2598-30-3

Basic information

• Product Name: 8-HYDROXY-QUINOLINE-5-CARBALDEHYDE
• Synonyms: IFLAB-BB F2108-0159;8-HYDROXY-QUINOLINE-5-CARBALDEHYDE;5g 1 pcs;5-Quinolinecarboxaldehyde,8-hydroxy-;8-hydroxy-5-Quinolinecarboxaldehyde
• CAS NO: 2598-30-3
• Molecular Formula: C₁₀H₇NO₂
• Molecular Weight: 173.17
• Mol File: 2598-30-3.mol
• Article Data: 25

Chemical Properties

• Melting Point: 178 °C
• Boiling Point: 383.1 °C at 760 mmHg
• Flash Point: 185.5 °C
• Appearance: /
• Density: 1.364 g/cm³
• Vapor Pressure: 2.05E-06mmHg at 25°C
• Refractive Index: 1.733
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• PKA: 3.88±0.10(Predicted)
• CAS DataBase Reference: 8-HYDROXY-QUINOLINE-5-CARBALDEHYDE(CAS DataBase Reference)
• NIST Chemistry Reference: 8-HYDROXY-QUINOLINE-5-CARBALDEHYDE(2598-30-3)
• EPA Substance Registry System: 8-HYDROXY-QUINOLINE-5-CARBALDEHYDE(2598-30-3)

Safety Data

• Hazard Codes: Xn
• Statements: 22-36/37/38
• Safety Statements: 26
• Hazardous Substances Data: 2598-30-3(Hazardous Substances Data)

Usage

Uses

8-Hydroxyquinoline-5-carbaldehyde is used in preparation of Polycyclic compounds.

InChI:InChI=1/C10H7NO2/c12-6-7-3-4-9(13)10-8(7)2-1-5-11-10/h1-6,13H

Synthetic route

8-quinolinol (148-24-3) + chloroform (67-66-3) → 8-hydroxyquinoline-5-carbaldehyde (2598-30-3)

Conditions	Yield
With tetrabutylammomium bromide In ethanol	24%
Stage #1: 8-quinolinol With sodium hydroxide In ethanol; water at 110℃; Stage #2: chloroform In ethanol; water at 70 - 110℃;	20%
Stage #1: 8-quinolinol With sodium hydroxide In ethanol; water at 40 - 65℃; Stage #2: chloroform With cetyltrimethylammonim bromide In ethanol; water at 65℃; for 8h; Stage #3: With water; acetic acid pH=5;	19.3%

8-quinolinol (148-24-3) + methylene chloride (74-87-3) → 8-hydroxyquinoline-5-carbaldehyde (2598-30-3)

Conditions	Yield
Stage #1: 8-quinolinol; methylene chloride With cetyltrimethylammonim bromide In ethanol for 0.5h; Stage #2: With water; sodium hydroxide In ethanol at 78℃; for 12h;	17%

8-quinolinol (148-24-3) + ethanol (64-17-5) → 8-hydroxyquinoline-5-carbaldehyde (2598-30-3)

Conditions	Yield
With cetyltrimethylammonim bromide; sodium hydroxide In chloroform; water for 20h; Reflux;	14.4%

8-quinolinol (148-24-3) + chloroform (67-66-3) → 8-hydroxyquinoline-5-carbaldehyde (2598-30-3) + 8-hydroxy-7-quinolinecarboxaldehyde (5683-78-3)

Conditions	Yield
With potassium hydroxide In ethanol; water for 4h; Reimer-Tiemann Phenol Formylation; Reflux; Inert atmosphere;	A 10.1% B n/a
With sodium hydroxide In ethanol; water at 100℃; for 12h;	A n/a B 3.0 g

5-(hydroxymethyl)-8-hydroxyquinoline (4053-44-5) + sodium 3-nitrobenzenesulfonate (127-68-4) → 8-hydroxyquinoline-5-carbaldehyde (2598-30-3)

Conditions	Yield
With sodium hydroxide; water at 120℃;

5-(2,2,2-trichloro-1-hydroxy-ethyl)-quinolin-8-ol (23218-68-0) → 8-hydroxyquinoline-5-carbaldehyde (2598-30-3)

