87674-14-4

Basic information

• Product Name: 1-(3-FLUORO-2-PYRIDYL)ETHANOL
• Synonyms: 1-(3-FLUORO-2-PYRIDYL)ETHANOL;3-FLUORO-A-METHYL-2-PYRIDINEMETHANOL;1-(3-Fluoro-2-pyridy)ethanol;1-(3-Fluoropyridin-2-yl)ethanol
• CAS NO: 87674-14-4
• Molecular Formula: C7H8FNO
• Molecular Weight: 141.14
• Product Categories: Pyridine;Pyridines
• Mol File: 87674-14-4.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 191.1 °C at 760 mmHg
• Flash Point: 69.4 °C
• Appearance: /
• Density: 1.196 g/cm³
• Vapor Pressure: 0.331mmHg at 25°C
• Refractive Index: 1.512
• PKA: 12.81±0.20(Predicted)
• CAS DataBase Reference: 1-(3-FLUORO-2-PYRIDYL)ETHANOL(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(3-FLUORO-2-PYRIDYL)ETHANOL(87674-14-4)
• EPA Substance Registry System: 1-(3-FLUORO-2-PYRIDYL)ETHANOL(87674-14-4)

Safety Data

• Hazardous Substances Data: 87674-14-4(Hazardous Substances Data)

Usage

InChI:InChI=1/C7H8FNO/c1-5(10)7-6(8)3-2-4-9-7/h2-5,10H,1H3

Upstream product

• 372-47-4 3-Fluoropyridine 
• 75-07-0 acetaldehyde 

Downstream Products

• 87674-20-2 1-(3-fluoropyridin-2-yl)ethanone 

Relevant articles and documents

REVIEW ON THE METALLATION OF ?-DEFICIENT HETEROAROMATIC COMPOUNDS; REGIOSELECTIVE ORTHO-LITHIATION OF 3-FLUOROPYRIDINE: DIRECTING EFFECTS AND APPLICATION TO SYNTHESIS OF 2,3- OR 3,4-DISUBSTITUTED PYRIDINES

Metallation of ?-deficient heterocyclic compounds is first reviewed, which shows the important recent developments in this research area.A particular aspect of this reaction is then given with the study of the 3-fluoropyridine metallation regioselectivity.Lithiation of 3-fluoropyridine is chemoselective at low temperatures using butyllithium-polyamine chelates or lithium diisopropylamide.Protophilic attack by these strong bases can be directed either at the 2- or 4-position depending on the lithiation conditions.Various reaction parameters are thus studied such as solvent, temperature, reaction time, lithium-chelating agent as well as metallating agent.The high regioselectivity of 3-fluoropyridine lithiation is theoretically discused, in particular in terms of kinetic of thermodynamic control of the metallation.Chelation between butyllithium and 3-fluoropyridine is proposed, which completely modifies the heterocycle reactivity toward the lithiating agent.This is confirmed by theoretical quantum calculations performed on different models of 3-fluoropyridine using the CNDO/2.These results allow to select the best 3-fluoropyridine-metallation conditions which lead to 3-fluoro-2-lithiopyridine on the one hand and to 3-fluoro-4-lithiopyridine on the other hand.Each of the lithiated isomers is then reacted with a great variety of electrophiles which gives very conveniently the corresponding 2,3- or 3,4-disubstituted pyridines.