroxy-5-methylphenyl)azo]phenyl]-

Hazard Traits - Carcinogenicity

Acetamide, N-[4-[(2-hydroxy-5-methylphenyl)azo]phenyl]-: Does not have an individual approval but may be used under an appropriate group standard

Other Safety InformationIMAP assessments - Acetamide, N-[4-[(2-hydroxy-5-methylphenyl)azo]phenyl]-: Human health tier II assessment
Fire HazardsFlash point data for this chemical are not available; however, it is probably combustible. (NTP, 1992)
Health HazardsSYMPTOMS: Exposure to this compound may cause allergic, contact-type dermatitis. It may also cause irritation.
Hazards SummaryAllergic contact dermatitis reported in textile workers; [Kanerva, p. 1791] May cause allergic contact dermatitis; [CAMEO] Danger of skin sensitization; [MAK]
Reactive GroupAmides and Imides
Special Reports · 2 items

Chemistry & industry

Uses & manufacturing

Uses · 6 items

CIR ingredient: Disperse Yellow 3

Used in textile dyes and in some semi-permanent hair dyes; [Kanerva, p. 1791]

Banned in UE for garment dyeing because potential skin sensitizer; Ullmann]

Textiles (Printing, Dyeing, or Finishing) [Category: Industry]

FOR DYEING TEXTILES, SHEEPSKINS & FURS, FOR COLORING POLYMETHYL METHACRYLATE & NYLON.

IN SURFACE DYEING OF CELLULOSE ACETATE

U.S. Imports · 2 items

(1977) 8.99X10+4 G (PRINCPL CUSTMS DISTS)

(1979) 1.12X10+7 G (PRINCPL CUSTMS DISTS)

U.S. Production · 2 items

(1977) PROBABLY GREATER THAN 1.36X10+7 G

(1979) 1.46X10+9 G

Consumption PatternsESSENTIALLY 100% AS A DYE
Methods of ManufacturingCONDENSATION OF DIAZOTIZED P-AMINOACETANILIDE WITH P-CRESOL
General Manufacturing Information · 2 items

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/

Applications · 4 items

DescriptionDisperse yellow 3 is an azoic dye responsible for occupational contact dermatitis in workers in the textile industry. It can be found in some semipermanent hair dyes.

UsesDisperse yellow 3 is used in dyeing textiles, sheepskins and furs; in coloring polymethyl methacrylate and nylon; in the surface dyeing of cellulose acetate; stocking dye.

UsesDisperse Yellow 3 is an azo disperse dye which is water insoluble. Disperse Yellow 3 can be used to dye polyester and acetate fibers. Dyes and metabolites, Environmental Testing.

Related reactions

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Compound notes

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On this pageBasic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
EC Number
220-600-8
Nikkaji
J33.575D
Boiling point
412.44 °C · 412.44°C (rough estimate)
Density
1.1385 · 1.1385 (rough estimate)
refractive index
1.56 · 1.5600 (estimate)
storage temp.
-20 °C, · -20°C, Inert atmosphere
solubility
Chloroform (Very Slightly), DMSO (Slightly, Sonicated), Methanol (Slightly, Sonicated)
Colour Index
11855 · 11855
form
powder
pka
8.74 · 8.74±0.43(Predicted)
color
Brownish-yellow powder
Water Solubility
32.32 ug/L · 32.32ug/L(25 ºC)
λmax
357 nm · 357 nm
ε(extinction coefficient)
6500 at · ≥6500 at 354-360nm in ethanol and water at 0.02g/L
BRN
1915225 · 1915225
Henry's Law Constant
6.6 · 6.6×105 mol/(m3Pa) at 25℃, Duchowicz et al. (2020)
Major Application
cleaning productscosmeticsenvironmentalfood and beveragespersonal care
Cosmetic Ingredient Review (CIR)
3 · Disperse Yellow 3 (2832-40-8)
InChI
1S/C15H15N3O2/c1-10-3-8-15(20)14(9-10)18-17-13-6-4-12(5-7-13)16-11(2)19/h3-9,20H,1-2H3,(H,16,19)
InChIKey
PXOZAFXVEWKXED-UHFFFAOYSA-N
SMILES
CC(=O)Nc1ccc(cc1)N=Nc2cc(C)ccc2O
Toxicology and Carcinogenesis
3 · Carcinogenesis Bioassay of Disperse Yellow 3 (CASRN 2832-40-8) in F344 Rats and B6C3F1 Mice (Feed Study)
CAS DataBase Reference
2832 · 2832-40-8(CAS DataBase Reference)
EWG's Food Scores
4 · 4
FDA UNII
890872 E2E · 0890872E2E
Proposition 65 List
3 · C.I. Disperse Yellow 3
IARC
3 · 3 (Vol. 48) 1990
NIST Chemistry Reference
3 · Disperse yellow 3,ci 11855(2832-40-8)
EPA Substance Registry System
3 · C.I. Disperse Yellow 3 (2832-40-8)
UNSPSC Code
85151701 · 85151701
NACRES
47 · NA.47
Symbol(GHS)
7 · GHS07,GHS08
Signal word
Warning
Hazard statements
317 · H317-H351
Precautionary statements
202 · P202-P261-P272-P280-P302+P352-P308+P313
PPE
3 · Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges
Hazard Codes
Xn
Risk Statements
40 · 40-43
Safety Statements
22 · 22-36/37-46
WGK Germany
2 · 2
RTECS
3662000 · AC3662000
TSCA
TSCA listed
HS Code
32041100 · 32041100
Storage Class
11 · 11 - Combustible Solids
Hazard Classifications
2 Skin · Carc. 2Skin Sens. 1
Hazardous Substances Data
2832 · 2832-40-8(Hazardous Substances Data)
Toxicity
50 intraperitoneal · LD50 intraperitoneal in mouse: 8080mg/kg

