1093880-37-5

Basic information

• Product Name: 6-Chloro-2-fluoropyridine-3-carboxaldehyde
• Synonyms: 6-Chloro-2-fluoropyridine-3-carboxaldehyde;6-chloro-2-fluoronicotinaldehyde;6-Chloro-2-fluoropyridine-3-carbaldehyde
• CAS NO: 1093880-37-5
• Molecular Formula: C₆H₃ClFNO
• Molecular Weight: 159.5455232
• Mol File: 1093880-37-5.mol

Chemical Properties

• Melting Point: 49-50 °C(Solv: hexane (110-54-3))
• Boiling Point: 255.5±35.0 °C(Predicted)
• Appearance: /
• Density: 1.444±0.06 g/cm3(Predicted)
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• PKA: -4.44±0.10(Predicted)
• CAS DataBase Reference: 6-Chloro-2-fluoropyridine-3-carboxaldehyde(CAS DataBase Reference)
• NIST Chemistry Reference: 6-Chloro-2-fluoropyridine-3-carboxaldehyde(1093880-37-5)
• EPA Substance Registry System: 6-Chloro-2-fluoropyridine-3-carboxaldehyde(1093880-37-5)

Safety Data

• Hazardous Substances Data: 1093880-37-5(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Synthesis:
6-Chloro-2-fluoropyridine-3-carboxaldehyde is used as a key reactant in the synthesis of various pharmaceutical compounds. Its unique structural features and reactivity make it a promising candidate for the development of new drugs with improved therapeutic properties.
Used in Organic Chemistry Research:
In the field of organic chemistry, 6-Chloro-2-fluoropyridine-3-carboxaldehyde serves as an important building block for the synthesis of complex organic molecules. Its reactivity and structural diversity allow researchers to explore novel reaction pathways and develop innovative synthetic strategies.
Used in the Synthesis of Phantasmidine:
6-Chloro-2-fluoropyridine-3-carboxaldehyde is used as a reactant in the synthesis of phantasmidine, a complex organic molecule, through a tandem intramolecular aldol reaction-intramolecular nucleophilic aromatic substitution sequence. This process results in the formation of the tetracyclic lactam, which is a crucial intermediate in the synthesis of phantasmidine and other related compounds.

Upstream product

• 20885-12-5 2-chloro-6-fluoropyridine 
• 68-12-2 N,N-dimethyl-formamide 

Downstream Products

• 1227509-94-5 6-chloro-2-fluoro-3-pyridinemethanol 
• 1227577-88-9 6-chloro-3-(chloromethyl)-2-fluoropyridine 
• 63725-52-0 6-chloro-1-methyl-1H-pyrazolo[3,4-b]pyridine 
• 63725-51-9 6-Chlor-1H-pyrazolo<3,4-b>pyridin 
• 1380584-11-1 (+)-phantasmidine Mosher's amide 
• 1380601-17-1 phantasmidine Mosher's amide 

Relevant articles and documents

Synthesis of phantasmidine

Reaction of 6-chloro-2-fluoro-3-pyridineacetamide with 1,2- bis(trimethylsilyloxy)cyclobutene in ether saturated with hydrogen chloride afforded the keto amide in 85% yield. In the key step, treatment of the keto amide with aqueous KOH in t-BuOH resulted in a tandem intramolecular aldol reaction-intramolecular nucleophilic aromatic substitution sequence to give the tetracylic lactam in 46% yield. Reduction of the lactam with BH3 in THF gave phantasmidine in 67% yield.

TRICYCLIC PIPERIDINE COMPOUNDS

The present invention relates to compounds of the formula (I) wherein R1a, R1b, R2, R3, (R4)n and ring (A) are as described in the description, to their preparation, to pharmaceutically acc

TRICYCLIC PIPERIDINE COMPOUNDS

The present invention relates to compounds of the formula (I), wherein R, R1a, R1b, R2, R3, and X are as described in the description, to their preparation, to pharmaceutically acceptable salts thereof, and to their use as pharmaceuticals, to pharmaceutical compositions containing one or more compounds of formula (I), to methods for the preparation of such compounds of formula (I), and especially to their use as TPH modulators.

Mosher's amide-based assignment of the absolute configuration of phantasmidine

The absolute configuration of phantasmidine was assigned by analysis of the two conformers of the two Mosher amides. The expected shielding of the protons adjacent to the nitrogen and large long range shielding (～1 ppm) of the cyclobutane methylene protons in 16major and the pyridine protons of 16minor by the phenyl group of the Mosher amide allows the assignment of absolute configuration as shown in Schemes 4 and 5.

PREPARATION OF PHANTASMIDINE AND ANALOGUES THEREOF

Described are methods of synthesizing phantasmidine and analogues thereof from commercially available starting materials. The compounds are useful as pharmacological probes and potential lead compounds for the development of selective nicotinic receptor therapeutics.