7295-44-5

Basic information

• Product Name: 4'-BROMOVALEROPHENONE
• Synonyms: P-BROMOVALEROPHENONE;1-(4-Bromophenyl)-1-pentanone;p-Bromophenyl butyl ketone;Valerophenone, 4'-bromo-;4'-BROMOVALEROPHENONE;4-BROMOVALEROPHENONE;1-(4-BROMO-PHENYL)-PENTAN-1-ONE;4-Bromophenyl n-butyl ketone
• CAS NO: 7295-44-5
• Molecular Formula: C₁₁H₁₃BrO
• Molecular Weight: 241.12
• EINECS: 230-729-1
• Product Categories: C11 to C12;Carbonyl Compounds;Ketones
• Mol File: 7295-44-5.mol
• Article Data: 12

Chemical Properties

• Melting Point: 34-36 °C(lit.)
• Boiling Point: 168-169 °C20 mm Hg(lit.)
• Flash Point: >230 °F
• Appearance: /
• Density: 1.3366 (rough estimate)
• Vapor Pressure: 0.00196mmHg at 25°C
• Refractive Index: 1.5290 (estimate)
• Storage Temp.: 0-10°C
• Solubility: Chloroform, Ethyl Acetate (Sparingly)
• CAS DataBase Reference: 4'-BROMOVALEROPHENONE(CAS DataBase Reference)
• NIST Chemistry Reference: 4'-BROMOVALEROPHENONE(7295-44-5)
• EPA Substance Registry System: 4'-BROMOVALEROPHENONE(7295-44-5)

Safety Data

• Hazard Codes: Xi
• Safety Statements: 24/25
• WGK Germany: 3
• TSCA: T
• HazardClass: IRRITANT
• Hazardous Substances Data: 7295-44-5(Hazardous Substances Data)

Usage

Description

4'-BROMOVALEROPHENONE is a yellow crystalline powder that is a derivative of Valerophenone, an aromatic ketone. It is commonly utilized in chemical synthesis studies and serves as a valuable tool in the investigation of various photochemical processes. Additionally, it acts as an inhibitor of the enzyme carbonyl reductase.

Uses

Used in Chemical Synthesis Studies:
4'-BROMOVALEROPHENONE is used as a synthetic compound for chemical synthesis studies, contributing to the development of new molecules and compounds with potential applications in various fields.
Used in Photochemical Process Research:
As a derivative of Valerophenone, 4'-BROMOVALEROPHENONE is used as a research tool for studying photochemical processes. Its involvement in these studies aids in understanding the behavior of molecules under different light conditions and their potential applications in various industries.
Used in Enzyme Inhibition Studies:
4'-BROMOVALEROPHENONE is used as an inhibitor of the enzyme carbonyl reductase, which plays a crucial role in various metabolic pathways. By inhibiting this enzyme, researchers can gain insights into its function and potential therapeutic applications in treating specific diseases or conditions.

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

Synthetic route

n-butyllithium (109-72-8, 29786-93-4) + 4-bromo-N-methoxy-N-methylbenzamide (192436-83-2) → 4'-bromovalerophenone (7295-44-5)

Conditions	Yield
In toluene at 20℃; for 1h;	99%

bromobenzene (108-86-1) + n-valeryl chloride (638-29-9) → 4'-bromovalerophenone (7295-44-5)

Conditions	Yield
With aluminium trichloride at 0 - 80℃; for 3h;	85%
With aluminium trichloride In chlorobenzene at 0 - 5℃; for 1.5h;	80%
With aluminium trichloride 0 deg C, 1 h then 80 deg C, 2 h;	78%

n-butyl magnesium bromide (693-03-8) + 4-bromo-N,N-dimethylbenzamide (18469-37-9) → 4'-bromovalerophenone (7295-44-5)

