Isoquinoline

HCID 8405CAS 119-65-3
Substructure searchFind similar structures

Basic information

Standard SMILES
c1ccc2cnccc2c1
InChIKey
AWJUIBRHMBBTKR-UHFFFAOYSA-N
Molecular formula
C9H7N
Average molar mass
129.16 g/mol
Monoisotopic mass
129.05784923

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 properties

XLogP
2.1
Topological polar surface area
12.9 Ų
Hydrogen bond donors
0
Hydrogen bond acceptors
1
Rotatable bonds
0
Heavy atoms
10

Experimental & physicochemical properties

LogP · 2 items

2.08

2.08

LogS-1.45
Density1.097-1.103
Solubility · 4 items

4520

4.52 mg/mL at 25 °C

Slightly soluble in water

Soluble (in ethanol)

Boiling Point · 3 items

243.2

242.00 to 243.00 °C. @ 760.00 mm Hg

242-243 °C

Melting Point · 2 items

26.47

25.5 - 26 °C

Physicochemical properties

Melting point
26 · 26-28 °C (lit.)
Boiling point
242 · 242-243 °C (lit.)
Density
1.099 g/mL · 1.099 g/mL at 25 °C (lit.)
vapor pressure
5 Pa · 5Pa at 20℃
FEMA
2978 · 2978 | ISOQUINOLINE
FLAVIS Number
14.001 · 14.001 | Isoquinoline

Safety & regulation

GHS classification

GHS Classification · 6 items

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.

Hazard information

Regulatory Information · 5 items

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 items

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

Toxicology

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

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

Regulatory information

Regulatory Information · 5 items

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

Safety data

PPE
Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges
wgk
2
tsca
TSCA listed
rtecs
NW6825000
ridadr
UN 2811 6.1/PG 3
hs_code
29334900

Chemistry & industry

Pharmacology

Metabolism/MetabolitesIsoquinoline has known human metabolites that include isoquinoline N-oxide.
Cellular LocationsCytoplasm；Extracellular

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；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 items

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 · 2 items

Plastics Material and Resin Manufacturing

Isoquinoline: ACTIVE

Applications · 3 items

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.

General DescriptionIsoquinoline 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.

Preparation methods · 1 item

PreparationBischler-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.

Upstream & downstream products

Additional notes · 1 item

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.

Related reactions

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Linked notes

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