563-70-2

Usage

Uses

Used in Pharmaceutical Industry:
Bromonitromethane is used as a key starting material for the preparation of the broad-spectrum antibiotic trovafloxacin, which contains the unique 3-azabicyclo[3.1.0]hexane ring system. This application highlights its importance in the development of life-saving medications.
Used in Chemical Synthesis:
Bromonitromethane is utilized in the synthesis of various organic compounds, such as 2-nitrobenzofuran, 2-nitro-2,3-dihydrobenzofuran-3-ols, nitrobenzothiophenes, nitrothiazoles, and polyfunctionalized nitrocyclopropanes. It also plays a role in the synthesis of 1-bromo-1-nitroalkan-2-ols and aryl nitromethanes, showcasing its versatility in creating a wide range of chemical products.
Used in Organic Chemistry Research:
Bromonitromethane serves as a bromine donor in various chemical reactions, making it a valuable tool for researchers in the field of organic chemistry.
Used in Umpolung Amide Synthesis:
In the field of organic chemistry, bromonitromethane is used in the production of various protected α-bromo nitroalkane donors, including Fmoc, which are essential for Umpolung amide synthesis. This application demonstrates its importance in peptide synthesis and the development of new pharmaceuticals.
Used in Synthesis of (Z)-1-Bromo-1-Nitroalkenes:
Bromonitromethane is employed in the preparation of (Z)-1-bromo-1-nitroalkenes through a sodium iodide-catalyzed Henry reaction. This process contributes to the synthesis of various organic compounds with potential applications in different industries.
Used in Cyclopropanation Reactions:
Bromonitromethane is utilized in diastereoand enantioselective cyclopropanation of β,γ-unsaturated α-ketoesters via a domino Michael-addition/intramolecular-alkylation strategy. This application highlights its role in the synthesis of complex organic molecules with potential applications in various fields, including pharmaceuticals and materials science.

Preparation

Bromonitromethane is commercially available and can also be easily prepared according to the procedures reported by Fishwick et al. A typical procedure is as following: freshly distilled nitromethane was stirred at 0℃ and bromine was dropped in 5 seconds. The resulted bromonitromethane could be used without further purification.

InChI:InChI=1/CH2BrNO2/c2-1-3(4)5/h1H2

Upstream product

• 60-29-7 diethyl ether 
• 506-68-3 bromocyane 
• 75-52-5 nitromethane 
• 64-17-5 ethanol 
• 100-63-0 phenylhydrazine 
• 22013-86-1 1-(2-bromo-2-nitrovinyl)-4-methoxybenzene 
• 85-44-9 phthalic anhydride 
• 7726-95-6 bromine 
• 7697-37-2 nitric acid 
• 100-97-0 hexamethylenetetramine 
• 7732-18-5 water 
• 107-18-6 allyl alcohol 
• 108-67-8 1,3,5-trimethyl-benzene 
• 123-31-9 hydroquinone 

Downstream Products

• 52-51-7 2-bromo-2-nitro-1,3-propanediol 
• 5437-60-5 2-bromo-2-nitro-1-ethanol 
• 106-37-6 1.4-dibromobenzene 
• 118871-57-1 (bromo-nitro-methylene)-(4-methyl-2-nitro-phenyl)-hydrazine 
• 7166-19-0 (2-bromo-2-nitroethenyl)benzene 
• 882-33-7 diphenyldisulfane 
• 104-92-7 1-bromo-4-methoxy-benzene 
• 29559-26-0 (p-methoxyphenyl)nitromethane 
• 106-39-8 bromochlorobenzene 
• 74-11-3 para-chlorobenzoic acid 
• 111441-96-4 nitromethyl-triphenyl-phosphonium; bromide 
• 791-28-6 Triphenylphosphine oxide 
• 78-40-0 triethyl phosphate 
• 622-42-4 1-nitro-1-phenylmethane 

Relevant academic research and scientific papers

Palladium(0)-Catalyzed Dearomatization of 2-Nitrobenzofurans through Formal (3+2) Cycloadditions with Vinylcyclopropanes: A Straightforward Access to Cyclopenta[ b ]benzofurans

In the context of the palladium-catalyzed dearomatization of electron-poor arenes, we report herein that various 2-nitrobenzofurans efficiently undergo a dearomative (3+2) cycloaddition with vinylcyclopropanes. This new method gives access to a wide variety of cyclo-penta[ b ]benzofuran derivatives in a straightforward manner.

