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1-[(2-ニトロ-4-メチルフェニル)アゾ]-2-ナフタレノール

Toluidine Red

HCID 17047
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
2425-85-6
標準SMILES
Cc1ccc(N=Nc2c(O)ccc3ccccc23)c([N+](=O)[O-])c1
InChIKey
ZLFVRXUOSPRRKQ-UHFFFAOYSA-N
分子式
C17H13N3O3
平均分子量
307.3 g/mol
単同位体質量
307.09569129

概要

Yellowish-red to red powder or solid. (NTP, 1992)

名称と識別子

優先名称
Toluidine Red
IUPAC
1-[(4-methyl-2-nitrophenyl)diazenyl]naphthalen-2-ol
現地名
1-[(2-ニトロ-4-メチルフェニル)アゾ]-2-ナフタレノール
英語名
Pigment Red 3
分子式
C17H13N3O3
分子量
307.3

名称と別名

2425-85-6Toluidine redHansa Red BHelio Red TonerSiegle Red BBPermanent Red 4RToluidine Red 3BFast Red RToluidine TonerIndependence RedHelio Fast Red RNChromatex Red J
名称をさらに表示
ハンザレッドBトルイジンレッド1-[(4-メチル-2-ニトロフェニル)アゾ]-2-ナフトールC.I.ピグメントレッド3赤色221号ファーストレッドA(顔料)1-[(4-メチル-2-ニトロフェニル)アゾ]-2-ナフタレノールDandCレッド35パーマネントレッド4R1-[(4-メチル-2-ニトロフェニル)アゾ]ナフタレン-2-オール1-[(2-ニトロ-4-メチルフェニル)アゾ]-2-ナフタレノールピグメント レッド3赤221CIピグメントレッド3ピグメントレッド-3トルイジンレッド標準品ピグメントレッド -3PR 3AKA221fastredjfastredrCI 12120fastredabfastredjehansaredb
Toluidine Red RDeep Fastona RedFastona Red BSilosol Red RNHansa Scarlet RBHansa Scarlet RNSiegle Red BSilosol Red RBN

データベース識別子

CAS
2425-85-6
PubChem CID
17047
DTXSID
DTXSID8021226
ChEMBL
CHEMBL2138372
ChEBI
CHEBI:82428
UNII
7K26S08256
EC Number
219-372-2
Nikkaji
J2.299.206F、J2.949.115A、J34.075H

物性

構造計算による物性

XLogP
4.8
極性表面積
90.8 Ų
水素結合供与体数
1
水素結合受容体数
5
回転可能結合数
2
重原子数
23
形式電荷
0
複雑度
451

実験および物理化学的性質

Chemical ClassesDyes -> Azo Dyes
CosmeticsCosmetic colorant
Density1.37 to 1.50 g/cu cm
Color/Form · 2 件

Yellowish red solid

Hue varies considerably with particle size and therefore several shades are commercially available.

Solubility · 3 件

less than 1 mg/mL at 72 °F (NTP, 1992)

Slightly soluble in ethanol and xylene; poorly soluble in ethers and ketones.

Slightly soluble in water(0.8 g/L) ethanol(0.7 g/L), ethylene glycol methyl ether(0.9 g/L), acetone, and benzene; very soluble in mineral spirits, aromatic hydrocarbons and plasticizers.

Endocrine DisruptorsPotential endocrine disrupting compound
DecompositionWhen heated to decomposition it emits toxic fumes of NOx.
Melting Point · 2 件

518 to 522 °F (NTP, 1992)

270 to 272 °C

Physical Description · 3 件

Yellowish-red to red powder or solid. (NTP, 1992)

CBI; Dry Powder

Yellowish-red to red solid; [CAMEO]

物理化学的性質

融点
270 · 270-272 °C(lit.)
沸点
447.81 °C · 447.81°C (rough estimate)
比重(密度)
1.1873 · 1.1873 (rough estimate)
屈折率
1.65 · 1.6500 (estimate)
溶解性
Chloroform (Slightly, Heated), DMSO (Slightly), Toluene (Very Slightly)
酸解離定数(Pka)
13.45 · 13.45±0.50(Predicted)
水溶解度
211 μg/L · 211μg/L at 20℃
Henry's Law Constant
8.2 · 8.2×106 mol/(m3Pa) at 25℃, HSDB (2015)
安定性
安定。湿気に敏感な場合があります。強力な酸化剤とは相容れない。
化粧品成分の機能
着色剤
LogP
5.4 at · 5.4 at 25℃
CAS データベース
2425 · 2425-85-6(CAS DataBase Reference)
NISTの化学物質情報
2 · 2-Naphthalenol, 1-[(4-methyl-2-nitrophenyl)azo]-(2425-85-6)
EPAの化学物質情報
3 · C.I. Pigment Red 3 (2425-85-6)

化学的性質

化学的特性red to orange powder

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 · 5 件

This chemical does not meet GHS hazard criteria for 56.9% (246 of 432) of all reports.

