| Identification | More | [Name]
3-Chloro-5-(trifluoromethyl)pyridin-2-amine | [CAS]
79456-26-1 | [Synonyms]
2,3,5-actf
2-AMINO-3-CHLORO-5-(TRIFLUOROMETHYL)PYRIDINE
3-CHLORO-5-(TRIFLUOROMETHYL)-2-PYRIDINAMINE
3-Chloro-5-(trifluoromethyl)-2-pyridylamine
3-CHLORO-5-(TRIFLUOROMETHYL)PYRIDIN-2-AMINE
LABOTEST-BB LT00012608
TIMTEC-BB SBB003584
3-CHLORO-5-(TRIFLUOROMETHYL)PYRIDINE-2-AMINE
2-Amino-3-Chloro-5-Trifluorome
2-Amino-3-chloro-5-(trifluoromethyl)pyridine 97%
2-Amino-3-chloro-5-(trifluoromethyl)pyridine97%
2-AMINO-3-CHLORO-5-TRIFLUOROMETHYLPYRIDI
ACTP
2-Amino-3-chloro-5-trifluoropyridine
2-Amino-3-Chloro-5-Trifluromethyl Pyridine
2-Amino-3-chloro-5-trifluoromethylpyridine ,98% | [EINECS(EC#)]
401-670-0 | [Molecular Formula]
C6H4ClF3N2 | [MDL Number]
MFCD00042154 | [Molecular Weight]
196.56 | [MOL File]
79456-26-1.mol |
| Chemical Properties | Back Directory | [Appearance]
Light yellow Cryst | [Melting point ]
86-90 °C (lit.) | [Boiling point ]
205°C | [density ]
1.4650 (estimate) | [vapor pressure ]
40.8Pa at 24.85℃ | [storage temp. ]
Keep in dark place,Inert atmosphere,2-8°C | [solubility ]
Chloroform (Slightly), Methanol (Slightly) | [form ]
Crystalline Powder | [pka]
1.79±0.49(Predicted) | [color ]
White to off-white | [Water Solubility ]
622mg/L at 25℃ | [Detection Methods]
GC | [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 Data | Back Directory | [Hazard Codes ]
Xn,Xi | [Risk Statements ]
R22:Harmful if swallowed.
R52/53:Harmful to aquatic organisms, may cause long-term adverse effects in the aquatic environment .
R36/37/38:Irritating to eyes, respiratory system and skin .
R20/21/22:Harmful by inhalation, in contact with skin and if swallowed . | [Safety Statements ]
S61:Avoid release to the environment. Refer to special instructions safety data sheet .
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection .
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S22:Do not breathe dust . | [WGK Germany ]
2
| [Hazard Note ]
Irritant | [HazardClass ]
IRRITANT | [HS Code ]
29339900 | [Storage Class]
11 - Combustible Solids | [Hazard Classifications]
Acute Tox. 4 Oral
Aquatic Chronic 3 |
| Hazard Information | Back Directory | [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 |
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