Name | 1,1'-[1,1'-biphenyl]-4,4'-diylbis[2-bromoethan-1-one] |
Synonyms | Einecs 223-785-3 4,4'-Bis(bromoacetyl)biphenyl 4,4'-Bis(2-bromoacetyl)biphenyl 1,1'-biphenyl-4,4'-diylbis(2-bromoethanone) 1,1'-(1,1'-Biphenyl-4,4'-diyl)bis(2-bromoethanone) Ethanone, 1,1'-(1,1'-biphenyl)-4,4'-diylbis(2-bromo- 2-Bromo-1-[4-[4-(2-bromoacetyl)phenyl]phenyl]ethanone 1,1'-[1,1'-biphenyl]-4,4'-diylbis[2-bromoethan-1-one] 1,1'-(1,1'-Biphenyl)-4,4'-diylbis(2-bromoethan-1-one) 4,4'-Bis(2-bromoacetyl)biphenyl 1,1'-(1,1'-Biphenyl)-4,4'-diylbis(2-bromoethan-1-one) |
CAS | 4072-67-7 |
EINECS | 223-785-3 |
InChI | InChI=1/C16H12Br2O2/c17-9-15(19)13-5-1-11(2-6-13)12-3-7-14(8-4-12)16(20)10-18/h1-8H,9-10H2 |
Molecular Formula | C16H12Br2O2 |
Molar Mass | 396.07 |
Density | 1.622±0.06 g/cm3(Predicted) |
Melting Point | 226-227 °C(Solv: benzene (71-43-2)) |
Boling Point | 464.8±30.0 °C(Predicted) |
Flash Point | 121.3°C |
Vapor Presure | 8.12E-09mmHg at 25°C |
Storage Condition | under inert gas (nitrogen or Argon) at 2-8°C |
Refractive Index | 1.625 |
HS Code | 29147000 |
EPA chemical information | Information provided by: ofmpub.epa.gov (external link) |
overview | 4,4 '-bis (2-bromoacetyl) biphenyl is a key intermediate in the synthesis of the anti-hepatitis C drug dhathavir. Dhaka Tamivir (Daclatasvir) is a new hepatitis C drug developed by Bristol-Myers Squibb in the United States. On July 24, 2015, the US FDA approved it for the treatment of chronic hepatitis C. Its trade name is Daklinza. It is an NS5A inhibitor and is suitable for adults infected with genes 1, 2, 3 and 4. Its chemical name is N,N'-[[1,1 '-biphenyl]-4,4'-diyl bis [1H-imidazol-5, 2-diyl-(2S)-2, 1-pyrrolidinyl [(1S)-1-(1-methylethyl) -2-oxo-2, 1-ethanediyl]] bis carbamate C, c'-dimethyl ester, the synthesis of 4,4 '-bis (2-bromoacetyl) biphenyl is reported in the literature. Biphenyl and bromoacetyl bromide are used as substrates and CS is used as the reaction solvent. Friedel acylation reaction occurs under the action of AlCl to obtain the product 4,4'-bis (2-bromoacetyl) biphenyl. |
application | 4,4 '-bis (2-bromoacetyl) biphenyl is an organic synthesis intermediate and a pharmaceutical intermediate, which can be used as a laboratory research and development process and a chemical medicine research and development process. |
Preparation | 4,4 '-bis (2-bromoacetyl) biphenyl The preparation method includes the following steps:(1) At the reaction temperature of -10 ℃ ~ 30 ℃, the catalyst and chlorinated alkane solvent are added to the reaction bottle to mix, the system is cooled to -10~30 ℃, the bromoacetyl bromide is added to the upward system dropwise, heat preservation and stirring for 10~30 minutes. The chlorinated alkane solution containing biphenyl is added dropwise to cause the Friedel-Crafts acylation reaction between bromoacetyl bromide and biphenyl to obtain the first mixed system. The chlorinated alkane solvent includes, but is not limited to: dichloromethane, 1, 2-dichloroethane, chloroform and/or carbon tetrachloride; the catalyst includes, but is not limited to: aluminum trichloride, zinc chloride and/or ferric chloride. (2) heating to room temperature and stirring continuously, adding anti-solvent to the first mixed system, and continuing the reaction at the reaction temperature of 20 ℃ ~ 60 ℃ for 0.5~8 hours to obtain a second mixed system containing 4,4 '-bis (2-bromoacetyl) biphenyl; the anti-solvent is selected from C3 ~ C10 alkanes, ethers and esters; C3 ~ C10 alkanes are selected from: n-hexane, n-heptane, cyclohexane, methylcyclohexane, pentane, octane, nonane, decane; ethers are selected from: petroleum ether, methyl tert-butyl ether, ether, ethylene glycol dimethyl ether, tetrahydrofuran, 2-methyltetrahydrofuran, isopropyl ether; esters are selected from: ethyl acetate, butyl acetate, isopropyl acetate; preferably n-hexane, cyclohexane, n-heptane, petroleum Ether; better n-heptane, cyclohexane. (3) Control the temperature of the second mixed system containing 4,4 '-bis (2-bromoacetyl) biphenyl at -5~25 ℃, stir for 2~5 hours, and filter to obtain 4,4'-bis (2-bromoacetyl) biphenyl crude product; the obtained crude product is beaten in water and dichloromethane solution at room temperature, filtered, and dried to obtain high-quality products 4,4 '-bis (2-bromoacetyl) biphenyl. |