Danger

H318 (18.8%): Causes serious eye damage [Danger Serious eye damage/eye irritation]

P264+P265, P273, P280, P305+P354+P338, P317, P391, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 432 reports by companies from 9 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

危険有害性情報

Regulatory Information · 5 件

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

Hazard Traits - Bioaccumulation; Environmental Persistence

2-Naphthalenol, 1-[2-(4-methyl-2-nitrophenyl)diazenyl]- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 2-Naphthalenol, 1-[2-(4-methyl-2-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-(4-methyl-2-nitrophenylazo)-2-naphthol (EC: 219-372-2)

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

Other Safety InformationIMAP assessments - 2-Naphthalenol, 1-[(4-methyl-2-nitrophenyl)azo]-: Human health tier I assessment
Fire HazardsFlash point data for this chemical are not available; however, it is probably combustible. (NTP, 1992)
Health HazardsSYMPTOMS: Symptoms of exposure to this compound may include pronounced coloring of the skin and blockage of the upper respiratory tract.
Hazards Summary · 1 件

Stains skin; May be absorbed through the skin; [CAMEO] An irritant; May cause serious injury to eyes; Possible sensitizer; Injury to adrenal glands, thyroid, spleen, liver, bone marrow, and kidneys in high-dose animal experiments; [MSDSonline]

Reactive GroupAzo, Diazo, Azido, Hydrazine, and Azide Compounds
Special ReportsDHHS/NTP; Toxicology & Carcinogenesis Studies of C.I. Pigment Red 3 in F344/N Rats and B6C3F1 Mice(Feed Studies) Technical Report Series No. 407 (1992) NIH Publication No. 92-3138
Reactivity AlertsExplosive
Reactivity Profile · 1 件

C.I. PIGMENT RED 3 may form toxic gases 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. May form flammable gases with alkali metals. Explosive combination can occur with strong oxidizing agents, metal salts, peroxides, and sulfides.

Air and Water ReactionsSensitive to moisture Dust suspensions in air can be explosive at certain concentrations. Insoluble in water.
Hazard Classes and CategoriesEye Dam. 1 (18.8%)

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.

Nonfire Spill Response · 1 件

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.

Disposal Methods · 1 件

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.

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 an organic vapor/acid gas cartridge (specific for organic vapors, HCl, acid gas and SO2) with a dust/mist filter. (NTP, 1992)

毒性情報

Environmental Fate · 3 件

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc of 2.0X10+5(SRC), determined from a structure estimation method(2), indicates that C.I. Pigment Red 3 is expected to be immobile in soil(SRC). Volatilization of C.I. Pigment Red 3 from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 1.2X10-11 atm-cu m/mole(SRC), using a fragment constant estimation method(3). C.I. Pigment Red 3 is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 3.7X10-11 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 2.0X10+5(SRC), determined from a structure estimation method(2), indicates that C.I. Pigment Red 3 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 1.2X10-12 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 6.5(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 3 , which has an estimated vapor pressure of 3.7X10-11 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 3 may be removed from the air by wet or dry deposition(SRC). C.I. Pigment Red 3 contains chromophores that absorb at wavelengths >290 nm(3) and therefore may be susceptible to direct photolysis by sunlight(SRC).

Adverse EffectsOccupational hepatotoxin - Secondary hepatotoxins: the potential for toxic effect in the occupational setting is based on cases of poisoning by human ingestion or animal experimentation.
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.[Available from: http://ntp-apps.niehs.nih.gov/ntp_tox/index.cfm?fuseaction=ntpsearch.searchresults&searchterm=2425-85-6]

安全データ

wgk
3
tsca
TSCA listed
rtecs
QK4247000
ridadr
UN 3077 9/PG 3
risk_code
41-50/53
hazard_code
Xi,N
safety_code
26-39-60-61
有毒物質データの
2425-85-6(Hazardous Substances Data)
発がん性評価について
IARC 3

化学と産業

用途と製造

Uses · 5 件

Used in paints, inks, plastics, rubber, cement, textile printing, and munitions; [HSDB]

Painting (Pigments, Binders, and Biocides) [Category: Paint]

Used in industrial finishes ... principal application is on air drying paints, and to a limited extent in printing inks.

