N-メチルアニリン 化学特性,用途語,生産方法
外観
無色～黄色, 澄明の液体
溶解性
エタノール及びアセトンに溶け、水に溶けにくい。
用途
有機合成中間体、各種染料?ゴム薬品?農薬?医薬?爆薬原料
化学的特性
N-Methylaniline is a yellow to light brown oily liquid with a weak, ammonia-like odor. soluble in ethanol, ether, chloroform, slightly soluble in water. Turns reddishbrown if left standing.
物理的性質
Colorless to yellow to pale brown liquid with a faint, ammonia-like odor. Odor threshold
concentration is 1.7 ppm (quoted, Amoore and Hautala, 1983).
使用
N-Methylaniline is used as a solvent and in organic synthesis. It is used in the production of cationic brilliant red FG, cationic pink B, reactive yellow brown KGR, etc. in the dye industry. N-methylaniline is an intermediate in the synthesis of the insecticide buprofezin and the herbicide mefenacet.
使用
N-methylaniline was used as raw material, and metal-organic skeleton material CAU-10pydc was used as catalyst to catalyze the reaction of CO
2 with n-methylaniline to produce N-methyl-N-phenylformamide in mild conditions and green solvent acetonitrile
[1]. Poly (N-methylaniline) (PNMA) was prepared by the electrooxidation of N-methylaniline in acidic aqueous solution. PNMA prepared in acidic aqueous solution with different organic solvents and anions had different conductivity. Such as the experimental group added acetonitrile, N, N-dimethylformamide and dimethylsulfoxide, and the experimental group which adding dimethylsulfoxide had the strongest conductivity
[2].
References:
[1] Zhiqiang Wang, Chenghua Deng, Xiao Liu, Wenmin Wang, Highly efficient conversion of CO2 into N-formamides catalyzed by a noble-metal-free aluminum-based MOF under mild conditions, 2023, 52, 11163-11167.
[2] Jun YANO , Hiroko YOSHIKAWA , Tomomi MUKAI , Sumio YAMASAKI , Akira KITANI, Effect of Anions and Added Organic Solvents of Polymerizing Solutions on the Conductivity of Poly (N-methylaniline), 2006, 74, 42-48.
定義
ChEBI: N-methylaniline is a methylaniline that is aniline carrying a methyl substituent at the nitrogen atom. It is a phenylalkylamine, a secondary amine and a methylaniline. It derives from an aniline.
製造方法
N-methylaniline was synthesized by the reaction of aniline with dimethyl sulfate. Dimethyl sulfate was added dropwise to the mixed solution of aniline and water below 10°C, stirred for 1 h, and then added dropwise with 30% sodium hydroxide solution. The upper layer is the organic phase, and the lower layer is extracted with benzene. After the benzene is recovered from the extract, the obtained oil Chemicalbook-like substance is combined with the organic phase to obtain a mixture of aniline, N-methylaniline and N,N-dimethylaniline. The mixture was treated with sulfuric acid, and the aniline formed sulfate crystals which were filtered off. N,N-dimethylaniline can be converted to N-methylaniline by the following reaction.
一般的な説明
Chemical oxidation of
N-methylaniline with dichromate (oxidant) has been studied by Raman spectroscopy.
危険性
Toxic by ingestion, inhalation, and skin
absorption. Methemoglobinemia and central nervous system impairment.
健康ハザード
Recommended Personal Protective Equipment: Approved respirator; rubber gloves; splash proof goggles; Symptoms Following Exposure: Inhalation causes dizziness and headache. Ingestion causes bluish discoloration (cyanosis) of lips, ear lobes, and fingernail beds. Liquid irritates eyes. Absorption through skin produces same symptoms as for ingestion; General Treatment for Exposure: INHALATION: remove victim to fresh air and call a physician at once; administer oxygen until physician arrives. INGESTION: give large amount of water; get medical attention at once. EYES or SKIN: flush with plenty of water for at least 15 min.; if cyanosis is present, shower with soap and warm water, with special attention to scalp and finger nails; remove any contaminated clothing; Toxicity by Inhalation (Threshold Limit Value): Data not available; Short-Term Inhalation Limits: Data not available; Toxicity by Ingestion: Data not available; Late Toxicity: Data not available; Vapor (Gas) Irritant Characteristics: Data not available; Liquid or Solid Irritant Characteristics: Data not available; Odor Threshold: Data not available.
