4'-(4-Bromophenyl)acetophenone supplier

Name
4-ACETYL-4'-BROMOBIPHENYL
EINECS 227-236-9
CAS No. 5731-01-1
Article Data23
CAS DataBase
Density 1.359 g/cm₃
Solubility
Melting Point 129-133 °C(lit.)
Formula C₁₄H₁₁BrO
Boiling Point 372.1 °C at 760 mmHg
Molecular Weight 275.145
Flash Point 76.7 °C
Transport Information UN 3077
Appearance White or pale brown solid
Safety 26-36-61
Risk Codes 36-51/53
Molecular Structure
Hazard Symbols Xi; N
Synonyms Acetophenone,4'-(p-bromophenyl)- (6CI,7CI,8CI);1-(4'-Bromobiphenyl-4-yl)ethanone;4-(4-Bromophenyl)acetophenone;4-Acetyl-4'-bromo-1,1'-biphenyl;4-Acetyl-4'-bromobiphenyl;4'-Bromo-4-acetylbiphenyl;NSC 58059;4'-(4-Bromophenyl)acetophenone;
PSA 17.07000
LogP 4.31870

Synthetic route

: 673-40-5
4-bromobenzenediazonium tetrafluoroborate

: potassium 4-acetylphenyltrifluoroborate

: 5731-01-1
4-bromo-4'-acetylbiphenyl

Conditions

Conditions	Yield
With palladium 10% on activated carbon In methanol Suzuki-Miyaura cross-coupling; Reflux; Under air;	91%

: 589-87-7
1,4-bromoiodobenzene

: 149104-90-5
4-acetylphenylboronic acid

: 5731-01-1
4-bromo-4'-acetylbiphenyl

Conditions

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 120℃; for 1h; Suzuki Coupling;	85%

: 92-66-0
4-bromo-1,1'-biphenyl

: 75-36-5
acetyl chloride

: 5731-01-1
4-bromo-4'-acetylbiphenyl

Conditions

Conditions	Yield
With aluminum (III) chloride In dichloromethane at 15℃; for 10.5h; Cooling with ice;	84.98%
With aluminium trichloride In dichloromethane at 0℃; for 6h;	69.6%
With aluminium trichloride In dichloromethane for 24h; Ambient temperature;	19%

: 92-66-0
4-bromo-1,1'-biphenyl

: 5731-01-1
4-bromo-4'-acetylbiphenyl

Conditions

Conditions	Yield
according to ref. 9.;	77%

: 92-66-0
4-bromo-1,1'-biphenyl

: 108-24-7
acetic anhydride

: 5731-01-1
4-bromo-4'-acetylbiphenyl

Conditions

Conditions	Yield
With aluminium trichloride In carbon disulfide for 1h; Heating;	77%
With aluminium trichloride In carbon disulfide

: 589-87-7
1,4-bromoiodobenzene

: 171364-81-1
1-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)ethanone

: 5731-01-1
4-bromo-4'-acetylbiphenyl

Conditions

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); caesium carbonate In N,N-dimethyl-formamide at 80℃; for 18h;	75%

: 92-86-4
4-(4-bromophenyl)bromobenzene

: 108-24-7
acetic anhydride

: 5731-01-1
4-bromo-4'-acetylbiphenyl

Conditions

Conditions	Yield
Stage #1: 4-(4-bromophenyl)bromobenzene With tri-n-butyllithium magnesate complex In tetrahydrofuran; hexane at 0℃; for 1.5h; Stage #2: acetic anhydride In tetrahydrofuran; hexane at -20℃; for 1h;	63%

: 5467-74-3
4-Bromophenylboronic acid

: 99-90-1
para-bromoacetophenone

: 5731-01-1
4-bromo-4'-acetylbiphenyl

Conditions

Conditions	Yield
With potassium carbonate In methanol at 25℃; for 5h; Wavelength; Suzuki-Miyaura Coupling; Inert atmosphere; Irradiation;	52%

: 5467-74-3
4-Bromophenylboronic acid

: 99-93-4
4-Hydroxyacetophenone

: 5731-01-1
4-bromo-4'-acetylbiphenyl

Conditions

Conditions	Yield
With potassium phosphate; 1,3-bis[(diphenylphosphino)propane]dichloronickel(II); 4-methyl-N-phenyl-N-tosylbenzenesulfonamide In 1,4-dioxane at 110℃; Suzuki-Miyaura Coupling; Inert atmosphere; Schlenk technique;	10%

