1744-12-3

Basic information

• Product Name: 2,2-DIFLUORO-BENZO[1,3]DIOXOLE-5,6-DIAMINE
• Synonyms: 5,6-DIAMINO-2,2-DIFLUORO-1,3-BENZODIOXOLE;5,6-DIAMINE-2,2-DIFLUORO-1,3-BENZODIOXOLE;2,2-DIFLUORO-BENZO[1,3]DIOXOLE-5,6-DIAMINE;2,2-Difluoro-benzo[1,3]dioxole-5,6-diamine ,97%;2,2-Difluorobenzo[d][1,3]dioxole-5,6-diaMine
• CAS NO: 1744-12-3
• Molecular Formula: C₇H₆F₂N₂O₂
• Molecular Weight: 188.13
• Mol File: 1744-12-3.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 2,2-DIFLUORO-BENZO[1,3]DIOXOLE-5,6-DIAMINE(CAS DataBase Reference)
• NIST Chemistry Reference: 2,2-DIFLUORO-BENZO[1,3]DIOXOLE-5,6-DIAMINE(1744-12-3)
• EPA Substance Registry System: 2,2-DIFLUORO-BENZO[1,3]DIOXOLE-5,6-DIAMINE(1744-12-3)

Safety Data

• Statements: 20/21/22-36/37/38
• Safety Statements: 26-36/37/39
• Hazardous Substances Data: 1744-12-3(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
2,2-DIFLUORO-BENZO[1,3]DIOXOLE-5,6-DIAMINE is used as a key intermediate in the synthesis of pharmaceuticals for its ability to contribute to the development of novel drug molecules. Its fluorinated and aromatic nature can enhance the pharmacokinetic and pharmacodynamic properties of the resulting compounds, potentially leading to improved therapeutic effects and reduced side effects.
Used in Agrochemical Industry:
In the agrochemical sector, 2,2-DIFLUORO-BENZO[1,3]DIOXOLE-5,6-DIAMINE is utilized as a building block for the creation of new agrochemicals. Its chemical structure can be tailored to target specific pests or diseases, offering a more efficient and environmentally friendly approach to crop protection.
Used in Materials Science:
2,2-DIFLUORO-BENZO[1,3]DIOXOLE-5,6-DIAMINE is employed in materials science for the development of innovative coatings, adhesives, and other functional materials. Its fluorinated benzene ring provides unique properties such as chemical resistance, thermal stability, and adhesion, which are valuable in various industrial applications.
Used in Polymer Synthesis:
As a monomer or a comonomer, 2,2-DIFLUORO-BENZO[1,3]DIOXOLE-5,6-DIAMINE is used in the synthesis of polymers with tailored properties. Its incorporation into polymer chains can result in materials with improved mechanical strength, thermal stability, and chemical resistance, suitable for a wide range of applications, from automotive to electronics industries.

Upstream product

• 1544-85-0 2,2-difluoro-benzo[1,3]dioxol-5-ylamine 
• 948-94-7 N-(2,2-difluorobenzo[d][1,3]dioxol-5-yl)acetamide 
• 1736-66-9 N-(2,2-difluoro-6-nitrobenzo[d][1,3]dioxol-5-yl)acetamide 
• 1644-86-6 2,2-difluoro-6-nitrobenzo[d][1,3]dioxol-5-amine 

Downstream Products

• 188028-35-5 6,6-difluoro[1,3]dioxolo[4,5-f]benzimidazole 

Relevant articles and documents

BENZIMIDAZOLE COMPOUND HAVING AN OPTIONALLY HALOGENATED ALKYLENEDIOXY GROUP OR SALT THEREOF, AGRICULTURAL AND HORTICULTURAL INSECTICIDE COMPRISING THE COMPOUND OR THE SALT, AND METHOD FOR USING THE INSECTICIDE

Provided are a benzimidazole compound represented by the general formula (1) {wherein R1 represents a hydrogen atom or a cyano group, R2 represents a (C1-C6) alkyl group, a (C1-C6) alkoxy (C1-C6) alkyl group, or a halo (C1-C6) alkyl group, R represents a (C1-C3) alkylene group or a halo (C1-C3) alkylene group, and m represents 0, 1, or 2}, or a salt thereof, an agricultural and horticultural insecticide comprising the compound or the salt as an active ingredient; an animal ectoparasite or endoparasite control agent comprising the compound or the salt as an active ingredient; and a method for using the insecticide or the agent.