Used in as a pigment in the manufacturing of paints, inks, plastics, rubber, textile printing

One of the most widely used of all red pigments on account of the bright scarlet hue, high tinctorial strength, good fastness to acids, alkalis and to light and economy. Some limitation is improved by the relatively poor fastness to organic solvents. Widely used in paints, printing inks, emulsion paints and distempers. Other uses are in synthetic resin lacquers and leather finishes, inks for foil and tinplate printing, paper coating and dyeing, wallpaper, linoleum, carbon papers, typewriter ribbons and student-grade artist materials. Rubber with good strength and fastness to vulcanisation but limited by solubility in rubber; celluloid, cellulose acetate, P/F, U/F, styrene and protein plastics but suffers from migration in some cases. Cement, because of fastness to lime. Textile printing for "print on" style with Aniline Black

U.S. Exports(1986) No Data
U.S. Imports(1983) 3.58X10+6 g
U.S. Production · 3 件

2023: 100,000 - <250,000 lb

(1984) 4.40X10+8 g

Production volumes for non-confidential chemicals reported under the Inventory Update Rule. [Table#4934]

Consumer UsesPigment
Industry UsesPigment
Methods of ManufacturingCoupling diazotized 2-nitro-4-methylaniline with 2-napthol
Household ProductsInformation on 4 consumer products that contain CI Red Pigment 3 in the following categories is provided:
Use ClassificationCosmetics -> Cosmetic colorant
General Manufacturing Information · 3 件

Synthetic Dye and Pigment Manufacturing

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

In full shade the pigment is very lightfast and weatherfast but shows poor tint lightfastness. It is characterized by poor fastness toward solvents and is likely to bloom in baking enamels.

応用分野

説明C.I. Pigment Red 3, 12120 [2425-85-6] is a good representative of monoazopigments of the β-naphthol type and is one of the most important organic pigments.

一般的な説明Yellowish-red to red powder or solid.

上流・下流製品情報

上流原料

亜硝酸ナトリウム塩酸4-メチル-2-ニトロアニリン2-ナフトール

下流製品

Alkyd resin paintVarious color amino baking enamel A04-9

サプライヤー89 社

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補足説明

定義本品は、平成15年厚労省令第126号に示される赤色221号である。

関連反応

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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
Soil Adsorption/Mobility · 1 件

Using a structure estimation method based on molecular connectivity indices(1), the Koc of C.I. Pigment Red 3 can be estimated to be 1.3X10+5(SRC). According to a classification scheme(2), this estimated Koc value suggests that C.I. Pigment Red 3 is expected to be immobile in soil.

Human Toxicity Excerpts · 3 件

/HUMAN EXPOSURE STUDIES/ Eight patients suffering from pigmented contact dermatitis caused by the commerical Brilliant Lake Red R were patch tested with purified Sudan I and its several chemical analogues. Positive reactions were observed to Sudan I, Orange SS, Brilliant Lake Red R, Vacanceine Red, Yellow OB and Sudan II. Negative tests were obtained with Toluidine Red /Pigment Red 3/, Permanent Orange, Lithol Red and Sudan III. ... The commerical Brilliant Lake Red R which has been said to be most important causative agent of pigmented contact dermatitis, contained Sudan I as a major impurity. The patients reacting to Brilliant Lake Red R always gave a positive reaction to Sudan I, but those reacting to Sudan I did not always give a positive reaction to Brilliant Lake Red R. This suggests that Sudan I is a potent sensitizer and may induce contact sensitivity and Brilliant Lake Red R itself is a weak sensitizer or a cross-reacting substance.

/SIGNS AND SYMPTOMS/ Toluidine Red may produce skin sensitization reactions in /humans/ and can be irritating to the skin.

/CASE REPORTS/ Eight patients suffering from pigmented contact dermatitis caused by the commercial Brilliant Lake Red R were patch tested with purified Sudan I and its several chemical analogs. Negative patch tests were obtained with toluidine red.

Artificial Pollution Sources · 1 件

C.I. Pigment Red 3's production and use as a red pigment for paints, inks, plastics, rubber, textiles, wallpaper, linoleum, carbon papers, typewriter ribbons, and student-grade artist materials(1,2) may result in its release to the environment through various waste streams(SRC).

