4'-Bromoacetophenone

Base Information

• Chemical Name: 4'-Bromoacetophenone
• CAS No.: 99-90-1
• Molecular Formula: C8H7BrO
• Molecular Weight: 199.047
• Hs Code.: 29147090
• European Community (EC) Number: 202-799-3,808-395-9
• NSC Number: 17541
• UNII: 7NB3XRY0C6
• DSSTox Substance ID: DTXSID4059203
• Nikkaji Number: J47.715J
• Wikidata: Q27268608
• Metabolomics Workbench ID: 133665
• ChEMBL ID: CHEMBL401928
• Mol file: 99-90-1.mol

Synonyms:4-Bromoacetophenone;p-Bromophenyl methyl ketone;Ethanone, 1-(4-bromophenyl)-;1-(4-Bromophenyl)ethanone;p-Bromoacetophenone;Methyl p-bromophenyl ketone;Ethanone, 1- (4-bromophenyl)-;Acetophenone, 4-bromo- (8CI);p-Bromo acetophenone;Acetophenone, 4-bromo-;4-Bromo Acetophenone;4-Bromoacetophenone 99%;

Chemical Property of 4'-Bromoacetophenone

Chemical Property:

• Appearance/Colour: white to light yellow crystals
• Melting Point: 108-110 °C(lit.)
• Refractive Index: 1.5540 (estimate)
• Boiling Point: 259.898 °C at 760 mmHg
• Flash Point: 94.278 °C
• PSA: 17.07000
• Density: 1.451 g/cm³
• LogP: 2.65170
• Storage Temp.: Store below +30°C.
• Solubility.: methanol: 0.1 g/mL, clear
• Water Solubility.: Soluble in Chloroform. Insoluble in water.
• XLogP3: 2.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 1
• Exact Mass: 197.96803
• Heavy Atom Count: 10
• Complexity: 125

Purity/Quality:

99.0% ^*data from raw suppliers

4’-Bromoacetophenone ^*data from reagent suppliers

Safty Information:

• Pictogram(s): C,Xi,Xn
• Hazard Codes: C,Xi,Xn
• Statements: 34-36/38-42/43-36/37/38-22
• Safety Statements: 26-36/37/39-45-22-36/37

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)C1=CC=C(C=C1)Br
• Uses: 4'-Bromoacetophenone is an important organic synthesis intermediate, widely used in synthetic medicine, pesticides, dyes, flavors and fragrances, perfumes, Intermediates of Liquid Crystals etc. Labeled 4?-Bromoacetophenone possess activity against positive phototaxis of Chlamydomonas cells. A fundamental starting material for organic synthesis.

Technology Process of 4'-Bromoacetophenone

There total 240 articles about 4'-Bromoacetophenone which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 95.0%

1-bromo-4-ethenyl-benzene (2039-82-9) → para-bromoacetophenone (99-90-1) + 1-(4-bromophenyl)ethanol (5391-88-8)

Guidance literature:

With triethylsilane; (1,2,3,4,8,9,10,11,15,16,17,18,22,23,24,25-Hexadecafluorophthalocyaninato)iron(II); oxygen; In ethanol; at 20 ℃; for 8.5h; under 760.051 Torr; chemoselective reaction; Sealed tube; Green chemistry;

DOI:10.1002/anie.201710370

Reference yield: 72.0%

p-bromophenacylmethylphenylselenonium perchlorate → selenoanisole (4346-64-9) + para-bromoacetophenone (99-90-1)

Guidance literature:

With methanol; samarium diiodide; In tetrahydrofuran; Ambient temperature;

Reference yield: 68.0%

pyrrolidine (123-75-1) + carbon dioxide (124-38-9,18923-20-1) + 4-bromoacetophenone tosylhydrazone (75230-51-2) → 1-bromo-4-ethenyl-benzene (2039-82-9) + 1-(4-bromophenyl)ethyl pyrrolidine-1-carboxylate + para-bromoacetophenone (99-90-1)

Guidance literature:

With water; potassium carbonate; In acetonitrile; at 120 ℃; for 24h; under 30003 Torr; Solvent; Concentration; Autoclave; Green chemistry;

DOI:10.1002/anie.201410605

upstream raw materials:

1-(4-bromophenyl)ethanol

3-(4-bromophenyl)-3-oxopropanoic acid

bromobenzene

acetic anhydride

Downstream raw materials:

4-piperidinoacetophenone

1-(2-(4-bromophenyl)-2-oxoethyl)pyridin-1-ium iodide

(E)-1-(4-bromophenyl)-3-(furan-2-yl)-2-propen-1-one

2-(4-bromo-phenyl)-6-iodo-quinoline-4-carboxylic acid

Refernces

Redox-neutral photochemical Heck-type arylation of vinylphenols activated by visible light

10.1039/c9sc06184c

The research focuses on the development of a redox-neutral photochemical Heck-type arylation of vinylphenols activated by visible light. The study discloses a method for the arylation of vinylphenols with non-activated aryl and heteroaryl halides under visible light irradiation, utilizing colored vinylphenolate anions as strong reducing photoactivators. These anions activate (hetero)aryl halides without the need for sacrificial reductants, leading to the formation of aryl radicals that couple with another molecule of vinylphenol to produce the desired arylation product in a regiospecific and stereoselective manner. The experiments involved the optimization of reaction conditions, evaluating the substrate scope with various (hetero)aryl halides, and conducting mechanistic investigations. Reactants included 4'-bromoacetophenone, methyl 4-hydroxycinnamate, and Cs2CO3 as the base, with DMSO as the solvent and blue LED light as the irradiation source. Analyses used to characterize the products and confirm the reaction mechanism included X-ray crystallography, UV-vis absorption spectra, Stern-Volmer quenching studies, and quantum yield determination.