72744-54-8

Usage

Uses

Used in Pharmaceutical Industry:
5-Bromo-1,3-benzodioxole-4-carboxaldehyde is used as an intermediate in the synthesis of various pharmaceutical compounds. Its unique chemical structure allows it to be a key component in the development of new drugs and medications.
Used in Fragrance and Flavor Industry:
5-BROMO-1 3-BENZODIOXOLE-4-CARBOXALDEHY& is used as a building block in the production of fragrances and flavors. Its sweet, floral odor makes it a valuable ingredient in creating a wide range of scents and tastes for various consumer products.
Used in Organic Chemistry Research:
5-Bromo-1,3-benzodioxole-4-carboxaldehyde is utilized in the synthesis of organic compounds and has potential applications in the field of organic chemistry. Its unique properties make it a valuable tool for researchers and scientists working on the development of new organic compounds and materials.
Used in Chemical Intermediates:
As a chemical intermediate, 5-Bromo-1,3-benzodioxole-4-carboxaldehyde plays a crucial role in the production of various chemical compounds. Its versatility in chemical reactions makes it an essential component in the synthesis of a wide range of products.

InChI:InChI=1/C8H5BrO3/c9-6-1-2-7-8(5(6)3-10)12-4-11-7/h1-3H,4H2

Upstream product

• 83983-71-5 6-bromo-2,3-dihydroxybenzaldehyde 
• 74-95-3 1,1-dibromomethane 
• 2635-13-4 1,2-(methylenedioxy)-4-bromobenzene 
• 68-12-2 N,N-dimethyl-formamide 
• 20035-41-0 6-bromo-2-hydroxy-3-methoxybenzaldehyde 
• 92252-86-3 1,1-diacetoxy-1-(2-acetoxy-3-methoxyphenyl)methane 
• 109548-06-3 6-Brom-2-acetoxy-3-methoxy-benzaldehyddiacetat 
• 492-88-6 3-ethoxysalicylaldehyde 
• 20035-45-4 6-bromo-3-ethoxy-2-hydroxybenzaldehyde 

Downstream Products

• 72744-56-0 5-bromobenzo[d][1,3]dioxole-4-carboxylic acid 
• 1099616-40-6 6,7-dipropyl-N-p-tolyl-8H-indeno[5,4-d][1,3]dioxol-8-amine 
• 1217171-65-7 5-(2-formylphenyl)-1,3-benzodioxole-4-carbaldehyde 
• 1268368-30-4 C₁₉H₁₄O₆ 
• 33458-77-4 7,14-dihydro-12bH-[1,3]dioxolo[4,5-i][1,3]dioxolo[4',5':4,5]benzo[1,2-c]phenanthridine-13-carboxylic acid benzyl ester 
• 1375467-89-2 C₂₇H₁₉NO₆ 
• 1375467-90-5 C₂₇H₂₁NO₆ 
• 1375467-84-7 C₂₇H₃₅NO₄Si 
• 1375467-85-8 C₂₉H₃₇NO₄Si 
• 1375467-86-9 C₂₀H₁₇NO₄ 
• 1375467-87-0 C₃₆H₄₁NO₆Si 
• 33458-78-5 (4bR^*,10bS^*)-5-benzyloxycarbonyl-2,3,7,8-bis(methylenedioxy)-4b,5,6,10b,11,12-hexahydrobenzophenanthridin-11-one 

Relevant academic research and scientific papers

Enantioselective Divergent Syntheses of (+)-Bulleyanaline and Related Isoquinoline Alkaloids from the Genus Corydalis

The isoquinoline alkaloids isolated from the genus Corydalis possess potent and diverse biological activities. Herein, a concise, divergent, and enantioselective route to access these natural products is disclosed. Key transformations of our approach incl

Re-engineering and synthesis of cytotoxic 2,3:7,8-di(alkylenedioxy)-extended analogs of quaternary sanguinarine chloride

A method was developed to synthesize 2,3:7,8-di(alkylenedioxy)-extended analogs of quaternary sanguinarine chloride. 1-Bromo-2-bromomethyl-3,4-alkylenedioxy benzenes and 6,7-alkylenedioxynaphthalen-1-amines were synthesized first. Reactions to construct the target compounds with these two series of synthons involved alterations on a published method for synthesizing 2,3,7,8-tetraoxygenated derivatives of benzo[c]phenanthridinium, substituting benzyl bromides for benzoic aldehydes, prolonging the radical annulation time, and conducting N-methylation with formic acid and NaBH4. All the target compounds showed the same or better in vitro growth inhibitory activities against cancer cell lines compared with the positive compound. The structure activity relationship relevant to cytotoxicity and lipophilicity of the target compounds was produced.