: 74-90-8
hydrogen cyanide

: 74415-08-0
2-(4'-Bromo-biphenyl-4-yl)-2-hydroxy-propionitrile

: 5731-01-1
4-bromo-4'-acetylbiphenyl

Conditions

Conditions	Yield
In 1,4-dioxane; water at 30℃; Equilibrium constant;

: 99-90-1
para-bromoacetophenone

12-phenylethynyl-6-methyl-5,6,7,12-tetrahydrodibenzo[c,f][1,5]azastibocine: 12-phenylethynyl-6-methyl-5,6,7,12-tetrahydrodibenzo[c,f][1,5]azastibocine

: 5731-01-1
4-bromo-4'-acetylbiphenyl

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: palladium(II) acetate; potassium acetate / dimethylformamide / 18 h / 80 °C 2: 75 percent / Cs2CO3; Pd(PPh3)4 / dimethylformamide / 18 h / 80 °C View Scheme

: 106-37-6
1.4-dibromobenzene

: 5720-05-8
4-methylphenylboronic acid

: 149104-90-5
4-acetylphenylboronic acid

A: 613-33-2
(4,4'-dimethyl-1,1'-biphenyl)

B: 50670-49-0
4-bromo-4'-methylbiphenyl

C: 5731-01-1
4-bromo-4'-acetylbiphenyl

D: 787-69-9
4,4'-diacetylbiphenyl

E: 5748-38-9
4-acetyl-4'-methylbiphenyl

Conditions

Conditions	Yield
Stage #1: 1.4-dibromobenzene; 4-acetylphenylboronic acid With (1-tert-butyl-4-{2-[(N,N-dimethylamino)methyl]phenyl}-3-phenyl-1H-1,2,4-triazol-4-ium-5-ide)palladium(II) dichloride for 1h; Suzuki-Miyaura Coupling; Inert atmosphere; Schlenk technique; Stage #2: 4-methylphenylboronic acid for 1h; Inert atmosphere; Schlenk technique;

...Expand

: 5731-01-1
4-bromo-4'-acetylbiphenyl

: 94512-73-9
2-bromo-1-(4'-bromo<1,1'-biphenyl>-4-yl)ethanone

Conditions

Conditions	Yield
With pol(vinylphenyltrimethylammoniumtribromide) resin In methanol; water at 65℃; for 1h;	96%
With bromine In dichloromethane at 20℃; for 48h;	88.6%
With bromine In acetic acid	87%

: 4460-86-0
asaraldehyde

: 5731-01-1
4-bromo-4'-acetylbiphenyl

: 1256153-24-8
1-[(4-(4-bromophenyl)phenyl)]-3-(2,4,5-trimethoxyphenyl)prop-2-en-1-one

Conditions

Conditions	Yield
In methanol at 75℃; Claisen-Schmidt condensation; Ionic liquid; Microwave irradiation;	96%

: 5731-01-1
4-bromo-4'-acetylbiphenyl

: 107-21-1
ethylene glycol

: 2-bromomethyl-2-[4-(4-bromophenyl)phenyl]-1,3-dioxolane

Conditions

Conditions	Yield
With pol(vinylphenyltrimethylammoniumtribromide) resin at 45℃; for 24h;	96%
With N-Bromosuccinimide at 20℃; for 24h;	92%

: 355-43-1
n-perfluorohexyl iodide

: 5731-01-1
4-bromo-4'-acetylbiphenyl

: 677324-87-7
C20H11F13O

Conditions

Conditions	Yield
With copper In dimethyl sulfoxide Heating;	93%

: 5731-01-1
4-bromo-4'-acetylbiphenyl

: 1159274-77-7
αα-dichloromethyl-4'-bromobiphenyl ketone

Conditions

Conditions	Yield
With 1,3-dichloro-5,5-dimethylhydantoin In acetonitrile at 20℃; for 0.75h; Inert atmosphere;	93%
Stage #1: 4-bromo-4'-acetylbiphenyl With ammonium chloride In acetonitrile for 0.0833333h; Stage #2: With 1,3-dichloro-5,5-dimethylhydantoin In acetonitrile at 35℃; for 12h;	93%

: 5731-01-1
4-bromo-4'-acetylbiphenyl

: 685114-64-1
4,4''''-dibromo-5''-(4'-bromo-[1,1'-biphenyl]-4-yl)-1,1':4',1'':3'',1''':4''',1''''-quinquephenyl

