71095-27-7

Usage

Uses

Used in Pharmaceutical Synthesis:
1-(6-bromo-1,3-benzodioxol-5-yl)ethanol is used as a key intermediate in the synthesis of pharmaceuticals for its versatile reactivity and functional groups that can be modified to create various medicinal compounds.
Used in Organic Chemistry Research and Development:
1-(6-bromo-1,3-benzodioxol-5-yl)ethanol serves as a valuable precursor in the production of other chemical compounds, contributing to the advancement of organic chemistry through research and development.
Used in the Synthesis of Other Organic Compounds:
1-(6-bromo-1,3-benzodioxol-5-yl)ethanol is utilized as a building block in the synthesis of a range of organic compounds, taking advantage of its unique structure and reactivity.

Upstream product

• 75-16-1 methylmagnesium bromide 
• 15930-53-7 6-bromo-3,4-methylenedioxybenzaldehyde 
• 6642-34-8 6-bromopiperonyl alcohol 
• 74-83-9 methyl bromide 
• 676-58-4 methylmagnesium chloride 
• 917-64-6 methyl magnesium iodide 
• 74-88-4 methyl iodide 
• 6329-73-3 1-benzo[1,3]dioxol-5-yl-ethanol 

Downstream Products

• 71095-26-6 1-(2′-bromo-4′,5′-methylenedioxyphenyl)ethan-1-one 
• 1233979-81-1 3-methyl-1-(p-tolylsulfonyl)-[1,3]dioxolo[4,5-f]indazole 
• 1233979-75-3 (Z)-N'-[1-(6-bromobenzo[d][1,3]dioxol-5-yl)ethylidene]-4-methylbenzenesulfonohydrazide 
• 41451-71-2 (+/-)-steganol 
• 41451-71-2 (+/-)-episteganol 
• 69174-44-3 Cyclohexyl-[1-{3,4,5-trimethoxy-2-[6-(2-methyl-[1,3]oxathiolan-2-yl)-benzo[1,3]dioxol-5-yl]-phenyl}-meth-(Z)-ylidene]-amine 
• 73252-70-7 dimethyl 2-<1'-(2'-bromoacetyl-4',5'-methylenedioxyphenyl)>-3,4,5-trimethoxybenzylmalonate 
• 73252-69-4 dimethyl 2-<1'-(2'-acetyl-4',5'-methylenedioxyphenyl)>-3,4,5-trimethoxybenzylmalonate 
• 69139-00-0 dimethyl 2-acetyl-4,5-methylenedioxy-4',5',6'-trimethoxy-1,1'-biphenyl-2'-β-methylenemalonate 
• 73252-63-8 2-<2''-(2''-methyl-1'',3''-dithianyl)>-4,5-methylenedioxy-4',5',6'-trimethoxy-1,1'-biphenyl-2'-carboxaldehyde 
• 41451-68-7 (+/-)-steganacin 
• 69138-99-4 dimethyl 2-<2''-(2''-methyl-1'',3''-oxathiolane)>-4,5-methylenedioxy-4',5',6'-trimethoxy-1,1'-biphenyl-2'-β-methylenemalonate 
• 69138-98-3 2-<2''-(2''-methyl-1'',3''-oxathiolane)>-4,5-methylenedioxy-4',5',6'-trimethoxy-1,1'-biphenyl-2'-carboxaldehyde 

Relevant academic research and scientific papers

α-Oxocarboxylic Acids as Three-Carbon Insertion Units for Palladium-Catalyzed Decarboxylative Cascade Synthesis of Diverse Fused Heteropolycycles

A novel palladium-catalyzed decarboxylative cascade cyclization for the assembly of diverse fused heteropolycycles by employing α-oxocarboxylic acids as three-carbon insertion units is reported. This protocol enables the synthesis of isoquinolinedione- and indolo[2,1-a]isoquinolinone-fused benzocycloheptanones in moderate to good yields by the use of different aryl iodides, including alkene-tethered 2-iodobenzamides and 2-(2-iodophenyl)-1H-indoles. Notably, the approach achieves simultaneous construction of both six- and seven-membered rings via sequential intramolecular carbopalladation, C-H activation, and decarboxylation.

Atmosphere-Controlled Palladium-Catalyzed Divergent Decarboxylative Cyclization of 2-Iodobiphenyls and α-Oxocarboxylic Acids

A novel palladium-catalyzed divergent decarboxylative cyclization of 2-iodobiphenyls and α-oxocarboxylic acids utilizing the atmosphere as a controlled switch is reported. Under the protection of a nitrogen atmosphere, tribenzotropones are synthesized by a [4 + 3] decarboxylative cyclization. Employing a palladium/O2 system enables a [4 + 2] decarboxylative cyclization to assemble triphenylenes. Notably, preliminary mechanistic studies indicate that the formation of triphenylenes involves a double decarboxylation.

