Isoquinoline
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Basic information
- CAS
119-65-3- Standard SMILES
c1ccc2cnccc2c1- InChIKey
AWJUIBRHMBBTKR-UHFFFAOYSA-N- Molecular formula
- C9H7N
- Average molar mass
- 129.16 g/mol
- Monoisotopic mass
- 129.05784923
Overview
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 member of isoquinolines, a mancude organic heterobicyclic parent, an azaarene and an ortho-fused heteroarene.
Names & identifiers
- Preferred name
- Isoquinoline
- IUPAC
- isoquinoline
- English name
- Isoquinoline
- Molecular formula
- C9H7N
- Molecular weight
- 129.16
Names & synonyms
ISOQUINOLINE119-65-32-Benzazine2-AzanaphthaleneLeucolinebeta-QuinolineIsochinolinBenzo[c]pyridine3,4-BenzopyridineBenzo(c)pyridineFEMA No. 2978DTXSID2047644
Show more names
ISOQUINOLINBenzopyridineFEMA 2978ISOQINOLINEIsoquinoL
JGX76Y85M6NSC-3395DTXCID0027644CHEBI:16092RefChem:792283204-341-87-methoxy-1,6-dimethylisoquinoline-5,8-dione2-Benzanine
Database identifiers
- CAS
119-65-3- PubChem CID
- 8405
- DTXSID
DTXSID2047644- ChEMBL
CHEMBL12315- ChEBI
CHEBI:16092- UNII
- JGX76Y85M6
- EC Number
- 204-341-8
- Nikkaji
- J43.394B
Properties
Computed structural propertiesFilling in
- XLogP
- 2.1
- Topological polar surface area
- 12.9 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 1
- Rotatable bonds
- 0
- Heavy atoms
- 10
- Formal charge
- 0
- Complexity
- 111
Experimental & physicochemical properties
Chemical Classes
Nitrogen Compounds -> Quinolines
Waste-water effluent contaminant
DrugsPharmaceuticals -> Listed in ZINC15
SpringerMaterials PropertiesAngular frequency
LogP
2.08
2.08
Food AdditivesFLAVORING AGENT OR ADJUVANT -> FDA Substance added to food
Density1.097-1.103
Flavoring AgentsEU Flavoring substances
Solubility
4.52 mg/mL at 25 °C
Slightly soluble in water
Soluble (in ethanol)
Boiling Point
242.00 to 243.00 °C. @ 760.00 mm Hg
242-243 °C
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
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]
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.
Warning
Hazard information
Regulatory Information
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)
REACH registered substance: Isoquinoline (EC: 204-341-8)
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
Acute Tox. 4 (> 99.9%)
Acute toxicity (Oral) - Category 4
Toxicology
Toxicological Information
Chemistry & industry
Pharmacology
Metabolism/MetabolitesIsoquinoline has known human metabolites that include isoquinoline N-oxide.
Cellular LocationsCytoplasm
Uses & manufacturing
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
Industry UsesCatalyst
Use Classification
Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes
Flavoring Agents -> JECFA Flavorings Index
Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes
Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes
Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes
General Manufacturing Information
Plastics Material and Resin Manufacturing
Isoquinoline: ACTIVE
Applications
DescriptionIsoquinoline, 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.
UsesIsoquinolines 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.
Related reactions
279 records
Compound notes
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