Conditions	Yield
Stage #1: 4-bromo-N,N-dimethylbenzamide With 2,6-di-tert-butyl-4-methylpyridine; trifluoromethylsulfonic anhydride In dichloromethane at -78 - 0℃; for 2h; Inert atmosphere; Stage #2: n-butyl magnesium bromide In diethyl ether; dichloromethane at -78℃; for 2h; Inert atmosphere; chemoselective reaction;	71%

n-butyllithium (109-72-8, 29786-93-4) + 4-(pyrrolidinocarbonyl)phenyl bromide (5543-27-1) → 4'-bromovalerophenone (7295-44-5)

Conditions	Yield
In hexane at 20℃; for 0.00555556h;	70%

butyl magnesium bromide (693-04-9) + 4-bromo-N-methoxy-N-methylbenzamide (192436-83-2) → 4'-bromovalerophenone (7295-44-5)

Conditions	Yield
In tetrahydrofuran at 0℃; for 3h; Grignard reaction;

4-chlorobenzoyl chloride (586-75-4) → 4'-bromovalerophenone (7295-44-5)

Conditions	Yield
Multi-step reaction with 2 steps 1: triethylamine / dichloromethane / 0 - 20 °C 2: hexane / 0.01 h / 20 °C View Scheme

4'-bromovalerophenone (7295-44-5) → (R)-1-(4-bromophenyl)pentan-1-ol

Conditions	Yield
Stage #1: 4'-bromovalerophenone With Dimethylphenylsilane; C28H32BNO2*CHF3O3S In toluene at 20℃; for 13h; Inert atmosphere; Stage #2: With methanol; potassium carbonate In toluene at 20℃; for 2h; Inert atmosphere; enantioselective reaction;	99%

ethyl trifluoroacetate, (383-63-1) + 4'-bromovalerophenone (7295-44-5) → 1,1,1-trifluoro-2-hexanone (360-34-9) + Ethyl 4-bromobenzoate (5798-75-4)

Conditions	Yield
Stage #1: ethyl trifluoroacetate, With sodium hydride In tetrahydrofuran at 20℃; for 0.166667h; Inert atmosphere; Schlenk technique; Stage #2: 4'-bromovalerophenone In tetrahydrofuran at 0 - 20℃; for 3h; Inert atmosphere; Schlenk technique; Stage #3: With hydrogenchloride In tetrahydrofuran; water at 0℃; for 0.25h; Inert atmosphere; Schlenk technique;	A n/a B 95%

4'-bromovalerophenone (7295-44-5) + phenylboronic acid (98-80-6) → 1-[1,1'-biphenyl]-4-yl-1-pentanone (42916-73-4)

Conditions	Yield
With potassium carbonate In ethanol; water at 20℃; for 4h; Suzuki-Miyaura coupling;	94%

4'-bromovalerophenone (7295-44-5) + ethylene glycol (107-21-1) → 2-(4'-bromophenyl)-2-butyl-1,3-dioxolane

Conditions	Yield
toluene-4-sulfonic acid In benzene for 16h; Heating / reflux; Dean-Stark apparatus;	92%

4-iodobenzoic acid ethyl ester (51934-41-9) + 4'-bromovalerophenone (7295-44-5) → ethyl 4'-pentanoylbiphenyl-4-carboxylate (1228685-42-4)

Conditions	Yield
Stage #1: 4-iodobenzoic acid ethyl ester With TurboGrignard In tetrahydrofuran at -20℃; for 0.333333h; Inert atmosphere; Stage #2: With lithium chlorozincate In tetrahydrofuran Inert atmosphere; Stage #3: 4'-bromovalerophenone With bis(dibenzylideneacetone)-palladium(0); ruphos In tetrahydrofuran at 25℃; for 0.0833333h; Negishi cross-coupling reaction; Inert atmosphere;	92%

4'-bromovalerophenone (7295-44-5) + 4-flourophenylmagnesium bromide (352-13-6) → 1-(4'-fluorobiphenyl-4-yl)pentan-1-one (1228685-44-6)

