2-Hydroxynicotinaldehyde

Base Information

• Chemical Name: 2-Hydroxynicotinaldehyde
• CAS No.: 36404-89-4
• Molecular Formula: C6H5NO2
• Molecular Weight: 123.111
• Hs Code.: 29333990
• European Community (EC) Number: 832-180-9
• DSSTox Substance ID: DTXSID10427668
• Nikkaji Number: J1.530.782J
• Wikidata: Q72480627
• Mol file: 36404-89-4.mol

Synonyms:2-hydroxynicotinaldehyde;36404-89-4;2-Oxo-1,2-dihydro-3-pyridinecarbaldehyde;2-oxo-1,2-dihydropyridine-3-carbaldehyde;2-oxo-1H-pyridine-3-carbaldehyde;32768-36-8;2-Hydroxy-pyridine-3-carbaldehyde;3-Pyridinecarboxaldehyde, 1,2-dihydro-2-oxo-;MFCD07698588;formylpyridone;hydroxynicotinaldehyde;2-Hydroxynicotinaldehyde, 97%;SCHEMBL1413944;DTXSID10427668;DNTYEVWEOFZXFE-UHFFFAOYSA-N;AKOS005070038;AKOS015856226;AB55041;CS-W003412;AC-23747;SY021292;2-oxo-1,2-dihydro-pyridine-3-carbaldehyde;2-oxo-1,2-dihydropyridine-3-carboxaldehyde;A6296;AM20070207;FT-0648018;EN300-300807;2Z-0720;J-510203;2-oxo-1,2-dihydro-3-pyridinecarbaldehyde, AldrichCPR;Z1198173495

Chemical Property of 2-Hydroxynicotinaldehyde

Chemical Property:

• Vapor Pressure: 0.001mmHg at 25°C
• Melting Point: 220-222 °C
• Refractive Index: 1.629
• Boiling Point: 303.966 °C at 760 mmHg
• PKA: 10.18±0.10(Predicted)
• Flash Point: 137.634 °C
• PSA: 49.93000
• Density: 1.327 g/cm³
• LogP: 0.18740
• Storage Temp.: 2-8°C
• XLogP3: -0.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 123.032028402
• Heavy Atom Count: 9
• Complexity: 203

Purity/Quality:

99% ^*data from raw suppliers

2-Hydroxynicotinaldehyde ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22-36
• Safety Statements: 26-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CNC(=O)C(=C1)C=O
• General Description: 2-Hydroxynicotinaldehyde serves as an effective transient directing group in Pd-catalyzed γ-C(sp3)-H oxygenation reactions of alkyl amines, enabling selective functionalization at γ-methyl positions. This method demonstrates broad substrate compatibility, accommodating diverse acids and alcohols to yield amine-containing esters and ethers, and is applicable to late-stage modifications of complex molecules. Its utility lies in simplifying the synthesis of mono-protected amino alcohols and hindered ethers, which are otherwise difficult to access.

Technology Process of 2-Hydroxynicotinaldehyde

There total 13 articles about 2-Hydroxynicotinaldehyde 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: 98.5%

2-chloro-3-carbaldehydepyridine (36404-88-3) → 2-oxo-1,2-dihydro-pyridine-3-carbaldehyde (36404-89-4,32768-36-8)

Guidance literature:

With hydrogenchloride; dihydrogen peroxide; In water; at 170 ℃; for 0.25h; under 11251.1 Torr;

DOI:10.1016/j.tet.2010.01.062

Reference yield: 75.2%

2-hydroxy-3-pyridinecarbaldehyde diacetate (114951-38-1) → 2-hydroxy-3-pyridinecarboxaldehyde (36404-89-4)

Guidance literature:

In water; for 0.5h; Heating;

Reference yield: 70.0%

2-hydroxy-3-hydroxymethylpyridine (42463-41-2) → 2-hydroxy-3-pyridinecarboxaldehyde (36404-89-4)

Guidance literature:

With manganese(IV) oxide; ethyl acetate; at 50 ℃; for 18h;

DOI:10.1016/j.ejmech.2020.112300

upstream raw materials:

2-hydroxy-3-hydroxymethylpyridine

2-hydroxy-3-pyridinecarbaldehyde diacetate

β-2',3'-O-isopropylidene nicotinamide riboside

3-pyridine carbaldehyde diacetate

Downstream raw materials:

1-ethyl-2-oxo-1,2-dihydro-pyridine-3-carbaldehyde

3-[(2-phenoxyphenylamino)methyl]pyridin-2-ol

5-chloro-2-hydroxynicotinaldehyde

tert-butyl (2-((3-formylpyridin-2-yl)oxy)ethyl)carbamate

Refernces

Transient Directing Group Enabled Pd-Catalyzed γ-C(sp³)-H Oxygenation of Alkyl Amines

10.1021/acscatal.0c01310

The research describes a novel method for the γ-C(sp3)–H oxygenation of free aliphatic amines, utilizing 2-hydroxynicotinaldehyde as a transient directing group and N-fluoro-2,4,6-trimethylpyridinium tetrafluoroborate as a bystanding oxidant. The purpose of this study was to develop a general protocol for the selective oxygenation at the γ-methyl positions of a wide range of aliphatic amines, which could be coupled with various aryl, heteroaryl, and aliphatic acids, as well as primary, secondary, and tertiary alcohols, to afford amine-containing esters and ethers. The conclusions highlight the method's broad applicability, good functional group tolerance, and its potential for late-stage functionalization of natural products and drug molecules, such as ibuprofen, isozepac, fenbufen, and lithocholic acid. This approach provides a more straightforward access to mono-protected amino alcohols and hindered ethers, which are challenging to synthesize using conventional methods.

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