2606-51-1

Basic information

• Product Name: 5-Bromomethylbenzo[1,3]dioxole
• Synonyms: 5-Bromomethylbenzo[1,3]dioxole;5-(BroMoMethyl)-1,3-benzodioxole;5-(BROMOMETHYL)-2H-1,3-BENZODIOXOLE
• CAS NO: 2606-51-1
• Molecular Formula: C₈H₇BrO₂
• Molecular Weight: 215.05
• Mol File: 2606-51-1.mol
• Article Data: 57

Chemical Properties

• Melting Point: 45-47 °C
• Boiling Point: 269.9°Cat760mmHg
• Flash Point: 126.2°C
• Appearance: /
• Density: 1.652g/cm³
• Vapor Pressure: 0.0117mmHg at 25°C
• Refractive Index: 1.609
• Storage Temp.: ?20°C
• BRN: 135376
• CAS DataBase Reference: 5-Bromomethylbenzo[1,3]dioxole(CAS DataBase Reference)
• NIST Chemistry Reference: 5-Bromomethylbenzo[1,3]dioxole(2606-51-1)
• EPA Substance Registry System: 5-Bromomethylbenzo[1,3]dioxole(2606-51-1)

Safety Data

• Hazard Codes: C
• Statements: 34-43-52
• Safety Statements: 26-36/37/39-45
• RIDADR: UN 3261 8 / PGII
• WGK Germany: 3
• Hazardous Substances Data: 2606-51-1(Hazardous Substances Data)

Usage

General Description

5-Bromomethylbenzo[1,3]dioxole is a chemical compound that belongs to the group of organic substances called aromatic carbocycles. This chemical stands distinct because of its significant role in numerous chemical reactions as a reagent. 5-Bromomethylbenzo[1,3]dioxole specifically has a molecular formula of C8H7BrO2, indicating the presence of eight carbon atoms, seven hydrogen atoms, one bromine atom, and two oxygen atoms in each molecule of this compound. While it is regularly leveraged in creating various synthesized compounds, adequate safety precautions must be observed while handling it due to its potential reactivity.

InChI:InChI=1/C8H7BrO2/c9-4-6-1-2-7-8(3-6)11-5-10-7/h1-3H,4-5H2

Upstream product

• 452-86-8 4-methyl-1,2-dihydroxybenzene 
• 120-57-0 piperonal 
• 7145-99-5 5-methyl-1,3-benzodioxole 
• 38227-87-1 2,2,6,6-tetramethylpiperidinyl-lithium 
• 495-76-1 piperonol 
• 10035-10-6 hydrogen bromide 
• 326-61-4 piperonyl acetate 

Downstream Products

• 22180-30-9 Diethyl α-piperonylmalonate 
• 393165-27-0 (1R,2R,3S,4S,5S,6R)-4,5-(isopropylidenedioxy)-3-[(tert-butyldimethylsilyl)oxy]-6-N-(3',4'-methylenedioxybenzyl)-N-(4'-methylphenylsulfonyl)-7-oxabicyclo[4.1.0]heptane 
• 215384-55-7 3,4-dimethoxybenzyl 3,4-(methylenedioxy)benzyl sulfoxide 
• 1394233-02-3 3-(2-methoxyphenyl)propynoic acid benzo[1,3]dioxol-5-ylmethylnaphthalen-1-ylamide 
• 933987-22-5 methyl 3-(2-piperonylphenyl)-2-diazo-3-oxopropanoate 
• 942506-54-9 methyl 3-(2-piperonylphenyl)-3-oxopropanoate 
• 580-73-4 (+/-)-hinokinin 
• 214783-17-2 5-(azidomethyl)benzo[d][1,3]dioxole 
• 137809-97-3 2,3-di(3',4'-(methylenedioxy)benzyl)-2-buten-4-olide 
• 942506-11-8 methyl 2-(benzo[d][1,3]dioxol-5-ylmethyl)benzoate 
• 732298-24-7 3-benzo[1,3]dioxol-5-ylmethyl-1-(2-tert-butyl-phenyl)-pyrrolidine-2,5-dione 
• 103844-15-1 (3,4-dioxymethylenephenyl)methyl phenyl sulfide 
• 725724-49-2 (R)-2-Benzo[1,3]dioxol-5-ylmethyl-1,4-bis-((4S,5R)-3,4-dimethyl-2-oxo-5-phenyl-imidazolidin-1-yl)-butane-1,4-dione 

Relevant articles and documents

Total synthesis of kingianinsA, D, and F

A synthesis fit for a king: The total synthesis of (±)-kingianinsA, D, and F has been achieved in ten steps. Key features include the gram-scale synthesis and partial reduction of a conjugated tetrayne to a (Z,Z,Z,Z)-tetraene, the domino 8π-6π electrocyclic ring closure of a (Z,Z,Z,Z)-tetraene, and the radical-cation-catalyzed formal Diels-Alder dimerization of functionalized bicyclo[4.2.0]octadiene precursors. Copyright

Synthesis and characterization of novel 1,3-benzodioxole tagged noscapine based ionic liquids with in silico and in vitro cytotoxicity analysis on HeLa cells

Ionic liquids (ILs) have proven themselves as a new class of anticancer compounds among the scientific community in the 21st century. With proven efficiency of ionic liquids here an attempt has been made on a legacy anticancer compound noscapine. In this study, a library of novel noscapine (Nos) based ionic liquids were synthesized and characterized using various techniques such as 1H, 13C NMR spectroscopy and Mass spectrometry. These novel Nos-based ionic liquids were studied by in silico assays including molecular docking analysis, which showed the [Pip-Nos]OAc and [Pip-Nos]OTf derivatives of Nos-based ionic liquids have high molecular binding with docking score ?336.19 kJ/mol and ?326.71 kJ/mol, respectively, much higher than the parent compound noscapine (?267.06 kJ/mol). Also, pharmacokinetics and pharmacodynamics properties analyses showed the favorable results with high drug likeliness. The lead compounds were further well validated with in vitro anticancer cytotoxicity assay on HeLa cancer cell line. The in vitro cytotoxicity analysis depicted the high anticancer potency of lead compounds with lower IC50 of acetate and triflate IL derivatives than the parent compound noscapine. In conclusion, the present study paves the way to elucidate the potential anticancer ionic liquids.

Homologation of Electron-Rich Benzyl Bromide Derivatives via Diazo C-C Bond Insertion

The ability to manipulate C-C bonds for selective chemical transformations is challenging and represents a growing area of research. Here, we report a formal insertion of diazo compounds into the "unactivated"C-C bond of benzyl bromide derivatives catalyzed by a simple Lewis acid. The homologation reaction proceeds via the intermediacy of a phenonium ion, and the products contain benzylic quaternary centers and an alkyl bromide amenable to further derivatization. Computational analysis provides critical insight into the reaction mechanism, in particular the key selectivity-determining step.