Preparation method of mandelamine compound

The invention discloses a preparation method of a mandelamine compound. The preparation method is a complete synthesis method for finally synthesizing a compound with a mandelamine parent by using a benzaldehyde compound as an initiator. An amido bond synthesis part adopts a polarity reversal reaction mechanism of using an amino segment to perform electrophilic attack on an acyl segment. The preparation method can be used for synthesizing multiple compounds which cannot be synthesized by the traditional method.

HYDRAZINE COMPOUND AS BLOOD COAGULATION FACTOR Xa INHIBITOR

Provided is a compound of formula (I) or a pharmaceutically acceptable salt thereof, wherein X is selected from a 3-9 membered carbon ring or its phenyl ring, and a 4-10 membered heterocyclic ring or its benzo ring; Y and Z are independently selected from 4-9 membered saturated heterocyclic rings respectively; RI-3 are independently selected from H, F, Cl, Br, I, CN, OH, SH,NH2, CHO, COOH respectively, or selected from C1-10 alkyls or heteroalkyls optionally substituted by R01, C3-10 alkyls ring hydrocarbon groups or heterocyclic hydrocarbon groups, C1-10 alkyls or heteroalkyls substituted by C3-10 ring hydrocarbon groups or heterocyclic hydrocarbon group. The compound can be used as an anticoagulant for treating and preventing thrombotic disorders, and can meet the real needs of selectivity and a potent inhibitor for coagulation Xa.

Chemical, biochemical and microbiological properties of a brominated nitrovinylfuran with broad-spectrum antibacterial activity

A di-bromo substituted nitrovinylfuran with reported broad-spectrum antibacterial activity was found to be a potent inhibitor of MurA, a key enzyme in peptidoglycan biosynthesis. Further characterization of the compound was carried out to assess its reactivity towards thiol nucleophiles, its stability and degradation under aqueous conditions, inhibitory potential at other enzymes, and antibacterial and cytotoxic activity. Our results indicate that the nitrovinylfuran derivative is reactive towards cysteine residues in proteins, as demonstrated by the irreversible inhibition of MurA and bacterial methionine aminopeptidase. Experiments with proteins and model thiols indicate that the compound forms covalent adducts with SH groups and induces intermolecular disulfide bonds, with the intermediate formation of a monobromide derivative. The parent molecule as well as most of its breakdown products are potent antibiotics with MIC values below 4 μg/mL and are active against multiresistant strains such as methicillin-resistant Staphylococcus aureus (MRSA). Further development of the bromonitrovinyl scaffold towards antibiotics with clinical relevance, however, requires optimization of the antibiotic-cytotoxic selectivity profile.

Synthesis of an amino moiety in trovafloxacin by using an in-expensive amidine base, N, N-diethylacetamidine

The simple and in-expensive amidine base, N.N-diethylacetamidine, has been prepared and utilized in the construction of bicyclic hetero compound, 4 and employed for further reduction of amidic carbonyl groups of 4 by using NaBH 4I2-THF condition which is an efficient and commercially viable method to prepare 5 towards the synthesis of amino moiety I, in Trovafloxacin 2 an antibacterial agent.

One-pot synthesis of substituted 3-amino-2-nitrothiophenes and selenophenes

In this work, we described an easy preparation of substituted 3-amino-2-nitrothiophenes and selenophenes. Substituted β-chloroacrylonitriles were reacted with sodium sulfide or sodium selenide and bromonitromethane to yield the expected compounds in a one-pot three-step procedure in good yields.

