563-70-2 Usage
Description
Bromonitromethane, also known as nitro-bromo-methane, is a versatile organic compound with the chemical formula CH2BrNO2. It is a clear yellow liquid and serves as a significant one-carbon synthon for the synthesis of various important organic intermediates. As a strong oxidizing agent, it exhibits properties similar to nitromethane.
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.
Check Digit Verification of cas no
The CAS Registry Mumber 563-70-2 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 5,6 and 3 respectively; the second part has 2 digits, 7 and 0 respectively.
Calculate Digit Verification of CAS Registry Number 563-70:
(5*5)+(4*6)+(3*3)+(2*7)+(1*0)=72
72 % 10 = 2
So 563-70-2 is a valid CAS Registry Number.
InChI:InChI=1/CH2BrNO2/c2-1-3(4)5/h1H2
563-70-2Relevant articles and documents
Palladium(0)-Catalyzed Dearomatization of 2-Nitrobenzofurans through Formal (3+2) Cycloadditions with Vinylcyclopropanes: A Straightforward Access to Cyclopenta[ b ]benzofurans
Ling, Johanne,Laugeois, Maxime,Michelet, Véronique,Ratovelomanana-Vidal, Virginie,Vitale, Maxime R.
supporting information, p. 928 - 932 (2018/02/14)
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.
HYDRAZINE COMPOUND AS BLOOD COAGULATION FACTOR Xa INHIBITOR
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Paragraph 0097, (2017/04/11)
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.
Synthesis of an amino moiety in trovafloxacin by using an in-expensive amidine base, N, N-diethylacetamidine
Madhusudhan,Balraju,Rajesh,Narayana, B. Venkata,Reddy
experimental part, p. 569 - 573 (2009/12/06)
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.
