65873-72-5

Basic information

• Product Name: 6-Methoxynicotinaldehyde
• Synonyms: 2-METHOXYPYRIDINE-5-CARBOXALDEHYDE;5-FORMYL-2-METHOXYPYRIDINE;3-FORMYL-6-METHOXYPYRIDINE;6-METHOXY-3-NICOTINALDEHYDE;6-METHOXY-3-PYRIDINECARBOXALDEHYDE;6-METHOXYNICOTINALDEHYDE;6-METHOXY-PYRIDINE-3-CARBALDEHYDE;3-Pyridinecarboxaldehyde, 6-methoxy- (9CI)
• CAS NO: 65873-72-5
• Molecular Formula: C₇H₇NO₂
• Molecular Weight: 137.14
• EINECS: 2017-001-1
• Product Categories: ALDEHYDE;Pyridine;pharmacetical;Pyridine series;Pyridines;Building Blocks;Boronic Acid;Aldehydes;C6 to C7;C7;Carbonyl Compounds;Chemical Synthesis;Heterocyclic Building Blocks;Organic Building Blocks;Heterocycle-Pyridine series
• Mol File: 65873-72-5.mol

Chemical Properties

• Melting Point: 51-54 °C(lit.)
• Boiling Point: 244.2 °C at 760 mmHg
• Flash Point: 225 °F
• Appearance: Off-white to light yellow/Crystalline Powder
• Density: 1.159 g/cm³
• Vapor Pressure: 0.0308mmHg at 25°C
• Refractive Index: 1.551
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• PKA: 1.60±0.10(Predicted)
• Water Solubility: insoluble
• CAS DataBase Reference: 6-Methoxynicotinaldehyde(CAS DataBase Reference)
• NIST Chemistry Reference: 6-Methoxynicotinaldehyde(65873-72-5)
• EPA Substance Registry System: 6-Methoxynicotinaldehyde(65873-72-5)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 65873-72-5(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
6-Methoxynicotinaldehyde is used as an intermediate for the synthesis of somatostatin SST3 receptor, a peptide hormone receptor that plays a crucial role in regulating various physiological processes, including growth hormone release, insulin secretion, and neurotransmission.
Used in Organic Synthesis:
6-Methoxynicotinaldehyde is used as a substrate in the synthesis of flavanones, a class of natural compounds with diverse biological activities, through an L-proline-catalyzed condensation with o-hydroxyarylketones. This method allows for the efficient and selective synthesis of flavanones, which can be further utilized in the development of pharmaceuticals, agrochemicals, and other applications.

InChI:InChI=1/C7H7NO2/c1-10-7-3-2-6(5-9)4-8-7/h2-5H,1H3

Upstream product

• 13472-85-0 2-methoxy-5-bromopyridine 
• 68-12-2 N,N-dimethyl-formamide 
• 15871-85-9 6-methoxynicotinonitrile 
• 58584-63-7 (6-methoxypyridin-3-yl)methanol 
• 26218-80-4 6-methoxy-nicotinic acid methyl ester 
• 59-67-6 nicotinic acid 
• 3099-50-1 3-trichloromethyl-pyridine 
• 1628-89-3 2-methoxypyridine 
• 7757-82-6 sodium sulfate 
• 563-41-7 semicarbazide hydrochloride 
• 107-31-3 Methyl formate 
• 20461-86-3 2,2-diethoxy acetic acid 
• 3510-66-5 2-Bromo-5-methylpyridine 
• 121643-49-0 3-dichloromethyl-6-methoxypyridine 

Downstream Products

• 106984-91-2 6-oxo-1,6-dihydropyridine-3-carbaldehyde 
• 123506-66-1 6-methoxy-4-methylnicotinaldehyde 
• 123506-67-2 6-methoxy-5-methylnicotinaldehyde 
• 220114-73-8 2-Methoxy-5-[(Z)-2-(3,4,5-trimethoxy-phenyl)-vinyl]-pyridine 
• 220114-73-8 2-Methoxy-5-[(E)-2-(3,4,5-trimethoxy-phenyl)-vinyl]-pyridine 
• 230648-45-0 1-isopropyl-6-oxo-1,6-dihydro-pyridine-3-carbaldehyde 
• 230648-43-8 1-ethyl-6-oxo-1,6-dihydropyridine-3-carbaldehyde 
• 140701-91-3 Methyl 2-benzyloxycarbonylamino-3-(2-methoxy-5-pyridyl)-propionate 
• 140681-92-1 3-aza-L-tyrosine 
• 31140-71-3 D-3-(2-Oxo-5-pyridyl)-alanine 

Relevant articles and documents

Simple synthetic process of 6-methoxypyridine-3-formaldehyde

The invention relates to a synthesis process of 6-methoxypyridine-3-formaldehyde, which comprises the following steps: 1, reacting 6-bromo-3-methylpyridine with sodium methylate under the condition ofa dry protic solvent to obtain 6-methoxy-3-methylpyridine; 2, carrying out bromination reaction on the 6-methoxy-3-methylpyridine obtained in the step 1 with a bromination reagent in an aprotic solvent under the action of a catalyst to obtain 5-(dibromomethyl)-2-methoxypyridine; and 3, carrying out a hydrolysis reaction on the 5-(dibromomethyl)-2-methoxypyridine prepared in the step 2 with an alkali in a mixed solvent of an aprotic solvent and water to prepare 6-methoxypyridine-3-formaldehyde. According to the invention, 6-bromo-3-methylpyridine is used as a main raw material, and is subjected to sodium methylate substitution, bromination and alkali metal hydroxide hydrolysis, such that a target compound is obtained. The method has the advantages of simple and accessible raw materials ineach step, simple process operation and mild reaction conditions, and is suitable for industrial amplification.

