4,4'-Bis(2-bromoacetyl)biphenyl Chemical Properties

Melting point:

226-227 °C(Solv: benzene (71-43-2))

Boiling point:

464.8±30.0 °C(Predicted)

Density 

1.622±0.06 g/cm3(Predicted)

storage temp. 

under inert gas (nitrogen or Argon) at 2-8°C

Appearance

Off-white to light brown Solid

InChI

InChI=1S/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

InChIKey

RTSLQVZQORGDQQ-UHFFFAOYSA-N

SMILES

C1(C2=CC=C(C(=O)CBr)C=C2)=CC=C(C(=O)CBr)C=C1

EPA Substance Registry System

Ethanone, 1,1'-[1,1'-biphenyl]-4,4'-diylbis[2-bromo- (4072-67-7)

Safety Information

HS Code 

29147000

4,4'-Bis(2-bromoacetyl)biphenyl Usage And Synthesis

Uses

4,4'-Bis(2-bromoacetyl)biphenyl is an intermediate in laboratory research and development.

Synthesis

To a reaction flask was added 138.8 g (1.04 mol, 2.9 eq.) of aluminum trichloride. 700 ml of dichloromethane was added and the system was cooled to 0-10 °C and stirred. 174.6 g (0.87 mol, 2.4 eq.) of bromoacetyl bromide was slowly added dropwise, controlling the temperature to be maintained at 0 to 10 °C during the dropwise addition. After the dropwise addition, stirring of the reaction mixture was continued for 10 to 30 minutes. Subsequently, 150 ml of dichloromethane solution containing 55.8 g (0.36 mol, 1.0 equiv) of biphenyl was slowly added. After the addition was completed, the reaction mixture was gradually warmed to room temperature with continuous stirring. Next, 200 ml of n-heptane was added to the system, the temperature was raised to reflux, and the reaction was maintained at this temperature for 4 to 5 hours until the alkaline reaction was complete and a large amount of product precipitated. The reaction mixture was continued to be stirred at room temperature for 3 to 5 hours, followed by diafiltration to give the crude product 4,4'-bis(2-bromoacetyl)biphenyl (I). The crude product I was suspended in 500 ml of water and stirred for 1 to 2 hours at room temperature and diafiltrated to give 4,4'-bis(2-bromoacetyl)biphenyl crude oil (II). The crude product II was pulped in 300 ml of dichloromethane, stirred for 1 to 2 hours at room temperature and filtered to give purified 4,4'-bis(2-bromoacetyl)biphenyl. Finally, the product was dried under vacuum at 70 °C to give 121.3 g solid with 99.4% purity and 84.9% yield.

References

[1] Patent: CN108727171, 2018, A. Location in patent: Paragraph 0049-0057
[2] Journal of Medicinal Chemistry, 1983, vol. 26, # 1, p. 104 - 107
[3] Journal of the American Pharmaceutical Association (1912-1977), 1954, vol. 43, p. 79,80
[4] Bulletin de la Societe Chimique de France, 1958, p. 1156,1158
[5] Chemical and Pharmaceutical Bulletin, 1971, vol. 19, p. 2262 - 2270

4,4'-Bis(2-bromoacetyl)biphenyl(4072-67-7)Related Product Information

• Acetylacetone
• PHENYL VALERATE
• FIREMASTER BP-6
• N-ACETYL-L-TYROSINE ETHYL ESTER
• Decabromodiphenyl oxide
• 2-Bromobiphenyl
• Acetylferrocene
• L-PICEIN
• Biphenyl
• PHENYL RESIN
• Phenylacetic acid
• 4'-Methylbiphenyl-4-carbaldehyde
• 4,4'-Diacetylbiphenyl
• 4,4'-Dimethylbiphenyl
• 2-Bromoacetophenone
• 2-Bromo-4'-methylacetophenone
• (2-Bromoethyl)benzene
• 2-BROMO-4'-PHENYLACETOPHENONE