| Identification | More | [Name]
2-Bromo-4-trifluoromethoxyaniline | [CAS]
175278-17-8 | [Synonyms]
2-BROMO-4-(TRIFLUOROMETHOXY)ANILINE
BUTTPARK 83\07-26
2-Bromo-4-(trifluoromethoxy)aniline 98%
2-Bromo-4-(trifluoromethoxy)aniline98% | [Molecular Formula]
C7H5BrF3NO | [MDL Number]
MFCD00203478 | [Molecular Weight]
256.02 | [MOL File]
175278-17-8.mol |
| Chemical Properties | Back Directory | [Appearance]
clear light yellow to orange-yellow liquid | [Boiling point ]
209 °C(lit.) | [density ]
1.693 g/mL at 25 °C(lit.)
| [refractive index ]
n20/D 1.504(lit.)
| [Fp ]
>230 °F
| [storage temp. ]
Keep in dark place,Inert atmosphere,Room temperature | [form ]
Liquid | [pka]
1.68±0.10(Predicted) | [color ]
Clear light yellow to orange-yellow | [Specific Gravity]
1.693 | [InChI]
InChI=1S/C7H5BrF3NO/c8-5-3-4(1-2-6(5)12)13-7(9,10)11/h1-3H,12H2 | [InChIKey]
ROSTYHNIIDIBEG-UHFFFAOYSA-N | [SMILES]
C1(N)=CC=C(OC(F)(F)F)C=C1Br | [CAS DataBase Reference]
175278-17-8(CAS DataBase Reference) |
| Safety Data | Back Directory | [Hazard Codes ]
Xi,T | [Risk Statements ]
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:Wear suitable protective clothing .
S37/39:Wear suitable gloves and eye/face protection . | [WGK Germany ]
3
| [Hazard Note ]
Toxic | [HazardClass ]
IRRITANT | [HS Code ]
29222990 | [Storage Class]
10 - Combustible liquids | [Hazard Classifications]
Eye Irrit. 2
Skin Irrit. 2
STOT SE 3 |
| Hazard Information | Back Directory | [Chemical Properties]
clear light yellow to orange-yellow liquid | [Synthesis]
General procedure for the synthesis of 2-bromo-4-trifluoromethoxyaniline from 4-(trifluoromethoxy)aniline: N-bromosuccinimide (3.62 g, 20.34 mmol) was slowly added to a solution of 4-(trifluoromethoxy)aniline (3.00 g, 16.9 mmol) in acetonitrile (30 mL) at 0 °C. The reaction mixture was gradually warmed to room temperature and stirred continuously for 4 hours. Upon completion of the reaction, the solvent was removed by distillation under reduced pressure to give the crude product. The crude product was purified by column chromatography using 10% ethyl acetate/hexane as eluent to give 2-bromo-4-trifluoromethoxyaniline as a brown oil (3.6 g, 83% yield). The structure of the product was confirmed by 1H NMR (400 MHz, CDCl3): δ 4.11 (broad single peak, 2H), 6.73 (double peak, 1H), 6.99 (double-double-heavy peak, 1H), and 7.31 (double-heavy peak, 1H).The LC-MS analysis showed that the [M-H]- peak was located at m/z 253.1. | [References]
[1] Patent: WO2015/100232, 2015, A2. Location in patent: Page/Page column 102
[2] Journal of Medicinal Chemistry, 2007, vol. 50, # 1, p. 113 - 128
[3] Patent: EP1183229, 2005, B1. Location in patent: Page/Page column 143-144
[4] Organic Letters, 2011, vol. 13, # 20, p. 5636 - 5639
[5] Journal of the American Chemical Society, 2016, vol. 138, # 40, p. 13147 - 13150 |
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