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5731-01-1 Usage

Chemical Properties

White or pale brown solid

Check Digit Verification of cas no

The CAS Registry Mumber 5731-01-1 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 5,7,3 and 1 respectively; the second part has 2 digits, 0 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 5731-01:
(6*5)+(5*7)+(4*3)+(3*1)+(2*0)+(1*1)=81
81 % 10 = 1
So 5731-01-1 is a valid CAS Registry Number.

5731-01-1 Well-known Company Product Price

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  • Alfa Aesar

  • (L13798)  4'-(4-Bromophenyl)acetophenone, 97%   

  • 5731-01-1

  • 25g

  • 748.0CNY

  • Detail
  • Alfa Aesar

  • (L13798)  4'-(4-Bromophenyl)acetophenone, 97%   

  • 5731-01-1

  • 100g

  • 2469.0CNY

  • Detail

5731-01-1SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name 4-ACETYL-4'-BROMOBIPHENYL

1.2 Other means of identification

Product number -
Other names 1-[4-(4-bromophenyl)phenyl]ethanone

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:5731-01-1 SDS

5731-01-1Synthetic route

4-bromobenzenediazonium tetrafluoroborate
673-40-5

4-bromobenzenediazonium tetrafluoroborate

potassium 4-acetylphenyltrifluoroborate

potassium 4-acetylphenyltrifluoroborate

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

4-bromo-4'-acetylbiphenyl

Conditions
ConditionsYield
With palladium 10% on activated carbon In methanol Suzuki-Miyaura cross-coupling; Reflux; Under air;91%
1,4-bromoiodobenzene
589-87-7

1,4-bromoiodobenzene

4-acetylphenylboronic acid
149104-90-5

4-acetylphenylboronic acid

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

4-bromo-4'-acetylbiphenyl

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 120℃; for 1h; Suzuki Coupling;85%
4-bromo-1,1'-biphenyl
92-66-0

4-bromo-1,1'-biphenyl

acetyl chloride
75-36-5

acetyl chloride

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

4-bromo-4'-acetylbiphenyl

Conditions
ConditionsYield
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%
4-bromo-1,1'-biphenyl
92-66-0

4-bromo-1,1'-biphenyl

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

4-bromo-4'-acetylbiphenyl

Conditions
ConditionsYield
according to ref. 9.;77%
4-bromo-1,1'-biphenyl
92-66-0

4-bromo-1,1'-biphenyl

acetic anhydride
108-24-7

acetic anhydride

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

4-bromo-4'-acetylbiphenyl

Conditions
ConditionsYield
With aluminium trichloride In carbon disulfide for 1h; Heating;77%
With aluminium trichloride In carbon disulfide
1,4-bromoiodobenzene
589-87-7

1,4-bromoiodobenzene

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

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

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

4-bromo-4'-acetylbiphenyl

Conditions
ConditionsYield
With tetrakis(triphenylphosphine) palladium(0); caesium carbonate In N,N-dimethyl-formamide at 80℃; for 18h;75%
4-(4-bromophenyl)bromobenzene
92-86-4

4-(4-bromophenyl)bromobenzene

acetic anhydride
108-24-7

acetic anhydride

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

4-bromo-4'-acetylbiphenyl

Conditions
ConditionsYield
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%
4-Bromophenylboronic acid
5467-74-3

4-Bromophenylboronic acid

para-bromoacetophenone
99-90-1

para-bromoacetophenone

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

4-bromo-4'-acetylbiphenyl

Conditions
ConditionsYield
With potassium carbonate In methanol at 25℃; for 5h; Wavelength; Suzuki-Miyaura Coupling; Inert atmosphere; Irradiation;52%
4-Bromophenylboronic acid
5467-74-3

4-Bromophenylboronic acid

4-Hydroxyacetophenone
99-93-4

4-Hydroxyacetophenone

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

4-bromo-4'-acetylbiphenyl

Conditions
ConditionsYield
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%
hydrogen cyanide
74-90-8

hydrogen cyanide

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

2-(4'-Bromo-biphenyl-4-yl)-2-hydroxy-propionitrile

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

4-bromo-4'-acetylbiphenyl

Conditions
ConditionsYield
In 1,4-dioxane; water at 30℃; Equilibrium constant;
para-bromoacetophenone
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

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

4-bromo-4'-acetylbiphenyl

Conditions
ConditionsYield
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
1.4-dibromobenzene
106-37-6

1.4-dibromobenzene

4-methylphenylboronic acid
5720-05-8

4-methylphenylboronic acid

4-acetylphenylboronic acid
149104-90-5

4-acetylphenylboronic acid

A

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

(4,4'-dimethyl-1,1'-biphenyl)

B

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

4-bromo-4'-methylbiphenyl

C

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

4-bromo-4'-acetylbiphenyl

D

4,4'-diacetylbiphenyl
787-69-9

4,4'-diacetylbiphenyl

E

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

4-acetyl-4'-methylbiphenyl

Conditions
ConditionsYield
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;
4-bromo-4'-acetylbiphenyl
5731-01-1

