3-Chloro-5-(trifluoromethyl)pyridin-2-amine Chemical Properties

Melting point:

86-90 °C (lit.)

Boiling point:

205°C

Density 

1.4650 (estimate)

vapor pressure 

40.8Pa at 24.85℃

storage temp. 

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

solubility 

Chloroform (Slightly), Methanol (Slightly)

pka

1.79±0.49(Predicted)

form 

Crystalline Powder

color 

White to off-white

Water Solubility 

622mg/L at 25℃

InChI

InChI=1S/C6H4ClF3N2/c7-4-1-3(6(8,9)10)2-12-5(4)11/h1-2H,(H2,11,12)

InChIKey

WXNPZQIRDCDLJD-UHFFFAOYSA-N

SMILES

C1(N)=NC=C(C(F)(F)F)C=C1Cl

LogP

2.59 at 20℃

CAS DataBase Reference

79456-26-1(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xn,Xi

Risk Statements 

22-52/53-36/37/38-20/21/22

Safety Statements 

61-36/37/39-26-22

WGK Germany 

2

HazardClass 

IRRITANT

HS Code 

29339900

MSDS

• Language:English Provider:SigmaAldrich

3-Chloro-5-(trifluoromethyl)pyridin-2-amine Usage And Synthesis

Chemical Properties

Light yellow Cryst

Uses

2-?Amino-?3-?chloro-?5-?trifluoromethylpyrid?ine acts as a reactant in the synthesis of novel imidazo[1,2-a]pyridine-coumarin hybrid molecules as inhibitors of NS5B in potential treatment of Hepititis C.

Definition

ChEBI: 3-Chloro-5-(trifluoromethyl)pyridin-2-amine is an aminopyridine.

Synthesis

Example 1: General procedure for the synthesis of 2-amino-3-chloro-5-trifluoromethylpyridine from 2,3-dichloro-5-trifluoromethylpyridine 1. Ammonolysis reaction: 2,3-dichloro-5-trifluoromethylpyridine (26.75 g, 0.125 mol) and water (25 ml) were added to an autoclave. After sealing, liquid ammonia (45 g, 2.85 mol) was added through a pressure bottle. The reaction mixture was heated to 80 °C and maintained for 9 h at 18-22 bar pressure. After cooling to room temperature, the intermediate 2-amino-3-chloro-5-trifluoromethylpyridine was obtained by filtration, washed with water and dried (22 g, 90% yield). 2. Condensation reaction: the above intermediate was dissolved in acetonitrile (230 ml), cooled to 5 ℃ and added solid KOH (12 g, 0.22 mol). A solution of 2,4-dichloro-3,5-dinitro-5-trifluoromethylbenzene (25 g, 0.08 mol) in acetonitrile (230 ml) was added slowly over 15 min under continuous cooling conditions. The reaction was gradually warmed up to 25°C for 4 hours and subsequently warmed up to 40°C for 2 hours. 3. Post-treatment: The reaction mixture was poured into water (1500 ml) and the pH was adjusted to about 4 with a 4N aqueous hydrochloric acid solution, followed by extraction with isopropyl acetate (2 x 750 ml). The organic phases were combined and concentrated to dryness to give the crude fludioxamine (43 g, 70% yield, 60% purity). The target product can be further purified by recrystallization.

References

[1] Patent: WO2014/198278, 2014, A1. Location in patent: Page/Page column 9; 17
[2] Heterocycles, 1984, vol. 22, # 1, p. 117 - 124
[3] Patent: US4349681, 1982, A

3-Chloro-5-(trifluoromethyl)pyridin-2-amine(79456-26-1)Related Product Information

• 2-Chloro-5-chloromethylpyridine
• Glycine
• Betaine
• 3-Aminopyridine
• Aniline
• Bis(2-ethylhexyl)amine
• 4-Methylpyridine
• 2-Aminopyridine
• 2-Amino-3-picoline
• 2-Chloro-5-trifluoromethylpyridine
• 4-Dimethylaminopyridine
• Epichlorohydrin
• ALTRENOGEST
• Tris(hydroxymethyl)aminomethane
• Difluorochloromethane
• Chloroacetic acid
• 3-AMINO-2-CHLORO-6-(TRIFLUOROMETHYL)PYRIDINE, 97% MIN.,3-AMINO-2-CHLORO-6-(TRIFLUOROMETHYL)PYRIDINE,2-CHLORO-6-(TRIFLUOROMETHYL)PYRIDIN-3-AMINE
• 6-chloro-4-(trifluoromethyl)pyridin-2-amine