Conditions	Yield
With methanol; sodium methylate

tetrachloromethane (56-23-5) + 8-quinolinol (148-24-3) + ethanol (64-17-5) + chloroform (67-66-3) + water (7732-18-5) → 8-hydroxyquinoline-5-carbaldehyde (2598-30-3)

8-quinolinol (148-24-3) → 8-hydroxyquinoline-5-carbaldehyde (2598-30-3)

Conditions	Yield
Multi-step reaction with 2 steps 1: water; hydrochloric acid; hydrogen chloride / und Behandeln des Reaktionsprodukts mit wss.Ammoniak oder wss.Natriumhydrogencarbonat-Loesung 2: water; NaOH-solution / 120 °C View Scheme
Multi-step reaction with 2 steps 1: concentrated sulfuric acid 2: methanol; sodium methylate View Scheme
Multi-step reaction with 2 steps 1: sulfuric acid / 70 °C / weitere Nebenprod. Verbindung C11H8Cl3NO2+ 0.5H2O 2: methanol; sodium methylate View Scheme

C13H15NO3 → 8-hydroxyquinoline-5-carbaldehyde (2598-30-3)

Conditions	Yield
Stage #1: C13H15NO3 With water; acetic acid at 60℃; Stage #2: With sodium hydrogensulfite In water at 60℃; Stage #3: With hydrogenchloride; sodium acetate more than 3 stages;

8-hydroxyquinoline-5-carbaldehyde (2598-30-3) + (1R,2R,4R)-6-Bicyclo[2.2.1]hept-5-en-2-yl-hexylamine → 5-{[(E)-(1R,2R,4R)-6-Bicyclo[2.2.1]hept-5-en-2-yl-hexylimino]-methyl}-quinolin-8-ol

Conditions	Yield
In benzene for 18h; Heating;	100%

8-hydroxyquinoline-5-carbaldehyde (2598-30-3) + 6-Bicyclo[2.2.1]hept-5-en-2-yl-hexylamine (511243-84-8) → 5-[(6-Bicyclo[2.2.1]hept-5-en-2-yl-hexylimino)-methyl]-quinolin-8-ol

Conditions	Yield
In benzene	100%

8-hydroxyquinoline-5-carbaldehyde (2598-30-3) + 3-aminopropyltriethoxysilane (919-30-2) → 5-(CHN(CH2)3Si(OC2H5)3)-8-hydroxyquinoline

Conditions	Yield
In ethanol for 12h; Heating;	100%

8-hydroxyquinoline-5-carbaldehyde (2598-30-3) + 4-methoxybenzoic acid hydrazide (3290-99-1) → N'-((8-hydroxyquinolin-5-yl)methylene)-4-methoxybenzohydrazide (700354-89-8)

Conditions	Yield
With hydrogenchloride In 1,4-dioxane; dimethyl sulfoxide at 20℃; for 18h;	99%

8-hydroxyquinoline-5-carbaldehyde (2598-30-3) + p-toluenesulfonyl chloride (98-59-9) → 5-formyl-8-p-toluenesulfonyloxyquinoline (10522-61-9)

Conditions	Yield
In dichloromethane at 20℃; Cooling with ice;	98%
In dichloromethane at 20℃; for 12h;	98%
Stage #1: 8-hydroxyquinoline-5-carbaldehyde With triethylamine In chloroform for 1h; Stage #2: p-toluenesulfonyl chloride In dichloromethane; chloroform at 20℃; for 13h; Cooling with ice;	84%

8-hydroxyquinoline-5-carbaldehyde (2598-30-3) + p-toluenesulfonyl chloride (98-59-9) → 5-formyl-8-tosyloxyquinoline

Conditions	Yield
In dichloromethane at 20℃; for 12h; Cooling with ice;	98%

8-hydroxyquinoline-5-carbaldehyde (2598-30-3) + 2,3,3-trimethyl-1-phenyl-3H-indol-1-ium perchlorate → 1-phenyl-2-[2-(8-hydroxyquinolin-5-yl)ethenyl]-3,3-dimethyl-3H-indolium perchlorate (1579297-59-8)

