Isoquinoline
- CAS No.
- 119-65-3
- Chemical Name:
- Isoquinoline
- Synonyms
- ISOQUINOLIN;LEUCOLINE;2-BENZAZINE;FEMA 2978;IsoquinoL;2-Benzanine;ISOCHINOLIN;ISOQINOLINE;ISOQUINOLINE;Isochinoline
- CBNumber:
- CB1690422
- Molecular Formula:
- C9H7N
- Molecular Weight:
- 129.16
- MOL File:
- 119-65-3.mol
- MSDS File:
- SDS
- Modify Date:
- 2024/6/28 14:36:33
| Melting point | 26-28 °C (lit.) |
|---|---|
| Boiling point | 242-243 °C (lit.) |
| Density | 1.099 g/mL at 25 °C (lit.) |
| vapor pressure | 5Pa at 20℃ |
| FEMA | 2978 | ISOQUINOLINE |
| refractive index |
n |
| Flash point | 225 °F |
| storage temp. | 2-8°C |
| solubility | 5g/l |
| form | Low Melting Solid |
| pka | 5.42(at 20℃) |
| color | Light brown |
| PH | 7.5 (5g/l, H2O, 20℃) |
| Odor | at 0.10 % in triacetin. sweet balsam herbal benzaldehyde anise |
| Odor Type | balsamic |
| Water Solubility | practically insoluble |
| Merck | 14,5222 |
| JECFA Number | 1303 |
| BRN | 107549 |
| Dielectric constant | 10.7（20℃） |
| InChIKey | AWJUIBRHMBBTKR-UHFFFAOYSA-N |
| LogP | 2.08 |
| Dissociation constant | 5.19 at 25℃ |
| CAS DataBase Reference | 119-65-3(CAS DataBase Reference) |
| NIST Chemistry Reference | Isoquinoline(119-65-3) |
| EPA Substance Registry System | Isoquinoline (119-65-3) |
SAFETY
Risk and Safety Statements
| Symbol(GHS) |  GHS06 |
|||||||||
|---|---|---|---|---|---|---|---|---|---|---|
| Signal word | Danger | |||||||||
| Hazard statements | H302-H311-H315-H319-H412 | |||||||||
| Precautionary statements | P264-P273-P280-P301+P312-P302+P352+P312-P305+P351+P338 | |||||||||
| Hazard Codes | T | |||||||||
| Risk Statements | 22-24-38-52/53-36/38-21/22-45 | |||||||||
| Safety Statements | 36/37-45-36/37/39-61-53 | |||||||||
| RIDADR | UN 2811 6.1/PG 3 | |||||||||
| WGK Germany | 2 | |||||||||
| RTECS | NW6825000 | |||||||||
| TSCA | Yes | |||||||||
| HazardClass | 6.1 | |||||||||
| PackingGroup | II | |||||||||
| HS Code | 29334900 | |||||||||
| Toxicity | LD50 orally in rats: 360 mg/kg (Smyth) | |||||||||
| NFPA 704 |
|
Isoquinoline price More Price(12)
| Manufacturer | Product number | Product description | CAS number | Packaging | Price | Updated | Buy |
|---|---|---|---|---|---|---|---|
| Sigma-Aldrich(India) | I28208 | Isoquinoline 97% | 119-65-3 | 5G | ₹2598 | 2022-06-14 | Buy |
| Sigma-Aldrich(India) | I28208 | Isoquinoline 97% | 119-65-3 | 100G | ₹5813.03 | 2022-06-14 | Buy |
| Sigma-Aldrich(India) | I28208 | Isoquinoline 97% | 119-65-3 | 500G | ₹18619 | 2022-06-14 | Buy |
| Sigma-Aldrich(India) | 68853 | Isoquinoline analytical standard | 119-65-3 | 1ML | ₹6365.1 | 2022-06-14 | Buy |
| Sigma-Aldrich(India) | 282162 | Isoquinoline technical grade, 90-92% | 119-65-3 | 100ML | ₹5185.18 | 2022-06-14 | Buy |
Isoquinoline Chemical Properties,Uses,Production
Description
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.
Chemical Properties
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.
