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化学名: | メチル エロー | 英語化学名: | Solvent Yellow 2 | 别名: | 4-(Dimethylamino)phenylazobenzene;4-(Phenylazo)-N,N-dimethylaniline;4-Dimethylaminoazobenzene,CI 11020;4-Dimethylaminoazobenzene,CI 11020 ph.eur;brilliantfastyellow;Butter OR Methyl Yellow;ButteryellowMethylyellow;C.I. Solvent Yellow 2 | CAS番号: | 60-11-7 | 分子式: | C14H15N3 | 分子量: | 225.29 | EINECS: | 200-455-7 | カテゴリ情報: | Azo;Analytical Chemistry;Indicator (pH);pH Indicators;Solvent Dyestuff | Mol File: | 60-11-7.mol | |
融点 | 111 °C (dec.)(lit.) | 沸点 | 356.8°C (rough estimate) | 比重(密度) | 1.1303 (rough estimate) | 蒸気圧 | 3 x 10-7 mmHg (estimated, NIOSH, 1997) | 屈折率 | 1.5770 (estimate) | 貯蔵温度 | Store at RT. | 溶解性 | Insoluble in water; soluble in ethanol, benzene, ether, chloroform,petroleum ether, mineralacids, oils | カラーインデックス | 11020 | 酸解離定数(Pka) | 3.226(at 25℃) | 外見 | Powder | 色 | Yellow | 酸塩基指示薬変色域(pH) | 2.9(red)-4(yellow/orange) | PH | 2.9-4.0 | 水溶解度 | 13.6 mg/L | 極大吸収波長 (λmax) | 408nm, 256nm, 508nm | Merck | 14,3229 | BRN | 746016 | 安定性: | Stable, but heat and light sensitive. Incompatible with strong oxidizing agents, strong acids. | 主な用途 | Electrochromic materials, sol-gel coatings, display device, inks, gasdetection apparatus, status assessment indetection apparatus, nematocides, hair dyes, diapers, food storage, status assessment inbreast cancer, detecting carbohydrates, bacteria, diagnosing cervical disease, wound dressing materials | CAS データベース | 60-11-7(CAS DataBase Reference) | IARC | 2B (Vol. 8, Sup 7) 1987 | NISTの化学物質情報 | Benzenamine, N,N-dimethyl-4-(phenylazo)-(60-11-7) | EPAの化学物質情報 | 4-Dimethylaminoazobenzene (60-11-7) |
| メチル エロー Usage And Synthesis |
外観 | 黄色〜黄赤色, 結晶性粉末〜粉末 | 溶解性 | 水に殆ど不溶。エタノールにやや溶けにくい。熱エタノール, アセトンに可溶。ジエチルエーテルにやや溶けにくく、エタノールに溶けにくく、水にほとんど溶けない。 | 解説 | C14H15N3(225.29).ジメチルイエロー(Dimethyl Yellow),バターイエロー(Butter Yellow)ともいう.アニリンとN,N-ジメチルアニリンの塩酸溶液に亜硝酸ナトリウム水溶液を加え,低温でジアゾカップリングすることにより得られる.黄色の結晶.融点117 ℃.染料および食品の着色料として使用されていたが,発がん性物質であることがわかったので,現在は使われていない.[CAS 60-11-7] 森北出版「化学辞典(第2版) | 用途 | 調製液原料。変異原性・がん原性物質試験研究用。 | 用途 | 染料、染料中間体 | 説明 | 4-N,N-Dimethylaminobenzene diazonium chloride is a
diazo compound found in diazo copy paper. It is
allergenic only when unexposed. | 化学的特性 | yellow to orange crystalline powder | 使用 | For determination of free HCl in gastric juice; spot test identification of peroxidized fats; pH indicator (red 2.9, yellow 4.0). | 使用 | Butter yellow was largely used as a food coloring agent. It was
also used for the determination of free hydrochloric acid in
gastric juice, for the spot test identification of peroxidized fats,
as a pH indicator, and as a laboratory reagent. | 使用 | Formerly used as a coloring agent in
foods, drugs, and cosmetics | 製造方法 | aniline diazotization, and N,N-dimethylaniline coupling. | 調製方法 | 4-Dimethylaminoazobenzene was produced in large quantities
in the early 1900s but is currently not produced in
any significant commercial quantity in the United States. | 定義 | A banned food coloring. | 一般的な説明 | Yellow crystalline leaflets or an orange powder. | 空気と水の反応 | Dust may form an explosive mixture in air. Insoluble in water. | 反応プロフィール | Solvent Yellow 2 can detonate, particularly if sensitized by the presence of metal salts or strong acids. 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. May react explosively with strong oxidizing agents, metal salts, peroxides, and sulfides. May react explosively with strong oxidizing agents, metal salts, peroxides, and sulfides. | 危険性 | Carcinogen. | 健康ハザード | 4-Dimethylamino-azobenzene (XIII) is the parent compound of the amino-azo dye carcinogens; it is also known in the earlier literature as Butter Yellow, because it was used to color butter and vegetable oils before its carcinogenic activity was discovered. Many derivatives of XIII have been prepared and tested for carcinogenic activity. In the rat, the amino-azo dye carcinogens, administered in the diet, specifically induce hepatomas. Tumor induction by most of the amino-azo dyes is delayed or inhibited by high dietary levels of riboflavin (vitamin B2) or protein. Replacement of the –N=N– azo linkage by –CH=CH–, as in 4-dimethylaminostilbene (XIV), results in widening the target tissue spectrum; XIV induces tumors in the liver, mammary gland, and ear duct. Mice are much more resistant than rats to the carcinogenic activity of both amino-azo dyes and aminostilbenes. | 火災危険 | Flash point data for Solvent Yellow 2 are not available. Solvent Yellow 2 is probably combustible. | 安全性プロファイル | Confirmed carcinogen
with experimental carcinogenic,
neoplastigenic, and tumorigenic data. Poison
by ingestion and intraperitoneal routes.
