15023-99-1

Basic information

• Product Name: 2,2-Dibromo-1,2-diphenylethanone
• Synonyms: 2,2-Dibromo-1,2-diphenylethanone;α,α-Dibromodeoxybenzoin
• CAS NO: 15023-99-1
• Molecular Formula: C₁₄H₁₀Br₂O
• Molecular Weight: 354.05
• Mol File: 15023-99-1.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 2,2-Dibromo-1,2-diphenylethanone(CAS DataBase Reference)
• NIST Chemistry Reference: 2,2-Dibromo-1,2-diphenylethanone(15023-99-1)
• EPA Substance Registry System: 2,2-Dibromo-1,2-diphenylethanone(15023-99-1)

Safety Data

• Hazardous Substances Data: 15023-99-1(Hazardous Substances Data)

Usage

Purification Methods

Crystallise α,α-dibromo deoxybenzoin from acetic acid, 50% aqueous EtOH (prisms, m 109-112o) or Et2O (m 112o). [Curtius & Lang J Prakt Chem 44 547 1891, Beilstein 7 H 436, 7 III 2114.]

Upstream product

• 451-40-1 phenyl benzyl ketone 
• 3469-17-8 2-diazo-1,2-diphenylethan-1-one 
• 4850-59-3 2,2,2-triphenoxy-4,5-diphenyl-2,2-dihydro-1,3,2-dioxaphospholene 
• 67-66-3 chloroform 
• 7726-95-6 bromine 
• 60-29-7 diethyl ether 
• 861533-66-6 2-methoxy-1,2,3,4-tetraphenyl-butane-1,4-dione 
• 5773-56-8 1,2-Diphenylethanol 
• 14447-41-7 (E)-1-bromo-1,2-diphenylethene 
• 501-65-5 diphenyl acetylene 
• 1484-50-0 desyl bromide 
• 134-81-6 benzil 
• 5344-88-7 benzil monohydrazone 

Downstream Products

• 65-85-0 benzoic acid 
• 134-81-6 benzil 
• 1056-32-2 2,2,4,5-tetraphenyl-2,3-dihydrofuran 
• 451-40-1 phenyl benzyl ketone 
• 5773-56-8 1,2-Diphenylethanol 
• 10035-10-6 hydrogen bromide 
• 1484-50-0 desyl bromide 
• 28925-53-3 α-phenyl-α-(p-tolylsulfonyl)acetophenone 

Relevant articles and documents

Electrochemical Oxidative Functionalization of Arylalkynes: Access to α,α-Dibromo Aryl Ketones

A general and effective protocol to synthesize α,α-dibromo aryl ketones has been developed via an electrochemical oxidative method. The reaction proceeds smoothly at room temperature in an undivided cell without the addition of external oxidants. In the reaction process, LiBr acts as both bromine source and supporting electrolyte. This electrooxidation strategy has good substrate applicability and functional group compatibility. Moreover, the reaction could be scaled up efficiently in a continuous flow cell. The target product could undergo further functionalization for the synthesis of some useful heterocyclic compounds. (Figure presented.).

Substituent Effect in the Synthesis of α,α-Dibromoketones, 1,2-Dibromalkenes, and 1,2-Diketones from the Reaction of Alkynes and Dibromoisocyanuric Acid

Internal alkynes reacted with dibromoisocyanuric acid/H2O to afford α,α-dibromoketone and 1,2-diketone derivatives. Diarylalkynes with activating groups provided 1,2-diketone derivatives as the major products, whereas diarylalkynes with a non-activating group or alkylarylalkynes gave α,α-dibromoketone derivatives as the major products. In addition, diarylalkynes with deactivating groups provided 1,2-dibromoalkenes. The reaction was conducted at room temperature and showed good yields in most cases. Reaction pathways have been proposed on the basis of experimental observations and density functional theory (DFT) calculations. (Figure presented.).

Water-controlled selective preparation of α-mono or α,α′-dihalo ketones: Via catalytic cascade reaction of unactivated alkynes with 1,3-dihalo-5,5-dimethylhydantoin

The control of a reaction that can produce multiple products from the same starting material is a highly attractive and challenging concept in organic synthesis. An efficient protocol for the selective synthesis of α-mono or α,α′-dihalo ketones via a water-controlled three-component thiourea-catalyzed cascade reaction of unactivated alkynes, 1,3-dihalo-5,5-dimethylhydantoin and water has been developed. α-Monohaloketones were obtained in aqueous acetone at 45 °C; conversely, α,α′-dihalo ketones were formed with pure water as the sole solvent at room temperature.

Catalyst-and metal-free rapid functionalizations of alkynes using TsNBr2

A very rapid (3-12 min) and efficient method has been developed for a one-pot synthesis of α,α-dibromoalkanones and β-bromoenol alkanoates directly from alkynes using N,N-dibromo-p-toluenesulfonamide (TsNBr2). The protocol is embellished with f

A facile synthesis of two series of multifunctional carbon compounds from α,α-dihalo ketones using allylsamarium bromide

The use of allylsamarium bromide to effect two different reactions on the common starting material, a,a-dihalo ketones, is presented. With DMF, α-halo-α-allyl aldehydes were obtained, while α-hydroxy- α-allyl aldehyde acetals were obtained in the presence of NaOMe/MeOH. Georg Thieme Verlag Stuttgart.

A facile one-pot synthesis of a?-halo-a?-allyl-aldehydes from a?,a?-Dihaloketoncs Using Allylsamarium Bromide and DMF

A convenient, one-pot synthesis of a range of a?-halo-a?-allyl aldehydes is described. The protocol involves the reaction of allylsamarium bromide with various a?,a?-dihalo ketones. A possible mechanism of the transformation is proposed.

A convenient and practical approach to α-diketones via reactions of internal aryl alkynes with N-iodosuccinimide/water

A convenient and practical approach to α-diketones via reactions of alkynes with N-iodosuccinimides/water at 70°C has been developed. Georg Thieme Verlag Stuttgart.