化学反応性
Reactivity with Water No reaction; Reactivity with Common Materials: May attack some forms of plastic; Stability During Transport: Stable; Neutralizing Agents for Acids and Caustics: Not pertinent; Polymerization: Not pertinent; Inhibitor of Polymerization: Not pertinent.
安全性プロファイル
Poison by ingestion and
intravenous routes. Moderately toxic by subcutaneous route. When heated to
decomposition it emits toxic fumes of NOx.
職業ばく露
The material is used as an intermediate
in organic synthesis, as a solvent and as an acid acceptor
発がん性
N-methyl aniline (1.95 g/kg of food) given
together with sodium nitrite (1.0 g/l of drinking
water) to Swiss mice resulted in a 17% incidence
of lung adenomas and a 14% incidence
of malignant lymphomas; there were no carcinogenic
effects in animals treated with Nmethyl
aniline alone, suggesting that in vivo
nitrosation is necessary for forming carcinogenic
nitrosamines.
In bacterial mutagenicity assays N-methyl
aniline was negative with or without metabolic
activation.
環境運命予測
Soil. Reacts slowly with humic acids or humates forming quinoidal structures (Parris, 1980).
輸送方法
UN2294 N-Methylaniline, Hazard Class: 6.1;
Labels: 6.1-Poisonous materials.
純化方法
Dry it with KOH pellets and fractionally distil it under vacuum. Acetylate, and the acetyl derivative is recrystallised to constant melting point (m 101-102o), then hydrolysed with aqueous HCl and distilled from zinc dust under reduced pressure. [Hammond & Parks J Am Chem Soc 77 340 1955, Beilstein 12 IV 241.]
廃棄物の処理
Controlled incineration
whereby oxides of nitrogen are removed from the effluent
gas by scrubber, catalytic or thermal device.
N-メチルアニリン 上流と下流の製品情報
原材料
準備製品
アストラゾン ピンク FG
2-クロロ-2',6'-ジメチルアセトアニリド
マラカイトグリーン
4-(TRIMETHYL-UREIDO)-BENZENESULFONYL CHLORIDE
2-(N-メチルアニリノ)エタノール
メチルフェニルカルバミド酸クロリド
1-[(3,4-ジメチルフェニル)アミノ]-1-デオキシ-D-リビトール
2-[[4-(ジメチルアミノ)フェニル]アゾ]-6-メトキシ-3-メチルベンゾチアゾール-3-イウム·メチルスルファート
1-アミノ-4-[[3-[(4,6-ジクロロ-1,3,5-トリアジン-2-イル)アミノ]-4-スルホフェニル]アミノ]-9,10-ジヒドロ-9,10-ジオキソ-2-アントラセンスルホン酸
4,4'-ビス(ジメチルアミノ)ベンゾフェノン
ベンゾチアゾール
2-メチル-1H-ピロロ[2,3-b]ピリジン
クリスタルバイオレット
メチルオレンジ
ヘキサメチルジシロキサン
N-フェニル-N-メチルベンジルアミン
[4-(ジメチルアミノ)フェニル]チオシアナート
メチレンブルー
N-Chloromethyl-N-phenylaminoformyl chloride
ブプロフェジン
4-ジメチルアミノベンズアルデヒド
アストラゾンブリリアントレッド4G
N-(2-ピペラジノ-アセチル)-N-メチルアニリン
イミノメタンアミン
1H-ピロロ[3,2-c]ピリジン
o-アセトアセトアニシジド
5-フルオロシトシン
4-[[4-クロロ-6-(メチルフェニルアミノ)-1,3,5-トリアジン-2-イル]アミノ]-2-[[[1-(2-クロロフェニル)-4,5-ジヒドロ-3-メチル-5-オキソ-1H-ピラゾール]-4-イル]アゾ]ベンゼンスルホン酸ナトリウム
2-アミノ-4,6-ジメトキシピリミジン
バニリン
2,6-ジメチルアニリン
4-(ジメチルアミノ)ベンゾフェノン
1-メチル-1-フェニルヒドラジン
リドカイン
2-(2-ベンゾチアゾリルオキシ)-N-メチル-N-フェニルアセトアミド
4,5-ジフェニル-1,3-ジオキソール-2-オン