Uses
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.
Preparation
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.
Definition
ChEBI: 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.
Production Methods
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.
General Description
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.
Health Hazard
The toxic properties of this compound aresimilar to those of quinoline. It is moderatelytoxic in rats and rabbits by oral routeand skin absorption. The oral LD50 value inrats is 360 mg/kg. The irritation effects onskin and eyes in rabbits were moderate tosevere. Carcinogenicity due to isoquinolinein animals or humans is not known. The histidinereversion–Ames test for mutagenicitywas inconclusive.
Synthesis
Isoquinoline is synthesized by isolation from coal tar. It represents 10% of the total Quinoline fraction.
Solubility in organics
Miscible with alcohol and oils
Purification Methods
Dry isoquinoline with Linde type 5A molecular sieves or Na2SO4 and fractionally distil at reduced pressure. Alternatively, it can be refluxed with, and distilled from, BaO. It is also purified by fractional crystallisation from the melt and distilled from zinc dust. It forms a phosphate (m 135o) and a picrate (m 223o), which are purified by crystallisation, and the free base can be recovered and distilled. [Packer et al. J Am Chem Soc 80 905 1958.] The procedure for purification via the picrate comprises the addition of quinoline to picric acid dissolved in the minimum volume of 95% EtOH to yield yellow crystals which are washed with EtOH and air dried before recrystallising from acetonitrile. The crystals are dissolved in dimethyl sulfoxide (previously dried over 4A molecular sieves) and passed through a basic alumina column, on which picric acid is adsorbed. The free base in the effluent is extracted with n-pentane and distilled under vacuum. Traces of solvent from small quantities are removed by vapour phase chromatography. The hydrochloride crystallises from EtOH with m 193o. [Mooman & Anton J Phys Chem 80 2243 1976, Beilstein 20 II 236, 20 III/IV 3410, 20/7 V 333.]
Isoquinoline Preparation Products And Raw materials
Raw materials
Preparation Products
1of4
chevron_right| Supplier | Tel | Country | ProdList | Advantage | Inquiry |
|---|---|---|---|---|---|
| ANJI BIOSCIENCES | +91-9000100077 +91-9000100077 | Hyderabad, India | 430 | 58 | Inquiry |
| chakrachem Lifesciences | +91 9902744663 | Hyderabad, India | 451 | 58 | Inquiry |
| JSK Chemicals | +919879767970 | Gujarat, India | 3756 | 58 | Inquiry |
| Otto Chemie Pvt Ltd | +91-2222070099 +91-2266382599 | Maharashtra, India | 429 | 58 | Inquiry |
| TCI Chemicals (India) Pvt. Ltd. | 1800 425 7889 | New Delhi, India | 6778 | 58 | Inquiry |
| CHEMSWORTH | +91-261-2397244 | New Delhi, India | 6707 | 30 | Inquiry |
| A.J Chemicals | 91-9810153283 | New Delhi, India | 6124 | 58 | Inquiry |
| Otto Chemie Pvt. Ltd. | +91 9820041841 | Mumbai, India | 5873 | 58 | Inquiry |
| Alfa Aesar | 1 800 209 7001 | Maharashtra, India | 6913 | 58 | Inquiry |
| Central Drug House(P) Ltd. | 91-11-49404040 | New Delhi, India | 6160 | 58 | Inquiry |
| Supplier | Advantage |
|---|---|
| ANJI BIOSCIENCES | 58 |
| chakrachem Lifesciences | 58 |
| JSK Chemicals | 58 |
| Otto Chemie Pvt Ltd | 58 |
| TCI Chemicals (India) Pvt. Ltd. | 58 |
| CHEMSWORTH | 30 |
| A.J Chemicals | 58 |
| Otto Chemie Pvt. Ltd. | 58 |
| Alfa Aesar | 58 |
| Central Drug House(P) Ltd. | 58 |
Related articles
- Isoquinoline - Synthesis, Applications and Scope
- Isoquinoline is an aromatic organic chemical compound, which is a structural isomer of quinoline. It is also known as leucolin....
- Nov 21，2019
119-65-3(Isoquinoline)Related Search:
1of4
chevron_right