BROMONITROMETHANE

Base Information

• Chemical Name: BROMONITROMETHANE
• CAS No.: 563-70-2
• Molecular Formula: CH2BrNO2
• Molecular Weight: 139.936
• Hs Code.: 29049095
• European Community (EC) Number: 209-258-0
• UNII: EG63P9EUR0
• DSSTox Substance ID: DTXSID7060338
• Nikkaji Number: J435I
• Wikidata: Q27277165
• ChEMBL ID: CHEMBL2335229
• Mol file: 563-70-2.mol

Synonyms:Bromonitromethane;Nitrobromomethane;a-Bromonitromethane;

Chemical Property of BROMONITROMETHANE

Chemical Property:

• Appearance/Colour: clear yellow liquid
• Vapor Pressure: 4.42mmHg at 25°C
• Melting Point: -28 °C
• Refractive Index: 1.485-1.495
• Boiling Point: 146-148 °C (750 mmHg)
• PKA: 7.22±0.29(Predicted)
• Flash Point: 35.4 °C
• PSA: 45.82000
• Density: 1.97 g/cm³
• LogP: 1.13870
• XLogP3: 0.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 138.92689
• Heavy Atom Count: 5
• Complexity: 39.4

Purity/Quality:

98%,99%, ^*data from raw suppliers

Bromonitromethane ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn,Xi,O
• Hazard Codes: Xn-O,Xi,O
• Statements: 8-36/37/38-20/21/22
• Safety Statements: 36/37/39-26-17-36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C([N+](=O)[O-])Br
• Uses: Bromonitromethane has received considerable attention as a one-carbon synthon for the synthesis of a variety of important organic intermediates. Bromonitromethane is a key starting material for the preparation of the broad-spectrum antibiotic trovafloxacin, which contains the interesting 3-azabicyclo[ 3.1.0]hexane ring system. it was used in the synthesis of 2-nitrobenzofuran and 2-nitro-2,3-dihydrobenzofuran-3-ols, nitrobenzo-thio-phenes, and nitrothiazoles, polyfunctionalized nitrocyclopropanes. It has also been utilized in the synthesis of 1-bromo-1-nitroalkan-2-ols and aryl nitromethanes. In addition, it could be used as a bromine donor. Bromonitromethane has been used:in production of various protected α-bromo nitroalkane donors (including Fmoc) for use in Umpolung amide synthesisin preparation of (Z)-1-bromo-1-nitroalkenes via sodium iodide-catalyzed Henry reactionin diastereo- and enantioselective cyclopropanation of β,γ-unsaturated a-ketoesters via domino Michael-addition/intramolecular-alkylation strategy

Technology Process of BROMONITROMETHANE

There total 31 articles about BROMONITROMETHANE which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 78.0%

nitromethane (75-52-5) → bromonitromethane (563-70-2)

Guidance literature:

With bromine; sodium bromide; sodium hydroxide; In water; at -10 ℃; for 0.5h; Inert atmosphere;

DOI:10.1055/s-0036-1591540

Reference yield:

water (7732-18-5) + 1-(2-bromo-2-nitrovinyl)-4-nitrobenzene (7559-38-8) → bromonitromethane (563-70-2) + hydrogen bromide (10035-10-6,12258-64-9) + nitric acid (7697-37-2,78989-43-2) + cis-nitrous acid (7782-77-6)

Guidance literature:

Reference yield:

β-bromo-2,β-dinitro-styrene + water (7732-18-5) → bromonitromethane (563-70-2) + hydrogen bromide (10035-10-6,12258-64-9) + nitric acid (7697-37-2,78989-43-2) + cis-nitrous acid (7782-77-6)

Guidance literature:

upstream raw materials:

diethyl ether

bromocyane

nitromethane

N-(2-bromo-2-nitro-1-phenyl-ethyl)-p-toluidine

Downstream raw materials:

(2-bromo-2-nitroethenyl)benzene

triethyl phosphate

benzyl-(5-nitro-4-phenyl-thiazol-2-yl)-amine

(Z)-2-bromo-2-nitro-1-phenylethene

Refernces

SYNTHESE DES NITRO-2 NAPHTO<1,2-b>FURANNES MONO-METHOXYLES SUR L'HOMOCYCLE EXTERIEUR

10.1016/0223-5234(87)90275-3

The research focuses on the synthesis of a series of nitro-naphtho[1,2-b]furans with methoxy groups on the external homocycle. The purpose of this study is to synthesize and characterize these compounds, which are of interest due to their potential mutagenic and carcinogenic properties, similar to the previously studied methoxy-7 nitro-2 naphtho[2,1-b]furane (R 7000). The researchers used methoxy-tetralones as starting materials, converting them into ortho-hydroxylated naphthaldehydes via a series of chemical reactions involving ethyl formate, sodium methoxide, and dichlorodicyanobenzoquinone. These intermediates were then treated with bromonitromethane and potassium carbonate, followed by dehydration in acetic anhydride to yield the desired nitro-naphtho[1,2-b]furans. The study concludes that this synthetic method is efficient, with overall yields ranging from 40% to 70% for the different compounds. The synthesized compounds are obtained in sufficient quantities for further biological testing, which will be detailed in subsequent studies.