Isoquinoline (HCID 8405)

이름 및 식별자

우선 이름: Isoquinoline
IUPAC: isoquinoline
현지명: 이소퀴놀린
영어명: Isoquinoline
분자식: C9H7N
분자량: 129.16

이름 및 동의어

ISOQUINOLINE119-65-32-Benzazine2-AzanaphthaleneLeucolinebeta-QuinolineIsochinolinBenzo[c]pyridine3,4-BenzopyridineBenzo(c)pyridineFEMA No. 2978DTXSID2047644

이름 더 보기

아이소퀴놀린이소퀴놀린ISOQUINOLINBenzopyridineFEMA 2978ISOQINOLINEIsoquinoL

JGX76Y85M6NSC-3395DTXCID0027644CHEBI:16092RefChem:792283204-341-87-methoxy-1,6-dimethylisoquinoline-5,8-dione2-Benzanine

데이터베이스 식별자

CAS: 119-65-3
PubChem CID: 8405
DTXSID: DTXSID2047644
ChEMBL: CHEMBL12315
ChEBI: CHEBI:16092
UNII: JGX76Y85M6
EC Number: 204-341-8
Nikkaji: J43.394B

물성

구조 계산 물성

XLogP: 2.1
극성 표면적: 12.9 Å²
수소 결합 공여자 수: 0
수소 결합 수용자 수: 1
회전 가능 결합 수: 0
무거운 원자 수: 10
형식 전하: 0
복잡도: 111

실험 및 물리화학적 성질

LogP · 2건

2.08

LogS-1.45

Density1.097-1.103

Solubility · 4건

4520

4.52 mg/mL at 25 °C

Slightly soluble in water

Soluble (in ethanol)

Boiling Point · 3건

243.2

242.00 to 243.00 °C. @ 760.00 mm Hg

242-243 °C

Melting Point · 2건

26.47

25.5 - 26 °C

물리화학적 성질

녹는점: 26 · 26-28 °C (lit.)
끓는 점: 242 · 242-243 °C (lit.)
밀도: 1.099 g/mL · 1.099 g/mL at 25 °C (lit.)
증기압: 5 Pa · 5Pa at 20℃
FEMA: 2978 · 2978 | ISOQUINOLINE
굴절률: 20 · n20/D 1.623(lit.)
인화점: 225 °F · 225 °F
저장 조건: 2 · 2-8°C
용해도: 5 g/L · 5g/L
산도 계수 (pKa): 5.42 · 5.42(at 20℃)
물리적 상태: 저융점 고체
색상: 연한 갈색
수소이온지수(pH): 7.5 · 7.5 (5g/l, H2O, 20℃)
냄새: 0.1 % · 트리아세틴 중 0.10%. 달콤한 발삼 허브 벤즈알데히드 아니스
냄새 유형: 발사믹
수용성: 실질적으로 불용성
비열: 1.52 J/ · Cp(liquid): 1.52 J/(g·K), at 25℃
JECFA Number: 1303 · 1303
Merck: 14 · 14,5222
BRN: 107549 · 107549
Henry's Law Constant: 5.2 · 5.2×10-2 mol/(m3Pa) at 25℃, Mackay et al. (2006)
Dielectric constant: 10.7 · 10.7(20℃)
InChI: 1S/C9H7N/c1-2-4-9-7-10-6-5-8(9)3-1/h1-7H
InChIKey: AWJUIBRHMBBTKR-UHFFFAOYSA-N
SMILES: c1ccc2cnccc2c1
LogP: 2.08 · 2.08
NIST: Isoquinoline(119-65-3)
EPA: Isoquinoline (119-65-3)

화학적 성질 · 1건

Isoquinoline is a colorless hygroscopic liquid at temperatures above its melting point with a heavy sweet balsamic, herbaceous odor. Impure samples can appear brownish, as is typical for nitrogen heterocycles. Isoquinoline is a slightly stronger base than quinoline (pKa=5.14) and has a larger dipole of 2.60D.

안전 및 규제

GHS 분류

GHS Classification · 6건

This chemical does not meet GHS hazard criteria for < 0.1% (1 of 1677) of reports.

Danger

H302 (> 99.9%): Harmful if swallowed [Warning Acute toxicity, oral]；H311 (99.6%): Toxic in contact with skin [Danger Acute toxicity, dermal]；H315 (93.4%): Causes skin irritation [Warning Skin corrosion/irritation]；H319 (93.4%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]

P262, P264, P264+P265, P270, P280, P301+P317, P302+P352, P305+P351+P338, P316, P321, P330, P332+P317, P337+P317, P361+P364, P362+P364, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 1677 reports by companies from 8 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.；Reported as not meeting GHS hazard criteria per 1 of 1677 reports by companies.；There are 7 notifications provided by 1676 of 1677 reports by companies with hazard statement code(s).；Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website.

유해성 정보

Regulatory Information · 5건

Chemical: Isoquinoline

Commission Regulation (EC) No 1565/2000 (Repealed by Com. Implementing Reg. (EU) No 872/2012)

Isoquinoline is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Isoquinoline are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)

Status: Active Update: 07-01-2011 https://echa.europa.eu/registration-dossier/-/registered-dossier/5236；Status: No longer Valid Update: 30-09-2010 https://echa.europa.eu/registration-dossier/-/registered-dossier/1356

Isoquinoline: Does not have an individual approval but may be used under an appropriate group standard

Hazards SummaryA moderate skin irritant; [RTECS] Safe when used as a flavoring agent in food; [JECFA] An irritant; Highly toxic by skin absorption; Harmful by ingestion; [Acros Organics MSDS] See Quinoline.