Synthesis of some 2-aminonitroethanes via tin(II)chloride mediated addition reaction of bromonitromethane to imines

In the presence of tin(II)chloride, bromonitromethane reacts with imines derived from aromatic aldehydes and ammonia to yield 2-amino-2-aromatic substituted nitroethane derivatives via an addition reaction in good yields.

Tin(II)chloride mediated addition reaction of bromonitromethane to aldehydes

Bromonitromethane adds to aliphatic aldehydes in the presence of tin(II) chloride to yield β-nitro alcohols via a Reformatsky-type reaction in high yields, while aromatic aldehydes give low yields. The products were characterized by IR, NMR, and mass spectroscopy and by elemental analysis.

Bromonitromethane. A Versatile Electrophile

Pathways in reactions of bromonitromethane with a variety of nucleophiles have been investigated.With thiolates, the electrophilic centre is bromine and the initial products are disulphides.When the thiolate ion itself carries an electrophilic centre such as carbonyl or cyano β-to sulphur, the product is a nitrothiophene derived from subsequent reaction of the first-formed disulphide with nitronate ion displaced in the initial process.This provides a generalisation of earlier nitrothiophene synthesis by this route.In reactions with arenesulphinate ion, the electrophilic centre is also bromine and equilibration between the initial reactants and the initial products, sulphonyl bromide and nitronate ion, is established.The components of the equilibrium subsequently react either with each other or with the solvent.Reactions with sulphides are slow and distal substituents such as hydroxy- or cyano- so much reduce reactivity that no reaction is observed.Dimethyl sulfide attacks bromonitromethane at the carbon atom,and subsequent attack on the nitromethyl sulphonium salt initially formed gives methylthionitromethane and trimethylsulphonium bromide.Iodide ion attacks at bromine to give iodine, presumably via iodine bromide, but with tervalent phosphorus nucleophiles, attack is at oxygen giving the corresponding oxides and HCN in a double deoxygenation sequence.For hydroxide, methoxide and hydride ions (from sodium borohydride), nucleophilic attack is at hydrogen and the nitronate ion produced is inert to further attack.There is no evidence of carbene formation by α-elimination.When the anion of bromonitromethane is allowed to react with tributylboron, the anionic migration-displacement which follows boron-carbon bond formation, yields 1-nitropentane.The anion of bromonitromethane is unreactive towards aldehydes and electrophilic alkenes.

Reactions of Salicylaldehydes with Bromonitromethane

Various salicylaldehydes were treated with bromonitromethane in the presence of an inorganic base to give 2-nitrobenzofuran derivatives, and the reaction mechanisms were investigated.The most remarkable feature of the reactions is that 3-hydroxysalicylaldehyde (1k) alone among various hydroxysalicylaldehydes (1b, k, n, r) gave 2-nitro-7-hydroxybenzofuran in good yield.Bromonitromethane reacted with salicylaldehydes at the aldehyde group exclusively to give 1-(2-hydroxyphenyl)-2-bromo-2-nitroethanols (14), followed by cyclization to produce mixtures consisting of cis- and trans-2-nitro-3-hydroxy-2,3-dihydrobenzofurans (8a, b; 9a, b; 10a, b).The stereochemistry of these products is discussed on the basis of the spectral data and chemical reactivities.The intermediates, 2,3-dihydrobenzofurans, underwent dehydration smoothly to give 2-nitrobenzofurans.Keywords - bromonitromethane; salicylaldehyde derivative; ring closure; 2-nitrobenzofuran derivative; cis-2-nitro-3-hydroxy-2,3-dihydrobenzofuran derivative; trans-2-nitro-3-hydroxy-2,3-dihydrobenzofuran derivative; 13C-NMR; stereochemistry; reaction mechanism