81474-47-7

Basic information

• Product Name: 6-BROMO-7-METHOXY-BENZO[1,3]DIOXOLE-5-CARBOXYLIC ACID METHYL ESTER
• Synonyms: 6-BROMO-7-METHOXY-BENZO[1,3]DIOXOLE-5-CARBOXYLIC ACID METHYL ESTER;Methyl6-bromo-7-methoxybenzo[d][1,3]dioxole-5-carboxylate;1,3-Benzodioxole-5-carboxylic acid, 6-bromo-7-methoxy-, methyl ester
• CAS NO: 81474-47-7
• Molecular Formula: C₁₀H₉BrO₅
• Molecular Weight: 289.07946
• Mol File: 81474-47-7.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 6-BROMO-7-METHOXY-BENZO[1,3]DIOXOLE-5-CARBOXYLIC ACID METHYL ESTER(CAS DataBase Reference)
• NIST Chemistry Reference: 6-BROMO-7-METHOXY-BENZO[1,3]DIOXOLE-5-CARBOXYLIC ACID METHYL ESTER(81474-47-7)
• EPA Substance Registry System: 6-BROMO-7-METHOXY-BENZO[1,3]DIOXOLE-5-CARBOXYLIC ACID METHYL ESTER(81474-47-7)

Safety Data

• Hazardous Substances Data: 81474-47-7(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
6-BROMO-7-METHOXY-BENZO[1,3]DIOXOLE-5-CARBOXYLIC ACID METHYL ESTER is used as a key intermediate in the synthesis of various organic compounds. Its unique structure allows for the formation of new chemical bonds and the creation of novel molecules with potential applications in various industries.
Used in Pharmaceutical Research:
6-BROMO-7-METHOXY-BENZO[1,3]DIOXOLE-5-CARBOXYLIC ACID METHYL ESTER is used as a starting material in the development of new drugs. Its unique structure and properties make it a valuable tool for medicinal chemists, who can use it to design and synthesize new pharmaceutical agents with potential therapeutic benefits.
Used in Chemical Industry:
6-BROMO-7-METHOXY-BENZO[1,3]DIOXOLE-5-CARBOXYLIC ACID METHYL ESTER is used as a building block in the creation of new materials with diverse applications in the chemical industry. Its unique structure and properties can contribute to the development of innovative products, such as advanced polymers, coatings, and other specialty chemicals.

Upstream product

• 848772-89-4 methyl 2-bromo-3-hydroxy-4,5-methylenedioxybenzoate 
• 77-78-1 dimethyl sulfate 
• 22934-58-3 methyl 7-methoxybenzo[d][1,3]dioxole-5-carboxylate 
• 67-71-0 dimethylsulfone 
• 15794-51-1 methyl 7-methoxy-6-nitro-1,3-benzodioxole-5-carboxylate 
• 3934-86-9 methyl 3,4-dihydroxy-5-methoxybenzoate 
• 526221-05-6 2-ethoxy-7-hydroxy-benzo[1,3]dioxole-5-carboxylic acid methyl ester 
• 142531-43-9 methyl 7-(benzyloxy)benzo[d][1,3]dioxole-5-carboxylate 
• 116119-01-8 methyl 7-hydroxybenzo[d][1,3]dioxole-5-carboxylate 
• 79831-86-0 methyl 3-(benzyloxy)-4,5-dihydroxybenzoate 
• 69829-46-5 methyl 7-hydroxy-2,2-diphenylbenzo[d]-1,3-dioxole-5-carboxylate 
• 99-24-1 methyl galloate 
• 149-91-7 3,4,5-trihydroxybenzoic acid 
• 848772-94-1 6-bromo-7-methoxy-2,2-diphenylbenzo[1,3]dioxole-5-carboxylic acid methyl ester 

Downstream Products

• 1084695-72-6 C₁₇H₁₄O₆ 
• 139006-77-2 eupomatilone-3 
• 870094-83-0 5-[7-methoxy-6-(3,4,5-trimethoxyphenyl)-benzo[1,3]dioxol-5-yl]-4-methyl-5H-furan-2-one 
• 870094-81-8 [7-methoxy-6-(3,4,5-trimethoxyphenyl)-benzo[1,3]dioxol-5-yl]methanol 
• 870094-82-9 7-methoxy-6-(3,4,5-trimethoxyphenyl)-benzo[1,3]dioxole-5-carboxaldehyde 
• 870094-80-7 7-methoxy-6-(3,4,5-trimethoxyphenyl)-benzo[1,3]dioxole-5-carboxylic acid methyl ester 

Relevant articles and documents

Gamma-bifendate intermediate, synthesis method thereof, and synthesis method of gamma-bifendate

The invention discloses a gamma-bifendate intermediate, a synthesis method thereof, and a synthesis method of gamma-bifendate. The gamma-bifendate intermediate is 4-methoxy-5, 6-methylenedioxy-2-methoxycarbonyl phenylboronic acid, and based on the gamma-bifendate intermediate, the invention further provides a novel synthesis method of gamma-bifendate. Ullmann reaction is not adopted, and Suzuki-Miyaura reaction is introduced as a key step of asymmetric synthesis, so that synthesis is simple, isomeride does not occur, the preparation process is optimized and upgraded, reaction steps are reduced, and reaction conditions are optimized.

