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4'-(4-Bromophenyl)acetophenone

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Name

4'-(4-Bromophenyl)acetophenone

EINECS 227-236-9
CAS No. 5731-01-1 Density 1.359 g/cm3
PSA 17.07000 LogP 4.31870
Solubility N/A 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 Molecular Structure of 5731-01-1 (4-ACETYL-4'-BROMOBIPHENYL) Hazard Symbols IrritantXi; DangerousN
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;

Article Data 23

4'-(4-Bromophenyl)acetophenone Synthetic route

673-40-5

4-bromobenzenediazonium tetrafluoroborate

potassium 4-acetylphenyltrifluoroborate

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%
589-87-7

1,4-bromoiodobenzene

149104-90-5

4-acetylphenylboronic acid

5731-01-1

4-bromo-4'-acetylbiphenyl

Conditions
ConditionsYield
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
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%
92-66-0

4-bromo-1,1'-biphenyl

5731-01-1

4-bromo-4'-acetylbiphenyl

Conditions
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
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%
5467-74-3

4-Bromophenylboronic acid

99-90-1

para-bromoacetophenone

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%
5467-74-3

4-Bromophenylboronic acid

99-93-4

4-Hydroxyacetophenone

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%
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
ConditionsYield
In 1,4-dioxane; water at 30℃; Equilibrium constant;

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;

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