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7,7,8,8-테트라시아노퀴노 디메탄

Tetracyanoquinodimethane

HCID 73697
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기본 정보개요이름 및 식별자물성안전 및 규제화학 및 산업관련 반응화합물 노트
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기본 정보

CAS
1518-16-7
표준 SMILES
N#CC(C#N)=c1ccc(=C(C#N)C#N)cc1
InChIKey
PCCVSPMFGIFTHU-UHFFFAOYSA-N
분자식
C12H4N4
평균 분자량
204.19 g/mol
단동위원소 질량
204.04359613

개요

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.

이름 및 식별자

우선 이름
Tetracyanoquinodimethane
IUPAC
2-[4-(dicyanomethylidene)cyclohexa-2,5-dien-1-ylidene]propanedinitrile
현지명
7,7,8,8-테트라시아노퀴노 디메탄
영어명
7,7,8,8-Tetracyanoquinodimethane
분자식
C12H4N4
분자량
204.19

이름 및 동의어

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
이름 더 보기
7,7,8,8-테트라사이아노퀴노이메탄7,7,8,8-테트라시아노퀴노디메탄Tetracyano 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

데이터베이스 식별자

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

물성

구조 계산 물성보충 중

XLogP
1
극성 표면적
95.2 Ų
수소 결합 공여자 수
0
수소 결합 수용자 수
4
회전 가능 결합 수
0
무거운 원자 수
16
형식 전하
0
복잡도
535

실험 및 물리화학적 성질

Chemical ClassesNitrogen Compounds -> Nitriles
SpringerMaterials PropertiesBand gap energy
Physical DescriptionGreen crystalline solid; [Alfa Aesar MSDS]

물리화학적 성질

녹는점
287 · 287-289 °C (dec.) (lit.)
끓는 점
332.67 °C · 332.67°C (rough estimate)
밀도
1.3596 · 1.3596 (rough estimate)
굴절률
1.5 · 1.5000 (estimate)
저장 조건
Sealed in dry,Room Temperature
물리적 상태
결정성 분말
색상
주황색-갈색에서 녹색
수용성
불용성
BRN
611604 · 611604
안정성
안정적인. 강산, 강염기, 강환원제, 강산화제와 호환되지 않습니다.
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|
NIST
2 · Propanedinitrile, 2,2'-(2,5-cyclohexadiene-1,4-diylidene)bis-(1518-16-7)
EPA
2 · Propanedinitrile, 2,2'-(2,5-cyclohexadiene-1,4-diylidene)bis- (1518-16-7)

화학적 성질

orange to green crystalline powder

안전 및 규제

안전 정보는 참고용이며, 공급업체의 물질안전보건자료(SDS), 관련 법규 및 전문가 평가를 대체하지 않습니다.

GHS 분류

GHS Classification · 4건

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.

유해성 정보

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%)

안전 및 보호

Protective Action Criteria (PAC) · 3건

0.18 [mg/m3]

2.0 [mg/m3]

12 [mg/m3]

독성 정보

Treatment · 1건

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 · 1건

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 · 1건

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).

안전 데이터

wgk
3
tsca
TSCA listed
rtecs
GU4850000
ridadr
3276
HS 번호
29269095
risk_code
22-20/21/22-23/24/25
hazard_code
Xn,Xi,T
safety_code
22-24/25-36/37-26-36-45
포장분류
II
위험 등급
6.1
위험 참고 사항
Irritant
Hazard Classifications
Acute Tox. 3 DermalAcute Tox. 3 InhalationAcute Tox. 3 Oral
스토리지 클래스
6.1A - Combustible acute toxic Cat. 1 and 2very toxic hazardous materials

화학 및 산업

약리 정보

Metabolism/Metabolites · 1건

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)

용도 및 제조

Uses · 2건

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
응용 분야 · 4건

개요7,7,8,8-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].

역사The 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].

용도7,7,8,8-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.

일반 설명7,7,8,8-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.

상·하류 제품 정보

하류 제품

5-메틸-1,3,4-옥사디아졸-2-일라민

추가 설명

정의ChEBI: A quinodimethane that is p-quinodimethane in which the methylidene hydrogens are replaced by cyano groups.

관련 반응

13건
반응 기록 만들기
HRID 26169 반응식
HRID 26169반응물로uspto-grants-1979_04
HRID 26170 반응식
HRID 26170촉매로uspto-grants-1979_04
HRID 85324 반응식
HRID 85324반응물로uspto-grants-2014_09
HRID 85325 반응식
HRID 85325반응물로uspto-grants-2014_09
HRID 485999 반응식
HRID 485999반응물로uspto-grants-1994_03
HRID 622615 반응식
HRID 622615반응물로uspto-grants-1988_09
HRID 903818 반응식
HRID 903818생성물로uspto-grants-1980_10
HRID 1164189 반응식
HRID 1164189반응물로uspto-grants-1983_01
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