476473-97-9

Basic information

• Product Name: 5-(chloromethyl)-2,2-difluorobenzo[d][1,3]dioxole
• Synonyms: 5-(chloromethyl)-2,2-difluorobenzo[d][1,3]dioxole;5-ChloroMethyl-2,2-difluoro-benzo[1,3]dioxole;5-(chloromethyl)-2,2-difluoro-2H-1,3-benzodioxole;5-(chloromethyl)-2,2-difluoro-1,3-benzodioxole;EOS-61002
• CAS NO: 476473-97-9
• Molecular Formula: C₈H₅ClF₂O₂
• Molecular Weight: 206.5739064
• Mol File: 476473-97-9.mol
• Article Data: 37

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 5-(chloromethyl)-2,2-difluorobenzo[d][1,3]dioxole(CAS DataBase Reference)
• NIST Chemistry Reference: 5-(chloromethyl)-2,2-difluorobenzo[d][1,3]dioxole(476473-97-9)
• EPA Substance Registry System: 5-(chloromethyl)-2,2-difluorobenzo[d][1,3]dioxole(476473-97-9)

Safety Data

• Hazardous Substances Data: 476473-97-9(Hazardous Substances Data)

Usage

Description

5-(Chloromethyl)-2,2-difluorobenzo[d][1,3]dioxole is an organic compound characterized by the presence of a chloromethyl group, two fluorine atoms, and a benzo[d][1,3]dioxole ring. This unique molecular structure endows it with specific chemical properties and potential applications in various fields.

Uses

Used in Pharmaceutical Industry:
5-(Chloromethyl)-2,2-difluorobenzo[d][1,3]dioxole is used as a key intermediate in the synthesis of substituted 5,6-dihydro-4H-pyrrolo[1,2-b]pyrazoles. These pyrrolobenzodiazepine derivatives are known for their ability to inhibit TGF-β (Transforming Growth Factor-beta) signal transduction, a critical pathway involved in various cellular processes, including cell proliferation, differentiation, and migration. By targeting this pathway, these compounds have potential applications in the development of therapeutic agents for the treatment of various diseases, such as cancer, fibrosis, and autoimmune disorders, where TGF-β signaling is dysregulated.

Upstream product

• 72768-97-9 (2,2-difluoro-1,3-benzodioxol-5-yl)methanol 
• 1634-04-4 tert-butyl methyl ether 
• 33070-32-5 5-bromo-2,2-difluoro-2H-1,3-benzodioxole 
• 656-46-2 2,2-difluoro-1,3-benzodioxole-5-carboxylic acid 
• 773873-95-3 2,2-difluorobenzo[1,3]dioxole-5-carboxylic acid methyl ester 
• 656-42-8 2,2-difluoro-2H-1,3-benzodioxole-5-carbaldehyde 
• 1583-59-1 2,2-difluoro-1,3-benzodioxole 
• 107-30-2 chloromethyl methyl ether 
• 50-00-0 formaldehyd 

