1583-59-1 Usage
Description
2,2-Difluoro-1,3-benzodioxole is an intermediate compound characterized as a colorless to pale yellow liquid. It is a difluoromethylated building block that is particularly useful in the synthesis of various benzodioxole-containing pharmaceutical active compounds and products for agricultural chemistry.
Uses
Used in Pharmaceutical Chemistry:
2,2-Difluoro-1,3-benzodioxole is used as a key intermediate for the synthesis of pharmaceutical products, specifically benzodioxole-containing active compounds. Its difluoromethylated structure contributes to the development of novel pharmaceutical agents with potential therapeutic applications.
Used in Agricultural Chemistry:
In the agricultural chemistry industry, 2,2-Difluoro-1,3-benzodioxole is utilized as an intermediate compound for the preparation of products that can enhance crop protection and management strategies.
Used in the Synthesis of Kv3 Inhibitors:
2,2-Difluoro-1,3-benzodioxole is employed as a crucial component in the synthesis of Kv3 inhibitors, which are compounds that target and modulate the activity of Kv3 potassium channels, playing a significant role in various physiological processes.
Used in the Preparation of Renin Inhibitors:
This intermediate compound is also used in the preparation of renin inhibitors, which are essential in the treatment of hypertension and other cardiovascular diseases by regulating the renin-angiotensin system.
Used in the Synthesis of Organofluorine Compounds:
2,2-Difluoro-1,3-benzodioxole serves as a versatile intermediate for the synthesis of a variety of new organofluorine compounds, such as 2-, 3-, and 4-(trifluoromethoxy)phenyllithiums, which can be used in selective aliphatic fluorination through halogen exchange under mild conditions.
Preparation
2,2-Difluoro-1,3-benzodioxole is prepared by reaction of 2,2-dichloro-1,3-benzodioxole with potassium fluoride in the presence of an effective quantity of a catalyst selected from potassium hydrogen fluoride, sodium hydrogen fluoride, cesium hydrogen fluoride, rubidium hydrogen fluoride, and quaternary ammonium hydrogen fluoride.
https://patents.google.com/patent/US5432290A/en
References
[1] E.Castagnetti, et al, Eur. J. Org. Chem., 2001, 2001(4), pp 691-695.
[2] L.Saint-Jalmes, J. F. Chem., 2006, 127(1), pp 85-90.
Check Digit Verification of cas no
The CAS Registry Mumber 1583-59-1 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 1,5,8 and 3 respectively; the second part has 2 digits, 5 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 1583-59:
(6*1)+(5*5)+(4*8)+(3*3)+(2*5)+(1*9)=91
91 % 10 = 1
So 1583-59-1 is a valid CAS Registry Number.
InChI:InChI=1/C7H4F2O2/c8-7(9)10-5-3-1-2-4-6(5)11-7/h1-4H
1583-59-1Relevant articles and documents
Fluorodesulfurization of Thionobenzodioxoles with Silver(I) Fluoride
Newton, Josiah J.,Brooke, Alan J.,Duhamel, Bastian,Pulfer, Jason M.,Britton, Robert,Friesen, Chadron M.
, p. 13298 - 13305 (2020)
Difluorobenzodioxole is an important functional group found in both pharmaceuticals and agrochemicals. The late-stage introduction of this functional group is challenged by typical fluorination conditions of HF and strong oxidants. Here, we demonstrate that a range of difluorobenzodioxoles can be prepared from catechols in two steps through conversion into thionobenzodioxoles, followed by desulfurative fluorination with silver(I) fluoride. These mild reaction conditions are compatible with a variety of functional groups and enable access to a range of functionalized difluorobenzodioxoles.
Preparation method of difluoropiperidine
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Paragraph 0020-0039; 0044-0047, (2018/09/08)
The invention relates to a preparation method of a drug intermediate, and particularly provides a preparation method of difluoropiperidine. The preparation method includes: adopting a microchannel reactor, and continuously and uniformly pumping a difluoropiperidine solution into a module A for pre-cooling; continuously and uniformly pumping fluorine mixed gas into a module B for pre-cooling; allowing mixing reaction sequentially in modules C, D, E and F, controlling reaction temperature at minus 40 DEG C-20 DEG C, and collecting a product after retaining for 5s-10min; subjecting the product towater washing, rectification, separation and purification to obtain difluoropiperidine. Difluoropiperidine prepared by the method has the advantages of high atom economy, quick reaction, low cost, little pollution, environment friendliness and safety.
4 - (2,2-difluoro -1,3-Benzodioxole-4-yl) pyrrole-3-nitrile synthetic method
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Paragraph 0045; 0055-0056; 0067; 0074; 0086-0087, (2018/07/10)
The invention discloses a synthetic method of 4-(2,2-difluoro-1,3-benzodioxole-4-yl)pyrrole-3-nitrile. The method comprises the following steps of: preparing an intermediate 2,2-difluorobenz-1,3-dioxole through reacting catechol with dibromodifluoromethane, and preparing an intermediate 2-cyano-3-(2,2-difluorobenz-1,3-dioxole-4-yl)-2-acrylate. The fludioxonil prepared by the synthetic method provided by the invention has the purity of more than 99.0% and the total yield of more than 45.0%; the synthetic method has the advantages of cheap and easily available raw materials, simple process, high product yield in each step, good purity, low production cost, applicability to batch industrial production and the like.
