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Home > Encyclopedia > 2-Fluoro-3-pyridinecarboxaldehyde

2-Fluoro-3-pyridinecarboxaldehyde

2-Fluoro-3-pyridinecarboxaldehyde structure

2-Fluoro-3-pyridinecarboxaldehyde 

structure
  • CAS No:

    36404-90-7

  • Formula:

    C6H4FNO

  • Chemical Name:

    2-Fluoro-3-pyridinecarboxaldehyde

  • Synonyms:

    3-Pyridinecarboxaldehyde,2-fluoro-;2-Fluoro-3-pyridinecarboxaldehyde;2-Fluoropyridine-3-carboxaldehyde;2-Fluoro-3-formylpyridine;2-Fluoronicotinaldehyde;2-Fluoropyridine-3-carbaldehyde

  • Categories:

    Pharmaceutical Intermediates  >  Heterocyclic Compound

2-Fluoro-3-pyridinecarboxaldehyde Basic Attributes

125.1

125.10

DTXSID00465675

2933399090

Characteristics

30

0.7

1.250 g/mL at 25 °C

50 °C @ Press: 3 Torr

164 °F

n20/D 1.520

Room temperature.

Safety Information

IRRITANT

3

36/37/38

26

Xn,Xi

Irritant

P261-P305 + P351 + P338

H302-H315-H319-H335

|Warning|H302 (97.56%): Harmful if swallowed [Warning Acute toxicity, oral]|P261, P264, P270, P271, P280, P301+P312, P302+P352, P304+P340, P305+P351+P338, P312, P321, P330, P332+P313, P337+P313, P362, P403+P233, P405, and P501|Aggregated GHS information provided by 41 companies from 4 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

2-Fluoro-3-pyridinecarboxaldehyde Use and Manufacturing

Methods of Manufacturing

A solution of (trimethylsilylmethyl) lithium (22 mL, 13.8 weight percent in hexanes) was charged to a 100 mL 3-NECK round-bottom flask and cooled TO-50 °C. A solution of 2-fluoropyridine (2.0 g), THF (25 mL) and DIISOPROPYLAMINE (0.13 mL) was added at less than-50 °C in 1 minute. After 3 hours, 1-formylpiperidine (2.4 g) was added in 1 min at less THAN-50 °C. The mixture was allowed to warm to room temperature and stir overnight. The reaction mixture was quenched with acetic acid (3 mL) and water (7 mL). The aqueous layer was separated and washed with 3x25 mL MTBE. All organic layers were combined, dried over MGS04 and concentrated in vacuo to leave 3.79 g of brown oil. This oil was chromatographed through silica gel, eluting with 15 percent EtOAc in hexanes, to afford 2. 24 g of 92. 4percent pure 2-FLUORO-3-PYRIDINECARBOXALDEHYDE (90percent yield, corrected for assay).

Uses

Through fluorine substitution and isoxazolone, naphthyridine for hydrogenolysis and cyclization can be generated.

Computed Properties

Molecular Weight:125.10
XLogP3:0.7
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:1
Exact Mass:125.027691913
Monoisotopic Mass:125.027691913
Topological Polar Surface Area:30
Heavy Atom Count:9
Complexity:107
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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