91511-83-0

Basic information

• Product Name: 1,3-Benzodioxole, 6-bromo-4-methoxy-
• Synonyms: 1,3-Benzodioxole, 6-bromo-4-methoxy-;6-Bromo-4-methoxy-1,3-benzodioxole
• CAS NO: 91511-83-0
• Molecular Formula: C₈H₇BrO₃
• Molecular Weight: 231.04
• Mol File: 91511-83-0.mol
• Article Data: 4

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 1,3-Benzodioxole, 6-bromo-4-methoxy-(CAS DataBase Reference)
• NIST Chemistry Reference: 1,3-Benzodioxole, 6-bromo-4-methoxy-(91511-83-0)
• EPA Substance Registry System: 1,3-Benzodioxole, 6-bromo-4-methoxy-(91511-83-0)

Safety Data

• Hazardous Substances Data: 91511-83-0(Hazardous Substances Data)

Usage

Explanation

The molecular formula represents the number of atoms of each element present in a molecule of the compound.

Explanation

It is a modified version of the parent compound benzodioxole, with additional functional groups.

Explanation

The bromine atom is a halogen that is attached to the benzodioxole ring at the 6th carbon atom.

Explanation

The methoxy group is an alkoxy functional group consisting of a methoxy (-OCH3) attached to the benzodioxole ring at the 4th carbon atom.

Explanation

The compound is used in the synthesis of various organic compounds and is also studied for its potential in developing new drugs and biologically active molecules.

Explanation

The compound has a pleasant and sweet aroma, making it a popular ingredient in perfumes and fragrances.

Explanation

Ongoing studies are being conducted to explore the compound's biological activity and its potential use in the development of medicinal products.

Explanation

The compound is still under investigation to better understand its properties, applications, and potential benefits in various fields.

Derivative of benzodioxole

Yes

Bromine atom

Attached at the 6th position

Methoxy group

Attached at the 4th position

Applications

Organic synthesis and pharmaceutical research

Fragrance

Aromatic and sweet

Biological activity

Potential medicinal properties

Ongoing research

Yes

Upstream product

• 75-11-6 diiodomethane 
• 38790-07-7 5-bromo-3-methoxybenzene-1,2-diol 
• 148-53-8 3-methoxy-2-hydroxybenzaldehyde 
• 5034-74-2 5-bromo-3-methoxysalicylaldehyde 
• 74-97-5 chlorobromomethane 
• 74-95-3 1,1-dibromomethane 

Downstream Products

• 791814-46-5 4-methoxy-6-{2-[2-(tetrahydro-pyran-2-yloxy)-ethyl]-phenyl}-benzo[1,3]dioxole-5-carbaldehyde 
• 791814-54-5 3-(4-methoxy-6-{2-[2-(tetrahydro-pyran-2-yloxy)-ethyl]-phenyl}-benzo[1,3]dioxol-5-yl)-N-methyl-acrylamide 
• 1026682-09-6 (3-{6-[2-(2-hydroxy-ethyl)-phenyl]-4-methoxy-benzo[1,3]dioxol-5-yl}-propyl)-methyl-carbamic acid tert-butyl ester 
• 1027510-17-3 [3-(4-methoxy-6-{2-[2-(tetrahydro-pyran-2-yloxy)-ethyl]-phenyl}-benzo[1,3]dioxol-5-yl)-propyl]-methyl-amine 
• 791814-58-9 3-(4-methoxy-6-{2-[2-(tetrahydro-pyran-2-yloxy)-ethyl]-phenyl}-benzo[1,3]dioxol-5-yl)-N-methyl-propionamide 
• 791814-66-9 methanesulfonic acid 2-(2-{6-[3-(tert-butoxycarbonyl-methyl-amino)-propyl]-7-methoxy-benzo[1,3]dioxol-5-yl}-phenyl)-ethyl ester 
• 791814-62-5 [3-(4-methoxy-6-{2-[2-(tetrahydro-pyran-2-yloxy)-ethyl]-phenyl}-benzo[1,3]dioxol-5-yl)-propyl]-methyl-carbamic acid tert-butyl ester 
• 136051-64-4 3'-hydroxy-5-methoxy-3,4-methylenedioxybiphenyl 
• 404953-32-8 (3(3S),4R)-4-(diphenylmethyl)-3-[3-(3,3-(3',4',5'-trimethoxyphenyl)-(3,4-methylenedioxy-5-methoxyphenyl))-propanoyl]-2-oxazolidinone 
• 404953-17-9 (4R)-4-(diphenylmethyl)-3-[3-(3,3-bis-3',4'-methylenedioxy-5'-methoxyphenyl)-propanoyl]-2-oxazolidinone 
• 109856-87-3 2-(3-methoxy-4,5-methylenedioxyphenyl)ethanol 
• 930793-27-4 (7-methoxy-1,3-benzodioxol)-5-yl-diphenylphosphine oxide 
• 484-28-6 cotarnone 

Relevant articles and documents

Chemoenzymatic Formal Total Synthesis of Pancratistatin from Narciclasine-Type Compounds via Myers Transposition: Model Study for a Short Conversion of Narciclasine to Pancratistatin

A formal total synthesis of pancratistatin was accomplished by conversion of advanced intermediates, used in the synthesis of narciclasine, to pancratistatin precursors via Myers' reductive transposition as the key strategic step. The synthesis began with the whole cell fermentation of m -dibromobenzene with JM109(pDTG601a), a recombinant strain that over-expresses toluene dioxygenase, which provided the corresponding cis -dihydrodiol 16 as a single isomer with complete optical purity. The key reductive transposition of the allylic alcohol 8a to olefin 9a allowed for further installation of the C-1/C-2 trans -diol, required for the pancratistatin scaffold, through the introduction of a cyclic sulfate and its subsequent opening. The formal synthesis of pancratistatin was accomplished in 14 steps (12 operations) from commercially available m -dibromobenzene. Experimental and spectral data are provided for all new compounds.

Application of the β-azidonation reaction to the synthesis of the antitumor alkaloid (+)-pancratistatin

o-Vanillin 21 was converted into 24 following literature procedures. Treatment of 24 with n-BuLi/THF followed by addition of 25 gave 26. Dehydration (POCL3/pyridine/DBU), hydrogenation and hydrolysis of 26 gave the ketone 29. Chirality was introduced by deprotonation of 29 with the lithium salt of (+)-bis(αmethylbenzyl)amine, followed by triisopropylsilyl trifluoromethanesulfonate to give 30 (95%). β-Azidonation of 30 with (PhiO)n/TMSN3 rapidly produced 31 (95%) as a mixture of trans- and cis- diastereomers in a 3.5:1 ratio. Reduction with LiAIH4 followed by methyl chloroformate/pyridine gave 32, which on treatment with MCPBA/CH2CL2/imidazole resulted in 33. Hydrolysis of 33 gave 34, which when exposed to KOBu(t)/HMPA at 90 °C resulted in 39. After conversion of 39 into enone 42, epoxidation with NaHCO3/H2O2/MeOH gave 43. Reduction of 43 with L-selectride followed by solvolysis with sodium benzoate in water gave 46, which was immediately acetylated to give 47. Lactam formation (Tf2O/DMAP) converted 47 into 48 and the regioisomer 49 (7:1). The mixture of 48 and 49 demethylated to give 50 and the acetate protecting groups removed to give (+)pancratistatin 1.