2356-16-3

Basic information

• Product Name: Triethyl 2-fluoro-2-phosphonoacetate
• Synonyms: 2-FLUORO-2-PHOSPHONOACETIC ACID TRIETHYL ESTER 95+%;ETHYL (DIETHOXYPHOSPHORYL)(FLUORO)ACETATE;2-Fluoro-2-(diethoxyphosphinyl)acetic acid ethyl ester;Fluoro(diethoxyphosphinyl)acetic acid ethyl ester;RIETHYL2-FLUORO-2-PHOSPHONOACETATE;Diethyl [(ethoxycarbonyl)fluoromethyl]phosphonate 96%;Ethyl (diethoxyphosphonyl)(fluoro)acetate, 2-Fluoro-2-phosphonoacetic acid triethyl ester;(Diethoxyphosphinyl)fluoroacetic Acid Ethyl Ester Ethyl (Diethoxyphosphinyl)fluoroacetate 2-Fluoro-2-phosphonoacetic Acid Triethyl Ester
• CAS NO: 2356-16-3
• Molecular Formula: C₈H₁₆FO₅P
• Molecular Weight: 242.18
• EINECS: -0
• Product Categories: Fluorinated Building Blocks;Fluorinating Reagents & Building Blocks for Fluorinated Biochemical Compounds;Horner-Emmons Reaction;Synthetic Organic Chemistry;Wittig & Horner-Emmons Reaction;C-C Bond Formation;Horner-Wadsworth-Emmons Reagents;Olefination;Phosphorus compounds
• Mol File: 2356-16-3.mol
• Article Data: 33

Chemical Properties

• Boiling Point: 75 °C0.01 mm Hg(lit.)
• Flash Point: 165 °F
• Appearance: clear colorless liquid
• Density: 1.194 g/mL at 25 °C(lit.)
• Vapor Pressure: 9.13E-05mmHg at 25°C
• Refractive Index: n20/D 1.425(lit.)
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• BRN: 1912161
• CAS DataBase Reference: Triethyl 2-fluoro-2-phosphonoacetate(CAS DataBase Reference)
• NIST Chemistry Reference: Triethyl 2-fluoro-2-phosphonoacetate(2356-16-3)
• EPA Substance Registry System: Triethyl 2-fluoro-2-phosphonoacetate(2356-16-3)

Safety Data

• Hazard Codes: Xi,F
• Statements: 36/37/38
• Safety Statements: 26-36-37/39
• WGK Germany: 3
• F: 10-21
• HazardClass: IRRITANT, FLAMMABLE
• Hazardous Substances Data: 2356-16-3(Hazardous Substances Data)

Usage

Chemical Properties

clear colorless liquid

Uses

Reactant for: Diels-Alder reactionsBiosynthesis of terpeneStereoselective synthesis of unsaturated esters, fluorides and nitriles from the reactions of aldehydes and ketones using Wadsworth-Emmons phosphonatesSynthesis of quinolonesHorner-Wadsworth-Emmons asymmetric hydrationAddition reactions and the subsequent application to click chemistryAsymmetric intermolecular Stetter reactions

Synthesis Reference(s)

The Journal of Organic Chemistry, 60, p. 4730, 1995 DOI: 10.1021/jo00120a014

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

Upstream product

• 401-55-8 ethyl bromofluoroacetate 
• 122-52-1 triethyl phosphite 
• 867-13-0 diethoxyphosphoryl-acetic acid ethyl ester 
• 541-41-3 chloroformic acid ethyl ester 
• 401-58-1 ethyl 2-fluoro-2-iodoacetate 
• 78-40-0 triethyl phosphate 
• 65094-25-9 diethyl dibromofluoromethylphosphonate 
• 7071-02-5 Potassium; (Z)-2-(diethoxy-phosphoryl)-1,2-bis-ethoxycarbonyl-ethenolate 
• 401-56-9 ethyl chlorofluoroacetate 
• 762-04-9 phosphonic acid diethyl ester 

Downstream Products

• 685-89-2 ethyl 2-fluoro-3-methyl-but-2-en-oate 
• 20397-58-4 ethyl (E)-2-fluoro-3-phenylacrylate 
• 79985-67-4 (2E,4E,6E)-2-Fluoro-5-methyl-7-(2,6,6-trimethyl-cyclohex-1-enyl)-hepta-2,4,6-trienoic acid ethyl ester 
• 79985-68-5 (2Z,4E,6E)-2-Fluoro-5-methyl-7-(2,6,6-trimethyl-cyclohex-1-enyl)-hepta-2,4,6-trienoic acid ethyl ester 
• 126275-39-6 ethyl 2,4-difluoro-5-phenyl-2(E),4(E)-pentadienoate 
• 85319-53-5 (2E,4Z,6Z)-2-Fluoro-5-methyl-7-(2,6,6-trimethyl-cyclohex-1-enyl)-hepta-2,4,6-trienoic acid ethyl ester 
• 138737-10-7 (E)-4-(tert-Butyl-dimethyl-silanyloxy)-2-fluoro-5-phenyl-7-(tetrahydro-pyran-2-yloxy)-hept-2-enoic acid ethyl ester 
• 138763-15-2 (E)-6-(tert-Butyl-diphenyl-silanyloxy)-6-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2-fluoro-4-(tetrahydro-pyran-2-yloxy)-hex-2-enoic acid ethyl ester 
• 110624-99-2 Fluoro-phosphono-acetic acid ethyl ester; compound with cyclohexylamine 
• 171916-53-3 triethyl 2-fluoro-3-oxo-2-phosphono-3-phenylpropanoate 
• 110915-28-1 (Z)-3-(4-cyanophenyl)-2-fluoroacrylic acid ethyl ester 
• 110915-64-5 (E)-3-(4-Cyano-phenyl)-2-fluoro-acrylic acid ethyl ester 
• 459-72-3 ethyl 2-fluoroacetate 
• 2253-33-0 Formylfluoressigsaeureaethylester 

Relevant articles and documents

A Convenient Synthesis of Ethyl (Diethoxyphosphoryl)fluoroacetate from Ethyl Fluoroacetate

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

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

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

Compounds of formula (I') and methods of their use and preparation, as well as compositions comprising compounds of formula (I').

HETEROARYL SUBSTITUTED AMINOPYRIDINE COMPOUNDS

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.