16619-55-9

Basic information

• Product Name: 2,2-DIBROMO-1,3-DIPHENYL-1,3-PROPANEDIONE
• Synonyms: 2,2-DIBROMO-1,3-DIPHENYL-1,3-PROPANEDIONE;DIBENZOYLDIBROMOMETHANE;Dibromodiphenylpropanedione;2,2-DibroMo-1,3-diphenylpropane-1,3-dione
• CAS NO: 16619-55-9
• Molecular Formula: C₁₅H₁₀Br₂O₂
• Molecular Weight: 382.05
• Mol File: 16619-55-9.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 403.2°C at 760 mmHg
• Flash Point: 98.5°C
• Appearance: /
• Density: 1.71g/cm³
• Vapor Pressure: 1.03E-06mmHg at 25°C
• Refractive Index: 1.648
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• CAS DataBase Reference: 2,2-DIBROMO-1,3-DIPHENYL-1,3-PROPANEDIONE(CAS DataBase Reference)
• NIST Chemistry Reference: 2,2-DIBROMO-1,3-DIPHENYL-1,3-PROPANEDIONE(16619-55-9)
• EPA Substance Registry System: 2,2-DIBROMO-1,3-DIPHENYL-1,3-PROPANEDIONE(16619-55-9)

Safety Data

• Hazardous Substances Data: 16619-55-9(Hazardous Substances Data)

Usage

General Description

2,2-Dibromo-1,3-diphenyl-1,3-propanedione is a chemical compound often used for its antimicrobial properties. Its molecular formula is C15H12Br2O2 and it is characterized by the presence of two bromine atoms and two phenyl groups attached to a propanedione moiety, commonly known as a beta-diketone. Its structure allows it to interact with and deactivate various types of bacteria and fungi, making it useful in areas such as health care, water treatment, and various industrial applications. As with many chemicals, proper handling is necessary due to potential health hazards, specifically its potential to cause irritation upon contact with skin or eyes, or if inhaled or swallowed.

InChI:InChI=1/C15H10Br2O2/c16-15(17,13(18)11-7-3-1-4-8-11)14(19)12-9-5-2-6-10-12/h1-10H

Upstream product

• 1907-69-3 (Z)-3-ethoxy-1,3-diphenylprop-2-en-1-one 
• 120-46-7 1,3-diphenylpropanedione 
• 94-41-7 benzalacetophenone 
• 67-66-3 chloroform 
• 62961-62-0 (Z)-3-hydroxy-1,3-diphenyl-2-propen-1-one 
• 7726-95-6 bromine 
• 75-15-0 carbon disulfide 

Downstream Products

• 6048-29-9 triphenylphenacylphosphonium bromide 
• 134898-30-9 2-Benzoyl-2-bromo-1,4-diphenyl-3-(triphenyl-λ⁵-phosphanylidene)-butane-1,4-dione 
• 134898-27-4 (1,2-Dibenzoyl-2-bromo-3-oxo-3-phenyl-propyl)-triphenyl-phosphonium; bromide 
• 942-60-9 5-phenyl-1,2,4-triazin-3-amine 
• 106-41-2 4-bromo-phenol 
• 120-46-7 1,3-diphenylpropanedione 
• 1116649-49-0 1,1-dicyano-2,2-dibenzoyl-3-phenylcyclopropane 
• 134898-29-6 3-Benzoyl-3-bromo-4-oxo-4-phenyl-2-(triphenyl-λ⁵-phosphanylidene)-butyric acid ethyl ester 
• 134898-28-5 3-Benzoyl-3-bromo-4-oxo-4-phenyl-2-(triphenyl-λ⁵-phosphanylidene)-butyric acid methyl ester 
• 134898-32-1 3-Benzoyl-2-bromo-4-oxo-4-phenyl-but-2-enoic acid ethyl ester 
• 134898-31-0 3-Benzoyl-2-bromo-4-oxo-4-phenyl-but-2-enoic acid methyl ester 
• 134898-33-2 2-benzoyl-3-bromo-1,4-diphenyl-but-2-ene-1,4-dione 
• 134898-25-2 (2-Benzoyl-2-bromo-1-methoxycarbonyl-3-oxo-3-phenyl-propyl)-triphenyl-phosphonium; bromide 
• 1779-58-4 (methyloxycarbonylmethyl)triphenylphosphonium bromide 

Relevant articles and documents

N,N-Dibromobenzenesulfonamide: A useful regenrable reagent for bromination of various carbanionic substrates

N,N-Dibromobenzenesulfonamide(dibromoamine-B), which is prepared easily in high yield, has been employed as effective brominating agent for carbanionic substrates under mild conditions. β-Diketones and β-ketoesters were brominated by this reagent without using any bases. The reagent can be recovered, rebrominated, and reused several times.

One-pot synthesis of α-bromo- and α-azidoketones from olefins by catalytic oxidation with in situ-generated modified IBX as the key reaction

Simple one-pot protocols for the syntheses of α-bromoketones and α-azidoketones starting from olefins have been developed by employing catalytic oxidation of the intermediary bromohydrins with in situ-generated modified IBX as the key reaction. The improved procedure involves initial formation of bromohydrin by the reaction of olefin with NBS in acetonitrile-water mixture (1:1) at rt followed by oxidation with in situ-generated 3,4,5,6-tetramethyl-2-iodoxybenzoic acid (TetMe-IBX), produced in catalytic amounts from 3,4,5,6-tetramethyl-2-iodobenzoic and Oxone. α-Bromoketones are further converted in the same pot to the corresponding α-azidoketones using NaN3/NaHCO3. The one-pot conversions are versatile for a variety of olefins that include cyclic as well as acyclic aliphatic olefins and electron-rich and electron-deficient styrenes. Chemoselective bromohydroxylation of electron-rich double bond and subsequent oxidation to the α-bromoketone is demonstrated for a substrate that contains both electron-rich and deficient double bonds.

Oxidative bromination of ketones using ammonium bromide and oxone

A highly efficient, environmentally safe and economic method for selective α-monobromination of aralkyl, cyclic, acyclic, 1,3-diketones and β-keto esters and α,α-dibromination of 1,3-diketones and β-keto esters without catalyst is reported using ammonium bromide as a bromine source and oxone as an oxidant. The reaction proceeds at ambient temperature and yields range from moderate to excellent. Bromination of unsymmetrical ketones takes place at the less substituted α-position predominantly. Aromatisation of tetralones is also carried out with this reagent system.