3583-02-6

Usage

Uses

Used in Pharmaceutical Industry:
2-BROMO-1,3,2-BENZODIOXAPHOSPHOLE is used as a synthetic intermediate for the development of pharmaceutical compounds. Its unique reactivity and coordination properties make it a valuable building block in the synthesis of complex molecules with potential therapeutic applications.
Used in Agrochemical Industry:
In the agrochemical sector, 2-BROMO-1,3,2-BENZODIOXAPHOSPHOLE serves as a key component in the synthesis of agrochemicals. Its ability to participate in a wide range of chemical reactions allows for the creation of novel compounds with potential applications in crop protection and pest control.
Used in Materials Science:
2-BROMO-1,3,2-BENZODIOXAPHOSPHOLE is utilized as a precursor in the development of advanced materials with specific properties. Its versatility in chemical reactions enables the synthesis of materials with tailored characteristics for use in various applications, such as sensors, catalysts, and functional coatings.
Used in Organic Synthesis:
As a ligand in transition metal-catalyzed reactions, 2-BROMO-1,3,2-BENZODIOXAPHOSPHOLE plays a crucial role in organic synthesis. Its unique coordination properties facilitate the formation of new chemical bonds and the construction of complex molecular structures, contributing to the discovery and development of novel organic compounds with diverse applications.

InChI:InChI=1/C6H4BrO2P/c7-10-8-5-3-1-2-4-6(5)9-10/h1-4H

Upstream product

• 120-80-9 benzene-1,2-diol 
• 1195-15-9 2-hydroxy-1,3,2-benzodioxaphosphole 
• 3712-44-5 2,2,2-tribromo-1,3,2-benzodioxaphosphole 
• 88399-68-2 2-(2,2,3,3-tetrafluoropropoxy)-4,5-benzo-1,3,2-dioxaphospholane 

Downstream Products

• 127054-66-4 2-hydroxyphenyl-2,2,3,3-tetrafluoropropylphosphoric acid 
• 4918-98-3 phosphoric acid 2-hydroxyphenyl phosphate 
• 205579-20-0 2-bromo-4-(4-bromophenyl)-2H-(4-bromobenzo)[e][1,2]oxaphosphorin-3-ene 2-oxide 
• 205579-17-5 2-bromo-4-(4-bromophenyl)-2H-benzo[e][1,2]oxaphosphorin-3-ene 2-oxide 

Relevant academic research and scientific papers

The Acceptor Properties of some Organophosphorus(V) Bromides

The acceptor properties of the organophosphorous(V) bromides PBr3(cat) (cat = benzene-1,2-diolate), PBr(cat)2, and PBr4Ph, and of the PBr3Ph(1+) cation, towards Lewis bases such as halide ions and uni- or bi-dentate pyridines have been investigated, mainl

Structure-property-reactivity studies on dithiaphospholes

The reaction of either toluene-3,4-dithiol or benzene dithiol with phosphorus(iii) trihalides generates the corresponding benzo-fused 1,3,2-dithiaphospholes, RC6H3S2PX (R = Me (1), R = H (2); X = Cl, Br, I). The P-chloro-dithiaphospholes undergo: (a) halogen abstraction reactions with Lewis acids forming phosphenium cations; (b) substitution with LiHMDS base and; (c) reduction chemistry with sodium metal to generate the P-P σ-bonded dimer, (RC6H3S2P)2. Reduction catalysis of aldehydes with pinacolborane using dithiaphospholes is compared with their dioxaphosphole and diazaphosphole counterparts as pre-catalysts, revealing interesting differences in the reactivity of this series of compounds.

Experiments towards the formation of 1,6-dehydroquadricyclane and density functional calculations on this and related molecules

1,6-Dibromoquadricyclane (6) was obtained from norbornadiene (11) by hydroboration, oxidation of the diol 12 to the diketone 14 and its conversion into 2,6-dibromonorbornadiene (20) using tribromodioxaphosphole 16b followed by treatment of the mixture 17/18 with potassium tert-butoxide in DMSO and photocyclization of 20. Reaction of 6 with tBuLi (2 equiv.) led to the formation of 1-bromo-6-lithioquadricyclane 7, the NMR spectra of which were observed up to 0°C. 7 did not lose LiBr to give 4, but could be trapped with H2O and chlorotrimethylsilane to give 21e (53%) and 21f (64%). Reaction of 6 with fBuLi (> 4 equiv.) gave rise to 1,6-dilithioquadricyclane (21c), whose NMR spectra could also be recorded. 21c was converted into the corresponding 1,6-disubstituted quadricyclanes with D2O (87%), chlorotrimethylsilane (92%), dimethyl sulfate (55%), methyl chloroformate (45%), iodine monochloride (62%), and p-toluenesulfonyl chloride (48%). - Density functional calculations using the B3LYP/6-31G* level of theory showed that 1,6-dehydroquadricyclane (4) is a local energy minimum in its singlet electronic state. 4 contains a unique structure with 4 condensed cyclopropane units. The parent hydrocarbons 27 and 28, hitherto unknown, are also local energy minima in their singlet electronic states.

Alkenyl bromides by brominative deoxygenation of ketones in one or two steps

The conversion of ketones into alkenyl bromides is accomplished in one or two steps by 2,2,2-tribromo-2,2-dihydro-1,3,2-benzodioxaphosphole or by the dibromomethyl methyl ether prepared therefrom. Investigations of the scope and limitations provide some hints for the preparative planning and improvement.