Conditions

Conditions	Yield
With boron tri(hydrogen sulphate) In neat liquid at 100℃; for 6h; Green chemistry;	91%
With Amberlyst 15 In toluene for 20h; Reflux;	45%
With trifluorormethanesulfonic acid In toluene for 14h; Heating;	38.9%

: 5731-01-1
4-bromo-4'-acetylbiphenyl

: 86-81-7
3,4,5-trimethoxy-benzaldehyde

: 109-77-3
malononitrile

: 1231255-61-0
6-(4'-bromobiphenyl-4-yl)-2-imino-4-(3,4,5-trimethoxyphenyl)-1,2-dihydropyridine-3-carbonitrile

Conditions

Conditions	Yield
With ammonium acetate In ethanol Reflux;	90%

...Expand

: 5731-01-1
4-bromo-4'-acetylbiphenyl

: 6287-38-3
3,4-dichlorobenzaldehyde

: 109-77-3
malononitrile

: 1231255-63-2
6-(4'-bromobiphenyl-4-yl)-4-(3,4-dichlorophenyl)-2-imino-1,2-dihydropyridine-3-carbonitrile

Conditions

Conditions	Yield
With ammonium acetate In ethanol Reflux;	90%

...Expand

: 423-39-2
1-iodo-2,2,3,3,4,4,5,5,5-nonafluorobutane

: 5731-01-1
4-bromo-4'-acetylbiphenyl

: 677324-84-4
C18H11F9O

Conditions

Conditions	Yield
With copper In dimethyl sulfoxide for 24h; Heating;	89%

: 5731-01-1
4-bromo-4'-acetylbiphenyl

: 105-36-2
ethyl bromoacetate

ethyl 3-hydroxy-3-(4'-bromo[1,1'-biphenyl]-4-yl)-butanoate: 610781-48-1
ethyl 3-hydroxy-3-(4'-bromo[1,1'-biphenyl]-4-yl)-butanoate

Conditions

Conditions	Yield
With zinc; iodine In benzene for 1.5h; Heating / reflux;	88.9%
With iodine; zinc In benzene for 1.5h; Heating / reflux;	88.9%

: 5731-01-1
4-bromo-4'-acetylbiphenyl

: 1670-14-0
benzamidine monohydrochloride

: 1122-91-4
4-bromo-benzaldehyde

C28H18Br2N2: C28H18Br2N2

Conditions

Conditions	Yield
Stage #1: 4-bromo-4'-acetylbiphenyl; 4-bromo-benzaldehyde With sodium hydroxide In ethanol at 20℃; for 8h; Stage #2: benzamidine monohydrochloride With sodium hydroxide In ethanol for 8h; Reflux;	86%

...Expand

: 5731-01-1
4-bromo-4'-acetylbiphenyl

: 1066-54-2
trimethylsilylacetylene

: 1086595-73-4
4'-[4-(trimethylsilylethynyl)phenyl]acetophenone

Conditions

Conditions	Yield
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine at 70℃; for 18h; Sonogashira coupling;	85%

: 5731-01-1
4-bromo-4'-acetylbiphenyl

: 86-81-7
3,4,5-trimethoxy-benzaldehyde

: 105-56-6
ethyl 2-cyanoacetate

: 1231255-64-3
6-(4'-bromobiphenyl-4-yl)-2-oxo-4-(3,4,5-trimethoxyphenyl)-1,2-dihydropyridine-3-carbonitrile

Conditions

Conditions	Yield
With ammonium acetate In ethanol Reflux;	85%

...Expand

: 5731-01-1
4-bromo-4'-acetylbiphenyl

: 105-56-6
ethyl 2-cyanoacetate

: 6287-38-3
3,4-dichlorobenzaldehyde

: 1231255-66-5
6-(4'-bromobiphenyl-4-yl)-4-(3,4-dichlorophenyl)-2-oxo-1,2-dihydropyridine-3-carbonitrile

Conditions

Conditions	Yield
With ammonium acetate In ethanol Reflux;	85%

...Expand

: 5731-01-1
4-bromo-4'-acetylbiphenyl

: potassium ferrocyanide

4-acetyl-4'-cyano-1,1'-biphenyl: 59211-64-2
4-acetyl-4'-cyano-1,1'-biphenyl

Conditions

Conditions	Yield
With dichloro[bis{1-(dicyclohexylphosphanyl)piperidine}]palladium; sodium carbonate In 1-methyl-pyrrolidin-2-one at 140℃; for 6h; Inert atmosphere;	85%

