36404-89-4

Basic information

• Product Name: 2-Hydroxynicotinaldehyde
• Synonyms: 2-OXO-1,2-DIHYDRO-3-PYRIDINECARBALDEHYDE;2-Hydroxynicotinaldehyde;2-Hydroxypyridine-3-carboxaldehyde;2-hydroxypyridine-3-carbaldehyde;1,2-dihydro-2-oxo-3-Pyridinecarboxaldehyde;2-Oxo-1,2-dihydropyridine-3-carbaldehyde;2-keto-1H-pyridine-3-carbaldehyde;2-oxo-1H-pyridine-3-carbaldehyde
• CAS NO: 36404-89-4
• Molecular Formula: C₆H₅NO₂
• Molecular Weight: 123.11
• Product Categories: Heterocycle-Pyridine series
• Mol File: 36404-89-4.mol
• Article Data: 10

Chemical Properties

• Melting Point: 220-222°
• Boiling Point: 303.966 °C at 760 mmHg
• Flash Point: 137.634 °C
• Appearance: /
• Density: 1.327 g/cm³
• Vapor Pressure: 0.001mmHg at 25°C
• Refractive Index: 1.629
• Storage Temp.: 2-8°C
• PKA: 10.18±0.10(Predicted)
• CAS DataBase Reference: 2-Hydroxynicotinaldehyde(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Hydroxynicotinaldehyde(36404-89-4)
• EPA Substance Registry System: 2-Hydroxynicotinaldehyde(36404-89-4)

Safety Data

• Hazard Codes: Xn
• Statements: 22-36
• Safety Statements: 26-24/25
• HazardClass: IRRITANT
• Hazardous Substances Data: 36404-89-4(Hazardous Substances Data)

Usage

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.

InChI:InChI=1/C6H5NO2/c8-4-5-2-1-3-7-6(5)9/h1-4H,(H,7,9)

Upstream product

• 14265-48-6 β-2',3'-O-isopropylidene nicotinamide riboside 
• 36404-88-3 2-chloro-3-carbaldehydepyridine 
• 109-09-1 2-chloropyridine 
• 98-92-0 nicotinamide 
• 102268-35-9 3-Carbamoyl-1-(2-hydroxy-3,4-dioxo-cyclobut-1-en-1-yl)pyridiniumhydroxid, inneres Salz 
• 71255-09-9 2-methoxynicotinaldehyde 
• 609-71-2 2-hydroxy-3-carboxypyridine 
• 114951-35-8 3-pyridinecarbaldehyde diacetate 1-oxide 
• 114951-44-9 3-pyridine carbaldehyde diacetate 
• 114951-38-1 2-hydroxy-3-pyridinecarbaldehyde diacetate 
• 42463-41-2 2-hydroxy-3-hydroxymethylpyridine 

Downstream Products

• 5693-71-0 2-oxo-2H-pyrano<2,3-b>pyridine 
• 138060-93-2 C₁₈H₁₈N₂O 
• 36404-92-9 (E)-3-(2'-hydroxypyridin-3-yl)prop-2-enoic acid 
• 35567-39-6 2-oxo-3-(3',4',5'-trimethoxyphenyl)-2H-pyrano<2,3-b>pyridine 
• 917391-96-9 1-ethyl-2-oxo-1,2-dihydro-pyridine-3-carbaldehyde 
• 614726-66-8 3-[4-Hydroxy-4-[(2-fluorophenyl)ethynyl)piperidino)methyl-1H-pyridin-2-one 
• 614725-21-2 1-(2-Oxo-1,2-dihydro-3-pyridylmethyl)-4-(2-methylphenoxymethyl)piperidine-4-carbonitrile 
• 36721-61-6 3-(hydroxymethyl)-1-methylpyridin-2(1H)-one 
• 51417-15-3 3-(chloromethyl)-1-methylpyridin-2(1H)-one 
• 79138-28-6 1-methyl-2-oxo-1,2-dihydropyridine-3-carbaldehyde 
• 614732-03-5 5-chloro-2-hydroxynicotinaldehyde 

Relevant articles and documents

Isolation and characterization of the fluorescent alkali product from diphosphopyridine nucleotide.

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Synthesis and pharmacological evaluation of N-benzyl substituted 4-bromo-2,5-dimethoxyphenethylamines as 5-HT2A/2C partial agonists

N-Benzyl substitution of phenethylamine 5-HT2A receptor agonists has dramatic effects on binding affinity, receptor selectivity and agonist activity. In this paper we examine how affinity for the 5-HT2A/2C receptors are influenced by N-benzyl substitution of 4-bromo-2,5-dimethoxyphenethylamine derivatives. Special attention is given to the 2′ and 3′-position of the N-benzyl as such compounds are known to be very potent. We found that substitutions in these positions are generally well tolerated. The 2′-position was further examined using a range of substituents to probe the hydrogen bonding requirements for optimal affinity and selectivity, and it was found that small changes in the ligands in this area had a profound effect on their affinities. Furthermore, two ligands that lack a 2′-benzyl substituent were also found to have high affinity contradicting previous held notions. Several high-affinity ligands were identified and assayed for functional activity at the 5-HT2A and 5-HT2C receptor, and they were generally found to be less efficacious agonists than previously reported N-benzyl phenethylamines.

THROMBIN INHIBITING 2-OXO-1, 2, 5, 6-TETRAHYDROPYRIDINE DERIVATIVES

There is provided a compound of formula (I) wherein R1, R2a, R2b, R3a, R3b, R4, R5a, R5b, R6 to R8, A and G have meanings given in the description, which compounds are useful as, or are useful as prodrugs of, competitive inhibitors of trypsin-like proteases, such as thrombin, and thus, in particular, in the treatment of conditions where inhibition of thrombin is beneficial (e.g. conditions, such as thrombo-embolisms, where inhibition of thrombin is required or desired, and/or conditions where anticoagulant therapy is indicated).