Carcinogen Classification · 6 件

CI Pigment Red 3

Group 3: Not classifiable as to its carcinogenicity to humans

Volume 57: (1993) Occupational Exposures of Hairdressers and Barbers and Personal Use of Hair Colourants; Some Hair Dyes, Cosmetic Colourants, Industrial Dyestuffs and Aromatic Amines

1993

1992

C.I. Pigment Red 3

Environmental Bioconcentration · 1 件

An estimated BCF of 10 was calculated for C.I. Pigment Red 3(SRC), using an estimated log Kow of 6.5(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 件

The Henry's Law constant for C.I. Pigment Red 3 is estimated as 1.2X10-12 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that C.I. Pigment Red 3 is expected to be essentially nonvolatile from water surfaces(2). The Henry's Law constant of C.I. Pigment Red 3 indicates that volatilization from moist soil surfaces is not expected(SRC). C.I. Pigment Red 3 is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 3.67X10-11 mm Hg(SRC), determined from a fragment constant method(3).

Non-Human Toxicity Excerpts · 5 件

/LABORATORY ANIMALS: Acute Exposure/ Toluidine Red ... was a mild eye irritant in rabbits.

/LABORATORY ANIMALS: Acute Exposure/ In rats, the acute oral toxicity /of Toluidine Red/ was low.

/LABORATORY ANIMALS: Subchronic or Prechronic Exposure/ Treatment of F344 rats and B6C3F1 mice with C.I. Pigment Red 3 in the diet (10, 5.0, 2.5, 1.25, 0.6 or 0.3%) for 14 and 90 days resulted in hematological alterations consistent with hemolytic anemia. Rats appeared to be more sensitive than mice to the hematological effects. Histological lesions were observed in rats and mice after exposure for 90 days. Target organs in the rat were the spleen, bone marrow, liver and kidney. Lesions in the spleen consisted of a hematopoietic cell proliferation, iron-positive pigment and congestion of the red pulp, and inflammation of the splenic capsule. Changes in the livers of rats consisted of hematopoietic cell proliferation and iron-positive pigment in Kupffer cells. Hematopoietic cell proliferation also occurred in the bone marrow of treated rats. The presence of iron-positive pigment and a slightly increased incidence of protein casts were seen in the kidney. Target organs in mice were the spleen, liver and kidney. Histological lesions in mice after exposure for 90 days included increased hematopoietic cell proliferation in the liver and spleen, and iron-positive pigment in the spleen. Mild cytomegaly of the renal tubular epithelia was also observed in exposed mice.

/LABORATORY ANIMALS: Chronic Exposure or Carcinogenicity/ Under the conditions of these 2-year feed studies, there was some evidence of carcinogenic activity of C.I. Pigment Red 3 in male F344/N rats as exhibited by increased incidences of benign pheochromocytomas of the adrenal gland. The marginal increase in the incidences of squamous cell papillomas of the skin and Zymbal's gland carcinomas may have been related to C.I. Pigment Red 3 administration. There was some evidence of carcinogenic activity of C.I. Pigment Red 3 in female F344/N rats as indicated by the increased incidence of hepatocellular adenomas. There was some evidence of carcinogenic activity of C.I. Pigment Red 3 in male B6C3F1 mice as exhibited by the increased incidences of tubule adenomas of the renal cortex and follicular cell adenomas of the thyroid gland. There was no evidence of carcinogenic activity of C.I. Pigment Red 3 in female B6C3F1 mice that received 12,500, 25,000, or 50,000 ppm. The incidences of mononuclear cell leukemia and preputial gland tumors in male rats and mononuclear cell leukemia, mammary gland fibroadenoma, and clitoral gland tumors in female rats were lower in the exposed groups. The incidences of liver foci were markedly increased in exposed male and female rats. The severity of chronic nephropathy was increased in male rats and to a lesser extent in female rats given C.I. Pigment Red 3. An increase in the severity of nephropathy was observed in male and female mice; cytomegaly (karyomegaly) of renal tubule epithelium was observed in male mice. Thyroid follicular cell hyperplasia occurred with an increased incidence in male and female mice receiving C.I. Pigment Red 3.

For more Non-Human Toxicity Excerpts (Complete) data for C.I. PIGMENT RED 3 (7 total), please visit the HSDB record page.

Evidence for Carcinogenicity · 1 件

Evaluation: There is inadequate evidence in humans for the carcinogenicity of CI Pigment Red 3. There is limited evidence in experimental animals for the carcinogenicity of CI Pigment Red 3. Overall evaluation: CI Pigment Red 3 cannot be classified as to its carcinogenicity to humans (Group 3).

Environmental Abiotic Degradation · 1 件

C.I. Pigment Red 3 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 3 does contains chromophores that absorb at wavelengths >290 nm(1) and therefore may be susceptible to direct photolysis by sunlight(SRC).

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