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
• Uses: This reagent was used as a catalytic transient directing group by Jin-Quan Yu′s lab for Pd(II)-catalyzed γ-C(sp3)-H arylation to couple free primary amines with aryl iodides. Reactions included Pd(OAc)2 683124 and low catalyst and directing group loading.

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:

3-[4-Hydroxy-4-[(2-fluorophenyl)ethynyl)piperidino)methyl-1H-pyridin-2-one

1-(2-Oxo-1,2-dihydro-3-pyridylmethyl)-4-(2-methylphenoxymethyl)piperidine-4-carbonitrile

(E)-N-hydroxy-3-(2-oxo-1-(3-(3-(trifluoromethyl)phenyl)propyl)-1,2-dihydropyridin-3-yl)acrylamide

(E)-N-hydroxy-3-(2-oxo-1-(3-(2-(trifluoromethyl)phenyl)propyl)-1,2-dihydropyridin-3-yl)acrylamide

Refernces

• 1、 Nocentini, Alessio,Supuran, Claudiu T.,?alubovskis, Raivis,Domra?eva, Ilona,Grandāne, Aiga. "Development of oxathiino[6,5-b]pyridine 2,2-dioxide derivatives as selective inhibitors of tumor-related carbonic anhydrases IX and XII". . . Retrieved 2020/05/25.
• 2、 Saubern, Simon,Macdonald, James M.,Ryan, John H.,Woodgate, Ruth C.J.,Louie, Theola S.,Fuchter, Matthew J.,White, Jonathan M.,Holmes, Andrew B.. "Tricyclic-isoxazolidine analogues via intramolecular 1,3-dipolar cycloaddition reactions of nitrones". experimental part. p. 2761 - 2767. Retrieved 2010/05/02.