Tetracyanoquinodimethane (HCID 73697)

概要

Tetracyanoquinodimethane is a quinodimethane that is p-quinodimethane in which the methylidene hydrogens are replaced by cyano groups. It is a nitrile, an alicyclic compound and a quinodimethane. It is functionally related to a p-quinodimethane.

名称と識別子

優先名称: Tetracyanoquinodimethane
IUPAC: 2-[4-(dicyanomethylidene)cyclohexa-2,5-dien-1-ylidene]propanedinitrile
現地名: 7,7,8,8-テトラシアノキノジメタン
英語名: 7,7,8,8-Tetracyanoquinodimethane
分子式: C12H4N4
分子量: 204.19

名称と別名

1518-16-77,7,8,8-TetracyanoquinodimethaneTCNQTetracyanoquinodimethaneTetracyanoquinodimethanTetracyano-p-quinodimethanePropanedinitrile, 2,2'-(2,5-cyclohexadiene-1,4-diylidene)bis-Tetracyanoquinodimethan(e)7,7,8,8-Tetracyano-p-quinodimethane7,7,8,8-Tetracyano-1,4-quinodimethan7,7',8,8'-Tetracyanoquinodimethane2-[4-(dicyanomethylidene)cyclohexa-2,5-dien-1-ylidene]propanedinitrile

名称をさらに表示

7,7,8,8-テトラシアノキノジメタン2,2'-(シクロヘキサ-2,5-ジエン-1,4-ジイリデン)ビス(プロパンジニトリル)2,2'-(2,5-シクロヘキサジエン-1,4-ジイリデン)ビス(プロパンジニトリル)2,2'-(2,5-シクロヘキサジエン-1,4-ジイリデン)ビス(マロノニトリル)1,4-ビス(ジシアノメチレン)-2,5-シクロヘキサジエンテトラシアノキノジメタン3,6-ビス(ジシアノメチレン)-1,4-シクロヘキサジエン2,2'-(2,5-シクロヘキサンジエン-1,4-ジイリデン)ビス(プロパンジニトリル)2,2'-(2,5-シクロヘキサジエン-1,4-ジイリデン)ビスプロパンジニトリル(2,5-シクロヘキサジエン-1,4-ジイリデン)ビス(マロノニトリル)2,5-シクロヘキサジエン-1,4-ジイリデンビス(マロノニトリル)2,2'-(シクロヘキサ-2,5-ジエン-1,4-ジイリデン)ビス(マロノニトリル)2,5-シクロヘキサジエン-1,4-ジイリデンビス(メタンジカルボニトリル)2,5-シクロヘキサジエン-1,4-ジイリデン-α,α'-ジマロノニトリル１，４ビス（ジシアノメチレン）シクロヘキサジエン7,7,8,8-テトラシアノキノジメタン (昇華精製品)1,4-ビス(ジシアノメチレン)シクロヘキサジエン1,4-ビス(ジシアノメチレン)シクロヘキサジエン (昇華精製品)7,7,8,8‐テトラシアノキノジメタン2,5-シクロヘキサジエン-1,4-ジイリデンジマロノニトリルTetracyano p-Quinone Dimethane2,2'-(Cyclohexa-2,5-diene-1,4-diylidene)dimalononitrileTIMTEC-BB SBB0004357,7,8,8-Tetracyanoqutetracyano-quinodimethaetracyanoquinodimethane7,7,8,8-Tetracyanodimethan

2,5-Cyclohexadiene-1,4-diylidenedimalononitrileHC6FB4H2KW2,5-Cyclohexadiene-delta(sup1alpha:4alpha)dimalononitrileNSC-1052372,5-Cyclohexadiene-delta1,alpha:4,alpha'-dimalononitrileDTXSID5061748CHEBI:524452,5-Cyclohexadiene-1,4-diylidene-alpha,alpha'-dimalononitrile

データベース識別子

CAS: 1518-16-7
PubChem CID: 73697
DTXSID: DTXSID5061748
ChEBI: CHEBI:52445
UNII: HC6FB4H2KW
EC Number: 216-174-8
Nikkaji: J38.157H

物性

構造計算による物性

XLogP: 1
極性表面積: 95.2 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: 16
形式電荷: 0
複雑度: 535

実験および物理化学的性質

Chemical ClassesNitrogen Compounds -> Nitriles

SpringerMaterials PropertiesBand gap energy

Physical DescriptionGreen crystalline solid; [Alfa Aesar MSDS]

