アクリジン 化学特性,用途語,生産方法
外観
うすい黄色～黄色～黄赤色粉末～結晶
外観
白色～褐色粉末～結晶
解説
アクリジン．コールタールから得られるアントラセン油に少量含まれる．ジフェニルアミンとギ酸を塩化亜鉛とともに加熱するか，ジフェニルアミン-2-カルボン酸に硫酸または塩化ホスホリルを作用させたのち，還元すると得られる．無色の針状結晶．融点109～110 ℃，沸点346 ℃．pKa 5.6(20 ℃)．100 ℃ で昇華しはじめる．水蒸気蒸留ができる．熱水にわずかに溶け，アルカリ性を示す．アルコール類，エーテル，炭化水素に易溶．希薄溶液は紫色の蛍光を出すが，アクリジンと酸から得られる黄色の塩は緑色の蛍光を出す．ハロゲン化アルキルまたはハロゲン化アリールと反応して，アクリジニウム塩をつくる．光の照射により二量化する．硫酸または水酸化カリウムと処理しても変化しない．二クロム酸カリウムで酸化するとアクリドンとなる．ニッケル触媒で還元するとアクリダン(9,10-ジヒドロアクリジン)となる．合成染料·殺菌剤(トリパフラピン)の原料，金属分析試薬として用いられる．皮膚や粘膜を強く刺激する性質がある．
用途
アントラセンの1つの炭素が窒素に置換した構造を持っている。色素や他の化合物の原料となる。プロフラビンなどアクリジン誘導体の多くは殺菌作用を持っている。アクリジンやその誘導体はDNAやRNAにインターカレートし、結合することができる。アクリジンオレンジ（N,N,N',N'-テトラメチルアクリジン-3.6-ジアミン）は核酸を選択的に染色する。
化学的特性
colourless to light yellow crystals
使用
manufacture of dyes and intermediates; some dyes derived from it are used as antiseptics, e.g. 9-aminoacridine, acriflavine and proflavine. The hydrochloride has been used as reagent for cobalt, iron and zinc.
定義
A colorless
crystalline heterocyclic compound
with three fused rings. Derivatives of acridine
are used as dyes and biological stains.
世界保健機関（WHO）
Acridine derivatives with antiseptic and disinfectant activity,
including acriflavine, proflavine and euflavine, were formerly used in the treatment
of infected wounds and burns. Such use has largely been discontinued on the
grounds that safer and more effective alternatives are now available. Following
demonstration of the mutagenic activity of proflavine in 1978 it was withdrawn from dental products in Denmark. Subsequently, euflavine was similarly withdrawn.
一般的な説明
Small colorless needle-like crystalline solid. Slightly soluble in hot water. Slightly denser than water. Contact may irritate skin, eyes, and mucous membranes. Sublimes before melting when heated. May be toxic by ingestion.
空気と水の反応
Slightly soluble in hot water.
反応プロフィール
Acridine neutralizes acids in exothermic reactions to form salts plus water. May be incompatible with isocyanates, halogenated organics, peroxides, phenols (acidic), epoxides, anhydrides, and acid halides. Flammable gaseous hydrogen may be generated in combination with strong reducing agents, such as hydrides. Burns to give toxic oxides of nitrogen.
健康ハザード
Inhalation irritates respiratory system and causes sneezing, crying, and vomiting. Contact with liquid irritates eyes, skin, and mucous membranes. At high temperature and during sun exposure, damage to the cornea, skin, and mucous membranes may occur following the liberation of Acridine vapor.
安全性プロファイル
Poison by ingestion, subcutaneous, and intravenous routes. Mutation data reported. A skin, eye, and mucous membrane irritant. When heated to decomposition it emits toxic fumes of NO,.
職業ばく露
Acridine and its derivatives are widely used in the production of dyestuffs, such as acriflavine, benzoflavine, and chrysaniline; and in the synthesis of pharmaceuticals; such as aurinacrine, proflavine, and rivanol. A constituent of coal tar, coal tar creosote; found in wastes from gas and tar plants and coke oven emissions. Incompatibilities: Strong acids, strong oxidizers.
輸送方法
UN2713 Acridine, Hazard Class: 6.1; Labels: 6.1-Poisonous materials
純化方法
Acridine has been crystallised twice from *benzene/cyclohexane, or from aqueous EtOH, then sublimed, removing and discarding the first 25% of the sublimate. The remainder is again crystallised and sublimed, discarding the first 10-15% [Wolf & Anderson J Am Chem Soc 77 1608 1955]. Acridine can also be purified by crystallisation from n-heptane and then from ethanol/water after pre-treatment with activated charcoal, or by chromatography on alumina with pet ether in a darkened room. Alternatively, acridine can be precipitated as the hydrochloride from *benzene solution by adding HCl, after which the base is regenerated, dried at 110o/50mm, and recrystallised to constant melting point from pet ether [Cumper et al. J Chem Soc 4518 1962]. The regenerated free base may be recrystallised, chromatographed on basic alumina, then vacuum-sublimed and zone-refined. [Williams & Clarke, J Chem Soc, Faraday Trans 1 73 514 1977, Albert, The Acridines Arnold Press 1966.] It can exist in five crystalline forms and is steam volatile. It is a strong IRRITANT to skin and mucous membranes and can become a chronic irritant— handle it with CARE. [Beilstein 20/8 V 199.]
不和合性
Acridine and its derivatives are widely used in the production of dyestuffs, such as acriflavine, benzoflavine, and chrysaniline; and in the synthesis of pharmaceuticals; such as aurinacrine, proflavine, and rivanol. A constituent of coal tar, coal tar creosote; found in wastes from gas and tar plants and coke oven emissions. Incompatibilities: Strong acids, strong oxidizers.
廃棄物の処理
Incineration with nitrogen oxide removal from the effluent gas by scrubber, catalytic, or thermal device.
アクリジン 上流と下流の製品情報
原材料
準備製品