Hazard Classes and Categories · 2건

Acute Tox. 4 (> 99.9%)；Acute Tox. 3 (99.6%)；Skin Irrit. 2 (93.4%)；Eye Irrit. 2 (93.4%)

Acute toxicity (Oral) - Category 4；Hazardous to the aquatic environment (Acute) - Category 3；Hazardous to the aquatic environment (Long-term) - Category 3

독성 정보

USGS Health-Based Screening Levels for Evaluating Water-Quality · 3건

Isoquinoline

Waste-water effluent contaminant

Smith, C.D. and Nowell, L.H., 2024. Health-Based Screening Levels for evaluating water-quality data (3rd ed.). DOI:10.5066/F71C1TWP

규제 정보

Regulatory Information · 5건

Chemical: Isoquinoline

Commission Regulation (EC) No 1565/2000 (Repealed by Com. Implementing Reg. (EU) No 872/2012)

Isoquinoline is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Isoquinoline are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)

Status: Active Update: 07-01-2011 https://echa.europa.eu/registration-dossier/-/registered-dossier/5236；Status: No longer Valid Update: 30-09-2010 https://echa.europa.eu/registration-dossier/-/registered-dossier/1356

Isoquinoline: Does not have an individual approval but may be used under an appropriate group standard

안전 데이터

wgk: 2
tsca: TSCA listed
rtecs: NW6825000
ridadr: UN 2811 6.1/PG 3
독성: LD50 orally in rats: 360 mg/kg (Smyth)
HS 번호: 29334900
risk_code: 22-24-38-52/53-36/38-21/22-45
hazard_code: T
safety_code: 36/37-45-36/37/39-61-53
포장분류: II
위험 등급: 6.1
기존화학 물질: KE-21757
Hazard Classifications: Acute Tox. 3 DermalAcute Tox. 4 OralAquatic Chronic 3Eye Irrit. 2Skin Irrit. 2
스토리지 클래스: 6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects

화학 및 산업

약리 정보

Metabolism/MetabolitesIsoquinoline has known human metabolites that include isoquinoline N-oxide.

Cellular LocationsCytoplasm；Extracellular

용도 및 제조

UsesPresent in coal tar; Used to make dyes, insecticides, antimalarials, and rubber accelerators; [Merck Index] Used as flavoring agent or adjuvant; [FDA]

U.S. Production2023: 25,000,000 - <75,000,000 lb；2022: 75,000,000 - <150,000,000 lb；2021: 150,000,000 - <500,000,000 lb；2020: 25,000,000 - <75,000,000 lb

Industry UsesCatalyst

Use Classification · 5건

Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes

Flavoring Agents -> JECFA Flavorings Index

Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes

General Manufacturing Information · 2건

Plastics Material and Resin Manufacturing

Isoquinoline: ACTIVE

응용 분야 · 3건

개요Isoquinoline, also known as 2-azanaphthalene, benzo[c]pyridine, or 2-benzanine, is a structural isomer of quinoline. It has structural and spectroscopic properties similar to quinoline. Isoquinoline was first isolated in 1885 by Hoogewerf and van Dorp from the quinoline fraction of coal tar by fractional crystallization. It is used to prepare dyes, insecticides, and antimalarial compounds, among other things.

용도Isoquinolines are used in the manufacture of dyes, paints, insecticides and antifungals. It is also used as a solvent for the extraction of resins and terpenes, and as a corrosion inhibitor.Isoquinoline (isq) has been used:in the preparation of cis-[(dcbH2)2Ru(isq)2](ClO4)2 [dcbH2 = 4,4′-(CO2H)2-2,2′-bipyridine].to investigate the toxicity of three two-ring and five three-ring azaarenes to the green alga Scenedesmus acuminatus and its relationship with molecular structure.

일반 설명Isoquinoline is one of the very few heterocyclic compounds in which numbering of the ring atoms does not start on the hetero atom.It consists of a benzene ring fused to the β- and Y-positions of a pyridine ring.Isoquinoline has an odor reminiscent of benzaldehyde and anise. Isoquinoline may be obtained from coal tar (238 - 250°C boiling fraction); it is isolated as the sulfate or as is by repeated freezing.

제조 방법 · 2건

생산 방법High-temperature coal tar contains an average of 0.2% isoquinoline. It is separated by distillation from the lower-boiling quinoline and the higherboiling 2-methylquinoline of the quinoline base mixture. Further refining is based on the fact that isoquinoline, in contrast to quinoline and 2-methylquinoline, cannot be hydrated but can be crystallized at low temperature. Isoquinoline can by synthesized, for example, via the Bischler–Napieralski reaction by cyclodehydration of N-acyl derivatives of b-phenylethylamine with Lewis acids and subsequent dehydrogenation.

Bischler-Napieralski synthesis is used to synthesize isoquinolines. β-phenylethylamine is acylated, and then cyclodehydrated using phosphoryl chloride, phosphorus pentoxide or other Lewis acids to yield dihydroisoquinoline, which can be aromatized by dehydrogenation with palladium, for example in the synthesis of papaverine, a pharmacologically active isoquinoline alkaloid.Pictet-Spengler synthesis is another method of preparing isoquinolines. β-phenylethylamine reacts with an aldehyde to produce an imine, which undergoes acid-catalysed cyclization, resulting in the synthesis of the tetrahydroisoquinoline system. Again, tetrahydroisoquinoline can be aromatized by palladium dehydrogenation to produce an isoquinoline system.

추가 설명 · 1건

정의ChEBI: Isoquinoline is an ortho-fused heteroarene that is a benzopyridine in which the N atom not directly attached to the benzene ring. It is a mancude organic heterobicyclic parent, an azaarene, an ortho-fused heteroarene and a member of isoquinolines.

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