2,3-Dichloro-5,6-dicyano-1,4-benzoquinone (HCID 6775)

概要

request from searcher

名称と識別子

優先名称: 2,3-Dichloro-5,6-dicyano-1,4-benzoquinone
IUPAC: 4,5-dichloro-3,6-dioxocyclohexa-1,4-diene-1,2-dicarbonitrile
現地名: 2,3-ジクロロ-5,6-ジシアノ-1,4-ベンゾキノン
英語名: 2,3-Dichloro-5,6-dicyano-1,4-benzoquinone
分子式: C8Cl2N2O2
分子量: 227

名称と別名

84-58-22,3-Dichloro-5,6-dicyano-1,4-benzoquinoneDichlorodicyanobenzoquinone2,3-Dichloro-5,6-dicyano-p-benzoquinone2,3-Dichloro-5,6-dicyanobenzoquinoneDichlorodicyano-p-benzoquinone1,4-CYCLOHEXADIENE-1,2-DICARBONITRILE, 4,5-DICHLORO-3,6-DIOXO-2,3-Dichloro-5,6-dicyanoquinone4,5-Dichloro-3,6-dioxo-1,4-cyclohexadiene-1,2-dicarbonitrile2,3-Dichloro-5,6-dicyano-p-quinone2,3-Dicyano-5,6-dichlorobenzoquinone2,3-Dicyano-5,6-dichloro-1,4-benzoquinone

名称をさらに表示

2,3-ジクロロ-5,6-ジシアノ-1,4-ベンゾキノン4,5-ジクロロ-3,6-ジヒドロキシベンゼン-1,2-ジカルボニトリル3,6-ジヒドロ-3,6-ジオキソ-4,5-ジクロロ-1,2-ベンゼンジカルボニトリル3,6-ジオキソ-4,5-ジクロロシクロヘキサ-1,4-ジエン-1,2-ジカルボニトリル1,4-ジオキソ-5,6-ジクロロ-2,5-シクロヘキサジエン-2,3-ジカルボニトリル3,6-ジヒドロキシ-4,5-ジクロロフタロニトリル2,3-ジクロロ-5,6-ジシアノ-2,5-シクロヘキサジエン-1,4-ジオン3,6-ジヒドロキシ-4,5-ジクロロベンゼン-1,2-ジカルボニトリル4,5-ジクロロ-3,6-ジヒドロキシフタロニトリル4,5-ジクロロ-3,6-ジオキソ-1,4-シクロヘキサジエン-1,2-ジカルボニトリル2,3-ジシアノ-5,6-ジクロロ-2,5-シクロヘキサジエン-1,4-ジオン2,3-ジクロロ-5,6-ジシアノ-p-ベンゾキノンジクロロジシアノキノン2,3-ジシアノ-5,6-ジクロロ-1,4-ベンゾキノン5,6-ジクロロ-2,3-ジシアノ-1,4-ベンゾキノン3,6-ジオキソ-4,5-ジクロロ-1,4-シクロヘキサジエン-1,2-ジカルボニトリル3,6-ジオキソ-4,5-ジクロロ1,4-シクロヘキサジエン-1,2-ジカルボニトリル２，３ジクロロ５，６ジシアノｐベンゾキノン2，3-ジクロロ-5，6-ジシアノベンゾキノン2,3‐ジクロロ‐5,6‐ジシアノベンゾキノンDDQ2,3-dicyano-5,6-dichloro-p-benzoquinone4,5-dichloro-3,6-dioxocyclohexa-1,4-diene-1,2-dicarbonitrile1,2-Dichloro-4,5-Dicyanobenzoquinone2，3-Dicyano-5，6-dichlorobenzoquinone2,3-dichloro-5,6-dicyano-4-benzoquinone

5,6-Dichloro-2,3-dicyano-p-benzoquinone5,6-Dicyano-2,3-dichloro-p-benzoquinone1H5KD39UH7NSC-401087RefChem:1330572,3-DDQDTXCID10818133201-542-2

データベース識別子

CAS: 84-58-2
PubChem CID: 6775
DTXSID: DTXSID7052577
ChEMBL: CHEMBL3759231
UNII: 1H5KD39UH7
EC Number: 201-542-2
Nikkaji: J4.898D、J510.000C