Downstream Products

• 68119-31-3 2-(2,2-difluorobenzo[d][1,3]dioxol-5-yl)acetonitrile 
• 862574-87-6 1-(2,2-difluorobenzo[d][1,3]dioxol-5-yl)cyclopropanecarbonitrile 
• 862574-88-7 1-(2,2-difluorobenzo[1,3]dioxol-5-yl)cyclopropane-1-carboxylic acid 
• 1152311-62-0 (R)-1-(2,2-difluorobenzo[d][1,3]dioxol-5-yl)-N-(1-(2,3-dihydroxypropyl)-6-fluoro-2-(1-hydroxy-2-methylpropan-2-yl)-1H-indol-5-yl)cyclopropanecarboxamide 
• 1294504-68-9 N-{1-[(2R)-3-(benzyloxy)-2-hydroxypropyl]-2-[1-(benzyloxy)-2-methylpropan-2-yl]-6-fluoro-1H-indol-5-yl}-1-(2,2-difluoro-2H-1,3-benzodioxol-5-yl)cyclopropane-1-carboxamide 
• 1160221-25-9 tert-butyl 3-(6-(1-(2,2-difluorobenzo[d][1,3]dioxol-5-yl)cyclopropane-1-carboxamido)-3-methylpyridin-2-yl)benzoate 
• 936727-05-8 Lumacaftor 
• 1160221-26-0 Lumacaftor hydrochloride 
• 1083168-23-3 1-(2,2-difluorobenzo[d][1,3]dioxol-5-yl)-N-(6-(5-fluoro-2-oxo-1,2-dihydropyridin-4-yl)-5-methylpyridin-2-yl)cyclopropanecarboxamide 
• 1083168-21-1 N-(6-(1-(2-cyanamido-2-oxoethyl)-6-oxo-1,6-dihydropyridin-3-yl)-5-methylpyridin-2-yl)-1-(2,2-difluorobenzo[d][1,3]dioxol-5-yl)cyclopropanecarboxamide 
• 1152274-56-0 3-(3-(1-(2,2-difluorobenzo[d][1,3]dioxol-5-yl)cyclopropanecarboxamido)isoquinolin-1-yl)benzoyl chloride 
• 1152274-47-9 1-(2,2-difluorobenzo[d][1,3]dioxol-5-yl)-N-(1-(4-(hydroxymethyl)phenyl)isoquinolin-3-yl)cyclopropanecarboxamide 
• 1152274-55-9 tert-butyl 3-(3-(1-(2,2-difluorobenzo[d][1,3]dioxol-5-yl)cyclopropanecarboxamido)isoquinolin-1-yl)benzoate 
• 1152274-36-6 2-(dimethylamino)ethyl 3-(3-(1-(2,2-difluorobenzo[d][1,3]dioxol-5-yl)cyclopropanecarboxamido)isoquinolin-1-yl)benzoate 

Relevant articles and documents

Pharmaceutical compositions for the treatment of cystic fibrosis transmembrane conductance regulator mediated diseases

The present invention features compositions comprising a plurality of therapeutic agents wherein the presence of one therapeutic agent enhances the properties of at least one other therapeutic agent. In one embodiment, the therapeutic agents are cystic fibrosis transmembrane conductance regulators (CFTR) such as a CFTR corrector or CFTR potentiator for the treatment of CFTR mediated diseases such as cystic fibrosis. Methods and kits thereof are also disclosed.

1 - (2, 2 - Difluorobenzene and [D] [1, 3] dioxo heterocyclic pentene -5 - yl) ring propyl nitrile of preparation method

The invention discloses a preparation method for 1-(2,2-difluoro-benzo[D][1,3]dioxol-5-yl)-cyclopropanecarbonitrile. The method comprises the following steps: 5-(chloromethyl)benzo[d][1,3]dioxole is prepared from 2,2-difluoro-1,3-benzodioxole through Blanc chloromethylation, and then is subjected to cyanation by utilization of cuprous cyanide, finally cyclization is carried out by utilization of 1-Bromo-2-chloroethane and a product is obtained. In the above method, cyanation is carried out by utilization of low-toxic cuprous cyanide, a weak organic base triethylamine deacid reagent is employed to carry out cyclization preparation and a target product is obtained, usage of dangerous lithium aluminum hydride and sodium cyanide is avoided, strong alkaline and high temperature conditions are avoided, and therefore hydrolysis of cyan in the product is avoided. The preparation method is low-toxic to the environment and the product yield and quality are raised. The process flow is simple and safe, the reaction process is easy to control, the cost is low, the yield is high, and the preparation method is suitable for industrialization.

Synthesis and biological evaluation of novel thiazole- VX-809 hybrid derivatives as F508del correctors by QSAR-based filtering tools

The most common CF mutation, F508del, impairs the processing and gating of CFTR protein. This deletion results in the improper folding of the protein and its degradation before it reaches the plasma membrane of epithelial cells. Present correctors, like VX809 only induce a partial rescue of the mutant protein. Our previous studies reported a class of compounds, called aminoarylthiazoles (AATs), featuring an interesting activity as correctors. Some of them show additive effect with VX809 indicating a different mechanism of action. In an attempt to construct more interesting molecules, it was thought to generate chemically hybrid compounds, blending a portion of VX809 merged to the thiazole scaffold. This approach was guided by the development of QSAR analyses, which were performed based on the F508del correctors so far disclosed in the literature. This strategy was aimed at exploring the key requirements turning in the corrector ability of the collected derivatives and allowed us to derive a predictive model guiding for the synthesis of novel hybrids as promising correctors. The new molecules were tested in functional and biochemical assays on bronchial CFBE41o-cells expressing F508del-CFTR showing a promising corrector activity.