Conditions	Yield
Stage #1: 4-flourophenylmagnesium bromide With lithium chlorozincate In tetrahydrofuran at 25℃; for 0.5h; Inert atmosphere; Stage #2: With 2-iodo-propane In tetrahydrofuran at 25℃; for 5h; Inert atmosphere; Stage #3: 4'-bromovalerophenone With bis(dibenzylideneacetone)-palladium(0); ruphos In tetrahydrofuran at 25℃; for 0.0833333h; Negishi cross-coupling reaction; Inert atmosphere;	91%

4'-bromovalerophenone (7295-44-5) + methyl iodide (74-88-4) → 1-(4-bromophenyl)-2,2-dimethylpentan-1-one (1313218-11-9)

Conditions	Yield
Stage #1: 4'-bromovalerophenone With sodium hydride In tetrahydrofuran; mineral oil at 20℃; for 0.516667h; Stage #2: methyl iodide In tetrahydrofuran; mineral oil for 3.05h; Reflux;	89%

4'-bromovalerophenone (7295-44-5) → phenyl butyl ketone (1009-14-9) + 1-(4-fluorophenyl)-1-pentanone (709-24-0)

Conditions	Yield
With potassium fluoride; C94H134O4P2Pd2; silver fluoride In cyclohexane at 110℃; for 14h; Sealed tube;	A 0.44% B 88%

4'-bromovalerophenone (7295-44-5) + p-ethoxycarbonylphenylboronic acid (4334-88-7) → ethyl 4'-pentanoylbiphenyl-4-carboxylate (1228685-42-4)

Conditions	Yield
With palladium 10% on activated carbon; potassium carbonate In 1,4-dioxane; water for 4h; Inert atmosphere; Reflux;	81%

4'-bromovalerophenone (7295-44-5) → 4-pentylbromobenzene (51554-95-1)

Conditions	Yield
With potassium hydroxide; hydrazine hydrate In diethylene glycol 130 deg C, 2 h then 200 deg C, 2 h;	80%
With potassium hydroxide; hydrazine hydrate In diethylene glycol at 130 - 180℃; for 6h;	71%

4'-bromovalerophenone (7295-44-5) + ethane-1,2-dithiol (540-63-6) → 2-(4-bromophenyl)-2-butyl-1,3-dithiolane (361348-09-6)

Conditions	Yield
With boron trifluoride diacetate	77%

bis[(trimethylsilyl)methyl](1,5-cyclooctadiene)palladium(II) (225931-80-6) + 4'-bromovalerophenone (7295-44-5) + C53H73O2P (1570098-46-2) → C64H86BrO3PPd

Conditions	Yield
In pentane at 20℃; for 24h; Inert atmosphere; Glovebox;	77%

4'-bromovalerophenone (7295-44-5) + phenylmanganese(II) chloride (71478-47-2) → 1-[1,1'-biphenyl]-4-yl-1-pentanone (42916-73-4)

Conditions	Yield
1,2-dimethoxyethane; bis(diphenylphosphino)propanepalladium(II) dichloride In tetrahydrofuran at 20℃; for 0.05h;	75%

4'-bromovalerophenone (7295-44-5) + N-methoxylamine hydrochloride (593-56-6) → C12H16BrNO

Conditions	Yield
With sodium acetate In ethanol; water for 2h; Reflux;	73%

4'-bromovalerophenone (7295-44-5) + tributylphenylstannane (960-16-7) → 4-biphenyl-4-yl-5-propyl-[1,2,3]thiadiazole

Conditions

Yield

Stage #1: 4'-bromovalerophenone With polystyrene-sulfonylhydrazide resin; acetic acid In tetrahydrofuran at 50℃; for 4h; Solid phase reaction; Stage #2: tributylphenylstannane; bis-triphenylphosphine-palladium(II) chloride In N,N-dimethyl-formamide at 90℃; for 24h; Solid phase reaction; Stille reaction; Stage #3: With thionyl chloride In 1,2-dichloro-ethane at 60℃; for 5h; Solid phase reaction; Hurd-Mori cyclization;

