Isochinolin
ISOQUINOLIN · LEUCOLINE · Benzopyridine · FEMA 2978 · 2-BENZAZINE · ISOQINOLINE · IsoquinoL · ISOCHINOLIN
Identifikatoren & physikalische Daten
| CAS No. | 119-65-3 |
|---|---|
| Summenformel | C9H7N |
| Durchschnittliche Molmasse | 129,16 g/mol |
| Monoisotopische Masse | 129,05784923 g/mol |
| SMILES | c1ccc2cnccc2c1 |
| InChIKey | AWJUIBRHMBBTKR-UHFFFAOYSA-N |
| PubChem CID | 8405 |
| ChEMBL | CHEMBL12315 |
| ChEBI | CHEBI:16092 |
| EC No. | 204-341-8 |
| DTXSID | DTXSID2047644 |
| Lokaler Name | Isochinolin |
Chemische & physikalische Eigenschaften
| XLogP | 2,1 |
|---|---|
| Polarare Oberfläche (TPSA) | 12,9 |
| H-Brücken-Donoren | 0 |
| H-Brücken-Akzeptoren | 1 |
| Frei drehbare Bindungen | 0 |
| Schwere Atome | 10 |
| Formalladung | 0 |
| Komplexität | 111 |
| LogP (Verteilungskoeffizient) | 2.08 |
| LogS | -1.45 |
| Dichte | 1.097-1.1031.099 g/mL at 25 °C (lit.) |
| Löslichkeit | 45204.52 mg/mL at 25 °CSlightly soluble in waterSoluble (in ethanol)5g/lpractically insoluble |
| Siedepunkt | 243.2242.00 to 243.00 °C. @ 760.00 mm Hg242-243 °C242-243 °C (lit.) |
| Schmelzpunkt | 26.4725.5 - 26 °C26-28 °C (lit.) |
| Brechungsindex | 1.621-1.627n20/D 1.623(lit.) |
| Physical Description | LiquidLiquid or hygroscopic solid with a pungent odor like anise oil mixed with benzaldehydemp = 26.48 deg C[Merck Index] Light brownmp = 24-28 deg C[Acros Organics MSDS]Colourless liquid, hygroscopic platelets when solidHeavy-sweet balsamic, herbaceous aroma |
| Dissociation Constants | 5.42 (at 20 °C) |
| Kovats Retention Index | 1225.21251126912481272.91250.712401241.6213.1912551261126812651275.51261.2214212.1214.14214.68214.41214.09215.611934195819551980 |
| Collision Cross Section | 122.3 Ų [M+H]+ [CCS Type: DTBuffer gas: N2Ionization: APCI+Dataset: TOXCASTSource Identifier: DTXSID2047644] |
| Dampfdruck | 5Pa at 20℃ |
| FEMA | 2978 | ISOQUINOLINE |
| Flammpunkt | 225 °F |
| Lagerbedingungen | 2-8°C |
| pKa (Säurekonstante) | 5.42(at 20℃) |
| Aggregatzustand | Low Melting Solid |
| Farbe | Light brown |
| pH | 7.5 (5g/l, H2O, 20℃) |
| Geruch | at 0.10 % in triacetin. sweet balsam herbal benzaldehyde anise |
| Geruchsart | balsamic |
| Spezifische Wärmekapazität | Cp(liquid): 1.52 J/(g·K), at 25℃ |
| JECFA Number | 1303 |
| Merck | 14,5222 |
| BRN | 107549 |
| Henry-Konstante | 5.2×10-2 mol/(m3Pa) at 25℃, Mackay et al. (2006) |
| Dielektrizitätskonstante | 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 (Verteilungskoeffizient) | 2.08 |
| CAS Datenbank | 119-65-3(CAS DataBase Reference) |
| NIST chemische Informationen | Isoquinoline(119-65-3) |
| EPA chemische Informationen | Isoquinoline (119-65-3) |
Sicherheit & Vorschriften
| GHS-Einstufung | This chemical does not meet GHS hazard criteria for < 0.1% (1 of 1677) of reports.DangerH302 (> 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. |
|---|---|
| Regulatorische Informationen | Chemical: IsoquinolineCommission 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/5236Status: No longer Valid Update: 30-09-2010 https://echa.europa.eu/registration-dossier/-/registered-dossier/1356Isoquinoline: Does not have an individual approval but may be used under an appropriate group standard |
| Gefahrenübersicht | A moderate skin irritant[RTECS] Safe when used as a flavoring agent in food[JECFA] An irritantHighly toxic by skin absorptionHarmful by ingestion[Acros Organics MSDS] See Quinoline. |
| Hazard Classes and Categories | Acute Tox. 4 (> 99.9%)Acute Tox. 3 (99.6%)Skin Irrit. 2 (93.4%)Eye Irrit. 2 (93.4%)Acute toxicity (Oral) - Category 4Hazardous to the aquatic environment (Acute) - Category 3Hazardous to the aquatic environment (Long-term) - Category 3 |
| USGS Health-Based Screening Levels for Evaluating Water-Quality | IsoquinolineWaste-water effluent contaminantSmith, C.D. and Nowell, L.H., 2024. Health-Based Screening Levels for evaluating water-quality data (3rd ed.). DOI:10.5066/F71C1TWP |
| Wassergefährdungsklasse (WGK) | 2 |
| TSCA-Inventar-Status | TSCA listed |
| UN-Transportnummer | UN 2811 6.1/PG 3 |
| Zollcode | 29334900 |
| RTECS-Nr. | NW6825000 |
| R-Sätze (R) | 22-24-38-52/53-36/38-21/22-45 |
| Toxizität | LD50 orally in rats: 360 mg/kg (Smyth) |
| Gefahrensymbole | T |
| Sicherheitshinweise (S) | 36/37-45-36/37/39-61-53 |
| Gefahrenklasse | 6.1Acute Tox. 3 DermalAcute Tox. 4 OralAquatic Chronic 3Eye Irrit. 2Skin Irrit. 2 |
| Verpackungsgruppe | II |
| Lagerklasse | 6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects |
Anwendungen & Verwendung
Beschreibung
Isoquinoline, 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.
Verwenden
Isoquinolines 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.
Herstellung & Synthese
synthetische
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.