10-Hydroxybenzo[h]quinoline

Base Information

• Chemical Name: 10-Hydroxybenzo[h]quinoline
• CAS No.: 33155-90-7
• Molecular Formula: C13H9NO
• Molecular Weight: 195.221
• Hs Code.: 29334900
• European Community (EC) Number: 679-961-9
• DSSTox Substance ID: DTXSID40954770
• Nikkaji Number: J256.570F,J1.758.464B
• Wikidata: Q72483274,Q69755188
• Mol file: 33155-90-7.mol

Synonyms:4-hydroxy-5-azaphenanthrene

Chemical Property of 10-Hydroxybenzo[h]quinoline

Chemical Property:

• Appearance/Colour: White powder
• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 103-105°C
• Refractive Index: 1.768
• Boiling Point: 420.621 °C at 760 mmHg
• PKA: 8.03±0.30(Predicted)
• Flash Point: 208.184 °C
• PSA: 33.12000
• Density: 1.307 g/cm³
• LogP: 3.09360
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility.: Soluble in acetone, chloroform and ethyl acetate.
• XLogP3: 1.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 195.068413911
• Heavy Atom Count: 15
• Complexity: 525

Purity/Quality:

99% ^*data from raw suppliers

5-Hydroxy-4-azaphenanthrene ^*data from reagent suppliers

Safty Information:

• Pictogram(s): R36/37/38:Irritating to eyes, respiratory system and skin.
• Hazard Codes: R36/37/38:Irritating to eyes, respiratory system and skin.
• Statements: 36/37/38
• Safety Statements: 26-37

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(=O)C2=C3C(=CC=CN3)C=CC2=C1
• General Description: 10-Hydroxybenzo[h]quinoline is a key intermediate used in the synthesis of π-conjugated polymers containing organoboron benzo[h]quinolate, contributing to enhanced optical properties such as improved fluorescence quantum yield and extended π-conjugation, which are beneficial for applications in chemical probes, photosensitizers, and optical sensing. Its incorporation into polymer backbones facilitates efficient energy transfer, leading to superior performance compared to low-molecular-mass analogs.

Technology Process of 10-Hydroxybenzo[h]quinoline

There total 3 articles about 10-Hydroxybenzo[h]quinoline which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 70.0%

ortho-methylbenzoic acid (118-90-1) + 10-bromobenzoquinoline (152583-10-3) → benzo[h]quinolin-10-ol (33155-90-7) + benzo[h]quinolin-10-yl 2-methylbenzoate

Guidance literature:

With potassium fluoride; silver carbonate; In para-xylene; at 120 ℃; Solvent;

DOI:10.1016/j.tetlet.2016.01.022

Reference yield: 65.0%

C13H9NO (865836-98-2) → benzo[h]quinolin-10-ol (33155-90-7) + 7-hydroxy-benzoquinoline (87707-11-7)

Guidance literature:

With hydrogenchloride; In ethanol; water; Heating;

DOI:10.1016/j.tetlet.2005.03.164

Reference yield:

C13H9NO (865836-98-2) → 7,8-benzoquinoline (230-27-3) + benzo[h]quinolin-10-ol (33155-90-7)

Guidance literature:

With trimethylsilyl iodide; In acetonitrile; at 20 ℃;

DOI:10.1016/j.tetlet.2005.03.164

upstream raw materials:

C₁₃H₉NO

ortho-methylbenzoic acid

10-bromobenzoquinoline

Downstream raw materials:

10-hydroxybenzo[h]quinolinatediphenylboron

bis(10-hydroxybenzo[h]quinolinato) beryllium

Refernces

Synthesis of π-Conjugated polymers containing organoboron benzo[ h ]quinolate in the main chain

10.1021/ma100814v

This research focused on the synthesis and characterization of π-conjugated polymers containing organoboron benzo[h]quinolate in the main chain, with the aim of leveraging their promising optical properties for applications such as chemical probes, photosensitizers, and optical sensing. The study demonstrated that the introduction of organoboron benzo[h]quinolate into the polymer backbone enhances the fluorescence quantum yield and leads to a bathochromic shift in the absorption peaks due to the extended π-conjugation. The researchers successfully prepared low-molecular-mass organoboron benzo[h]quinolate complexes and main-chain-type organoboron benzo[h]quinolate polymers using Sonogashira-Hagihara coupling in moderate yields. Key chemicals used in the process included 10-hydroxybenzo[h]quinoline, triphenylborane, 1,4-diethynyl-2,5-dihexadecyloxybenzene, and 1,4-diethynyl-2-perfluorooctyl-5-trifluoromethylbenzene, among others. The conclusions highlighted the efficient energy transfer from the π-conjugated main chain to the benzo[h]quinolate ligand, resulting in higher quantum yields for the polymers compared to the low-molecular-mass model compound.