74213-24-4

Usage

Uses

Used in Organic Synthesis:
1,1-Dibromoformaldoxime is used as a reagent for the preparation of substituted 3-bromo-isoxazoles through cycloaddition reactions with alkynes. This application is valuable for the synthesis of complex organic molecules and the development of new pharmaceuticals and chemical compounds.
In the Chemical Industry:
1,1-Dibromoformaldoxime is utilized in the synthesis of various organic compounds, including substituted isoxazoles, which are important building blocks in the creation of pharmaceuticals, agrochemicals, and other specialty chemicals. Its ability to undergo cycloaddition with alkynes makes it a valuable tool for chemists in the chemical industry for the development of novel and efficient synthetic routes.

Synthesis Reference(s)

Tetrahedron Letters, 25, p. 387, 1984 DOI: 10.1016/S0040-4039(00)99890-3

InChI:InChI=1/CHBr2NO/c2-1(3)4-5/h5H

Upstream product

• 3545-80-0 hydroxyiminoacetic acid 
• 69676-53-5 2-(hydroxyimino)propanedioic acid 
• 92114-96-0 mercury fulminate 
• 15736-98-8 sodium cyanate 
• 298-12-4 Glyoxilic acid 
• 168208-95-5 glyoxylic acid aldoxime 
• 62812-66-2 (Z)-hydroxyimino-acetic acid 
• 3545-78-6 N-hydroxyglycine 
• 859074-29-6 2-hydroxyimino-malonomonohydroxamic acid 
• 7732-18-5 water 
• 7726-95-6 bromine 
• 57913-56-1 2-hydroxyimino-acetohydroxamic acid 
• 51060-05-0 fulminic acid 

Downstream Products

• 10557-74-1 3-bromo-5-phenylisoxazole 
• 86256-88-4 3-bromo-4,5-dihydro-5-phenyl-isoxazole 
• 128993-06-6 3-Bromo-4-phenyl-4,5-dihydro-isoxazole 
• 124498-15-3 5-Chloromethyl-3-bromoisoxazole 
• 121596-84-7 5-<(benzyloxycarbonylamino)methyl>-3-bromo-2-isoxazoline 
• 110165-06-5 (4S,5S)-3-Bromo-5-methyl-4-phenyl-4,5-dihydro-isoxazole 
• 110164-86-8 (4S,5R)-3-Bromo-4-methyl-5-phenyl-4,5-dihydro-isoxazole 
• 142259-50-5 N-Benzyloxycarbonyl-2-(3-bromisoxazol-5-yl)-3,3,3-trifluoralanin-methylester 
• 126458-77-3 (4S,5S,5'S)-3'-Bromo-4,5,5'-triphenyl-4,5,4',5'-tetrahydro-[3,5']biisoxazolyl 
• 126458-77-3 (4R,5R,5'S)-3'-Bromo-4,5,5'-triphenyl-4,5,4',5'-tetrahydro-[3,5']biisoxazolyl 
• 115328-81-9 (S,R)-3-bromo-5-aminomethyl-4,5-dihydroisoxazole 
• 143005-81-6 (R)-(3-bromo-4,5-dihydroisoxazol-5-yl)methanamine 
• 143005-79-2 (S)-(3-bromo-4,5-dihydroisoxazol-5-yl)methanamine 
• 2763-93-1 5-Aminomethyl-3-bromoisoxazole 

Relevant academic research and scientific papers

Asymmetric Total Syntheses of Kopsia Indole Alkaloids

The asymmetric total syntheses of a group of structurally complex Kopsia alkaloids, (?)-kopsine, (?)-isokopsine, (+)-methyl chanofruticosinate, (?)-fruticosine, and (?)-kopsanone, has been achieved. The key strategies for the construction of the molecular complexity in the targets included an asymmetric Tsuji–Trost rearrangement to set the first quaternary carbon center at C20, an intramolecular cyclopropanation by diazo decomposition to install the second and third quaternary carbon centers at C2 and C7, respectively, and a SmI2-promoted acyloin condensation to assemble the isokopsine core. A radical decarboxylation of an isokopsine-type intermediate results in a thermodynamic partial rearrangement to give N-decarbomethoxyisokopsine and N-decarbomethoxykopsine, two key intermediates for the syntheses of Kopsia alkaloids with different subtype core structures.