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

Reactivity AlertsExplosive
Reactivity Profile · 1 item

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).

Air and Water ReactionsAzo dyes can be explosive when suspended in air at certain concentrations. Insoluble in water.
Hazard Classes and Categories · 4 items

Skin Sens. 1 (100%)

Carcinogenicity - category 2

Skin sensitization - Category 1

Carc. 2

Safety & protection

Fire FightingFires involving this material can be controlled with a dry chemical, carbon dioxide or Halon extinguisher. (NTP, 1992)
First Aid · 1 item

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.

Cleanup Methods · 2 items

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.

Nonfire Spill Response · 1 item

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.

Personal Protective Equipment (PPE) · 1 item

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)

Toxicology

Adverse EffectsSkin Sensitizer - An agent that can induce an allergic reaction in the skin.
Toxicity Summary · 2 items

The CIR Panel concludes that the available data are insufficient to support the safety of Disperse Yellow 3 for use in cosmetic products.

The available data are insufficient to support safety, but the ingredient is not used

Ongoing Test Status · 1 item

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=2832-40-8]

Human Toxicity Excerpts · 4 items

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.

Carcinogen Classification · 6 items

Disperse Yellow 3

Group 3: Not classifiable as to its carcinogenicity to humans

Volume 48: (1990) Some Flame Retardants and Textile Chemicals, and Exposures in the Textile Manufacturing Industry

1990

1989

C.I. Disperse Yellow 3

Non-Human Toxicity Excerpts · 2 items

1 ADENOMA & 6 CARCINOMAS OF BLADDER ... IN 7/23 STOCK MICE SURVIVING 25 WK AFTER IMPLANTATION OF PELLETS OF CI DISPERSE YELLOW 3 IN CHOLESTEROL. ... 4 PAPILLOMAS & 5 CARCINOMAS OF BLADDER OCCURRED IN 77 MICE GIVEN IMPLANTS OF CHOLESTEROL ALONE & SURVIVING @ 25 WK. RESULTS WERE OF BORDERLINE SIGNIFICANCE.

POLLUTANT IN RIVER WATER SUPPLY OF NORTHERN GEORGIA CAUSED ABERRATIONS IN SQUASH PREPN FROM R CLAMITANS, INCL ARE GAPS, DICENTRICS, RINGS & BREAKS.

Evidence for Carcinogenicity · 1 item

Evaluation: There is limited evidence for the carcinogenicity of Disperse Yellow 3 in experimental animals. No data were available from studies in humans on the carcinogenicity of Disperse Yellow 3. Overall evaluation: Disperse Yellow 3 is not classifiable as to its carcinogenicity to humans (Group 3).

Probable Routes of Human ExposureBeauticians 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/
National Toxicology Program Studies · 1 item

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.

Safety data

PPE
Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges
wgk
2
tsca
TSCA listed
rtecs
AC3662000
hs_code
32041100
Toxicity
LD50 intraperitoneal in mouse: 8080mg/kg
risk_code
40-43
Signal word
Warning
Symbol(GHS)
GHS07,GHS08
hazard_code
Xn
safety_code
22-36/37-46
Storage Class
11 - Combustible Solids
Hazard statements
H317-H351
Hazard Classifications
Carc. 2Skin Sens. 1
Precautionary statements
P202-P261-P272-P280-P302+P352-P308+P313
Hazardous Substances Data
2832-40-8(Hazardous Substances Data)

General DescriptionBrownish-yellow powder.

