Isoquinoline (HCID 8405)

Namen und Bezeichner

Bevorzugter Name: Isoquinoline
IUPAC: isoquinoline
Lokaler Name: Isochinolin
Englischer Name: Isoquinoline
Summenformel: C9H7N
Molmasse: 129.16

Namen und Synonyme

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

Weitere Namen anzeigen

ISOQUINOLINBenzopyridineFEMA 2978ISOQINOLINEIsoquinoL

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

Datenbank-Bezeichner

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

Eigenschaften

Berechnete Struktureigenschaften

XLogP: 2,1
Polarare Oberfläche (TPSA): 12,9 Å²
H-Brücken-Donoren: 0
H-Brücken-Akzeptoren: 1
Frei drehbare Bindungen: 0
Schwere Atome: 10
Formalladung: 0
Komplexität: 111

Experimentelle und physikochemische Eigenschaften

LogP · 2 Einträge

2.08

LogS-1.45

Density1.097-1.103

Solubility · 4 Einträge

4520

4.52 mg/mL at 25 °C

Slightly soluble in water

Soluble (in ethanol)

Boiling Point · 3 Einträge

243.2

242.00 to 243.00 °C. @ 760.00 mm Hg

242-243 °C

Melting Point · 2 Einträge

26.47

25.5 - 26 °C

Physikochemische Eigenschaften

Schmelzpunkt: 26 · 26-28 °C (lit.)
Siedepunkt: 242 · 242-243 °C (lit.)
Dichte: 1.099 g/mL · 1.099 g/mL at 25 °C (lit.)
Dampfdruck: 5 Pa · 5Pa at 20℃
FEMA: 2978 · 2978 | ISOQUINOLINE
Brechungsindex: 20 · n20/D 1.623(lit.)
Flammpunkt: 225 °F · 225 °F
storage temp.: 2 · 2-8°C
Löslichkeit: 5 g/l · 5g/l
pka: 5.42 · 5.42(at 20℃)
Aggregatzustand: Low Melting Solid
Farbe: Light brown
PH: 7.5 · 7.5 (5g/l, H2O, 20℃)
Geruch (Odor): 0.1 % · at 0.10 % in triacetin. sweet balsam herbal benzaldehyde anise
Geruchsart: balsamic
Wasserlöslichkeit: practically insoluble
Spezifische Wärmekapazität: 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
CAS Datenbank: 119 · 119-65-3(CAS DataBase Reference)
NIST chemische Informationen: Isoquinoline(119-65-3)
EPA chemische Informationen: Isoquinoline (119-65-3)

Sicherheit und Regulatorisches

GHS-Klassifizierung

GHS Classification · 6 Einträge

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.

Gefahrenhinweise

Regulatory Information · 5 Einträge

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 · 2 Einträge

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

Toxikologische Informationen

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

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

Regulatorische Informationen

Regulatory Information · 5 Einträge

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

Sicherheitsdaten

wgk: 2
tsca: TSCA listed
ridadr: UN 2811 6.1/PG 3
hs_code: 29334900
RTECS-Nr.: NW6825000
risk_code: 22-24-38-52/53-36/38-21/22-45
Toxizität: LD50 orally in rats: 360 mg/kg (Smyth)
hazard_code: T
safety_code: 36/37-45-36/37/39-61-53
hazard_class: 6.1
packing_group: II
Speicherklasse: 6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects
Hazard Classifications: Acute Tox. 3 DermalAcute Tox. 4 OralAquatic Chronic 3Eye Irrit. 2Skin Irrit. 2

Chemie und Industrie

Pharmakologische Informationen

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

Cellular LocationsCytoplasm；Extracellular

Verwendung und Herstellung

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 · 5 Einträge

Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes

Flavoring Agents -> JECFA Flavorings Index

Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes

General Manufacturing Information · 2 Einträge

Plastics Material and Resin Manufacturing

Isoquinoline: ACTIVE

Anwendungen · 2 Einträge

BeschreibungIsoquinoline, 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.

VerwendenIsoquinolines 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.

Darstellung · 1 Eintrag

synthetischeBischler-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.

Ergänzende Hinweise · 1 Eintrag

DefinitionChEBI: 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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Isochinolin

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