이소퀴놀린
아이소퀴놀린 · 이소퀴놀린 · ISOQUINOLIN · LEUCOLINE · Benzopyridine · FEMA 2978 · 2-BENZAZINE · ISOQINOLINE
식별자 및 물리적 특성
| CAS No. | 119-65-3 |
|---|---|
| 분자식 | C9H7N |
| 평균 분자량 | 129.16 g/mol |
| 단동위원소 질량 | 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 |
| 현지명 | 이소퀴놀린 |
화학 및 물리적 성질
| XLogP | 2.1 |
|---|---|
| 극성 표면적 | 12.9 |
| 수소 결합 공여자 수 | 0 |
| 수소 결합 수용자 수 | 1 |
| 회전 가능 결합 수 | 0 |
| 무거운 원자 수 | 10 |
| 형식 전하 | 0 |
| 복잡도 | 111 |
| LogP(분배 계수) | 2.08 |
| LogS | -1.45 |
| 밀도 | 1.097-1.1031.099 g/mL at 25 °C (lit.) |
| 용해도 | 45204.52 mg/mL at 25 °CSlightly soluble in waterSoluble (in ethanol)5g/L |
| 끓는 점 | 243.2242.00 to 243.00 °C. @ 760.00 mm Hg242-243 °C242-243 °C (lit.) |
| 녹는점 | 26.4725.5 - 26 °C26-28 °C (lit.) |
| 굴절률 | 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] |
| 증기압 | 5Pa at 20℃ |
| FEMA | 2978 | ISOQUINOLINE |
| 인화점 | 225 °F |
| 저장 조건 | 2-8°C |
| pKa(산도 계수) | 5.42(at 20℃) |
| 물리적 상태 | 저융점 고체 |
| 색상 | 연한 갈색 |
| pH | 7.5 (5g/l, H2O, 20℃) |
| 냄새 | 트리아세틴 중 0.10%. 달콤한 발삼 허브 벤즈알데히드 아니스 |
| 향취 유형 | 발사믹 |
| 용해도 | 실질적으로 불용성 |
| 비열 | Cp(liquid): 1.52 J/(g·K), at 25℃ |
| JECFA Number | 1303 |
| Merck | 14,5222 |
| BRN | 107549 |
| 헨리 상수 | 5.2×10-2 mol/(m3Pa) at 25℃, Mackay et al. (2006) |
| 유전율 | 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(분배 계수) | 2.08 |
| NIST | Isoquinoline(119-65-3) |
| EPA | Isoquinoline (119-65-3) |
화학적 성질
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 | 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. |
|---|---|
| 규제 정보 | 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 |
| 유해성 요약 | 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. |
용도
개요
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.
용도
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.
일반 설명
Isoquinoline 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 및 합성 방법
생산 방법
High-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.
제조 방법
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.