| Identification | More | [Name]
3-BROMO-5-NITROBENZOTRIFLUORIDE | [CAS]
630125-49-4 | [Synonyms]
1-BROMO-3-NITRO-5-(TRIFLUOROMETHYL)BENZENE
3-BROMO-5-NITROBENZOTRIFLUORIDE
3-Bromo-5-nitrobenzotrifluoride 97%
3-Bromo-5-nitrobenzotrifluoride97%
BENZENE,1-BROMO-3-NITRO-5
5-bromo-3-nitrobenzotrifluoride | [Molecular Formula]
C7H3BrF3NO2 | [MDL Number]
MFCD03788719 | [Molecular Weight]
270 | [MOL File]
630125-49-4.mol |
| Chemical Properties | Back Directory | [Boiling point ]
223.7±35.0 °C(Predicted) | [density ]
1.788±0.06 g/cm3(Predicted) | [refractive index ]
1.515 | [storage temp. ]
Sealed in dry,Room Temperature | [solubility ]
Chloroform (Slightly), Methanol (Slightly) | [form ]
Oil | [color ]
Colourless | [InChI]
InChI=1S/C7H3BrF3NO2/c8-5-1-4(7(9,10)11)2-6(3-5)12(13)14/h1-3H | [InChIKey]
YHTVYRKVFAFVLP-UHFFFAOYSA-N | [SMILES]
C1(Br)=CC(C(F)(F)F)=CC([N+]([O-])=O)=C1 | [CAS DataBase Reference]
630125-49-4(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 . | [Hazard Note ]
Irritant | [HazardClass ]
IRRITANT | [HS Code ]
29049090 |
| Hazard Information | Back Directory | [Description]
3-Bromo-5-nitrobenzotrifluoride is an important organic synthetic compound and a pharmaceutical intermediate component. It can be used in the preparation of SOS1 degraders and nilotinib hydrochloride. | [Chemical Properties]
Yellow liquid | [Uses]
3-Bromo-5-nitrobenzotrifluoride is an efficient D-glucosamine-based copper catalyst for C-X couplings and its application in synthesis of nilotinib intermediate. 3-Bromo-5-nitrobenzotrifluoride is also an intermediate for Nilotinib (N465300). | [Synthesis]
Example 14 Synthesis of 1-bromo-3-nitro-5-trifluoromethylbenzene (XI): To a solution of 1-nitro-3-trifluoromethylbenzene (41.1 mL, 300 mmol, 97%, purchased from Aldrich) in dichloromethane (240 mL) was slowly added 98% sulfuric acid (45.7 mL, 840 mmol) over a 10 minute period. The two-phase mixture obtained with vigorous stirring was heated to 35 °C and 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione (total 53.1 g, 180 mmol) was added in six equal portions over 5 hours. The mixture was continued to be stirred at 35 °C for 19 h. HPLC analysis showed more than 97% conversion of the starting material. After the reaction mixture was cooled to room temperature, it was added dropwise to a stirred aqueous 2 M NaOH solution (210 mL) at 0-5 °C over 20 min, during which time it was cooled in an ice-water bath, and the internal temperature was briefly raised to about 35 °C. The reaction mixture was then cooled to room temperature, and the internal temperature was raised to about 35 °C. The reaction mixture was then cooled to room temperature. The two layers were separated and the aqueous layer was extracted with hexane (3 x 200 mL). The combined organic layers were washed sequentially with water (200 mL), 5% aqueous sodium bisulfite (2 x 200 mL), 8% aqueous NaHCO3 (200 mL), and 10% aqueous NaCl (200 mL), followed by evaporation of the solvent at 45 °C under reduced pressure. The resulting liquid was distilled at 0.71 mbar and a bath temperature of 70-80 °C to give 1-bromo-3-nitro-5-trifluoromethylbenzene as a light yellow liquid in 89.6% yield (1H-NMR purity about 95%).1H-NMR (400 MHz, CDCl3): δ 8.11 (m, 1H), 8.45 (m, 1H), 8.58-8.59 (m, 1H). 1H). Boiling point: ca. 68 °C (0.71 mbar). | [References]
[1] Patent: WO2006/135640, 2006, A2. Location in patent: Page/Page column 25-26
[2] RSC Advances, 2015, vol. 5, # 2, p. 1522 - 1528
[3] Patent: US2016/311777, 2016, A1. Location in patent: Paragraph 0028 |
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