Conditions	Yield
In butan-1-ol for 0.5h; Reflux;	97%

8-hydroxyquinoline-5-carbaldehyde (2598-30-3) + C15H17N3O4S → 4-ethoxy-N-(4-(2-((8-hydroxyquinolin-5-yl)methylene)hydrazine-1-carbonyl)phenyl)benzenesulfonamide

Conditions	Yield
With hydrogenchloride In 1,4-dioxane; dimethyl sulfoxide at 20℃; for 18h;	93%

8-hydroxyquinoline-5-carbaldehyde (2598-30-3) + C11H11N3O3S2 (380427-32-7) → N-(4-(2-((8-hydroxyquinolin-5-yl)methylene)hydrazine-1-carbonyl)phenyl)thiophene-2-sulfonamide

Conditions	Yield
With hydrogenchloride In 1,4-dioxane; dimethyl sulfoxide at 20℃; for 18h;	90%

8-hydroxyquinoline-5-carbaldehyde (2598-30-3) + 4-Bromo-N-(4-hydrazinocarbonyl-phenyl)-benzenesulfonamide (59256-25-6) → 4-bromo-N-(4-(2-((8-hydroxyquinolin-5-yl)methylene)hydrazine-1-carbonyl)phenyl)benzenesulfonamide

Conditions	Yield
With hydrogenchloride In 1,4-dioxane; dimethyl sulfoxide at 20℃; for 18h;	88%

Nicotinic acid hydrazide (553-53-7) + 8-hydroxyquinoline-5-carbaldehyde (2598-30-3) → 8-hydroxy-quinoline-5-carbaldehyde nicotinoylhydrazone

Conditions	Yield
With formic acid In ethanol for 8h; Reflux;	86%

poly(styrene-p-aminomethylstyrene), styrene:p-aminomethylstyrene ratio 2:1; monomer(s): styrene; 4-vinylbenzyl chloride + 8-hydroxyquinoline-5-carbaldehyde (2598-30-3) → polymer, styrene:5-((4-vinyl-benzylimino)methyl)quinolin-8-ol fragments ratio = 2:1; monomer(s): styrene; 4-vinylbenzyl chloride; 5-formyl-8-hydroxyquinoline

Conditions	Yield
In tetrahydrofuran for 24h; Heating;	85%

8-hydroxyquinoline-5-carbaldehyde (2598-30-3) → C20H14N4O2

Conditions	Yield
With hydrazine In ethanol for 0.333333h;	84%

8-hydroxyquinoline-5-carbaldehyde (2598-30-3) + 4,4-difluoro-8-(4-aminophenyl)-3,5-dimethyl-4-bora-3a,4a-diaza-s-indacene → C29H25BF2N4O (1296130-60-3)

Conditions	Yield
With acetic acid In ethanol; dichloromethane for 5h; Reflux;	84%

5-chloro-2-thiophenecarboxylic acid hydraizde (351983-31-8) + 8-hydroxyquinoline-5-carbaldehyde (2598-30-3) → 5-chloro-N'-((8-hydroxyquinolin-5-yl)methylene)thiophene-2-carbohydrazide

Conditions	Yield
With hydrogenchloride In 1,4-dioxane; dimethyl sulfoxide at 20℃; for 18h;	83%

8-hydroxyquinoline-5-carbaldehyde (2598-30-3) + N-propylheptakis(isobutyl)POSS-3,5-diaminobenzamide (1220715-67-2) → C58H87N5O15Si8 (1322137-90-5)

Conditions	Yield
In ethanol for 30h; Inert atmosphere; Reflux;	82%

2-thienylhydrazide (2361-27-5) + 8-hydroxyquinoline-5-carbaldehyde (2598-30-3) → N'-((8-hydroxyquinolin-5-yl)methylene)thiophene-2-carbohydrazide

Conditions	Yield
With hydrogenchloride In 1,4-dioxane; dimethyl sulfoxide at 20℃; for 18h;	82%

8-hydroxyquinoline-5-carbaldehyde (2598-30-3) + 4-(dimethylamino)benzohydrazide (19353-92-5) → 4-(dimethylamino)-N'-((8-hydroxyquinolin-5-yl)methylene)benzohydrazide