4-bromo-4'-acetylbiphenyl

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

2-bromo-1-(4'-bromo<1,1'-biphenyl>-4-yl)ethanone

Conditions
ConditionsYield
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 acid87%
asaraldehyde
4460-86-0

asaraldehyde

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

4-bromo-4'-acetylbiphenyl

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

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

Conditions
ConditionsYield
In methanol at 75℃; Claisen-Schmidt condensation; Ionic liquid; Microwave irradiation;96%
4-bromo-4'-acetylbiphenyl
5731-01-1

4-bromo-4'-acetylbiphenyl

ethylene glycol
107-21-1

ethylene glycol

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

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

Conditions
ConditionsYield
With pol(vinylphenyltrimethylammoniumtribromide) resin at 45℃; for 24h;96%
With N-Bromosuccinimide at 20℃; for 24h;92%
n-perfluorohexyl iodide
355-43-1

n-perfluorohexyl iodide

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

4-bromo-4'-acetylbiphenyl

C20H11F13O
677324-87-7

C20H11F13O

Conditions
ConditionsYield
With copper In dimethyl sulfoxide Heating;93%
4-bromo-4'-acetylbiphenyl
5731-01-1

4-bromo-4'-acetylbiphenyl

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

αα-dichloromethyl-4'-bromobiphenyl ketone

Conditions
ConditionsYield
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%
4-bromo-4'-acetylbiphenyl
5731-01-1

4-bromo-4'-acetylbiphenyl

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

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

Conditions
ConditionsYield
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%
4-bromo-4'-acetylbiphenyl
5731-01-1

4-bromo-4'-acetylbiphenyl

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

3,4,5-trimethoxy-benzaldehyde

malononitrile
109-77-3

malononitrile

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

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

Conditions
ConditionsYield
With ammonium acetate In ethanol Reflux;90%
4-bromo-4'-acetylbiphenyl
5731-01-1

4-bromo-4'-acetylbiphenyl

3,4-dichlorobenzaldehyde
6287-38-3

3,4-dichlorobenzaldehyde

malononitrile
109-77-3

malononitrile

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

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

Conditions
ConditionsYield
With ammonium acetate In ethanol Reflux;90%
1-iodo-2,2,3,3,4,4,5,5,5-nonafluorobutane
423-39-2

1-iodo-2,2,3,3,4,4,5,5,5-nonafluorobutane

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

4-bromo-4'-acetylbiphenyl

C18H11F9O
677324-84-4

C18H11F9O

Conditions
ConditionsYield
With copper In dimethyl sulfoxide for 24h; Heating;89%
4-bromo-4'-acetylbiphenyl
5731-01-1

4-bromo-4'-acetylbiphenyl

ethyl bromoacetate
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
ConditionsYield
With zinc; iodine In benzene for 1.5h; Heating / reflux;88.9%
With iodine; zinc In benzene for 1.5h; Heating / reflux;88.9%
4-bromo-4'-acetylbiphenyl
5731-01-1

4-bromo-4'-acetylbiphenyl

benzamidine monohydrochloride
1670-14-0

benzamidine monohydrochloride

4-bromo-benzaldehyde
1122-91-4

4-bromo-benzaldehyde

C28H18Br2N2

C28H18Br2N2

Conditions
ConditionsYield
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%
4-bromo-4'-acetylbiphenyl
5731-01-1

4-bromo-4'-acetylbiphenyl

trimethylsilylacetylene
1066-54-2

trimethylsilylacetylene

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

4'-[4-(trimethylsilylethynyl)phenyl]acetophenone

Conditions
ConditionsYield
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine at 70℃; for 18h; Sonogashira coupling;85%
4-bromo-4'-acetylbiphenyl
5731-01-1

4-bromo-4'-acetylbiphenyl

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

3,4,5-trimethoxy-benzaldehyde

ethyl 2-cyanoacetate
105-56-6

ethyl 2-cyanoacetate

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

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

Conditions
ConditionsYield
With ammonium acetate In ethanol Reflux;85%
4-bromo-4'-acetylbiphenyl
5731-01-1

4-bromo-4'-acetylbiphenyl

ethyl 2-cyanoacetate
105-56-6

ethyl 2-cyanoacetate

3,4-dichlorobenzaldehyde
6287-38-3

3,4-dichlorobenzaldehyde

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

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

Conditions
ConditionsYield
With ammonium acetate In ethanol Reflux;85%
4-bromo-4'-acetylbiphenyl
5731-01-1

4-bromo-4'-acetylbiphenyl

potassium ferrocyanide

potassium ferrocyanide

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

4-acetyl-4'-cyano-1,1'-biphenyl

Conditions
ConditionsYield
With dichloro[bis{1-(dicyclohexylphosphanyl)piperidine}]palladium; sodium carbonate In 1-methyl-pyrrolidin-2-one at 140℃; for 6h; Inert atmosphere;85%
4-bromo-4'-acetylbiphenyl
5731-01-1

4-bromo-4'-acetylbiphenyl

ortho-anisaldehyde
135-02-4

ortho-anisaldehyde

malononitrile
109-77-3

malononitrile

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

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

Conditions
ConditionsYield
With ammonium acetate In ethanol Reflux;85%
1-iodoheptadecafluorooctane
507-63-1

