1644-86-6

Basic information

• Product Name: 2,2-Difluoro-6-nitro-benzo[1,3]dioxol-5-ylamine
• Synonyms: 2,2-Difluoro-6-nitro-benzo[1,3]dioxol-5-ylamine;4,5-[(DifluoroMethylene)dioxy]-2-nitro-aniline;2,2-difluoro-6-nitrobenzo[d][1,3]dioxol-5-amine
• CAS NO: 1644-86-6
• Molecular Formula: C7H4F2N2O4
• Molecular Weight: 218.11
• Product Categories: Chemical Amines;Amines;Heterocycles
• Mol File: 1644-86-6.mol
• Article Data: 3

Chemical Properties

• Melting Point: 140-1410C
• Appearance: /
• Refractive Index: 1.593
• Storage Temp.: Refrigerator
• Solubility: DMSO (Slightly), Methanol (Slightly)
• CAS DataBase Reference: 2,2-Difluoro-6-nitro-benzo[1,3]dioxol-5-ylamine(CAS DataBase Reference)
• NIST Chemistry Reference: 2,2-Difluoro-6-nitro-benzo[1,3]dioxol-5-ylamine(1644-86-6)
• EPA Substance Registry System: 2,2-Difluoro-6-nitro-benzo[1,3]dioxol-5-ylamine(1644-86-6)

Safety Data

• Hazardous Substances Data: 1644-86-6(Hazardous Substances Data)

Usage

Chemical Properties

Yellow Solid

Uses

2,2-Difluoro-6-nitro-benzo[1,3]dioxol-5-ylamine (cas# 1644-86-6) is a compound useful in organic synthesis.

InChI:InChI=1/C7H4F2N2O4/c8-7(9)14-5-1-3(10)4(11(12)13)2-6(5)15-7/h1-2H,10H2

Upstream product

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

Downstream Products

• 1744-12-3 2,2-difluorobenzo[d][1,3]dioxole-5,6-diamine 

Relevant articles and documents

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.

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