Conditions	Yield
With hydrogenchloride In 1,4-dioxane; dimethyl sulfoxide at 20℃; for 18h;	82%

8-hydroxyquinoline-5-carbaldehyde (2598-30-3) + 2-phenoxybenzoic acid hydrazide (43038-37-5) → N'-((8-hydroxyquinolin-5-yl)methylene)-2-phenoxybenzohydrazide

Conditions	Yield
With hydrogenchloride In 1,4-dioxane; dimethyl sulfoxide at 20℃; for 18h;	82%

poly(styrene-p-aminomethylstyrene), styrene:p-aminomethylstyrene ratio 9:1; monomer(s): styrene; 4-vinylbenzyl chloride + 8-hydroxyquinoline-5-carbaldehyde (2598-30-3) → polymer, styrene:5-((4-vinyl-benzylimino)methyl)quinolin-8-ol fragments ratio = 9:1; monomer(s): styrene; 4-vinylbenzyl chloride; 5-formyl-8-hydroxyquinoline

Conditions	Yield
In tetrahydrofuran for 24h; Heating;	80%

8-hydroxyquinoline-5-carbaldehyde (2598-30-3) + 4,4-difluoro-8-(4-aminophenyl)-3,5-dimethyl-4-bora-3a,4a-diaza-s-indacene → C27H21BF2N4O (1296130-59-0)

Conditions	Yield
With acetic acid In ethanol; dichloromethane for 5h; Reflux;	80%

1-aminohydantoin (6301-02-6) + 8-hydroxyquinoline-5-carbaldehyde (2598-30-3) → 1-(((8-hydroxyquinolin-5-yl)methylene)amino)imidazolidine-2,4-dione

Conditions	Yield
With hydrogenchloride In 1,4-dioxane; dimethyl sulfoxide at 20℃; for 18h;	78%

8-hydroxyquinoline-5-carbaldehyde (2598-30-3) + N-dodecyl-3,5-diaminobenzamide (141505-16-0) → C39H43N5O3 (1322137-91-6)

Conditions	Yield
In ethanol for 30h; Inert atmosphere; Reflux;	77%

8-hydroxyquinoline-5-carbaldehyde (2598-30-3) + 3-<(Diethylamino)sulfonyl>benzoic Acid Hydrazide (96134-80-4) → N,N-diethyl-3-(2-((8-hydroxyquinolin-5-yl)methylene)hydrazine-1-carbonyl)benzenesulfonamide

Conditions	Yield
With hydrogenchloride In 1,4-dioxane; dimethyl sulfoxide at 20℃; for 18h;	76%

[iridium(III)(μ-chloro)(2-phenylpyridine)2]2 + 8-hydroxyquinoline-5-carbaldehyde (2598-30-3) → [κ2(N,O)-5-formyl-8-quinolinato]bis[κ2(C2,N)-2-phenylpyridine]ridium(III)

Conditions	Yield
With triethylamine In ethanol; dichloromethane Ar, an excess of quinoline deriv., refluxed for 20 h; solvent removed (vac.), residue washed (hot methanol), ppt filtered; TGA, MAS, NMR;	75.5%

8-hydroxyquinoline-5-carbaldehyde (2598-30-3) + 4-amino-N,N-dimethylaniline (99-98-9) → 5-[(4'-N,N-dimethyl)phenyliminomethyl]-8-hydroxyquinoline

Conditions	Yield
In ethanol for 4h; Heating;	74%

8-hydroxyquinoline-5-carbaldehyde (2598-30-3) + 4-hydroxybenzoic acid hydrazide (5351-23-5) → 4-hydroxy-N'-((8-hydroxyquinolin-5-yl)methylene)benzohydrazide (17076-04-9)

Conditions	Yield
With hydrogenchloride In 1,4-dioxane; dimethyl sulfoxide at 20℃; for 18h;	73%

8-hydroxyquinoline-5-carbaldehyde (2598-30-3) + 2-(1H-benzo[d][1,2,3]triazol-1-yl)acetohydrazide (122502-94-7) → 8-hydroxyquinoline-5-carbaldehyde-(benzotriazol-1′-acetyl)hydrazone (1425802-82-9)