Asymmetric Synthesis and Application of Chiral Spirosilabiindanes

Reported here is the development of a class of chiral spirosilabiindane scaffolds by Rh-catalyzed asymmetric double hydrosilation, for the first time. Enantiopure SPSiOL (spirosilabiindane diol), a new type of chiral building block for the preparation of various chiral ligands and catalysts, was readily prepared on greater than 10 gram scale using this protocol. The potential of this new spirosilabiindane scaffold in asymmetric catalysis was preliminarily demonstrated by development of the corresponding monodentate phosphoramidite ligands (SPSiPhos), which were used in both a Rh-catalyzed hydrogenation and a Pd-catalyzed intramolecular carboamination.

1-HYDROXY-1,3-DIHYDROBENZO[c][1,2]OXABOROLES AND THEIR USE AS HERBICIDES

Provided herein are 1-hydroxy-1,3-dihydrobenzo[c][1,2]oxaboroles and their derivatives, and compositions and methods of use thereof as herbicides.

PdII-Catalyzed Oxidative Tandem aza-Wacker/Heck Cyclization for the Construction of Fused 5,6-Bicyclic N,O-Heterocycles

A PdII-catalyzed oxidative tandem cyclization was developed for the construction of fused 5,6-bicyclic N, O-heterocycles. This reaction was enabled by the combined use of a 3-methylpyridine ligand and pentafluorobenzoic acid additive. A range of heterocyclic products with different substituents could be prepared in moderate to good yields via this methodology. Several transformations, including a scaled-up preparation of product 2 a, were also carried out showing the good applicability of our methodology.

One-Pot Asymmetric Synthesis of Alkylidene 1-Alkylindan-1-ols Using Br?nsted Acid and Palladium Catalysis

A one-pot catalytic enantioselective allylboration/Mizoroki-Heck reaction of 2-bromoaryl ketones has been developed for the asymmetric synthesis of 3-methyleneindanes bearing a tertiary alcohol center. Br?nsted acid-catalyzed allylboration with a chiral BINOL derivative was followed by a palladium-catalyzed Mizoroki-Heck cyclization, resulting in selective formation of the exo-alkene. This novel protocol provides a concise and scalable approach to 1-alkyl-3-methyleneindan-1-ols in high enantiomeric ratios (up to 96:4 er). The potential of these compounds as chiral building blocks was demonstrated with efficient transformation to optically active diol and amino alcohol scaffolds.

Preparation of isoindolinones via a palladium-catalyzed diamination

A Pd(II)-catalyzed cyclization using oxidative olefin diamination was developed for the preparation of isoindolinones from ortho-olefinic N-methoxybenzamides. Using the optimized reaction conditions, the desired products were obtained in up to 90% yield using NFSI as the oxidant. This reaction provides an efficient and direct access to isoindolinones with amine functionality, an important drug skeleton.

Facile synthesis of 1-naphthols through a copper-catalyzed arylation of methyl ketones with o-bromoacetophenones

The coupling reactions of simple methyl ketones with o-bromoacetophenones and subsquential cyclization reactions were realized to produce a range of 1-naphthols. These cascade reactions were initiated by a rare Cu-catalyzed arylation reaction of methyl ketones with aromatic bromides.

Palladium-Catalyzed Aerobic Aminooxygenation of Alkenes for Preparation of Isoindolinones

A palladium-catalyzed intramolecular isoindolinone-forming aminooxygenation of alkenes with 1 atm of oxygen as oxidant is reported. A variety of functionalized alkenes and carboxylic acids can be used, and high yields were observed. Preliminary mechanistic studies revealed that the aminooxygenation products were formed through the oxidation of a C-PdII species using a strong oxidant, peroxide, which is generated in situ from a Pd(OAc)2/bpy/O2/HOAc catalytic system.

Substitution controlled functionalization of ortho -bromobenzylic alcohols via palladium catalysis: Synthesis of chromenes and indenols

An efficient domino Pd-catalyzed transformation of simple ortho-bromobenzyl tertiary alcohols to chromenes is presented. Their formation is believed to proceed via the formation of a five-membered palladacycle, which, in turn, involves in an intermolecular homocoupling with the second ortho- bromobenzyltertiary alcohol to yield the homo-biaryl bond followed by intramolecular C-O bond formation. Interestingly, when there is an allylic substituent on the benzylic carbon atom, a chemoselective switch was observed, which preferred intramolecular Heck coupling and gave indenols. Further, it has been confirmed that the tertiary alcohol functionality is indispensible to give the coupled products, whereas the use of primary/secondary benzylic alcohols furnished the simple carbonyl products via a possible reductive debromination followed by oxidation due to the availability of β-hydrogen(s).