3-Chloro-5-(trifluoromethyl)-2-pyridinamine
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3-Chloro-5-(trifluoromethyl)-2-pyridinamine
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CAS No:
79456-26-1
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Formula:
C6H4ClF3N2
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Chemical Name:
3-Chloro-5-(trifluoromethyl)-2-pyridinamine
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Synonyms:
2-Pyridinamine,3-chloro-5-(trifluoromethyl)-;3-Chloro-5-(trifluoromethyl)-2-pyridinamine;2-Amino-3-chloro-5-trifluoromethylpyridine;5-(Trifluoromethyl)-3-chloro-2-pyridinylamine
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CAS No:
3-Chloro-5-(trifluoromethyl)-2-pyridinamine Basic Attributes
196.56
196.56
401-670-0
DTXSID00345807
2933399090
Characteristics
38.9
2
White to off-white Crystalline Powder
1.5±0.1 g/cm3
86-90 °C(lit.)
205°C
75.7±27.3 °C
1.502
Safety Information
IRRITANT
NONH for all modes of transport
2
22-52/53-36/37/38-20/21/22
61-36/37/39-26-22
Xn,Xi
Irritant
P273
H302-H412
|Warning|H302: Harmful if swallowed [Warning Acute toxicity, oral]|P264, P270, P273, P301+P312, P330, and P501|H302 (97.44%): Harmful if swallowed [Warning Acute toxicity, oral]|Aggregated GHS information provided by 39 companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]|P261, P264, P270, P271, P273, P280, P301+P312, P302+P352, P304+P340, P305+P351+P338, P312, P321, P330, P332+P313, P337+P313, P362, P403+P233, P405, and P501|Aggregated GHS information provided by 3 companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
3-Chloro-5-(trifluoromethyl)-2-pyridinamine Use and Manufacturing
Conversion of 2, 3-dichloro-5-(trifluoromethyl)pyridine to Fluazinam. 2, 3-dichloro-5-(trifluoromethyl)pyridine (26, 75 g, 0.125 mole) and water (25 ml) was added to an autoclave. The autoclave was closed and liquid ammonia (45 g, 2, 85 mole) was added from a pressure bottle. The autoclave was heated to 80°C for 9 hours at a pressure between 22 and 18 bar. The reaction was cooled to room temperature and the intermediate, 2-amino-3- chloro-5-(trifluoromethyl)pyridine was obtained by filtration, washing with water and drying (22 g, 90percent). The intermediate was dissolved in acetonitril (230 ml). The solution was cooled to 5 °C and KOH (s., 12 g, 0.22 mole) was added. A solution of 2, 4-dichloro-3, 5-dinitro-5-(trifluoromethyl)benzene (25 g, 0.08 mole) in acetonitrile (230 ml) was added over 15 minutes with continuous cooling. The temperature was raised to 25 °C for four hours followed by a a temperature increase and kept at 40 °C for two hours. The mixture was added to 1500 ml of water, neutralised to a pH around 4 with 4N HCl (aq) and extracted with isopropyl acetate (2 x 750 ml). The organic phase was evaporated to dryness to get crude Fluazinam (43 g, 70 percent yield, 60 percent purity). The Fluazinam can be further purified by recrystallisation.[0048] Preparation of 2-amino, 3-chloro, 5- trifluoromethylpyridine .[0049] 35, 0 grams (0, 176 moles) of 2-fluoro, 3-chloro, 5- trifluoromethylpyridine and 82, 8 grams (93, 1 ml) of THF are put into an autoclave of 250 ml. After degassing the system with nitrogen, 6, 8 grams (0, 4 moles) of NH
Computed Properties
Molecular Weight:196.56
XLogP3:2
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:5
Exact Mass:196.0015103
Monoisotopic Mass:196.0015103
Topological Polar Surface Area:38.9
Heavy Atom Count:12
Complexity:161
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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3-Chloro-5-(trifluoromethyl)-2-pyridinamine
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