2-chloro-3-fluoropyridin-4-aMine Chemical Properties

Boiling point:

271.9±35.0 °C(Predicted)

Density 

1.449±0.06 g/cm3(Predicted)

storage temp. 

under inert gas (nitrogen or Argon) at 2–8 °C

pka

2.81±0.42(Predicted)

form 

powder

color 

Brown

InChI

InChI=1S/C5H4ClFN2/c6-5-4(7)3(8)1-2-9-5/h1-2H,(H2,8,9)

InChIKey

VUGYOFOYGPXOFL-UHFFFAOYSA-N

SMILES

C1(Cl)=NC=CC(N)=C1F

Safety Information

HS Code 

2933399990

2-chloro-3-fluoropyridin-4-aMine Usage And Synthesis

Uses

2-Chloro-3-fluoro-4-aminopyridine is a highly useful class of pyridine derivatives, serving as an important pharmaceutical and pesticide intermediate. It can be used as a viscosity modifier, in the synthesis of anti-peptic ulcer drug pelenzapine, diazepine anti-HIV drugs, leukotriene biosynthesis inhibitors, and as a pharmaceutical intermediate for insecticides. Furthermore, 2-chloro-3-fluoro-4-aminopyridine and its derivatives can also be used as raw materials for food additives, ultra-efficient quenching catalysts, and directly as pharmaceutical and analytical reagents.

Synthesis

TFA (5 mL) was added to a solution of (2- chloro-3-fluoropyridin-4-yl)carbamic acid fert-butyl ester (1.9 g, 7.7 mmol) in DCM (10 mL). The solution was stirred at ambient temperature for 5 hours and concentrated under reduced pressure. The resultant residue was dissolved in DCM and purified by column chromatography on an NH2 cartridge (0-10 per cent MeOH in DCM) to afford 2-chloro-3-fluoropyridin-4-aMine as a beige solid (0.96 g, 94 per cent yield). NMR (400 MHz, CDC13): δ 7.82 (d, J = 5.4 Hz, 1H), 6.60 (t, J= 5.8 Hz, 1H), 4.38 (br s, 2H).

References

[1] Patent: WO2012/35039, 2012, A1. Location in patent: Page/Page column 97
[2] Patent: US2015/203455, 2015, A1. Location in patent: Paragraph 0461; 0463
[3] Patent: WO2015/110378, 2015, A1. Location in patent: Paragraph 00263; 00312
[4] Patent: US9440929, 2016, B2. Location in patent: Page/Page column 59; 60
[5] Patent: WO2017/12647, 2017, A1. Location in patent: Paragraph 0502

2-chloro-3-fluoropyridin-4-aMine(1227577-03-8)Related Product Information

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