物性

構造計算による物性

XLogP: 1.6
極性表面積: 81.7 Å²
水素結合供与体数: 0
水素結合受容体数: 4
回転可能結合数: 0
重原子数: 14
形式電荷: 0
複雑度: 464

実験および物理化学的性質

Chemical ClassesNitrogen Compounds -> Other Aromatics (Nitrogen)

SpringerMaterials PropertiesNuclear quadrupole resonance spectroscopy

Physical DescriptionYellow to orange solid; [Merck Index] Dark yellow powder; [Alfa Aesar MSDS]

物理化学的性質

融点: 210 · 210-215 °C (dec.)(lit.)
沸点: 301.8 · 301.8±42.0 °C(Predicted)
比重(密度): 1.75 · 1.7500 (estimate)
貯蔵温度: 30 °C · Store below +30°C.
溶解性: ベンゼン、メタノール、酢酸、ジオキサンに可溶。クロロホルムおよびジクロロメタンにわずかに溶ける。
外見: 結晶性粉末または結晶
色: 黄色からオレンジ
水溶解度: 反応する
Merck: 14 · 14,3063
BRN: 747939 · 747939
InChI: 1S/C8Cl2N2O2/c9-5-6(10)8(14)4(2-12)3(1-11)7(5)13
InChIKey: HZNVUJQVZSTENZ-UHFFFAOYSA-N
SMILES: ClC1=C(Cl)C(=O)C(C#N)=C(C#N)C1=O
CAS データベース: 84 · 84-58-2(CAS DataBase Reference)
NISTの化学物質情報: 1 · 1,4-Cyclohexadiene-1,2-dicarbonitrile, 4,5-dichloro-3,6-dioxo-(84-58-2)
EPAの化学物質情報: 1 · 1,4-Cyclohexadiene-1,2-dicarbonitrile, 4,5-dichloro-3,6-dioxo- (84-58-2)

化学的性質

化学的特性yellow to orange powder

安全と法規制

GHS分類

GHS Classification · 4 件

Danger

H301 (100%): Toxic if swallowed [Danger Acute toxicity, oral]

P261, P264, P264+P265, P270, P272, P280, P301+P316, P302+P352, P305+P351+P338, P321, P330, P333+P317, P337+P317, P362+P364, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 77 reports by companies from 11 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

危険有害性情報

Regulatory Information · 3 件

Chemical: 1,4-Cyclohexadiene-1,2-dicarbonitrile, 4,5-dichloro-3,6-dioxo-

Status: Active Update: 01-03-2023 https://echa.europa.eu/registration-dossier/-/registered-dossier/21337

2,3-Dichloro-5,6-dicyano-p-benzoquinone: Does not have an individual approval but may be used under an appropriate group standard

Hazards Summary · 1 件

Intraperitoneal LD50 (mouse) = 31 mg/kg; Intravenous LD50 (mouse) = 13 mg/kg; [RTECS] Decomposed by water; [Merck Index] Reacts with water evolving toxic gases; An irritant; Toxic by ingestion; [Alfa Aesar MSDS] See Hydroquinone. See NITRILES.

Hazard Classes and CategoriesAcute Tox. 3 (100%)

安全データ

F: 21
wgk: 3
tsca: TSCA listed
rtecs: GU4825000
ridadr: UN 3439 6.1/PG 3
hs_code: 29269095
risk_code: 25-29-41-37/38-20/21-23/24/25
化審法: (3)-1822
hazard_code: T
safety_code: 22-24/25-37-45-36/37-26-36/37/39
hazard_class: 6.1
packing_group: II
毒劇物取締法: 劇物
Hazard Classifications: Acute Tox. 3 Oral
ストレージクラス: 6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects

化学と産業

用途と製造

UsesUsed in steroid synthesis (oxidizing agent); [Merck Index]

General Manufacturing Information1,4-Cyclohexadiene-1,2-dicarbonitrile, 4,5-dichloro-3,6-dioxo-: ACTIVE

応用分野 · 3 件

用途有機合成中に、酸化剤として使用，ステロイド化学でのアクリルアルコール類を酸化し、対応するα,β-不飽和ケトンの合成に使用，有機ELを構成するキャリア輸送層に使用。

説明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.

使用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.

調製方法 · 2 件

製造方法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

純化方法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.]