Conditions	Yield
In ethanol for 10h; Reflux;	72%

8-hydroxyquinoline-5-carbaldehyde (2598-30-3) + benzoic acid hydrazide (613-94-5) → N'-((8-hydroxyquinolin-5-yl)methylene)benzohydrazide (17076-07-2)

Conditions	Yield
With hydrogenchloride In 1,4-dioxane; dimethyl sulfoxide at 20℃; for 18h;	72%

8-hydroxyquinoline-5-carbaldehyde (2598-30-3) + 2,6-diisopropylbenzenamine (24544-04-5) → 5-[(E)-{[2,6-di(propan-2-yl)phenyl]imino}methyl]quinolin-8-ol

Conditions	Yield
In chloroform for 40h; Reflux; Inert atmosphere;	71.1%

Upstream product

• 148-24-3 8-quinolinol 
• 67-66-3 chloroform 
• 56-23-5 tetrachloromethane 
• 64-17-5 ethanol 
• 7732-18-5 water 
• 74-87-3 methylene chloride 
• 23218-68-0 5-(2,2,2-trichloro-1-hydroxy-ethyl)-quinolin-8-ol 
• 4053-44-5 5-(hydroxymethyl)-8-hydroxyquinoline 
• 127-68-4 sodium 3-nitrobenzenesulfonate 

Downstream Products

• 5541-67-3 5-methyl-8-quinolinol 
• 2240-70-2 2-[trans-2-(8-hydroxy-[5]quinolyl)-vinyl]-1,3,3-trimethyl-3H-indolium; chloride 
• 700354-89-8 N'-((8-hydroxyquinolin-5-yl)methylene)-4-methoxybenzohydrazide 
• 17076-07-2 N'-((8-hydroxyquinolin-5-yl)methylene)benzohydrazide 
• 1138320-13-4 C₁₈H₁₂N₂O₄ 
• 833488-09-8 C₁₈H₁₂BrNO₂ 

Relevant articles and documents

Selective fluorescence turn-on of a prefluorescent azomethine with Zn 2+

A prefluorescent conjugated azomethine (4) was prepared by condensing 8-hydroxyquinoline-5-carbaldehyde with 2-amine thiophene. The fluorescence of the azomethine was quenched in organic solvents including dichloromethane, methanol, DMSO, and DMF. However, the fluorescence of 4 was selectively revived in the presence of zinc and an absolute quantum yield Φfl = 0.15 was measured.

8-hydroxyquinoline-substituted boron-dipyrromethene compounds: Synthesis, structure, and OFF-ON-OFF type of pH-sensing properties

A series of four novel 8-hydroxyquinoline-substituted boron-dipyrromethene derivatives, namely 4,4-difluoro-8-(5-(8-hydroxyquinoline))-3,5-dimethyl-4-bora- 3a,4a-diaza-s-indacene (1), 4,4-difluoro-8-(5-(8-hydroxyquinoline))-1,3,5,7- tetramethyl-4-bora-3a,4a-diaza-s-indacene (2), 4,4-difluoro-8-(5-azastyryl-(8- hydroxyquinoline))-3,5-dimethyl-4-bora-3a,4a-diaza-s-indacene (3), and 4,4-difluoro-8-(5-azastyryl-(8-hydroxyquinoline))-1,3,5,7-tetramethyl-4-bora-3a, 4a-diaza-s-indacene (4), have been synthesized and characterized by a series of spectroscopic methods. The molecular structures of 1 and 2 have been determined by single-crystal X-ray diffraction analyses. The two methyl substituents attached at C-1 and C-7 positions of boron-dipyrromethene (Bodipy) in compound 2 was revealed to prevent the free rotation of the 8-hydroxyquinoline (8-HQ) moiety, resulting in an almost vertical 8-HQ-Bodipy configuration of this compound. This is obviously different from those for 1 with the dihedral angle between 8-hydroxyquinoline and Bodipy moieties of 65.44 and 66.79° due to the lack of methyl substituents in the latter compound. The intense fluorescence from the Bodipy subunit of these compounds was revealed to gradually get diminished along with either decreasing or increasing the pH value under acidic and basic conditions, respectively, in particular for 1, 2, and 4 because of the photoinduced intramolecular electron transfer from excited Bodipy moiety to 8-HQ unit and just an opposite process. This renders these compounds the first OFF-ON-OFF type of pH-dependent fluorescent sensors. Nevertheless, both the intrinsic fluorescence of these compounds and their fluorescent quenching properties along with the change in the pH value have been found to depend on the steric configuration as well as the linking group between 8-hydroxyquinoline and Bodipy moieties, revealing the effect of molecular structure on their fluorescence properties.

