2,4'-Dibromoacetophenone

Base Information

• Chemical Name: 2,4'-Dibromoacetophenone
• CAS No.: 99-73-0
• Molecular Formula: C8H6Br2O
• Molecular Weight: 277.943
• Hs Code.: 29147090
• European Community (EC) Number: 202-783-6
• NSC Number: 6224
• UNII: PN0FRW1G4Z
• DSSTox Substance ID: DTXSID4059201
• Nikkaji Number: J3.227A
• Wikidata: Q27286634
• ChEMBL ID: CHEMBL142826
• Mol file: 99-73-0.mol

Synonyms:2,4-dibromoacetophenone;4-bromophenacyl bromide;alpha-para-dibromoacetophenone;bromophenacyl bromide;bromophenacylbromide;p-bromophenacyl bromide;PBPAB

Chemical Property of 2,4'-Dibromoacetophenone

Chemical Property:

• Appearance/Colour: off-white crystals or powder
• Melting Point: 108-110 °C(lit.)
• Refractive Index: 1.5560 (estimate)
• Boiling Point: 310.4 °C at 760 mmHg
• Flash Point: 114.1 °C
• PSA: 17.07000
• Density: 1.848 g/cm³
• LogP: 3.02670
• Storage Temp.: 2-8°C
• Sensitive.: Lachrymatory
• Water Solubility.: Soluble in dimethyl sulfoxide (5 mg/ml), methanol (20 mg/ml), toluene and ethanol. Insoluble in water.
• XLogP3: 3.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 2
• Exact Mass: 277.87649
• Heavy Atom Count: 11
• Complexity: 139

Purity/Quality:

98% ^*data from raw suppliers

4-Bromophenacyl bromide 98+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s): C
• Hazard Codes: C
• Statements: 34
• Safety Statements: 26-36/37/39-45

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Other Classes -> Aromatic Ketones, Halogenated
• Canonical SMILES: C1=CC(=CC=C1C(=O)CBr)Br
• Uses: Undergoes condensation reactions with aldehydes in the presence of SnCl21 or SmI32 to afford α,β-unsaturated ketones. Also useful in the esterification of carboxylic acids.3 Identification of carboxylic acids. 2,4'-Dibromoacetophenone is used as a reagent for analysis of fatty acids by HPLC as 4-bromophenacyl esters, for use in the protection of phenols and carboxylic acids. It undergoes condensation reactions with aldehydes in the presence of SnCl2 or SmI3 to afford α,β-unsaturated ketones. It is also useful in the esterification of carboxylic acids.

Technology Process of 2,4'-Dibromoacetophenone

There total 49 articles about 2,4'-Dibromoacetophenone 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: 98.0%

bromobenzene (108-86-1,52753-63-6) + 2-Bromoacetyl bromide (598-21-0) → para-bromophenacyl bromide (99-73-0,132309-76-3)

Guidance literature:

With aluminium trichloride; In 1,2-dichloro-ethane; for 4h; Ambient temperature;

DOI:10.3987/com-97-7820

Reference yield: 97.0%

1-bromo-4-(1-bromovinyl)benzene (69151-18-4) → para-bromophenacyl bromide (99-73-0,132309-76-3)

Guidance literature:

With iron(III) trifluoromethanesulfonate; 2-((4R,5R)-1-((4-(tert-butyl)phenyl)sulfonyl)-4,5-diphenylimidazolidin-2-yl)-6-((4R,5R)-1-((4-(tert-butyl)phenyl)sulfonyl)-4,5-diphenylimidazolidin-2-yl)pyridine; oxygen; In 1,2-dichloro-ethane; at 75 ℃; for 16h; under 760.051 Torr; chemoselective reaction; Green chemistry;

DOI:10.1021/jacs.5b03956

Reference yield: 95.0%

2-bromo-1-(4-bromophenyl)ethanone oxime (57342-22-0) → para-bromophenacyl bromide (99-73-0,132309-76-3)

Guidance literature:

With tris[trinitratocerium(IV)] paraperiodate; at 90 ℃; for 0.166667h;

upstream raw materials:

2-bromoacetyl chloride

bromobenzene

1-(4-bromo-phenyl)-2-diazo-ethanone

α,α,α-tribromoacetophenone

Downstream raw materials:

1-ethyl-1-(4-bromo-phenacyl)-piperidinium; bromide

1-(p-bromophenacyl)pyridinium bromide

1-(4-bromo-phenacyl)-3-hydroxy-pyridinium; bromide

2-(4-bromophenyl)imidazo[1,2-a]pyridine

Refernces

• 1、 -. "Thiazole ring-containing amide compounds as well as preparation method and application thereof". Paragraph 0044; 0051; 0078; 0081; 0150; 0155; 0234; 0239. . Retrieved 2021/06/23.
• 2、 Abay, Efrem,Barry, Clifton E.,Basarab, Gregory S.,Boshoff, Helena I. M.,Boyle, Grant A.,Chibale, Kelly,Eyermann, Charles J.,Fienberg, Stephen,Ghorpade, Sandeep R.,Khonde, Lutete Peguy,Lawrence, Nina,Lenaerts, Anne J.,Massoudi, Lisa M.,Myers, Timothy G.,Myrick, Alissa,Nchinda, Aloysius T.,Njoroge, Mathew,Reddy, Virsinha,Robertson, Gregory T.,Singh, Vinayak,Sirgel, Frederick A.,Su, Qin,Van Helden, Paul D.,Müller, Rudolf. "1,3-Diarylpyrazolyl-acylsulfonamides as Potent Anti-tuberculosis Agents Targeting Cell Wall Biosynthesis in Mycobacterium tuberculosis". supporting information. p. 12790 - 12807. Retrieved 2021/09/11.