Conformationally constrained penta(hetero)cyclic molecular architectures by photoassisted diversity-oriented synthesis

Intramolecular cycloadditions of photogenerated azaxylylenes provide access to unprecedented polyheterocyclic scaffolds, which are suitable for subsequent postphotochemical modifications to further grow molecular complexity. Here, we explore approaches to the rapid "assembly" of new photoprecursors with nitrogen- or oxygen-rich tethers capable of producing potential pharmacophores and also compatible with subsequent 1,3-dipolar cycloadditions to furnish pentacyclic heterocycles with new structural cores, a minimal number of rotatable bonds, and a high content of sp3-hybridized carbon atoms. The modular assembly of the photoprecursors and the potential variety of postphotochemical modifications of the primary photoproducts provide a framework for the combinatorial implementation of this synthetic strategy.

Total Synthesis of Actinophyllic Acid

Herein we report a total synthesis of the indolohydroazocine natural product actinophyllic acid. The target molecule was retrosynthetically deconvoluted to render a greatly simplified and symmetrical [4.4.1] bicyclic trienone, the desymmetrization of which was carefully examined under a variety of conditions, including oxidative, reductive, and transition-metal-catalyzed transformations. Ultimately, the successful synthetic strategy featured chemoselective catalytic dihydroxylation, desymmetrizing nitrile oxide dipolar cycloaddition, and palladium-catalyzed aminoarylation to sequentially modify the three olefins within the trienone, followed by a late-stage reductive cascade indolization and alkylation to complete the target molecule.

Three-dimensional heterocycles: New uracil-based structures obtained by nucleophilic substitution at the sp2 carbon of bromoisoxazoline

The regioisomeric cycloadducts of bromonitrile oxide and N-benzoyl-2,3-oxazanorborn- 5-ene were easily prepared and elaborated into a novel class of uracil-based scaffolds. The key-synthetic step is the nucleophilic substitution at the sp2 carbon atom of the bromoisoxazoline three-dimensional heterocycles. The protocol to perform the nucleophilic substitution of uracil anions was optimized and adapted to the steric requirements of the substrates. A library of pyrimidine derivatives was prepared in very good yields and the products were fully characterized. They are proposed as nucleoside analogues and as synthons for β-turn motifs within PNA structures.

Synthetic method 3 - bromo -5, 5 - dimethyl -4 and 5 -dihydroisoxazole

The invention discloses a synthetic method of 3 - bromo -5, 5 - dimethyl -4 and 5 -dihydroisoxazole, which comprises the continuous synthesis of intermediate dibromoformaldehyde oxime and the synthesis of the product 3 - bromo -5, 5 - dimethyl -4 and 5 -dihydroisoxazole. To the method, the production route is improved firstly through dehydration condensation of glyoxylic acid and hydroxylamine hydrochloride, the obtained intermediate does not need to be discharged, and a bromination reagent is directly added. 1,3 - Dipole ring addition reaction produces the target product, can realize whole production route in-process target product overall yield's improvement, reduces by-product and the generation of three wastes, can also realize the recovery of solvent, and easy and simple to handle, and whole process used raw materials and solvent price are low, are favorable to the control cost, especially be fit for industrial production.