Application of the palladium-catalysed norbornene-assisted catellani reaction towards the total synthesis of (+)-linoxepin and isolinoxepin

Our ongoing effort towards the development of highly selective transition-metal-catalysed C-H activation processes has led to the expansion of the Catellani reaction. In a Pd0/PdII/Pd IV-catalysed domino reaction, an aryl iodide, alkyl iodide and tert-butyl acrylate were combined to synthesize the carbon framework of the novel lignan (+)-linoxepin. The enantioselective synthesis highlights the work accomplished in our group and provides an excellent procedure for the reliable and scalable synthesis of architecturally complex scaffolds. This report outlines the synthetic approaches towards this interesting class of biologically active molecules. After the key Catellani/Heck reaction, our synthesis features a Leimeux-Johnson oxidation and a titanium tetrachloride mediated aldol condensation. Finally, a tuneable Mizoroki-Heck reaction was performed to furnish not only the natural product (+)-linoxepin but also its isoform, which we have named isolinoxepin. The enantioselective total synthesis of the natural product (+)-linoxepin has been accomplished in eight steps starting from commercial materials. The key Pd-catalysed Catellani step served to combine aryl iodide, alkyl iodide and tert-butyl acrylate in a domino sequence. By tuning the final Heck reaction, both the natural product and its structural isomer were synthesized. Copyright

Total synthesis of (+)-linoxepin by utilizing the catellani reaction

Molecular intelligence: The structurally novel lignan (+)-linoxepin is synthesized in an eight-step sequence. The enantioselective synthesis features the palladium-catalyzed Catellani reaction as the key step. In this highly convergent multicomponent reaction, two new carbon-carbon bonds are formed, one of which results from a C-H bond functionalization. Copyright

(+)-Dinapsoline: An efficient synthesis and pharmacological profile of a novel dopamine agonist

A highly convergent synthesis was developed for the novel dopamine agonist dinapsoline (12) (Ghosh, D.; Snyder, S. E.; Watts, V. J.; Mailman, R. B.; Nichols, D. E. 8,9-Dihydroxy-2,3,7, 11b-tetrahydro-1H-naph[1,2,3-de]isoquinoline: A Potent Full Dopamine D1 Agonist Containing a Rigid β-Phenyldopamine Pharmacophore. J. Med. Chem. 1996, 39 (2), 549-555). The crucial step in the new synthesis was a free radical-initiated cyclization to give the complete dinapsoline framework. The improved synthesis required half as many steps as the original procedure (Nichols, D. E.; Mailman, R.; Ghosh, D. Preparation of novel naphtho[1,2,3-de]isoquinolines as dopamine receptor ligands. PCT Int. Appl. WO 9706799 A1, Feb 27, 1997). One of the late-stage intermediates (11) was resolved into a pair of enantiomers. From there, the (R)-(+)-12 (absolute configuration by x-ray) of dinapsoline was identified as the active enantiomer. In unilateral 6-hydroxydopamine (6-OHDA)-lesioned rats, (+)-dinapsoline showed robust rotational behavior comparable to that of an external benchmark, trans- 4,5,5a,6,7,11b-hexahydro-2-propylbenzo[f]thieno[2,3-c]quinoline-9,10-diol, hydrochloride 18 (Michaelides, M. R.; Hong, Y. Preparation of heterotetracyclic compounds as dopamine agonists. PCT Int. Appl. WO 9422858 A1, Oct 13, 1994).

Synthesis and Reactions of 1,3-Benzodioxoledicarboxaldehydes. A Contribution to the Structure Elucidation of Nepenthone-A

We describe the preparation of 1,3-Benzodioxole-5,6-dicarboxaldehyde (1d) and 1,3-Benzodioxole-4,5-dicarboxaldehyde (3h).Under especially mild conditions also the synthesis of 4,7-Dimethoxy-1,3-benzodioxole-5,6-dicarboxaldehyde (4g) can be achieved.Its re

3-ETHOXY-2-HYDROXYBENZALDEHYDE AS A STARTING COMPOUND FOR SYNTHESIS OF ISOQUINOLINE ALKALOIDS

3-Ethoxy-2-hydroxybenzaldehyde (I) was used to prepare 6-bromo-2,3-dihydroxybenzaldehyde (V), 6-bromo-2,3-methylenedioxybenzaldehyde (VIa), 6-bromo-2,3-methylenedioxybenzoic acid (VIIa), and for new synthesis of compounds II, IIIa, IIIb, IV, VIb, VIIb, VIIIa, VIIIb, IXa and IXb.