Sodium chlorodifluoroacetate

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Sodium chlorodifluoroacetate
NaCF2ClCO2.svg
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.015.988 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 217-586-0
PubChem CID
UNII
  • InChI=1S/C2HClF2O2.Na/c3-2(4,5)1(6)7;/h(H,6,7);/q;+1/p-1
    Key: MRTAVLDNYYEJHK-UHFFFAOYSA-M
  • C(=O)(C(F)(F)Cl)[O-].[Na+]
Properties
C2ClF2NaO2
Molar mass 152.46 g·mol−1
Appearancewhite solid
Melting point 196–198 °C (385–388 °F; 469–471 K)
Hazards
GHS labelling: [1]
GHS-pictogram-exclam.svg
Warning
H315, H319, H335
P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Sodium chlorodifluoroacetate is the organofluorine compound with the formula CF2ClCO2Na. [2] It is a salt formed by neutralization of chlorodifluoroacetic acid with sodium hydroxide. The compound, a white solid, is of interest as a source of difluorocarbene:

CF2ClCO2Na → NaCl + CF2 + CO2

This reaction is conducted in a hot solution also containing the substrate. Diglyme is a typical solvent. [2] The conversion of sodium chlorodifluoroacetate is proposed to start with decarboxylation, which generates the carbanion ClF2C.

One set of applications is difluorocyclopropanation. Thermal decomposition of sodium chlorodifluoroacetate in the presence of triphenylphosphine and an aldehyde allows for a Wittig-like reactions [3] In this case, (C6H5)3P=CF2 is proposed as an intermediate.

Related Research Articles

Decarboxylation is a chemical reaction that removes a carboxyl group and releases carbon dioxide (CO2). Usually, decarboxylation refers to a reaction of carboxylic acids, removing a carbon atom from a carbon chain. The reverse process, which is the first chemical step in photosynthesis, is called carboxylation, the addition of CO2 to a compound. Enzymes that catalyze decarboxylations are called decarboxylases or, the more formal term, carboxy-lyases (EC number 4.1.1).

<span class="mw-page-title-main">Lithium aluminium hydride</span> Chemical compound

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<span class="mw-page-title-main">Sodium borohydride</span> Chemical compound

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<span class="mw-page-title-main">Lithium perchlorate</span> Chemical compound

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<span class="mw-page-title-main">Iodine monochloride</span> Chemical compound

Iodine monochloride is an interhalogen compound with the formula ICl. It is a red-brown chemical compound that melts near room temperature. Because of the difference in the electronegativity of iodine and chlorine, this molecule is highly polar and behaves as a source of I+. Discovered in 1814 by Gay-Lussac, iodine monochloride is the first interhalogen compound discovered.

<span class="mw-page-title-main">Organolead chemistry</span>

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1,1,2-Trichloro-1,2,2-trifluoroethane, also called trichlorotrifluoroethane or CFC-113, is a chlorofluorocarbon. It has the formula Cl2FC−CClF2. This colorless, volatile liquid is a versatile solvent.

<span class="mw-page-title-main">Fluorine perchlorate</span> Chemical compound

Fluorine perchlorate, also called perchloryl hypofluorite is the rarely encountered chemical compound of fluorine, chlorine, and oxygen with the chemical formula ClO
4
F
or FOClO
3
. It is an extremely unstable gas that explodes spontaneously and has a penetrating odor.

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The Pinnick oxidation is an organic reaction by which aldehydes can be oxidized into their corresponding carboxylic acids using sodium chlorite (NaClO2) under mild acidic conditions. It was originally developed by Lindgren and Nilsson. The typical reaction conditions used today were developed by G. A. Kraus. H.W. Pinnick later demonstrated that these conditions could be applied to oxidize α,β-unsaturated aldehydes. There exist many different reactions to oxidize aldehydes, but only a few are amenable to a broad range of functional groups. The Pinnick oxidation has proven to be both tolerant of sensitive functionalities and capable of reacting with sterically hindered groups. This reaction is especially useful for oxidizing α,β-unsaturated aldehydes, and another one of its advantages is its relatively low cost.

<span class="mw-page-title-main">Ethyl bromodifluoroacetate</span> Chemical compound

Ethyl bromodifluoroacetate is an ester with the chemical formula F2BrCH−CO2CH2CH3. It can be used to introduce the CF2 group when synthesising chemical compounds. It is a colorless to yellow liquid. It is an ethyl ester of bromodifluoroacetic acid.

<span class="mw-page-title-main">Phenylsodium</span> Chemical compound

Phenylsodium C6H5Na is an organosodium compound. Solid phenylsodium was first isolated by Nef in 1903. Although the behavior of phenylsodium and phenyl magnesium bromide are similar, the organosodium compound is very rarely used.

References

  1. "Sodium chlorodifluoroacetate". pubchem.ncbi.nlm.nih.gov.
  2. 1 2 Taschner, Michael J. (2001). "Sodium Chlorodifluoroacetate". Encyclopedia of Reagents for Organic Synthesis. doi:10.1002/047084289X.rs058. ISBN   0-471-93623-5.
  3. Fuqua, Samuel A.; Duncan, Warren G.; Silverstein, Robert M. (1967). "β,β-Difluorostyene". Organic Syntheses. 47: 49. doi:10.15227/orgsyn.047.0049.