2,3-디클로로-5,6-디시아노-1,4-벤조퀴논

2,3-디클로로-5,6-디시아노-1,4-벤조퀴논 속성

2,3-디클로로-5,6-디시아노-1,4-벤조퀴논 MSDS

DDQ

2,3-디클로로-5,6-디시아노-1,4-벤조퀴논 C화학적 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.]

2,3-디클로로-5,6-디시아노-1,4-벤조퀴논 준비 용품 및 원자재

원자재

준비 용품

2,3-디클로로-5,6-디시아노-1,4-벤조퀴논 공급 업체

공급자	전화	이메일	국가	제품 수	이점
Hangzhou Qiwei Pharmatech Co.,Ltd	13282840061	mw@qwpharmatech.com	China	109	58
Hebei Yanxi Chemical Co., Ltd.	+8617531153977	allison@yan-xi.com	China	5854	58
Firsky International Trade (Wuhan) Co., Ltd	+8615387054039	admin@firsky-cn.com	China	427	58
Capot Chemical Co.,Ltd.	+86-（0）57185586718 +86-13336195806	sales@capot.com	China	29730	60
Henan Tianfu Chemical Co.,Ltd.	+86-0371-55170693 +86-19937530512	info@tianfuchem.com	China	21628	55
Zjartschem	+86-571 87238903	jocelynpan@zjarts.com	CHINA	988	58
Tianjin Zhongxin Chemtech Co., Ltd.	86-22-66880623 +8618622897568	sales@tjzxchem.com	China	572	58
career henan chemical co	+86-0371-86658258 +8613203830695	sales@coreychem.com	China	29858	58
NINGBO INNO PHARMCHEM CO., LTD.	13867897135	sales@nbinno.com	CHINA	923	58
Hubei Jusheng Technology Co.,Ltd.	18871490254	linda@hubeijusheng.com	CHINA	28172	58

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