Experimental teratogenic and reproductive
effects. Human mutation data reported.
When heated to decomposition it emits
toxic fumes of NOx | 職業ばく露 | Tumorigen,Drug, Mutagen; Reproductive Effector DAB is used for coloring polishes and other wax products, polystyrene, petrol,soap, and as a chemical indicator. Human exposure to DABcan occur through either inhalation or skin absorption. | 応急処置 | If this chemical gets into the eyes, remove anycontact lenses at once and irrigate immediately for at least15 min, occasionally lifting upper and lower lids. Seek medical attention immediately. If this chemical contacts theskin, remove contaminated clothing and wash immediatelywith soap and water. Seek medical attention immediately. Ifthis chemical has been inhaled, remove from exposure,begin rescue breathing (using universal precautions, including resuscitation mask) if breathing has stopped and CPR ifheart action has stopped. Transfer promptly to a medicalfacility. Contact a physician, hospital, or poison center atonce. If the victim is unconscious or convulsing, do notinduce vomiting or give anything by mouth. Assure that thepatient’s airway is open and if conscious and not convulsing, give a glass of water to dilute the substance. Vomitingshould not be induced without a physician’s advice. | 発がん性 | 4-Dimethylaminoazobenzene is reasonably anticipated to be a human carcinogen based on sufficient evidence of carcinogenicity fromstudies in experimental animals. | 環境運命予測 | Chemical/Physical. Releases toxic nitrogen oxides when heated to decomposition (Sax and
Lewis, 1987).
At influent concentrations of 1.0, 0.1, 0.01, and 0.001 mg/L, the GAC adsorption capacities
were 249, 140, 83, and 48 mg/g, respectively (Dobbs and Cohen, 1980). | 貯蔵 | Color Code—Blue: Health Hazard/Poison: Storein a secure poison location. Prior to working with DAB youshould be trained on its proper handling and storage. Storein a cool, dry place and protect from exposure to light andair. A regulated, marked area should be established wherethis chemical is handled, used, or stored in compliance withOSHA Standard 1910.1045. | 輸送方法 | Dyes, solid, toxic, n.o.s. require a label of“POISONOUS/TOXIC MATERIALS.” 4-Dimethylaminoazo-benzene falls in Hazard Class 6.1; Packing Group III. | Properties and Applications | yellow to red light yellow. Light yellow powder, melting point 115 ℃ (yellow flaky crystal). Insoluble in water, soluble in ethanol for yellow solution, in oil soluble. In concentrated sulfuric acid to yellow, red after diluted solution; . Mainly used for Aviation fuel TETRAETHYLLEAD stability agent and pH indicator, also used in paraffin, polystyrene, oil and soap stain
Standard
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Light Fastness
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Heat-resistant(℃)
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Water
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Sodium Carbonate(5%)
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Hydrochloric acid(5%)
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Melting point
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Stable
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ISO
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General
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113.5-115
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120
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Poor
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Well
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Poor
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| 純化方法 | Crystallise the dye from acetic acid or isooctane, or from 95% EtOH by adding hot water and cooling. Dry it over KOH under vacuum at 50o. [Beilstein 6 IV 448.] CARCINOGEN. | Toxicity evaluation | Butter yellow exists as a stable crystalline material at normal
temperature and pressure. It is insoluble in water, but soluble in
organic solvents such as alcohol, chloroform, ether, petroleum
ether, mineral acids, oils, and pyridine. Its octanol/water partition
coefficient is 4.58, vapor pressure is 3.3×10-7 mm Hg;
and Henry’s law constant is 7.1×10-9 atm-m3 mol-1.
Butter yellow may be released into the environment as
a result of its manufacture and use in the consumer products.
It may bind to the soil and when released into water, may
bioconcentrate in aquatic organisms, or may be adsorbed into
the sediment. If released in the atmosphere, it may undergo
direct photolysis. | 不和合性 | None reported. |
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