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Sigma-Aldrich

2-Fluoro-4-methylpyridine

98%

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Synonym(s):
2-Fluoro-4-picoline
Empirical Formula (Hill Notation):
C6H6FN
CAS Number:
Molecular Weight:
111.12
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22

Assay

98%

refractive index

n20/D 1.472 (lit.)

bp

160-161 °C (lit.)

density

1.078 g/mL at 25 °C (lit.)

SMILES string

Cc1ccnc(F)c1

InChI

1S/C6H6FN/c1-5-2-3-8-6(7)4-5/h2-4H,1H3

InChI key

ZBFAXMKJADVOGH-UHFFFAOYSA-N

General description

2-Fluoro-4-methylpyridine, also known as 2-fluoro-4-picoline, can be prepared based on Talik′s procedure from 2-amino-5-methylpyridine via diazotization. The effect of substituents on spectral properties of 2-fluoro-6-methylpyridine has been investigated based on 13C NMR, UV and IR spectral data.

Application

2-Fluoro-4-methylpyridine may be used in the preparation of:
  • 2-Fluoro-4-(iodomethyl)pyridine
  • 4-(4-fluorophenyl)-5-(2-fluoropyridin-4-yl)-1,3-dihydroimidazol-2-thione
  • 2-fluoro-4-pyridinemethanol
  • 2-fluoro-4-pyridinemethanol, 4-methylbenzenesulfonate
  • 10,10-bis[(2-fluoro-4-pyridinyl)methyl]-9(10H)-anthracenone
  • 2-fluoro-3-iodo-5-methylpyridine
  • 2-fluoro-4-pyridinecarboxylic acid

Pictograms

Exclamation mark

Signal Word

Warning

Hazard Statements

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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2-Fluoro-4-pyridinylmethyl analogues of linopirdine as orally active acetylcholine release-enhancing agents with good efficacy and duration of action.
Earl RA, et al.
Journal of Medicinal Chemistry, 41(23), 4615-4622 (1998)
Efficient Pyridinylmethyl Functionalization: Synthesis of 10,10-Bis[(2-fluoro-4-pyridinyl)methyl]-9(10H)-anthracenone (DMP 543), an Acetylcholine Release Enhancing Agent.
Pesti JA, et al.
Journal of Oral Pathology & Medicine, 65(23), 7718-7722 (2000)
Towards the improvement of the synthesis of novel 4 (5)-aryl-5 (4)-heteroaryl-2-thio-substituted imidazoles and their p38 MAP kinase inhibitory activity.
Laufer S and Koch P.
Organic & Biomolecular Chemistry, 6(3), 437-439 (2008)
First metalation of aryl iodides: directed ortho-lithiation of iodopyridines, halogen-dance, and application to synthesis.
Rocca P, et al.
The Journal of Organic Chemistry, 58(27), 7832-7838 (1993)
The13C NMR, UV and IR spectra of 2-fluoropyridine methyl derivatives.
Puszko A and Ciurla H.
Chemistry of Heterocyclic Compounds, 35(6), 677-687 (1999)

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