2356-16-3 Usage
Description
Triethyl 2-fluoro-2-phosphonoacetate is a clear colorless liquid that serves as a versatile reagent in various chemical reactions and processes. It is known for its ability to participate in a range of applications, including Diels-Alder reactions, biosynthesis of terpenes, and stereoselective synthesis of unsaturated esters, fluorides, and nitriles.
Uses
Used in Organic Chemistry:
Triethyl 2-fluoro-2-phosphonoacetate is used as a reactant for Diels-Alder reactions, which are important in the synthesis of complex organic compounds. It is also utilized in the biosynthesis of terpenes, a large and diverse class of organic compounds produced by a variety of organisms.
Used in Stereoselective Synthesis:
Triethyl 2-fluoro-2-phosphonoacetate is used as a reactant for the stereoselective synthesis of unsaturated esters, fluorides, and nitriles from the reactions of aldehydes and ketones using Wadsworth-Emmons phosphonates. This application is crucial in the development of enantiomerically pure compounds, which are essential in the pharmaceutical industry.
Used in Synthesis of Quinolones:
Triethyl 2-fluoro-2-phosphonoacetate is employed as a reactant in the synthesis of quinolones, a class of antibacterial agents that are widely used in the treatment of various bacterial infections.
Used in Horner-Wadsworth-Emmons Asymmetric Hydration:
Triethyl 2-fluoro-2-phosphonoacetate is used as a reactant in the Horner-Wadsworth-Emmons asymmetric hydration, a reaction that allows for the formation of chiral phosphonates, which are valuable intermediates in the synthesis of biologically active molecules.
Used in Addition Reactions and Click Chemistry:
Triethyl 2-fluoro-2-phosphonoacetate is used in addition reactions, which are then applied to click chemistry, a set of powerful and versatile reactions that allow for the rapid and efficient assembly of complex molecules from smaller units.
Used in Asymmetric Intermolecular Stetter Reactions:
Triethyl 2-fluoro-2-phosphonoacetate is used as a reactant in asymmetric intermolecular Stetter reactions, which are important for the synthesis of biologically active molecules with high enantioselectivity.
Synthesis Reference(s)
The Journal of Organic Chemistry, 60, p. 4730, 1995 DOI: 10.1021/jo00120a014
Check Digit Verification of cas no
The CAS Registry Mumber 2356-16-3 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 2,3,5 and 6 respectively; the second part has 2 digits, 1 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 2356-16:
(6*2)+(5*3)+(4*5)+(3*6)+(2*1)+(1*6)=73
73 % 10 = 3
So 2356-16-3 is a valid CAS Registry Number.
InChI:InChI=1/C8H16FO5P/c1-4-12-8(10)7(9)15(11,13-5-2)14-6-3/h7H,4-6H2,1-3H3/t7-/m1/s1
2356-16-3Relevant articles and documents
A Convenient Synthesis of Ethyl (Diethoxyphosphoryl)fluoroacetate from Ethyl Fluoroacetate
Elkik, Elias,Imbeaux, Michele
, p. 861 - 862 (1989)
A new synthesis of ethyl (diethoxyphosphoryl)fluoroacetate starting from ethyl fluoroacetate is described for a mole scale.This synthesis does not require the use of special equipment for fluorine chemistry since no hydrogen fluoride is evolved.
Synthesis of fluorinated phosphonoacetate derivatives of carbocyclic nucleoside monophosphonates and activity as inhibitors of HIV reverse transcriptase
Hamilton, Chris J.,Roberts, Stanley M.
, p. 1051 - 1056 (1999)
The syntheses of compounds 8-10 are described; the compounds showed some activity as inhibitors of HIV reverse transcriptase (IC50 ≥ 365 μM).
Preparation of triethyl 2-fluoro-2-phosphonoacetate
Patois,Savignac
, p. 1317 - 1322 (1994)
Triethyl 2-fluoro-2-phosphonoacetate was prepared in one step from dibromofluoromethyl phosphonate and ethyl chloroformate.
INHIBITORS OF BRUTON'S TYROSINE KINASE AND METHODS OF THEIR USE
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Page/Page column 161; 165-166; 339, (2018/06/30)
Compounds of formula (I') and methods of their use and preparation, as well as compositions comprising compounds of formula (I').
HETEROARYL SUBSTITUTED AMINOPYRIDINE COMPOUNDS
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Page/Page column 178, (2017/01/09)
Disclosed are compounds of Formula (I) Formula(I) or salts thereof, wherein HET is a heteroaryl selected from oxazolyl, pyrazolyl, imidazo[l,2-b]pyridazin-3-yl, and pyrazolo[l,5-a]pyrimidin-3-yl, wherein said heteroaryl is attached to the pyridinyl group in the compound of Formula (I) by a carbon ring atom in the heteroaryl and wherein said heteroaryl is substituted with zero to 2 Rb; and R1, R3, and Rb are define herein. Also disclosed are methods of using such compounds as modulators of IRAK4, and pharmaceutical compositions comprising such compounds. These compounds are useful in treating, preventing, or slowing inflammatory and autoimmune diseases, or in the treatment of cancer.
