6-Methoxyquinoline

HCID 14860
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Basic information

CAS
5263-87-6
Standard SMILES
COc1ccc2ncccc2c1
InChIKey
HFDLDPJYCIEXJP-UHFFFAOYSA-N
Molecular formula
C10H9NO
Average molar mass
159.18 g/mol
Monoisotopic mass
159.06841391

Overview

6-methoxyquinoline is an aromatic ether that is quinoline substituted at position 6 by a methoxy group. It is a member of quinolines and an aromatic ether.

Names & identifiers

Preferred name
6-Methoxyquinoline
IUPAC
6-methoxyquinoline
English name
6-Methoxyquinoline
Molecular formula
C10H9NO
Molecular weight
159.18

Names & synonyms

6-Methoxyquinoline5263-87-6Quinoline, 6-methoxy-Methyl 6-quinolyl ether5S1U3125ADNSC-1954DTXSID9063746FEMA NO. 4640CHEBI:72822RefChem:104961DTXCID0041224226-077-2
Show more names
6-quinanisole6-methoxy-quinolinTIMTEC-BB SBB008352Methoxyquinoline,95%6-Methoxyquinoline6-6-Methoxyquinoline>
6-Methoxy-quinolinep-QuinanisoleMFCD00006800NSC 1954CHEMBL15200UNII-5S1U3125AD6-methoxyquinolin6-methoxy quinoline

Database identifiers

CAS
5263-87-6
PubChem CID
14860
DTXSID
DTXSID9063746
ChEMBL
CHEMBL15200
ChEBI
CHEBI:72822
UNII
5S1U3125AD
EC Number
226-077-2
Nikkaji
J54.285G

Properties

Computed structural properties

XLogP
2.2
Topological polar surface area
22.1 Ų
Hydrogen bond donors
0
Hydrogen bond acceptors
2
Rotatable bonds
1
Heavy atoms
12

Experimental & physicochemical properties

Chemical ClassesNitrogen Compounds -> Quinolines
SpringerMaterials PropertiesChemical shift
LogP2.2
Food AdditivesFLAVORING AGENT OR ADJUVANT -> FDA Substance added to food
Density1.151-1.154 (20º)
Solubility · 2 items

Very slightly soluble in water

Soluble (in ethanol)

Physicochemical properties

Melting point
18 · 18-20 °C (lit.)
Boiling point
140 · 140-146 °C/15 mmHg (lit.)
Density
1.15 g/mL · 1.15 g/mL at 20 °C (lit.)
refractive index
20 · n20/D 1.625(lit.)
FEMA
4640 · 4640 | 6-METHOXYQUINOLINE
Flash point
230 °F · >230 °F

Safety & regulation

GHS classification

GHS Classification · 4 items

Warning

H302 (20%): Harmful if swallowed [Warning Acute toxicity, oral]

P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P317, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 10 reports by companies from 6 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Hazard information

Hazards SummaryMay cause irritation; [Sigma-Aldrich MSDS] See Quinoline.
Hazard Classes and CategoriesAcute Tox. 4 (20%)

Safety data

F
8
PPE
Eyeshields, Gloves, multi-purpose combination respirator cartridge (US)
wgk
3
tsca
TSCA listed
hs_code
29334990
risk_code
36/37/38

Chemistry & industry

Uses & manufacturing

Use Classification · 2 items

Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes

Flavoring Agents -> JECFA Flavorings Index

General Manufacturing InformationQuinoline, 6-methoxy-: INACTIVE
Applications · 2 items

Uses6-Methoxyquinoline is a useful sythetic intermediate

Uses6-Methoxyquinoline is used as a precursor in the synthesis of:Fluorescent zinc and chlorine sensors.5-Amino-2-aroylquinolines as potent tubulin polymerization inhibitors.3-Fluoro-6-methoxyquinoline derivatives as inhibitors of bacterial DNA gyrase and topoisomerase.Cobalt-based ternary metal-organic complex as singleion magnets.

Preparation methods · 1 item

PreparationCurrently, the Skraup synthesis method is mostly used for the synthesis of 6-methoxyquinoline. The Skraup synthesis method involves reacting aromatic amines, glycerol or α,β-unsaturated aldehydes or ketones, sulfuric acid and nitrobenzene (corresponding to the aromatic amine used), arsenic pentoxide or ferric chloride and other oxidizing agents together to generate quinoline and its derivatives.

Upstream & downstream products

Suppliers100 total

国药集团化学试剂有限公司86-21-63210123 · [email protected]
河北凡博医药科技有限公司15588346797
北京华美互利生物化工010-56205725 · [email protected]
梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
郑州阿尔法化工有限公司+86-18530059196 · [email protected]

Additional notes

DefinitionChEBI: An aromatic ether that is quinoline substituted at position 6 by a methoxy group.

Related reactions

36 records
New reaction record

Compound notes

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