| Identification | More | [Name]
4-Bromo-3-fluorobenzonitrile | [CAS]
133059-44-6 | [Synonyms]
3-FLUORO-4-BROMOBENZONITRILE
4-BROMO-3-FLUOROBENZONITRILE
4-Bromo-3-fluorobenzonitrile97% | [Molecular Formula]
C7H3BrFN | [MDL Number]
MFCD07782069 | [Molecular Weight]
200.01 | [MOL File]
133059-44-6.mol |
| Chemical Properties | Back Directory | [Melting point ]
54-58 C | [Boiling point ]
230.1±20.0 °C(Predicted) | [density ]
1.69±0.1 g/cm3(Predicted) | [storage temp. ]
Sealed in dry,Room Temperature | [form ]
powder to crystal | [color ]
White to Almost white | [InChI]
InChI=1S/C7H3BrFN/c8-6-2-1-5(4-10)3-7(6)9/h1-3H | [InChIKey]
QBKXYSXQKRNVRQ-UHFFFAOYSA-N | [SMILES]
C(#N)C1=CC=C(Br)C(F)=C1 | [CAS DataBase Reference]
133059-44-6(CAS DataBase Reference) |
| Safety Data | Back Directory | [Hazard Codes ]
T,Xi,Xn | [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:Wear suitable protective clothing . | [Hazard Note ]
Toxic | [HazardClass ]
IRRITANT | [HS Code ]
2926907090 |
| Hazard Information | Back Directory | [Chemical Properties]
White to light brown solid | [Uses]
4-Bromo-3-fluorobenzonitrile is a fluorobenzonitrile that is used in the preparation of ethylene. This chemical can also be used in the synthesis of pharmaceuticals and dyes. 4-Bromo-3-fluorobenzonitrile has been shown to have antimutagenicity and DNA repair abilities, which are due to its ability to inhibit carcinogen metabolism by binding to the enzyme cytochrome P450 2E1. 4-Bromo-3-fluorobenzonitrile also prevents cross linking of collagen by reacting with amino groups on lysine residues, which leads to a decrease in cardiac toxicity. | [Synthesis]
Step 2: Synthesis of 4-bromo-3-fluorobenzonitrile
Sodium sulfite (0.97 g, 14.117 mmol) was added to sulfuric acid (6 mL) in batches at 5 °C, followed by stirring at room temperature for 30 min. The reaction mixture was cooled to 0 °C, acetic acid (9.8 mL) was added slowly and stirring was continued for 5 min. After that, 4-amino-3-fluorobenzonitrile (1.6 g, 11.764 mmol) was added in small portions. The mixture was stirred at room temperature for 1 hour. Subsequently, a solution of copper (I) bromide (2.5 g, 17.647 mmol) was added to the aqueous solution. Hydrobromic acid (6 mL) was added slowly at 10 °C. The resulting mixture was stirred overnight at room temperature and the progress of the reaction was monitored by thin layer chromatography (TLC). Upon completion of the reaction, water was added and extracted with ether. The organic layer was dried with anhydrous sodium sulfate and concentrated under reduced pressure. The crude product was purified by column chromatography on silica gel (100-200 mesh) using a hexane solution containing 2% ethyl acetate as eluent, resulting in 4-bromo-3-fluorobenzonitrile (0.8 g, 34.7% yield) as a white solid. Mass spectrum (MS): 201.1 [M + 1]. | [References]
[1] Patent: US2017/291894, 2017, A1. Location in patent: Paragraph 0536-0538 |
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