2,3-디클로로-5,6-디시아노-1,4-벤조퀴논

그림문자(GHS)

• 그림문자(GHS)

  

• 신호 어

  Danger

• 유해·위험 문구

  H301：삼키면 유독함

• 예방조치문구

  P264：취급 후에는 손을 철저히 씻으시오.

  P264：취급 후에는 손을 철저히 씻으시오.

  P270：이 제품을 사용할 때에는 먹거나, 마시거나 흡연하지 마시오.

  P301+P310：삼켰다면 즉시 의료기관(의사)의 진찰을 받으시오.

  P405：밀봉하여 저장하시오.

  P501：...에 내용물 / 용기를 폐기 하시오.

2,3-디클로로-5,6-디시아노-1,4-벤조퀴논 MSDS

• DDQ

2,3-디클로로-5,6-디시아노-1,4-벤조퀴논 화학적 특성, 용도, 생산

• 개요

  2,3-Dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) has a variety of applications. DDQ is a deprotection agent for ketals, acetals, and thioacetals. It is a useful electron transfer reagent for synthesis of quinolones and an oxidizing agent used to synthesize steroids. Additionally, DDQ is used with Ph3P to synthesize 1,2-benzisoxazoles.

• 화학적 성질

  yellow to orange powder

• 용도

  An oxidizing agent, especially in steroid synthesis.
  2,3-Dichloro-5,6-dicyano-1,4-benzoquinone is used as a reagent for oxidative couplings and cyclization reactions and dehydrogenation of alcohols, phenols and steroid ketones. It is also used in the synthesis of 1,2-benzisoxazoles. It is a useful electron-transfer reagent for synthesis of quinolines from imines and alkynes or alkenes.

• 제조 방법

  The first synthesis of 2,3-Dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) was described by J.Thiele and F.Guntber in 1906. However, no interest was shown in the compound until Linstead and co-workers discovered its extraordinary potency as a dehydrogenating agent. Its oxidation potential is greater than that of any other known quinone.
  2,3-Dichloro-5,6-Dicyanobenzoquinone (DDQ). A New Preparation

• 주요 응용

  2,3-Dichloro-5,6-dicyano-p-benzoquinone (DDQ) can be used as:
  A deprotecting reagent for a variety of compounds, such as thioacetals, acetals, and ketals.
  An electron-transfer reagent for the synthesis of quinolines from imines and alkynes or alkenes.
  An effective reagent for the benzylic and allylic C?H functionalization.
  An oxidizing agent for the synthesis of functionalized furans and benzofurans.
  A reagent with Ph3P in an efficient synthesis of 1,2-benzisoxazoles.

• Mechanism of action

  2,3-Dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) has many applications in the oxidation of various organic compounds such as ketones, alcohols, phenols, aromatic compounds, heterocyclic structures, etc. Apart from that, the presence of two chlorine atoms and two nitrile groups on the benzoquinone ring may also behave as a potential chlorinating agent. Consequently, DDQ could act simultaneously as the chlorinating agent and the oxidant. It can also remove the protective functional groups during deprotections of different chemical entities. For dehydrogenation by DDQ, the mechanism includes the transfer of hydride to the quinone oxygen followed by the transfer of a proton to the phenolate ion[1].

• Safety

  DDQ reacts with water to release highly toxic hydrogen cyanide (HCN). A low-temperature and weakly acidic environment increases the stability of DDQ.

• Purification Methods

  Crystallise DDQ from CHCl3, CHCl3/*benzene (4:1), or *benzene and store it at 0o. [Pataki & Harvey J Org Chem 52 2226 1987, Beilstein 10 H 902, 10 II 635, 10 IV 3521.]

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