트리페닐렌

Triphenylene

HCID 9170CAS 217-59-4

기본 정보

표준 SMILES
c1ccc2c(c1)c1ccccc1c1ccccc21
InChIKey
SLGBZMMZGDRARJ-UHFFFAOYSA-N
분자식
C18H12
평균 분자량
228.3 g/mol
단동위원소 질량
228.09390038

개요

Triphenylene is an ortho-fused polycyclic arene consisting of four fused benzene rings.

이름 및 식별자

우선 이름
Triphenylene
IUPAC
triphenylene
현지명
트리페닐렌
영어명
Triphenylene
분자식
C18H12
분자량
228.29

이름 및 동의어

TRIPHENYLENE217-59-49,10-BenzophenanthreneIsochrysene9,10-BenzphenanthreneBenzo(l)phenanthreneBenzo[l]phenanthrene1,2,3,4-DibenznaphthaleneDTXSID9059757NSC-5745518WX3373I0CHEBI:33080
이름 더 보기
트라이페닐렌트리페닐렌Triphenylene,98%benzo(1)phenanthreneriphenyleneTriphenylene 98%Triphenylene >benzo(l)phenathrene
RefChem:191904DTXCID7036537205-922-9MFCD00001108triphenylene (purity)1,2:3,4-Dibenznaphthalene53814-75-8triphenylen

데이터베이스 식별자

CAS
217-59-4
PubChem CID
9170
DTXSID
DTXSID9059757
ChEMBL
CHEMBL1797416
ChEBI
CHEBI:33080
UNII
18WX3373I0
EC Number
205-922-9
Nikkaji
J6.134D

물성

구조 계산 물성

XLogP
4.9
극성 표면적
0 Ų
수소 결합 공여자 수
0
수소 결합 수용자 수
0
회전 가능 결합 수
0
무거운 원자 수
18

실험 및 물리화학적 성질

PolymersOther Classes -> Polycyclic Aromatic Hydrocarbons
SpringerMaterials Properties13C nuclear magnetic resonance spectrum
LogP5.84
Physical DescriptionLight yellow powder, insoluble in water; [MSDSonline]
Collision Cross Section143.6 Ų [M*]+

물리화학적 성질

녹는점
195 · 195-198 °C(lit.)
끓는 점
438 °C · 438 °C(lit.)
밀도
1.302 · 1.302
굴절률
1.55 · 1.5500 (estimate)
인화점
438 °C · 438°C
저장 조건
Sealed in dry,Room Temperature

화학적 성질

white to beige crystalline needles

안전 및 규제

유해성 정보

Hazards SummaryAn irritant; [MSDSonline] See POLYCYCLIC AROMATIC HYDROCARBONS.

독성 정보

TreatmentThere is no know antidote for PAHs. Exposure is usually handled with symptomatic treatment. (L10)
Health EffectsPAHs are carcinogens and have been associated with the increased risk of skin, respiratory tract, bladder, stomach, and kidney cancers. They may also cause reproductive effects and depress the immune system. (L10)
Exposure RoutesOral (L10) ; inhalation (L10)
Toxicity Summary · 1건

The ability of PAH's to bind to blood proteins such as albumin allows them to be transported throughout the body. Many PAH's induce the expression of cytochrome P450 enzymes, especially CYP1A1, CYP1A2, and CYP1B1, by binding to the aryl hydrocarbon receptor or glycine N-methyltransferase protein. These enzymes metabolize PAH's into their toxic intermediates. The reactive metabolites of PAHs (epoxide intermediates, dihydrodiols, phenols, quinones, and their various combinations) covalently bind to DNA and other cellular macromolecules, initiating mutagenesis and carcinogenesis. (L10, L23, A27, A32)

Signs and SymptomsAcute exposure to PAHs causes irritation and inflammation of the skin and lung tissue. (A10)
Carcinogen Classification · 6건

Triphenylene

Group 3: Not classifiable as to its carcinogenicity to humans

Volume Sup 7: Overall Evaluations of Carcinogenicity: An Updating of IARC Monographs Volumes 1 to 42, 1987; 440 pages; ISBN 92-832-1411-0 (out of print)

2010

2005

3, not classifiable as to its carcinogenicity to humans. (L135)

안전 데이터

wgk
3
rtecs
YK2925000
ridadr
UN 3077 9/PG 3
HS 번호
29029090
risk_code
41-50/53
hazard_code
Xi,N

화학 및 산업

약리 정보

Metabolism/Metabolites · 1건

PAH metabolism occurs in all tissues, usually by cytochrome P-450 and its associated enzymes. PAHs are metabolized into reactive intermediates, which include epoxide intermediates, dihydrodiols, phenols, quinones, and their various combinations. The phenols, quinones, and dihydrodiols can all be conjugated to glucuronides and sulfate esters; the quinones also form glutathione conjugates. (L10)

용도 및 제조

Uses · 1건

PAHs are released into the environment via the combustion of fossil fuels, coke oven emissions and vehicle exhausts, as well as naturally from forest fires and vocanic eruptions. PAHs from these sources may contaminate nearly water systems. They are also found in coal tar and charbroiled food. (L10)

응용 분야 · 2건

용도Triphenylene is a polycyclic aromatic hydrocarbon (PAH) that can be isolated from coal tar. Triphenylene emits fluorescence in the ultraviolet region and is a useful compound for developing semiconductor devices.

일반 설명Triphenylene belongs to the class of polycyclic aromatic hydrocarbons, which is commonly employed as a substrate for use as a precursor for the synthesis of graphenes, carbon nanotubes, buckminsterfullerenes as well as polycyclic heteroaromatics.

제조 방법 · 1건

Triphenylene synthesis: 2-Chlorobenzoic acid(78mg, 0.5mmol), iodonium salt (236mg, 0.55mmol), palladium acetate (2.8mg, 0.0125mmol), potassium carbonate (152mg, 1.1mmol) were dissolved in 3mL of NMP solvent was heated to 110 °C and stirred for 17 hours, cooled to room temperature, extracted with ethyl acetate, washed with saturated sodium chloride solution, dried over anhydrous sodium sulfate, filtered, concentrated, and subjected to column chromatography to obtain 92 mg of triphenylene as a white solid, The yield was 80%.

추가 설명

정의ChEBI: Triphenylene is an ortho-fused polycyclic arene consisting of four fused benzene rings.

관련 반응

10건

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