61441-09-6

Usage

Uses

Used in Pharmaceutical Industry:
Methyl 6-bromobenzo[d][1,3]dioxole-5-carboxylate is used as a key intermediate in the synthesis of various pharmaceuticals for its ability to be incorporated into the molecular structures of biologically active compounds.
Used in Agrochemical Industry:
Methyl 6-bromobenzo[d][1,3]dioxole-5-carboxylate is used as a building block in the development of agrochemicals, contributing to the creation of effective products for agricultural applications.
Used in Organic Synthesis:
Methyl 6-bromobenzo[d][1,3]dioxole-5-carboxylate is used as a versatile reagent in organic synthesis, allowing for the construction of complex organic molecules and the development of new chemical entities with potential applications in various fields.

InChI:InChI=1/C9H7BrO4/c1-12-9(11)5-2-7-8(3-6(5)10)14-4-13-7/h2-3H,4H2,1H3

Upstream product

• 7112-80-3 4-amino-benzo[1,3]dioxole-5-carboxylic acid methyl ester 
• 60546-62-5 6-bromopiperonylic acid 
• 149-73-5 trimethyl orthoformate 
• 67-56-1 methanol 
• 420-37-1 trimethoxonium tetrafluoroborate 
• 148160-25-2 (6-bromo(2H-benzo[3,4-d]1,3-dioxolen-5-yl))-N,N-diethylcarboxamide 
• 94-53-1 Piperonylic acid 
• 74-88-4 methyl iodide 
• 15930-53-7 6-bromo-3,4-methylenedioxybenzaldehyde 

Downstream Products

• 64511-19-9 6-(2-carboxy-phenyl)-benzo[1,3]dioxole-5-carboxylic acid 
• 65171-06-4 (bis-methoxycarbonyl-1,2,3 propyl-1)-6 methoxycarbonyl-2' methylenedioxy-4',5' trimethoxy-2,3,4 biphenyle 
• 2436-96-6 1-nitro-2-(2-nitrophenyl)benzene 
• 52886-06-3 hippadine 
• 40141-86-4 [1,3]dioxolo[4,5-j]-6(5H)-phenanthridinone 
• 97456-40-1 C₁₆H₁₄BrNO₂ 
• 97456-93-4 {6-[2-(2-Amino-ethyl)-3-bromo-phenyl]-benzo[1,3]dioxol-5-yl}-methanol 
• 97456-38-7 6-(3-Bromo-2-bromomethyl-phenyl)-benzo[1,3]dioxole-5-carboxylic acid methyl ester 
• 97456-37-6 6-(3-Bromo-2-cyanomethyl-phenyl)-benzo[1,3]dioxole-5-carboxylic acid methyl ester 
• 61038-90-2 (+/-)-isostegane 
• 41451-68-7 (+/-)-steganacin 
• 41451-71-2 (+/-)-episteganol 
• 41451-71-2 (+/-)-steganol 
• 906563-77-7 methyl 6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzo[d][1,3]dioxole-5-carboxylate 

Relevant academic research and scientific papers

Total Synthesis of Zephycarinatines via Photocatalytic Reductive Radical ipso-Cyclization

We report herein a nonbiomimetic strategy for the total synthesis of the plicamine-type alkaloids zephycarinatines C and D. The key feature of the synthesis is a stereoselective reductive radical ipso-cyclization using visible-light-mediated photoredox ca

Efficient and rapid synthesis of N-substituted isoquinolin-1-ones under mild conditions: Facile access to doryanine derivatives

We describe the simple and efficient synthesis of N-substituted isoquinolin-1-one derivatives. Initiating with the coupling of benzoic acids containing vinyl ethers with different amines, followed by rapid intramolecular cyclization under acidic conditions at room temperature, N-substituted isoquinolin-1-ones were furnished in high yields. The utility of this simple and mild cyclization method was demonstrated through the practical synthesis of natural product doryanine and its analogues.

Pd-Catalyzed/Iodide-Promoted α-Arylation of Ketones for the Regioselective Synthesis of Isocoumarins

A variety of isocoumarins have been synthesized directly from 2-halobenzoates and ketones through a palladium-catalyzed α-arylation step followed by an intramolecular cyclization process. The addition of iodide anions to the reaction mixture increased yields and selectivities especially when 2-bromobenzoates were employed. This phosphine-free one-pot synthesis features a high functional group tolerance and gives access to richly decorated isocoumarins. This general methodology was successful in the total synthesis of Xyridin A, an important natural product with antibacterial and antifungal activity.