71%

4'-bromovalerophenone (7295-44-5) → 4,4'-Divaleryl-biphenyl

Conditions	Yield
With C24H38N2O6; palladium diacetate In water at 60℃; for 6h; Inert atmosphere;	66%

4'-bromovalerophenone (7295-44-5) + C63H80F5O2PPd → 1-(4-fluorophenyl)-1-pentanone (709-24-0)

Conditions	Yield
With p-bromobutylbenzene In (2)H8-toluene at 20℃; for 12h; Inert atmosphere; Glovebox;	66%

4'-bromovalerophenone (7295-44-5) + N-(2,2-dimethoxyethyl)-N-methylformamide → C17H26BrNO4

Conditions	Yield
With lithium diisopropyl amide In tetrahydrofuran at 25℃; for 0.0166667h;	63%

4'-bromovalerophenone (7295-44-5) + phenylmagnesium chloride (100-59-4) → 1-[1,1'-biphenyl]-4-yl-1-pentanone (42916-73-4)

Conditions	Yield
Stage #1: phenylmagnesium chloride With titanium(IV) tetraethanolate In tetrahydrofuran at 0℃; Stage #2: 4'-bromovalerophenone With 1,3-bis[2,6-diisopropylphenyl]imidazolium chloride; bis(acetylacetonate)nickel(II) In tetrahydrofuran at -10℃; for 6h; Further stages.;	60%

4'-bromovalerophenone (7295-44-5) + butyraldehyde (123-72-8) → 1-(4-butyrylphenyl)pentan-1-one

Conditions	Yield
With nickel(II) iodide; potassium phosphate; tetrakis(tetrabutylammonium)decatungstate(VI); 4,4'-di-tert-butyl-2,2'-bipyridine In acetonitrile at 20℃; for 4h; Schlenk technique; Inert atmosphere; Irradiation;	60%

4'-bromovalerophenone (7295-44-5) + bis(tri-n-butyltin) (813-19-4) → 4-tributylstannylvalerophenone

Conditions	Yield
	58%

4'-bromovalerophenone (7295-44-5) + 3,4-(OCH2O)-C6H3-X, X = lithium or magnesium halide → C18H18O3

Conditions	Yield
Stage #1: 3,4-(OCH2O)-C6H3-X, X = lithium or magnesium halide With titanium(IV) tetraethanolate In tetrahydrofuran at 0℃; Stage #2: 4'-bromovalerophenone With 1,3-bis[2,6-diisopropylphenyl]imidazolium chloride; bis(acetylacetonate)nickel(II) In tetrahydrofuran at -10℃; for 6h; Further stages.;	57%

4'-bromovalerophenone (7295-44-5) + 2-chloro-benzaldehyde (89-98-5) → 4-Bromobenzoic acid (586-76-5) + (E)-1-chloro-2-(pent-1-en-1-yl)benzene (14717-30-7) + 1-(4-Bromo-phenyl)-2-[1-(2-chloro-phenyl)-meth-(E)-ylidene]-pentan-1-one

Conditions	Yield
With boron trifluoride diacetate In hexane for 4h; Aldol-Grob reaction; Heating;	A 54% B n/a C n/a

bis[(trimethylsilyl)methyl](1,5-cyclooctadiene)palladium(II) (225931-80-6) + 4'-bromovalerophenone (7295-44-5) + AlPhos → C63H80BrF4O2PPd

Conditions	Yield
In pentane at 20℃; for 24h; Inert atmosphere; Glovebox;	47%

4'-bromovalerophenone (7295-44-5) → (E)-1-(4-bromophenyl)pent-2-ene-1,4-dione (1172582-14-7)