1-iodoheptadecafluorooctane

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

4-bromo-4'-acetylbiphenyl

C22H11F17O
677324-91-3

C22H11F17O

Conditions
ConditionsYield
With copper In dimethyl sulfoxide Heating;84%
4-bromo-4'-acetylbiphenyl
5731-01-1

4-bromo-4'-acetylbiphenyl

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

5731-01-1Relevant articles and documents

Pure Deep Blue Light-Emitting Diodes from Alternating Fluorene/Carbazole Copolymers by Using Suitable Hole-Blocking Materials

Lu, Jianping,Tao, Ye,D'iorio, Marie,Li, Yuning,Ding, Jianfu,Day, Michael

, p. 2442 - 2449 (2004)

The influences of the carbazole content on the photophysical, electrochemical, and electroluminescent properties of alternating fluorene/carbazole copolymers PFnCz (n = 1, 2, 3) with well-defined chemical structures have been systematically investigated. The incorporation of carbazole units into the polyfluorene (PF) backbone resulted in a blue shift of both the absorption and photoluminescence (PL) emission peaks, improved PL thermal stability, raised HOMO energy levels, and thus facilitated hole injection into the copolymers. Pure deep blue electroluminescence (EL) with narrow with (full width at the half-maximum) (39-52 nm) and negligible low-energy emission bands was successfully achieved from the PFnCz copolymers by using l,3,5-tris(4′-fluorobiphenyl-4-yl)benzene (F-TBB) as a hole-blocking layer and Alq3 as an electron injection/transporting layer. This device configuration stabilized the blue emission from the PF derivatives. An efficiency of 0.72 cd/A at a luminance of 100 cd/m2 was obtained even with aluminum metal as the cathode.

-

Adrova,N.A. et al.

, (1962)

-

Understanding the remarkable difference in liquid crystal behaviour between secondary and tertiary amides: The synthesis and characterisation of new benzanilide-based liquid crystal dimers

Strachan, Grant J.,Harrison, William T. A.,Storey, John M. D.,Imrie, Corrie T.

, p. 12600 - 12611 (2021/06/17)

A number of liquid crystal dimers have been synthesised and characterised containing secondary or tertiary (N-methyl) benzanilide-based mesogenic groups. The secondary amides all form nematic phases, and we present the first example of an amide to show the twist-bend nematic (NTB) phase. Only two of the correspondingN-methylated dimers formed a nematic phase and with greatly reduced nematic-isotropic transition temperatures. Characterisation using 2D ROESY NMR experiments, DFT geometry optimisation and X-ray diffraction reveal that there is a change in the preferred conformation of the benzanilide core on methylation, fromZtoE. The rotational barrier around the N-C(O) bond has been measured using variable temperature1H NMR spectroscopy. This dramatic change in shape accounts for the remarkable difference in liquid crystalline behaviour between these secondary and tertiary amide-based materials.

Carboncarbon bond forming reactions: Application of covalently anchored 2,4,6-triallyloxy-1,3,5-triazine (TAT) Pd(II) complex over modified surface of SBA-15 to Heck, Suzuki, Sonogashira and Hiyama cross coupling reactions

Singh, Chandani,Jawade, Kiran,Sharma, Priti,Singh, Anand P.,Kumar, Pradeep

, p. 11 - 15 (2015/06/08)

A highly active SBA-15-TAT-Pd(II) catalyst was synthesized from organofunctionalized SBA-15 and 2,4,6-triallyloxy-1,3,5-triazine. The catalyst was employed in carrying out Heck, "copper-free" Sonogashira, Suzuki and Hiyama cross coupling reactions. Under the optimized conditions the catalyst displays excellent catalytic activity in delivering the desired products in good to excellent yields. The catalytic system exhibited superior activity regarding the time taken for the completion of reaction, isolation, Pd loading (0.62 mmol%) and yields of products as compared to the earlier reported heterogeneous SBA-15 anchored Pd catalysts. The catalyst could be recycled and reused for five times without any appreciable loss of catalytic activity.

Nickel-catalyzed one-pot Suzuki-Miyaura cross-coupling of phenols and arylboronic acids mediated by N,N-ditosylaniline

Chen, Liangshun,Lang, Hongyue,Fang, Lei,Zhu, Mengyun,Liu, Jinqian,Yu, Jianjun,Wang, Limin

supporting information, p. 4953 - 4957 (2014/08/18)

An efficient method for the construction of two distinct C aryl-Caryl bonds through the Ni-catalyzed Suzuki-Miyaura cross-coupling of phenols with arylboronic acids has been developed. This reaction proceeds through the in situ tosylation of phenols by using N,N-ditosylaniline as the sulfonylating reagent, which is highly active, markedly stable, and easily prepared. The scope with respect to the coupling partners - phenols and boronic acids - is broad, and sensitive functional groups are tolerated. Phenols, especially those containing an unprotected amino group, which are generally problematic for coupling under conventional one-pot conditions, are also viable substrates in this transformation.

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