4'-BROMOVALEROPHENONE Chemical Properties

Melting point:

34-36 °C(lit.)

Boiling point:

168-169 °C20 mm Hg(lit.)

Density 

1.3366 (rough estimate)

refractive index 

1.5290 (estimate)

Flash point:

>230 °F

storage temp. 

Sealed in dry,Room Temperature

solubility 

Chloroform, Ethyl Acetate (Sparingly)

form 

Solid

color 

Tan

λmax

325nm(Heptane)(lit.)

InChI

InChI=1S/C11H13BrO/c1-2-3-4-11(13)9-5-7-10(12)8-6-9/h5-8H,2-4H2,1H3

InChIKey

STYJKBMRWQQJIS-UHFFFAOYSA-N

SMILES

C(C1=CC=C(Br)C=C1)(=O)CCCC

CAS DataBase Reference

7295-44-5(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Safety Statements 

24/25

WGK Germany 

3

TSCA 

T

HazardClass 

IRRITANT

HS Code 

29147000

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

4'-BROMOVALEROPHENONE Usage And Synthesis

Chemical Properties

yellow crystalline powder

Uses

4′-Bromovalerophenone may be used in chemical synthesis studies.

Uses

4'-Bromovalerophenone is a derivative of Valerophenone, which is an aromatic ketone that is often used as a tool in the study of various photochemical processes. Valerophenone is also an inhibitor of the enzyme carbonyl reductase.

Synthesis

GENERAL PROCEDURE: Trifluoromethanesulfonic anhydride (Tf2O, 1.2 eq.) was slowly added dropwise to a solution of 4-bromo-N,N-dimethylbenzamide (1.0 eq.) and 2,6-di-tert-butyl-4-methylpyridine (DTBMP, 1.2 eq.) in dichloromethane (CH2Cl2, 5 mL) cooled to -78 °C. The reaction mixture was gradually warmed up to 0 °C over 2 hours. Subsequently, a solution of butylmagnesium bromide (1.0 eq.) in ether (Et2O) was slowly added dropwise to the reaction mixture at -78 °C and stirring was continued at the same temperature for 2 hours. After completion of the reaction, the reaction was quenched with 15% aqueous hydrochloric acid (5 mL). The organic layer was separated and the aqueous phase was extracted with ether (3 x 5 mL). The organic layers were combined, washed with saturated saline, dried over anhydrous sodium sulfate (Na2SO4), filtered and concentrated under reduced pressure. The residue was purified by silica gel fast column chromatography to obtain the target product 4-bromovalerophenone. For the separation of the by-product N,N-dimethyl-4-bromobenzamide, the aqueous phase was alkalized with 15% aqueous sodium hydroxide (6 mL) and extracted with dichloromethane (3 x 10 mL). The organic layers were combined, dried over anhydrous sodium sulfate (Na2SO4), filtered and concentrated under reduced pressure. The residue was purified by silica gel fast column chromatography to give N,N-dimethyl-4-bromobenzamide.

References

[1] Tetrahedron, 2015, vol. 71, # 24, p. 4248 - 4254

4'-BROMOVALEROPHENONE(7295-44-5)Related Product Information

• 1-BROMO-4-N-HEPTANOYLBENZENE
• 4'-BROMOVALEROPHENONE
• 4-BROMOPENTANOPHENONE
• Valerophenone
• 5-(4-BROMOPHENYL)-5-OXOVALERONITRILE
• 2-(2-(4-BROMOPHENYL)-2-OXOETHYL)-5,5-DIMETHYLCYCLOHEXANE-1,3-DIONE
• CIS-2-[2-(4-BROMOPHENYL)-2-OXOETHYL]CYCLOHEXANE-1-CARBOXYLIC ACID
• TRANS-2-[2-(4-BROMOPHENYL)-2-OXOETHYL]CYCLOHEXANE-1-CARBOXYLIC ACID
• TRANS-2-(4-BROMOBENZOYL)CYCLOPENTANE-1-CARBOXYLIC ACID
• 1-(4-BROMOPHENYL)-6-CHLORO-1-OXOHEXANE
• 5-(4-BROMOPHENYL)-5-OXOVALERIC ACID
• CIS-2-(4-BROMOBENZOYL)-1-CYCLOHEXANE-CARBOXYLIC ACID
• TRANS-2-[2-(4-BROMOPHENYL)-2-OXOETHYL]CYCLOPENTANE-1-CARBOXYLIC ACID
• ETHYL 5-(4-BROMOPHENYL)-5-OXOVALERATE
• 1-(4-BROMOPHENYL)-7-CHLORO-1-OXOHEPTANE
• P-BROMOPHENYL N-HEPTYL KETONE
• ETHYL 6-(4-BROMOPHENYL)-6-OXOHEXANOATE
• ETHYL 4-(4-BROMOPHENYL)-4-OXO-2-(PHENYLCARBONYL)BUTANOATE