チオサリチル酸 化学特性,用途語,生産方法
外観
白色～うすい黄色、結晶性粉末～粉末
溶解性
熱水に微溶。エタノール, 酢酸に易溶。氷酢酸、エタノールに可溶。熱湯に難溶。エタノールに溶け、水にほとんど溶けない。
解説
C
6H
4(SH)COOH．一般にチオサリチル酸とよばれるが，サリチル酸のどの酸素が硫黄に置き換わったのかはっきりしないので，安息香酸のオルト位に－SHが置換したことを示す名称が正式名とされている．分析試薬として，また医薬や染料合成の原料として使われる．
用途
分析試薬、医薬・染料中間体、重金属キレート剤、塩ビ安定剤、感光性樹脂原料。
効能
鎮痛薬, 解熱薬
化学的特性
Thiosalicylic acid, (o-mercapto benzoic acid), a sulfur-yellow solid that softens at 158 °C (316 °F), has a melting point of 164 °C (327 °F). It sublimes, is slightly soluble in hot water but freely soluble in glacial acetic acid and alcohol, and yields dithiosalicylic acid, upon exposure to air.
使用
Thiosalicylic acid acts as a trapping agent, which is useful in the desulfenylation of 3-indolyl sulfides. It is used to prepare macrocyclic diamides by condensation with diamines. Further, it is used as a precursor to drug, which finds application for the treatment of atherosclerosis and melanoma. In addition to this, it is involved in the preparation of vaccine preservative thiomersal and thioindigo dyestuff.
定義
ChEBI: Thiosalicylic acid is a sulfanylbenzoic acid that is the 2-sulfanyl derivative of benzoic acid. It has a role as a non-narcotic analgesic and an antipyretic. It is a conjugate acid of a thiosalicylate(1-).
製造方法
Thiosalicylic acid can be prepared from anthranilic acid via diazotization followed by the addition of sodium sulfide and then reduction with zinc. It can also prepared by heating o-halogenated benzoic acids with alkaline hydrosulfide in presence of copper.
主な応用
thiosalicylic acid can be used as:
A nucleophilic trapping agent for the desulfenylation of 3-indolyl sulfides to obtain 3-unsubstituted indoles.
A starting material to prepare 2′-mercaptoacetophenone, which is used in the synthesis of thioflavanone by reacting with lithium diisopropylamide and benzaldehyde.
A stabilizing agent in the synthesis of metal nanoparticles.
It can also be used to prepare 2-thioxanthone-thioacetic acid bimolecular system, which is used as a photoinitiator for free radical polymerization.
反応性
Hydroxythioxanthones are readily obtained with good regioselectivity from the reaction of thiosalicylic acid with phenols effected by a mixture of methanesulfonic acid and alumina.
合成方法
2-ハロ安息香酸と水硫化ナトリウムとの反応
純化方法
Crystallise the thio acid from hot EtOH (4mL/g), after adding hot distilled water (8mL/g) and boiling with charcoal. The hot solution is filtered, cooled, the solid is collected and dried in vacuo (P2O5). Crystallise it from AcOH and sublime in vacuo.[Beilstein 10 IV 272.]
チオサリチル酸 上流と下流の製品情報
原材料
準備製品