Conditions	Yield
With oxygen; copper diacetate; palladium diacetate; trifluoroacetic acid In dimethyl sulfoxide at 80℃; for 48h;	45%

4'-bromovalerophenone (7295-44-5) + C64H86FO3PPd → 1-(4-fluorophenyl)-1-pentanone (709-24-0)

Conditions	Yield
With p-bromobutylbenzene In (2)H8-toluene at 20℃; for 12h; Inert atmosphere; Glovebox;	31%

Upstream product

• 108-86-1 bromobenzene 
• 638-29-9 n-valeryl chloride 
• 693-04-9 butyl magnesium bromide 
• 192436-83-2 4-bromo-N-methoxy-N-methylbenzamide 
• 693-03-8 n-butyl magnesium bromide 
• 18469-37-9 4-bromo-N,N-dimethylbenzamide 
• 109-72-8 n-butyllithium 
• 5543-27-1 4-(pyrrolidinocarbonyl)phenyl bromide 
• 586-75-4 4-chlorobenzoyl chloride 

Downstream Products

• 51554-95-1 4-pentylbromobenzene 
• 91428-17-0 α-<4-Brom-phenyl>-pentylamin 
• 99859-32-2 1-(4-bromo-3-nitro-phenyl)-pentan-1-one 
• 1009-14-9 phenyl butyl ketone 
• 586-76-5 4-Bromobenzoic acid 
• 14717-30-7 (E)-1-chloro-2-(pent-1-en-1-yl)benzene 
• 42916-73-4 1-[1,1'-biphenyl]-4-yl-1-pentanone 
• 361348-09-6 2-(4-bromophenyl)-2-butyl-1,3-dithiolane 
• 198758-23-5 2-bromo-1-(4-bromophenyl)pentan-1-one 
• 850352-59-9 2-pyrrolidin-1-yl-1-(4'-bromo-phenyl)-pentan-1-one 
• 850442-93-2 1-(4-N-methylpyrrolephenyl)-2-pyrrolidin-1-yl-pentan-1-one 
• 361348-17-6 1-bromo-4-(1,1-difluoropentyl)benzene 
• 124388-30-3 p-pentylphenylmagnesium bromide 
• 121219-17-8 2,3-difluoro-4'-pentylbiphenyl 

Relevant articles and documents

A Fast and General Route to Ketones from Amides and Organolithium Compounds under Aerobic Conditions: Synthetic and Mechanistic Aspects

We report that the nucleophilic acyl substitution reaction of aliphatic and (hetero)aromatic amides by organolithium reagents proceeds quickly (20 s reaction time), efficiently, and chemoselectively with a broad substrate scope in the environmentally responsible cyclopentyl methyl ether, at ambient temperature and under air, to provide ketones in up to 93 % yield with an effective suppression of the notorious over-addition reaction. Detailed DFT calculations and NMR investigations support the experimental results. The described methodology was proven to be amenable to scale-up and recyclability protocols. Contrasting classical procedures carried out under inert atmospheres, this work lays the foundation for a profound paradigm shift of the reactivity of carboxylic acid amides with organolithiums, with ketones being straightforwardly obtained by simply combining the reagents under aerobic conditions and with no need of using previously modified or pre-activated amides, as recommended.

A general method for the direct transformation of common tertiary amides into ketones and amines by addition of Grignard reagents

The direct transformation of amides into ketones by addition of organometallic reagents has attracted the attention of organic chemists for a long time. However limited methods are reliable for common amides and have found synthetic applications. Here we report a method featuring in situ activation of tertiary amides with triflic anhydride (Tf2O) followed by addition of Grignard reagents. The method displays a good generality in scope for both amides and Grignard reagents, and it can be viewed as the acylation of Grignard reagents using amides as stable and selective acylating agents. Moreover, this deaminative alkylation reaction provides a mild method for the N-Deacylation of amides to give free amines.

Parallel synthesis of 1,2,3-thiadiazoles employing a 'catch and release' strategy

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