Preparation method of pyroxasulfone intermediate

The invention discloses a preparation method of a pyroxasulfone intermediate, which comprises the following steps: by taking glyoxylic acid as an initial raw material, carrying out condensation reaction on the glyoxylic acid and hydroxylamine to generate 2-(hydroxyimino) acetic acid; then carrying out bromination reaction in the presence of sodium bromate and sodium hydrogen sulfite to generate dibromoformaldoxime; and finally, carrying out cyclization reaction with isobutene to generate the pyroxasulfone intermediate that is 3-bromo-5,5-dimethyl-4,5-dihydroisoxazole. The bromination reaction temperature is 10-60 DEG C, and the molar ratio of glyoxylic acid to sodium bromate to sodium hydrogen sulfite is 1: 2-1: 4. According to the method disclosed by the invention, the bromine is slowly released through the reaction of the sodium bromate and the sodium hydrogen sulfite, the reaction is relatively mild and easy to control, byproducts are not easy to generate, the product generated by introducing isobutene does not need to be rectified to remove impurities, and the yield is relatively high.

Synthesis method and application of pyroxasulfone

The invention relates to the technical field of pesticides, and provides a synthesis method of pyroxasulfone, which comprises the steps of: (1) carrying out a hydroxyalkylation reaction, a fluoromethylation reaction and a chlorination reaction on a reaction body (I) to obtain an intermediate 2; and (2) mixing an intermediate 1 and the intermediate 2, adding water to separate out an organic phase to obtain a transition intermediate, and adding a solvent and an oxidizing agent for reaction to obtain pyroxasulfone. The invention further provides application of pyroxasulfone to pesticides. The pyroxasulfone is prepared by the synthesis method. According to the invention, the overall yield of the target product can be increased, the generation of by-products can be reduced, the generation of three wastes is perfectly reduced, and the recycling of the solvent is realized.

PROCESS FOR PREPARATION OF BROMO FORMIMINE COMPOUNDS

The present invention discloses an improved process for the preparation of bromo-formimine compounds. More particularly, the present invention discloses an improved process for the preparation of bromo-formimine compounds, wherein bromine anion is recycled by using a suitable oxidizing agent.

Synthesis and Synthetic Application of Chloro- And Bromofuroxans

Furoxans are potentially useful heteroaromatic units in pharmaceuticals and agrichemicals. However, the applications for furoxan-based compounds have been hampered due to the underdevelopment of their synthetic methods. Herein, we report a new synthetic approach for the synthesis of chloro- and bromofuroxans. The starting materials were dichloro- and dibromofuroxans, and the substituents were directly introduced to the furoxan ring in a modular fashion. The synthesized monohalofuroxans served as substrates for the installation of a second substituent to prepare further functionalized furoxans.

In vivo evaluation of two tissue transglutaminase PET tracers in an orthotopic tumour xenograft model

Background: The protein cross-linking enzyme tissue transglutaminase (TG2; EC 2.3.2.13) is associated with the pathogenesis of various diseases, including cancer. Recently, the synthesis and initial evaluation of two high-potential radiolabelled irreversible TG2 inhibitors were reported by us. In the present study, these two compounds were evaluated further in a breast cancer (MDA-MB-231) tumour xenograft model for imaging active tissue transglutaminase in vivo. Results: The metabolic stability of [11C]1 and [18F]2 in SCID mice was comparable to the previously reported stability in Wistar rats. Quantitative real-time polymerase chain reaction analysis on MDA-MB-231 cells and isolated tumours showed a high level of TG2 expression with very low expression of other transglutaminases. PET imaging showed low tumour uptake of [11C]1 (approx. 0.5 percentage of the injected dose per gram (%ID/g) at 40–60?min p.i.) and with relatively fast washout. Tumour uptake for [18F]2 was steadily increasing over time (approx. 1.7 %ID/g at 40–60?min p.i.). Pretreatment of the animals with the TG2 inhibitor ERW1041E resulted in lower tumour activity concentrations, and this inhibitory effect was enhanced using unlabelled 2. Conclusions: Whereas the TG2 targeting potential of [11C]1 in this model seems inadequate, targeting of TG2 using [18F]2 was achieved. As such, [18F]2 could be used in future studies to clarify the role of active tissue transglutaminase in disease.