Nitrogen-containing biaromatic ring compounds as well as preparation method and application thereof

The invention relates to nitrogen-containing biaromatic ring compounds, a preparation method and an application, namely a pharmaceutical composition consisting of the compound as an effective component, a preparation method and an application of the compound in resisting liver cancer. A series of nitrogen-containing biaromatic ring compounds with novel structures are synthesized, generation of miRNA is induced by regulating TRBP, a good anti-liver cancer effect is shown, small molecules have a relatively strong inhibiting effect on proliferation of liver cancer cells, individual compounds even have a better curative effect than enoxacin, no similar structure has the effect before, and the compounds have good development prospects.

Towards the Total Synthesis of Schisandrene: Stereoselective Synthesis of the Dibenzocyclooctadiene Lignan Core

A stereoselective synthesis of the dibenzocyclooctadiene lignan core of the natural product schisandrene is described. Starting from readily available gallic acid, the synthetic strategy involves Suzuki-Miyaura cross-coupling, Stille reaction, and ring-closing metathesis (RCM) in the reaction sequence. The required asymmetric center at C-7′ was established by an asymmetric reduction of a keto compound using the Corey-Bakshi-Shibata (CBS) catalyst. In our approach, the eight-membered ring was achieved by RCM for the first time.

Nitrogen-Containing Biphenyl Compounds, Pharmaceutical Compositions of Same, Preparation Methods and Anti-HIV-1 Uses Thereof

Nitrogen-containing biphenyl compounds as represented by formula (I), pharmaceutically acceptable salts or derivatives thereof, pharmaceutical compositions, and preparation methods therefore, and anti-HIV-1 use of the compound. Each substituent group in formula (I) is as defined in the description.

An improved method for the synthesis of γ-DDB

A mild and efficient method for the synthesis γ-DDB has been developed through anhydride-linker assisted intramolecular Ullmann reaction. Highly regioselective bromination of differentially protected gallate was realized by virtue of the introduction of NBS.

Asymmetrie synthesis of (+)- and (-)-wuweizisu C stereoisomers and their chemosensitizing effects on multidrug-resistant cancer cells

Total syntheses of the dibenzocyclooctadiene natural product wuweizisu C in its (-)-form [(S)-1] and its (+)-form [(R)-l] were achieved in 19 steps, starting from commercially available gallic acid. In the key step, the asymmetric biphenyl axis was constructed by an oxazoline-mediated Ullmann reaction to provide either the P or Mbiaryl product in 68% yield and >99% de, depending on the configuration of the oxazoline. The efficiency of this total synthesis was excellent, as the syntheses of (S)-1 and (R)-1 from, intermediate 7 each proceeded in 13 steps with an overall yield of 6.8%. (S)-1 and (R)-1 were evaluated as chemosensitizers for multidrug-resistant cancers.

Synthesis of unsymmetrical biphenyls as potent cytotoxic agents

Twenty-six unsymmetrical biphenyls were synthesized and evaluated for cytotoxic activity against DU145, A549, KB and KB-Vin tumor cell lines. Three compounds 27, 35 and 40 showed very potent activity against the HTCL panel with an IC50 value range of 0.04-3.23 μM. In addition, fourteen active compounds were all more potent against the drug-resistant KB-Vin cell line than the parental KB cell line. Preliminary SAR analysis indicated that two bulky substituents on the 2,2′-positions of unsymmetrical biphenyl skeleton are necessary and crucial for in vitro anticancer activity, thus providing a good starting point to develop unsymmetrical biphenyls as novel anticancer agents.

Multi-functionalization of gallic acid towards improved synthesis of α- and β-DDB

The synthesis of mono-, di- and trisubstituted gallic acids and their ester with similar or different groups including different acetal and ketals is described. Regioselective bromination on two ortho-positions of methyl gallate, which is very crucial for many organic syntheses, was achieved in high yield and purity. The α- and β-DDB were synthesized in high overall yield and purity from the regioselective bromoderivatives.

Efficient synthesis of γ-DDB

Synthesis of γ-DDB, which is another family member of α-DDB (dimethyl 4,4′-dimethoxy-5,6,5′,6 ′- dimethylenedioxybiphenyl-2,2′- dicarboxylate), is described. The unsymmetric isomer (γ-DDB) was constructed by a linker-directed intramolecular Ullmann coupling reaction, followed by the cleavage of the linker and re-esterification.

Synthesis, separation, and theoretical studies of chiral biphenyl lignans (α- and β-DDB)

Two biphenyl lignans, α- and β-DDB (1 and 2, respectively) were efficiently synthesized without contamination by other regio-isomers. The different yields of the Ullmann coupling reactions for the synthesis of 1 and 2 were rationalized by calculating steric hindrance, stability, entropy change, and heat-of-formation values. The enantiomers of 1 and 2 were readily separated by HPLC on a chiral stationary phase. Their configurations were assigned based on the Cotton effect of the authentic natural products.