A covalently bonded AlQ3/SiO2 hybrid material with blue light emission by a conventional sol-gel approach

We report the design and synthesis of a covalently bonded AlQ 3/SiO2 hybrid material with strong blue light emission by a sol-gel approach, which make AlQ3 solution-processable and chemically stable. The Royal Society of Chemistry 2006.

Characterization of N-hexadecyl-5-iminomethyl-8-hydroxyquinoline and oriented crystallization of CuSO4?5H2O under its monolayer

A new amphiphilic ligand, N-hexadecyl-5-iminomethyl-8-hydroxyquinoline (HIHQ), has been synthesized in a convenient method and the characteristics of its monolayer on pure water and on a subphase containing copper ions investigated. LB films of HIHQ were studied by small angle X-ray scattering, UV-VIS and XPS spectra. An oriented crystallization was examined at the monolayer/water interface. A good selection of the (110) crystal face of CuSO4?SH2O occurred at the solid state of the monolayer due to the perfect match between this crystal face and the definite lattice structure of the monolayer.

Design and synthesis of Alq3-functionalized polymers

Synthesis of an Alq3-containing monomer and its chain-growth polymerization were demonstrated via ring-opening metathesis polymerization. Polymerization was complete within 12 h under mild polymerization conditions and solubility could be tailored via the incorporation of a comonomer. All copolymers retained the absorption and emission properties of Alq3 in solution. This indicated that the polymer coil did not interfere with the luminescence properties of the pendant Alq3 groups.

Imine derivative and 8-hydroxyquinoline derivative cadmium complex dye sensitizer, preparation method and application thereof

The invention relates to a D (-A-pi-A) 2-type imine derivative and 8-hydroxyquinoline derivative cadmium complex dye sensitizer (BDTT-PCd) as shown in a formula 1, a preparation method and applicationthereof. The dye sensitizer is a D (-A-pi-A) 2 complex synthesized by reacting an imine derivative containing functional groups like an auxiliary electron acceptor (A), a pi bridge, a main electron acceptor (A), an anchoring group and the like with an 8-hydroxyquinoline derivative cadmium complex and an electron donor (D) benzodithiophene bithiophene (BDTT) through a Heck coupling reaction. Experiments show that the dye-sensitized solar cell taking BDTT-PCd as the dye sensitizer shows good effects in photovoltaic performance tests: the photoelectric conversion efficiency (PCE) reaches 8.82%,the dye thermal decomposition temperature reaches 320DEG C or above, the thermal stability is high, the requirements of photovoltaic materials can be met, and the dye sensitizer has certain prospectsin development and application of dye-sensitized solar cells. The structure of the complex BDTT-PCd is shown as formula 1 in the specification.

Four D-A ’ - (π-A)2 Polysalicylaldehyde Schiff base derivative alloy metal complex as well as preparation method and application thereof

The invention relates to four 1-D A (π-’ -) shown A. 2 The polymeric salicylaldehyde Schiff base derivative alloy belongs to the complex BDTT-SP-Cd. The invention BDTT-SP-Zn, BDTT-SP-Cu and BDTT-SP-Ni, and a preparation method and application thereof, wherein the metal complex formed by coordination of functionalized salicylaldehyde Schiff base derivative as a main ligand and a metal serves as an electron donor BDTT and D-Heck D (π-A A) synthesized by ’ - reaction. 2 The photoelectrical conversion efficiency is BDTT, SP, Cd and BDTT BDTT Zn, the thermal decomposition temperature of the dye-SP sensitized Cu 203 °C Ni solar BDTT cell SP is SP or more, the thermal stability is good, and the dye-sensitized solar cell has a certain prospect in the 8.07% aspect 7.63% of 6.79% the 6.11% development and application of the dye-sensitized solar cell.