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N-[4-[(2-ヒドロキシ-5-メチルフェニル)アゾ]フェニル]アセトアミド

C.I. Disperse Yellow 3

HCID 17811
ノート反応
基本情報概要名称と識別子物性安全と法規制化学と産業関連反応化合物ノート
部分構造検索類似構造を探す

基本情報

CAS
2832-40-8
標準SMILES
CC(=O)Nc1ccc(N=Nc2cc(C)ccc2O)cc1
InChIKey
PXOZAFXVEWKXED-UHFFFAOYSA-N
分子式
C15H15N3O2
平均分子量
269.3 g/mol
単同位体質量
269.11642673

概要

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

名称と識別子

優先名称
C.I. Disperse Yellow 3
IUPAC
N-[4-[(2-hydroxy-5-methylphenyl)diazenyl]phenyl]acetamide
現地名
N-[4-[(2-ヒドロキシ-5-メチルフェニル)アゾ]フェニル]アセトアミド
英語名
Disperse Yellow 3
分子式
C15H15N3O2
分子量
269.3

名称と別名

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
名称をさらに表示
アセタミンイエローCGカヤロンファストイエロGジスパースファストイエローGノバロンイエロー2GNシバセットイエロー2GCカルコシンイエローGCペルリトンイエローGセリニルホシエリイエローGDカルコシンイエローGCNシラファストイエローGKCAアセタートファストイエローGアマセルイエローGジアセリトンファストイエローGミクロセチルイエローGRアセタートファストイエローGニロキノンイエロー4JC.I.ソルベントイエロー77ジスパーソルプリンティングイエローGナセランファストイエローCGインターケムジスパースイエローGHyellowzZlut diYellow ZCI 11855NCI-C53781c.i.3/11855C.I. 3/11855

物性

構造計算による物性

XLogP
2.9
極性表面積
74.1 Ų
水素結合供与体数
2
水素結合受容体数
4
回転可能結合数
3
重原子数
20
形式電荷
0
複雑度
351

実験および物理化学的性質

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

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 件

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]

物理化学的性質

融点
268 · 268-270 °C(lit.)
沸点
412.44 °C · 412.44°C (rough estimate)
比重(密度)
1.1385 · 1.1385 (rough estimate)
屈折率
1.56 · 1.5600 (estimate)

安全と法規制

安全情報は参考情報です。供給元の安全データシート(SDS)、適用法令、専門家による評価に代わるものではありません。

GHS分類

GHS Classification · 6 件

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)

危険有害性情報

Regulatory Information · 3 件

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 件

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

化学と産業

用途と製造

Uses · 6 件

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 件

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

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

U.S. Production · 2 件

(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 件

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/

応用分野 · 4 件

用途ポリメチルメタクリレート&ナイロンを着色するための紡織

説明Disperse 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.

使用Disperse 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.

一般的な説明Brownish-yellow powder.

調製方法

関連反応

0 件
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化合物ノート

読み込み中…

このページの内容基本情報概要名称と識別子物性安全と法規制化学と産業関連反応化合物ノート
estoneyellowgn
fenacetyellowg
Serisol fast yellow gdAcetate Fast Yellow GCibacet yellow 2gcCibacete yellow gbaNovalon yellow 2gnCalcosyn Yellow GCSafaritone yellow GAcetamine Yellow CG

データベース識別子

CAS
2832-40-8
PubChem CID
17811
DTXSID
DTXSID6021450
ChEMBL
CHEMBL1590721
ChEBI
CHEBI:53617
UNII
0890872E2E
EC Number
220-600-8
Nikkaji
J33.575D
貯蔵温度
-20 °C, · -20°C, Inert atmosphere
溶解性
Chloroform (Very Slightly), DMSO (Slightly, Sonicated), Methanol (Slightly, Sonicated)
外見
powder
酸解離定数(Pka)
8.74 · 8.74±0.43(Predicted)
色
黄褐色の粉末
水溶解度
32.32 ug/L · 32.32ug/L(25℃)
BRN
1915225 · 1915225
Henry's Law Constant
6.6 · 6.6×105 mol/(m3Pa) at 25℃, Duchowicz et al. (2020)
主な用途
洗浄剤化粧品環境食品および飲料パーソナルケア
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
CAS データベース
2832 · 2832-40-8(CAS DataBase Reference)
NISTの化学物質情報
3 · Disperse yellow 3,ci 11855(2832-40-8)
EPAの化学物質情報
3 · C.I. Disperse Yellow 3 (2832-40-8)
Reactivity AlertsExplosive
Reactivity Profile · 1 件

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 件

Skin Sens. 1 (100%)

Carcinogenicity - category 2

Skin sensitization - Category 1

Carc. 2

安全と保護具

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

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 件

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 件

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 件

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)

毒性情報

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

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 件

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 件

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 件

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 件

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 件

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 件

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.

安全データ

wgk
2
tsca
TSCA listed
rtecs
AC3662000
毒性
LD50 intraperitoneal in mouse: 8080mg/kg
hs_code
32041100
risk_code
40-43
化審法
一般化学物質
hazard_code
Xn
safety_code
22-36/37-46
Hazard Classifications
Carc. 2Skin Sens. 1
ストレージクラス
11 - Combustible Solids
有毒物質データの
2832-40-8(Hazardous Substances Data)

製造方法N-(4-aminophenyl)acetamide diazo, and to a p-Cresolcoupling

上流・下流製品情報

上流原料

p-クレゾール4'-アミノアセトアニリド

サプライヤー56 社

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補足説明

定義ChEBI: 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.