| Identification | More | [Name]
4-TRIFLUOROMETHYL-THIAZOL-2-YLAMINE | [CAS]
349-49-5 | [Synonyms]
2-AMINO-4-(TRIFLUOROMETHYL)THIAZOLE
4-(TRIFLUOROMETHYL)-1,3-THIAZOL-2-AMINE
4-TRIFLUOROMETHYL-THIAZOL-2-YLAMINE
4-TRIFLUOROMETHYL-THIAZOLE-2YLAMINE
4-(trifluoromethyl)thiazol-2-amine | [Molecular Formula]
C4H3F3N2S | [MDL Number]
MFCD00832759 | [Molecular Weight]
168.14 | [MOL File]
349-49-5.mol |
| Chemical Properties | Back Directory | [Melting point ]
60-62°C | [Boiling point ]
125-128 °C(Press: 22 Torr) | [density ]
1.557±0.06 g/cm3(Predicted) | [storage temp. ]
Keep in dark place,Inert atmosphere,2-8°C | [form ]
crystalline solid | [pka]
1.90±0.10(Predicted) | [color ]
Yellow | [InChI]
InChI=1S/C4H3F3N2S/c5-4(6,7)2-1-10-3(8)9-2/h1H,(H2,8,9) | [InChIKey]
OVMGTNMCYLZGLS-UHFFFAOYSA-N | [SMILES]
S1C=C(C(F)(F)F)N=C1N | [CAS DataBase Reference]
349-49-5(CAS DataBase Reference) |
| Safety Data | Back Directory | [Hazard Codes ]
Xi | [Risk Statements ]
R20/21/22:Harmful by inhalation, in contact with skin and if swallowed .
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection . | [RIDADR ]
UN2811 | [WGK Germany ]
3 | [HazardClass ]
IRRITANT | [HS Code ]
2934100090 |
| Hazard Information | Back Directory | [Uses]
4-(Trifluoromethyl)-2-thiazolamine can be used to prepare phenethylthiazolylthiourea analogs as HIV-1 reverse transcriptase inhibitors. 4-(Trifluoromethyl)-2-thiazolamine can also be used to synthesize 2-amino benzamide derivatives as allosteric glucokinase activators. | [Synthesis]
General procedure for the synthesis of 2-amino-4-trifluoromethylthiazole from 3-bromo-1,1,1-trifluoroacetone and thiourea: Thiourea (4.0 g, 52.3 mmol) and 3-bromo-1,1,1-trifluoropropan-2-one (5.5 mL, 10 g, 52.3 mmol) were added to ethanol (100 mL) and the reaction was heated for 2 hours at 50 °C. After completion of the reaction, it was cooled to room temperature and the reaction solution was concentrated to dryness. The residue was dissolved in water and the pH was adjusted with 2 M NaOH solution to >12. Subsequently, four extractions were performed with ether. The organic extracts were combined, dried with sodium sulfate, filtered and concentrated in vacuum. The resulting crude product was purified by silica gel column chromatography (CH2Cl2 as eluent) to afford 2-amino-4-trifluoromethylthiazole (6.9 g, 79% yield). es/MS m/z 169 (M + 1)+. | [References]
[1] Patent: WO2008/36579, 2008, A1. Location in patent: Page/Page column 43
[2] Journal of Heterocyclic Chemistry, 1991, vol. 28, # 4, p. 907 - 911
[3] Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 1988, vol. 27, # 1-12, p. 1051 - 1053
[4] Journal of Organic Chemistry, 1955, vol. 20, p. 499,505
[5] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1981, p. 2335 - 2339 |
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