Preparation methods

PreparationN-(4-aminophenyl)acetamide diazo, and to a p-Cresolcoupling

Upstream & downstream products

Upstream raw materials

p-Cresol4'-Aminoacetanilide

Suppliers56 total

Hebei Chuanghai Biotechnology Co., Ltd+86-17732866630 · [email protected]
湖北盛明安化工有限公司13928406992 · [email protected]
杭州品高化工有限公司0571-87658025 · [email protected]
上海赛可锐生物科技有限公司021-58000709 13120558703 · [email protected]
梯希爱(上海)化工贸易有限公司021-61109150 · [email protected]
Protheragen-ING+86-15618352007 · [email protected]
山东洛克化工有限公司17653113209 13065062079 · [email protected]
上海艾梯西生物科技有限公司18721763493 · [email protected]
超彩实业有限公司0574-83851061 · [email protected]
TargetMol 中国(陶术生物)400-821-0310 15002144251 · [email protected]
艾科试剂4008-755-333 18080918076 · [email protected]
苏州亚科科技股份有限公司0512-87182055 13451648594 · [email protected]
上海将来实业股份有限公司400-0066400 13621662912 · [email protected]
成都零六生物科技有限公司400-1166-196 13458535857 · [email protected]
天津普西唐生物医药科技有限公司010-60605840 · [email protected]
杭州杰恒化工有限公司0571-87396432 · [email protected]
陕西缔都医药化工有限公司029-81024372 17792795018 · [email protected]
天津阿尔塔科技有限公司022-6537-8550 15522853686 · [email protected]
山东智尚新材料有限公司+8617653113209 · [email protected]
武汉匠信生物科技有限公司19272768272 18007157445 · [email protected]
艾吉析科技(上海)有限公司17717235263 17717235263 · [email protected]
河南沃咖斯生物科技有限公司18537671377 · [email protected]
杭州迈昂进出口有限公司0571-56076803 18667038366 · [email protected]
南京艾比克斯生化科技有限公司025-87193546 18652950785 · [email protected]
上海西陇生化科技有限公司021-52907766-8042
上海源叶生物科技有限公司18916372613 · [email protected]
成都标样生物科技有限公司028-81700200 13308200041 · [email protected]
上海颖心实验室设备有限公司021-021-59178156 15300768757 · [email protected]
山东西亚化学有限公司4009903999 13395398332 · [email protected]
湖北世腾化工科技有限公司19086915685 18971850150 · [email protected]
山东小野化学股份有限公司0539-6362799 20)
Shaanxi Didu New Materials Co. Ltd+86-86-17392712779 +86-13289823923 · [email protected]
杭州洁汉化工有限公司+86-571-86217390; +8618058761490 · [email protected]
江苏艾康生物医药研发有限公司025-58859352 13913916777 · [email protected]
河南天孚化工有限公司+86-0371-55170693 +86-19937530512 · [email protected]
厦门盈融达化工有限公司+86-0592-6210733 · [email protected]
上海吉至生化科技有限公司021-4009004166/18616739031 18616739031 · [email protected]
career henan chemical co+86-0371-86658258 · [email protected]
深圳聚合生化科技有限公司+86-400-002-6226 13028896684 · [email protected]
SHANDONG ZHI SHANG CHEMICAL CO.LTD0531-68652808 18953170293 · [email protected]
海蔚化学86-21-51086038 · [email protected]
爆牛贸易重庆有限公司+86-023-6139-8061 +86-86-13650506873 · [email protected]
XIAMEN AMITY INDUSTRY AND TRADE CO., LTD.+8618950047208 · [email protected]
SHANGHAI KEAN TECHNOLOGY CO., LTD.+8613817748580 · [email protected]
武汉卡米克科技有限公司18162538168 · [email protected]
BOC Sciences+1-631-485-4226 · [email protected]
上海安谱实验科技股份有限公司18502138905 · [email protected]
广东翁江化学试剂有限公司0751-2815983 13927872582 · [email protected]
北京百灵威科技有限公司18210857532 18210857532 · [email protected]
HANGZHOU LEAP CHEM CO., LTD.+86-571-87711850 +8619957148339 · [email protected]

Additional notes

DefinitionChEBI: 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.