: 5731-01-1
4-bromo-4'-acetylbiphenyl

: 135-02-4
ortho-anisaldehyde

: 109-77-3
malononitrile

: 2-amino-6-(4'-bromobiphenyl-4-yl)-4-(2-methoxyphenyl)nicotinonitrile

Conditions

Conditions	Yield
With ammonium acetate In ethanol Reflux;	85%

...Expand

: 507-63-1
1-iodoheptadecafluorooctane

: 5731-01-1
4-bromo-4'-acetylbiphenyl

: 677324-91-3
C22H11F17O

Conditions

Conditions	Yield
With copper In dimethyl sulfoxide Heating;	84%

: 5731-01-1
4-bromo-4'-acetylbiphenyl

: 73183-34-3
bis(pinacol)diborane

1-(4'-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-[1,1'-biphenyl]-4-yl)ethan-1-one: 269410-19-7
1-(4'-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-[1,1'-biphenyl]-4-yl)ethan-1-one

Conditions

Conditions	Yield
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate In N,N-dimethyl-formamide Reflux;	84%

4'-(4-Bromophenyl)acetophenone Specification

The 4'-(4-Bromophenyl)acetophenone, with the CAS registry number 5731-01-1 and EINECS registry number 227-236-9, has the systematic name of 1-(4'-bromobiphenyl-4-yl)ethanone. It is a kind of white or pale brown solid, and belongs to the product categories: Aromatic Halides (substituted); Biphenyl & Diphenyl ether; Electronic Chemicals; Bromine Compounds; Biphenyls (Building Blocks for Liquid Crystals); Building Blocks for Liquid Crystals; Functional Materials; C13 to C14; Carbonyl Compounds; Ketones. And the molecular formula of the chemical is C₁₄H₁₁BrO.

The characteristics of 4'-(4-Bromophenyl)acetophenone are as followings: (1)ACD/LogP: 4.42; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 4.42; (4)ACD/LogD (pH 7.4): 4.42; (5)ACD/BCF (pH 5.5): 1335.87; (6)ACD/BCF (pH 7.4): 1335.87; (7)ACD/KOC (pH 5.5): 6012.02; (8)ACD/KOC (pH 7.4): 6012.02; (9)#H bond acceptors: 1; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 2; (12)Polar Surface Area: 17.07 Å²; (13)Index of Refraction: 1.592; (14)Molar Refractivity: 68.56 cm³; (15)Molar Volume: 202.4 cm³; (16)Polarizability: 27.18×10^-24cm³; (17)Surface Tension: 42.3 dyne/cm; (18)Density: 1.359 g/cm³; (19)Flash Point: 76.7 °C; (20)Enthalpy of Vaporization: 61.92 kJ/mol; (21)Boiling Point: 372.1 °C at 760 mmHg; (22)Vapour Pressure: 9.83E-06 mmHg at 25°C.

Preparation of 4'-(4-Bromophenyl)acetophenone: 4'-(4-Bromophenyl)acetophenonecan be prepared by acetyl chloride and 4-bromo-biphenyl. The reaction will need reagent aluminum chloride, and the menstruum CH₂Cl₂. The reaction time is 6 hours with temperature of 0°C, and the yield is about 69.6%.

Uses of 4'-(4-Bromophenyl)acetophenone: It can react with hydrogen cyanide; copper(1+) salt. This reaction will need reagent N-methylpyrrolidin-2-one. The reaction time is 4 hours with temperature of 185°C, and the yield is about 60%.

You should be cautious while dealing with 4'-(4-Bromophenyl)acetophenone. It irritates to eyes. It is also toxic to aquatic organisms, and may cause long-term adverse effects in the aquatic environment. Therefore, you had better take the following instructions: Avoid release to the environment. Refer to special instructions safety data sheet; Wear suitable protective clothing, gloves and eye/face protection; In case of contacting with eyes, rinse immediately with plenty of water and seek medical advice.

Addtionally, the following datas could be converted into the molecular structure:
(1)SMILES: Brc2ccc(c1ccc(C(=O)C)cc1)cc2;
(2)InChI: InChI=1/C14H11BrO/c1-10(16)11-2-4-12(5-3-11)13-6-8-14(15)9-7-13/h2-9H,1H3;
(3)InChIKey: UUVKNCRMWPNBNM-UHFFFAOYAY-N;

Product Name

4-ACETYL-4'-BROMOBIPHENYL

Synthetic route

4'-(4-Bromophenyl)acetophenone Specification

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