AD-35 preparation technology

The invention discloses a new preparation method of a benzodioxole derivative (AD-35) shown by the formula (I). The method comprises the following steps: with piperic acid as a raw material, performing bromination, esterification, cyaniding, cyclopropane

Novel derivatives of indole and pyrrole, method for the production thereof and pharmaceutical compositions containing same

The invention relates to compounds of formula (I), wherein Ra, Rb, Rc, Rd, R3, R4, R5, A1, A2, T and W are as defined in the description. The invention also relates to drugs containing same.

INDOLE AND PYRROLE COMPOUNDS, A PROCESS FOR THEIR PREPARATION AND PHARMACEUTICAL COMPOSITIONS CONTAINING THEM

Compounds of formula (I): wherein Ra, Rb, Rc, Rd, R3, R4, R5, A1, A2, T and W are as defined in the description. Medicinal products containing the same whic

Synthesis of N-substituted benzo[c][1,7]- and benzo[c][1,8] phenanthrolin-(5H)-6-ones through a Pd-mediated Suzuki-Miyaura heteroaryl-aryl coupling reaction

In the course of the search for non-camptothecin topoisomerase I inhibitors we have undertaken the synthesis of N-substituted benzo[c][1,7]- and benzo[c][1,8]phenanthrolinone derivatives. An intermolecular Suzuki-Miyaura heteroaryl-aryl coupling reaction was planned as the key step. Then a nitro reduction followed by a concomitant lactamization achieved the construction of the tetracycle structures. This methodology permitted a rapid and efficient elaboration of biologically potent compounds.

Comparative study of the Kumada, Negishi, Stille, and Suzuki - Miyaura reactions in the synthesis of the indole alkaloids hippadine and pratosine

The total synthesis of hippadine by a tandem metalation/cross-coupling/ lactamization strategy was investigated starting from either 7-bromoindole or a 6-halogenated methyl piperonate. The Kumada and Negishi cross-coupling reactions failed to provide any of the desired product. However, the Stille and Suzuki reactions furnished hippadine in low yields starting from the electron-deficient methyl 6-iodo- and 6-bromopiperonate, respectively. Starting from the metalated indole, only the Suzuki reaction occurred, affording hippadine in 67-74% and pratosine in 62% isolated yield.

Synthesis of 7-deoxypancratistatin from carbohydrates by the use of olefin metathesis

The stereocontrolled synthesis of (+)-7-deoxypancratistatin is described. The convergent synthesis has been achieved by two different strategies, both of which commence from a pentose and piperonal. The latter is converted into allylic bromide 7, which is then coupled with a protected methyl 5-deoxy-5-iodo-D-ribofuranoside in the presence of zinc metal. The first strategy involves a total of only 13 steps from D-ribose and piperonal, but suffers from a low yield in the zinc-mediated reaction between ribofuranoside 9, benzylamine, and bromide 7.The second strategy involves a total of 18 steps from D-xylose and piperonal. The former is converted into ribofuranoside 28, which is coupled with bromide 7 in the presence of zinc, and this is followed by ring-closing olefin metathesis. Subsequent Overman rearrangement, dihydroxylation. and deprotection then affords the natural product.

A direct and mild conversion of tertiary aryl amides to methyl esters using trimethyloxonium tetrafluoroborate: A very useful complement to directed metalation reactions

The scope and generality of a direct process for the conversion of tertiary amides directly to methyl esters has been investigated. The process involves a two-step, one pot procedure in which a tertiary amide is first treated with trimethyloxonium tetrafluoroborate to generate an imidate intermediate which is then hydrolyzed, generally by the addition of saturated aqueous sodium bicarbonate solution. Although this process fails for aliphatic amides, very good yields are realized for a variety of amides derived from aromatic carboxylic acids. Steric hindrance at the N-alkyl group is well tolerated; thus N,N-dimethyl, -diethyl, and -diisopropyl amides can all be utilized successfully. (C) 2000 Elsevier Science Ltd.