Synthesis of carbon-11-labeled CK1 inhibitors as new potential PET radiotracers for imaging of Alzheimer's disease

The reference standards methyl 3-((2,2-difluoro-5H-[1,3]dioxolo[4′,5′:4,5]benzo[1,2-d]imidazol-6-yl)carbamoyl)benzoate (5a) and N-(2,2-difluoro-5H-[1,3]dioxolo[4′,5′:4,5]benzo[1,2-d]imidazol-6-yl)-3-methoxybenzamide (5c), and their corresponding desmethylated precursors 3-((2,2-difluoro-5H-[1,3]dioxolo[4′,5′:4,5]benzo[1,2-d]imidazol-6-yl)carbamoyl)benzoic acid (6a) and N-(2,2-difluoro-5H-[1,3]dioxolo[4′,5′:4,5]benzo[1,2-d]imidazol-6-yl)-3-hydroxybenzamide (6b), were synthesized from 5-amino-2,2-difluoro-1,3-benzodioxole and 3-substituted benzoic acids in 5 and 6 steps with 33% and 11%, 30% and 7% overall chemical yield, respectively. Carbon-11-labeled casein kinase 1 (CK1) inhibitors, [11C]methyl 3-((2,2-difluoro-5H-[1,3]dioxolo[4′,5′:4,5]benzo[1,2-d]imidazol-6-yl)carbamoyl)benzoate ([11C]5a) and N-(2,2-difluoro-5H-[1,3]dioxolo[4′,5′:4,5]benzo[1,2-d]imidazol-6-yl)-3-[11C]methoxybenzamide ([11C]5c), were prepared from their O-desmethylated precursor 6a or 6b with [11C]CH3OTf through O-[11C]methylation and isolated by HPLC combined with SPE in 40–45% radiochemical yield, based on [11C]CO2 and decay corrected to end of bombardment (EOB). The radiochemical purity was >99%, and the molar activity (MA) at EOB was 370–740 GBq/μmol with a total synthesis time of ～40-min from EOB.

BIFLUORODIOXALANE-AMINO-BENZIMIDAZOLE KINASE INHIBITORS FOR THE TREATMENT OF CANCER, AUTOIMMUNEINFLAMMATION AND CNS DISORDERS

The invention relates to a compound of the general formula (I) or a physiologically functional derivative, solvate or salt thereof, (I) wherein A is a bond, alkyl or alkoxy optionally substituted with one or more R" as defined herein, *-N(R"')CO-, *-CON(R"')-, *-N(R'")CON(R"')-, -S-, -SO-, *-N(R'")-, *-N(R'")CO-, *-CON(R'")-, -CO-, *-COO-, *-OOC-, *-S02N(R"')-, -S02, or *-N(R"')-SO2-, wherein R"' is as defined herein and * specifies the point of attachment to X; X is aryl, cycloalkyl, aralkyl, heterocyclyl or heteroaryl, which may be substituted with one or more Rx further described herein; L is a bond or *-N(RN)CO-, *-CON(RN)-, *-N(RN)-, *-C=N(RN)-, *-N(RN)-alkyI-, *-alkyl-N(RN)-, *-N(RN)CON(RN)-, *-CO-, *-S02-, alkyl, *-alkyl-0-alkyl-, *-NCO-CH=CH-, *-CH=CH-CONH-, * -S02N(RN)-, *-N(RN)S02-, or heterocyclyl, wherein * specifies the point of attachment to X; Y is H, alkyl, aryl, aralkyl, cycloalkyl, heterocyclyl or heteroaryl, which may be substituted with one or more RY further described herein; and R and RN are further described herein; as well as their use as a medicament, a pharmaceutical composition comprising them, a method of treatment or prevention of a medical condition entailing the administration thereof, and the use thereof in the manufacture of a medicament for the treatment or prevention of a medical condition, particularly autoimmune inflammatory disorders, CNS disorders, sleeping disorders, or proliferative diseases including cancer. The invention further relates to a specific process for the preparation of said compounds.

Difluoro-dioxolo-benzoimidazol-benzamides as potent inhibitors of CK1δ and ε with nanomolar inhibitory activity on cancer cell proliferation

Deregulation of CK1 (casein kinase 1) activity can be involved in the development of several pathological disorders and diseases such as cancer. Therefore, research interest in identifying potent CK1-specific inhibitors is still increasing. A previously p