物理化学的性質

融点: 287 · 287-289 °C (dec.) (lit.)
沸点: 332.67 °C · 332.67°C (rough estimate)
比重(密度): 1.3596 · 1.3596 (rough estimate)
屈折率: 1.5 · 1.5000 (estimate)
貯蔵温度: Sealed in dry,Room Temperature
外見: 結晶性粉末
色: オレンジブラウンからグリーン
水溶解度: 不溶性
BRN: 611604 · 611604
安定性: 安定。強酸、強塩基、強還元剤、強酸化剤とは相容れない。
InChI: InChI=1S/C12H4N4/c13-5-11(6-14)9-1-2-10(4-3-9)12(7-15)8-16/h1-4H
InChIKey: PCCVSPMFGIFTHU-UHFFFAOYSA-N
SMILES: C1(=C(C#N)C#N)C=CC(=C(C#N)C#N)C=C1 |c:8,t:0|
CAS データベース: 1518 · 1518-16-7(CAS DataBase Reference)
NISTの化学物質情報: 2 · Propanedinitrile, 2,2'-(2,5-cyclohexadiene-1,4-diylidene)bis-(1518-16-7)
EPAの化学物質情報: 2 · Propanedinitrile, 2,2'-(2,5-cyclohexadiene-1,4-diylidene)bis- (1518-16-7)

化学的性質

化学的特性orange to green crystalline powder

安全と法規制

GHS分類

GHS Classification · 4 件

Danger

H301+H311+H331 (87%): Toxic if swallowed, in contact with skin or if inhaled [Danger Acute toxicity, oral; acute toxicity, dermal; acute toxicity, inhalation]

P261, P262, P264, P270, P271, P280, P301+P316, P301+P317, P302+P352, P304+P340, P316, P317, P321, P330, P361+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 46 reports by companies from 4 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

危険有害性情報

Regulatory Information7,7,8,8-Tetracyanoquinonedimethane: Does not have an individual approval but may be used under an appropriate group standard

Hazards SummaryIntravenous LD50 (mouse) = 56 mg/kg; [RTECS] May cause irritation; Harmful by ingestion and skin absorption; Toxic by inhalation; [Alfa Aesar MSDS] See NITRILES.

Hazard Classes and CategoriesAcute Tox. 3 (89.1%)

安全と保護具

Protective Action Criteria (PAC) · 3 件

0.18 [mg/m3]

2.0 [mg/m3]

12 [mg/m3]

毒性情報

Treatment · 1 件

Antidotes to cyanide poisoning include hydroxocobalamin and sodium nitrite, which release the cyanide from the cytochrome system, and rhodanase, which is an enzyme occurring naturally in mammals that combines serum cyanide with thiosulfate, producing comparatively harmless thiocyanate. Oxygen therapy can also be administered. (L97)

Health Effects · 1 件

Exposure to high levels of cyanide for a short time harms the brain and heart and can even cause coma, seizures, apnea, cardiac arrest and death. Chronic inhalation of cyanide causes breathing difficulties, chest pain, vomiting, blood changes, headaches, and enlargement of the thyroid gland. Skin contact with cyanide salts can irritate and produce sores. (L96, L97)

Exposure RoutesOral (L96) ; inhalation (L96) ; dermal (L96)

Toxicity Summary · 1 件

Organic nitriles decompose into cyanide ions both in vivo and in vitro. Consequently the primary mechanism of toxicity for organic nitriles is their production of toxic cyanide ions or hydrogen cyanide. Cyanide is an inhibitor of cytochrome c oxidase in the fourth complex of the electron transport chain (found in the membrane of the mitochondria of eukaryotic cells). It complexes with the ferric iron atom in this enzyme. The binding of cyanide to this cytochrome prevents transport of electrons from cytochrome c oxidase to oxygen. As a result, the electron transport chain is disrupted and the cell can no longer aerobically produce ATP for energy. Tissues that mainly depend on aerobic respiration, such as the central nervous system and the heart, are particularly affected. Cyanide is also known produce some of its toxic effects by binding to catalase, glutathione peroxidase, methemoglobin, hydroxocobalamin, phosphatase, tyrosinase, ascorbic acid oxidase, xanthine oxidase, succinic dehydrogenase, and Cu/Zn superoxide dismutase. Cyanide binds to the ferric ion of methemoglobin to form inactive cyanmethemoglobin. (L97)

Signs and SymptomsCyanide poisoning is identified by rapid, deep breathing and shortness of breath, general weakness, giddiness, headaches, vertigo, confusion, convulsions/seizures and eventually loss of consciousness. (L96, L97)

Carcinogen ClassificationNo indication of carcinogenicity to humans (not listed by IARC).