Reversible Folding of a β-Hairpin Peptide by a Metal-Chelating Amino Acid

5-(1-Hydroxy-pyridin-2(1H)-onyl)-l-alanine (Hop) is a N-hydroxy-1,2-pyridone functionalized α-amino acid with the desired metal-chelating properties of DOPA (3,4-dihydroxy phenylalanine) but without its unwanted redox activity. The Fmoc-protected amino acid Fmoc-l-Hop(tBu)-OH (11) was synthesized from glycine phosphonate followed by enzymatic hydrolysis of the methyl ester yielding the Hop l-isomer in 96 % ee. The amino acid 11 is used in automated peptide synthesis for the assembly of a 14mer β-hairpin peptide with the sequence [dsb1, 14]H-CHXETGKHGHKLVC-OH (X=W, l-Hop). While the 10 π electron containing indole side chain of l-Trp in peptide 14 completes the formation of a hydrophobic cluster and results in 90 % folding, the folded fraction is significantly decreased to approximately 30 % for the 6 π electron l-Hop side chain in peptide 16. Metal chelation of Ga3+ reconstitutes the folding of 16 to above 60 % due to the formation of the Ga(16)3 trimer. The chelation process of 16 is monitored by NMR spectroscopy and the subsequent release of Ga3+ by a competitive metal chelator exemplifies the reversible oligomerization of peptide epitopes by metal chelation, bearing the opportunity to synthesize protein-sized aggregates on the basis of reversible chemistry in water.

Visible-Light-Promoted Nickel- and Organic-Dye-Cocatalyzed Formylation Reaction of Aryl Halides and Triflates and Vinyl Bromides with Diethoxyacetic Acid as a Formyl Equivalent

A simple formylation reaction of aryl halides, aryl triflates, and vinyl bromides under synergistic nickel- and organic-dye-mediated photoredox catalysis is reported. Distinct from widely used palladium-catalyzed formylation processes, this reaction proceeds by a two-step mechanistic sequence involving initial in situ generation of the diethoxymethyl radical from diethoxyacetic acid by a 4CzIPN-mediated photoredox reaction. The formyl-radical equivalent then undergoes nickel-catalyzed substitution reactions with aryl halides and triflates and vinyl bromides to form the corresponding aldehyde products. Significantly, besides aryl bromides, less reactive aryl chlorides and triflates and vinyl halides serve as effective substrates for this process. Since the mild conditions involved in this reaction tolerate a plethora of functional groups, the process can be applied to the efficient preparation of diverse aromatic aldehydes.

SPIROCYCLIC HAT INHIBITORS AND METHODS FOR THEIR USE

Compounds having a structure of Formula (IX) or a stereoisomer, tautomer or pharmaceutically acceptable salt thereof, wherein R1, R2a, R2b, R3a, R3b, R4a, R4b, Q1----Q2, R6, R7, A, B, W, x, and y are as defined herein and are provided. Pharmaceutical compositions comprising such compounds and methods for treating various HAT-related conditions or diseases, including cancer, by administration of such compounds are also provided.

NOVEL TETRAHYDROPYRIDOPYRIMIDINES AND TETRAHYDROPYRIDOPYRIDINES FOR THE TREATMENT AND PROPHYLAXIS OF HEPATITIS B VIRUS INFECTION

The invention provides novel compounds having the general formula (I): wherein R1, R2, R3, Q, U,W, Z, X and Y are as described herein, compositions including the compounds and methods of using the compounds. These compounds are HbsAg inhibitors and are useful as medicaments for the treatment or prophylaxis of HBV infection.

HETEROARYL SUBSTITUTED HETEROCYCLYL SULFONES

The invention relates to aryl substituted heterocyclyl sulfones as voltage gated calcium channel blockers, to pharmaceutical compositions containing these compounds and also to these compounds for use in the treatment and/or prophylaxis of pain and further diseases and/or disorders.

Lewis basicity modulation of N-heterocycles: A key for successful cross-metathesis

Cross-metathesis involving N-heteroaromatic olefinic derivatives is disclosed. The introduction of an appropriate substituent on the heteroaromatic ring decreases the Lewis basicity of the nitrogen atom, thus preventing the deactivation of the ruthenium-centered catalyst. The reaction is quite general in terms of both N-heterocycles and olefinic partners.

Noncryogenic synthesis of functionalized 2-methoxypyridines by halogen-magnesium exchange using lithium dibutyl(isopropyl)magnesate(1-) and lithium chloride

2-Methoxypyridines functionalized in the 3-, 5-, or 6-position and 2,6-dimethoxypyridines functionalized in the 3-position were prepared from the corresponding bromo or iodo analogues by using lithium dibutyl(isopropyl) magnesate(1-) and lithium chloride

TRPA1 ANTAGONISTS

Compounds of formula (I), wherein R1, R2, R3, and Y are defined in the description are TRPA1 antagonists. Compositions comprising such compounds and methods for treating conditions and disorders using such compounds and compositions are also disclosed.

Efficient synthesis of 5-functionalised 2-methoxypyridines and their transformation to bicyclic d-lactams, both accessed using magnesium ?ate? complexes as key reagents

Simple and efficient synthesis of 5-functionalised ?2-methoxypyridines from 5-bromo-2-methoxypyridine using ?[n-Bu3Mg]Li performed in noncryogenic conditions is described. Application of 5-functionalised 2-methoxypyridines in the synthesis of 1-substitute