安全データ

wgk: 3
tsca: TSCA listed
rtecs: GU4850000
ridadr: 3276
hs_code: 29269095
risk_code: 22-20/21/22-23/24/25
化審法: (3)-1798
hazard_code: Xn,Xi,T
hazard_note: Irritant
safety_code: 22-24/25-36/37-26-36-45
hazard_class: 6.1
packing_group: II
毒劇物取締法: 劇物
Hazard Classifications: Acute Tox. 3 DermalAcute Tox. 3 InhalationAcute Tox. 3 Oral
ストレージクラス: 6.1A - Combustible acute toxic Cat. 1 and 2very toxic hazardous materials

化学と産業

薬理情報

Metabolism/Metabolites · 1 件

Organic nitriles are converted into cyanide ions through the action of cytochrome P450 enzymes in the liver. Cyanide is rapidly absorbed and distributed throughout the body. Cyanide is mainly metabolized into thiocyanate by either rhodanese or 3-mercaptopyruvate sulfur transferase. Cyanide metabolites are excreted in the urine. (L96)

用途と製造

Uses · 2 件

Synthetic Polymer MALDI Matrix Compounds

Tetracyanoquinodimethane is an electron-acceptor that is used to prepare charge transfer salts, which are of interest in the area of molecular electronics. (L614)

General Manufacturing InformationPropanedinitrile, 2,2'-(2,5-cyclohexadiene-1,4-diylidene)bis-: ACTIVE

応用分野 · 5 件

解説2,2′-(2,5-cyclohexadiene-1,4-diylidene)bispropanedinitrile．C12H4N4(204.19)．略称TCNQ．シクロヘキサン-1,4-ジオンとマロノニトリルとを縮合させて1,4-ビス(ジシアノメチレン)シクロヘキサンとし，ついで臭素化，脱臭化水素して合成する．"橙色の結晶．分解点297～298 ℃．アセトニトリル，ジオキサン，THFなどに可溶．強力な電子受容体として分子錯体を形成するほか，多数の単純および複雑陰イオンラジカル塩，M＋ (TCNQ)n(n ＝ 1，4/3，3/2，2)などを与え，高電導性のものも多い．電導性および光電導性複合材料として，ケミカルコンデンサーなどの電子材料，電子写真用感光材料に用いられる．[CAS 1518-16-7]森北出版「化学辞典（第2版）

説明7,7,8,8-tetracyanoquinodimethane (TCNQ), with a LUMO at 4.5 eV, is known for the charge-transfer salts formed by its radical anion TCNQ inphotovoltaic, light-emitting diodes, and organic field-effect transistordevices. TCNQ and its derivativeshave been used as dopants, leading to an increase in hole mobility or to the lowering of injectionbarriers. One classic example of such is the treatment of tetrathiafulvene (TTF), an electron donor with TCNQ. TFF and TCNQ form an ion pair, the TTF-TCNQ complex. This process of doping leads to the crystallisation of the ion pair into a one-dimensionally stacked polymer. This polymer consists of segregated stacks of cations and anions of the donors and the acceptors, respectively. The complex crystal is an organic semiconductor that exhibits metallic electric conductivity [1, 2].

来歴The first report on the electrical conductivity in an organic solid appeared in 1954, namely, a perylene—bromine complex with a room-temperature conductivity of 0.1 S cm1. In 1960, the organic acceptor Tetracyanoquinodimethane (TCNQ; 7,7,8,8-Tetracyanoquinodimethane) was synthesized, as well as a great number of its conducting charge-transfer complexes and radical ion salts. In the 1970s, the organic donor TTF led to the first organic metal TTF-TCNQ. Its room-temperature conductivity (500 S cm1) increases with a decrease in the temperature to the value of 6000 S cm1 at 60 K, where a metal-insulator transition occurs[1].

使用7,7,8,8-Tetracyanoquinodimethane is an electron-acceptor molecule used to form charge-transfer superconductors. It is an effective catalyst used for the -chlorination of carboxylic acids using chlorosulfonic acid; the presence of TCNQ suppresses competing free-radical chlorination.

一般的な説明7,7,8,8-Tetracyanoquinodimethane (TNCQ) is a strong electron acceptor as it has four cyano groups and π-conjugation bonds that form charge transferring chains and ion radical salts which are mainly used as p-dopants for the fabrication of a variety of semiconductor applications.