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Sigma-Aldrich

Cäsiumpivalat

98%

Synonym(e):

Caesium-2,2-dimethylpropionat, Caesiumtrimethylacetat

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About This Item

Empirische Formel (Hill-System):
C5H9O2Cs
CAS-Nummer:
20442-70-0
Molekulargewicht:
234.03
MDL-Nummer:
MFCD10567040
UNSPSC-Code:
12352302
PubChem Substanz-ID:
329761643
NACRES:
NA.22

Assay

98%

Form

powder

mp (Schmelzpunkt)

344-348 °C

SMILES String

[Cs+].CC(C)(C)C([O-])=O

InChI

1S/C5H10O2.Cs/c1-5(2,3)4(6)7;/h1-3H3,(H,6,7);/q;+1/p-1

InChIKey

LGVUAXNPXVXCCW-UHFFFAOYSA-M

Allgemeine Beschreibung

Cesium pivalate is an organic base widely used in palladium-catalyzed cross-coupling and carbonylation reactions due to its solubility in organic solvents.

Anwendung

Cesium pivalate can be used as a base to synthesize:
  • Fluoren-9-one derivatives by cyclocarbonylation of o-halobiaryls in the presence of palladium catalyst.
  • Fused heterocycles (dihydrobenzofurans and indolines) from o-bromo phenol and aniline precursors via Pd-catalyzed intramolecular coupling of two C(sp3)-H bonds.
  • Amides and esters derivatives containing a quaternary β-carbon atom by Pd-catalyzed C-H activation and amino/alkoxycarbonylation reaction.
It can also be used as a base in the palladium-catalyzed Mizoroki-Heck reaction.

Piktogramme

Exclamation mark
GHS07

Signalwort

Warning

Gefahreneinstufungen

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Zielorgane

Respiratory system

Lagerklassenschlüssel

11 - Combustible Solids

WGK

WGK 3

Flammpunkt (°F)

Not applicable

Flammpunkt (°C)

Not applicable

Persönliche Schutzausrüstung

dust mask type N95 (US), Eyeshields, Gloves

Analysenzertifikate (COA)

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Tomáš Čarný et al.
Angewandte Chemie (International ed. in English), 59(43), 18980-18984 (2020-07-22)
The 1,4-palladium shift strategy allows the functionalization of remote C-H bonds that are difficult to reach directly. Reported here is a domino reaction proceeding by C(sp3 )-H activation, 1,4-palladium shift, and amino- or alkoxycarbonylation, which generates a variety of amides
M A Campo et al.
Organic letters, 2(23), 3675-3677 (2000-11-14)
The synthesis of various substituted fluoren-9-ones has been accomplished by a novel palladium-catalyzed cyclocarbonylation of o-halobiaryls. The cyclocarbonylation of 4'-substituted-2-iodobiphenyls produces very high yields of 2-substituted fluoren-9-ones bearing either electron-donating or electron-withdrawing substituents. 3'-Substituted 2-iodobiphenyls afford in excellent yields with
Ronan Rocaboy et al.
Angewandte Chemie (International ed. in English), 58(41), 14625-14628 (2019-08-10)
The intramolecular coupling of two C(sp3 )-H bonds to forge a C(sp3 )-C(sp3 ) bond is enabled by 1,4-Pd shift from a trisubstituted aryl bromide. Contrary to most C(sp3 )-C(sp3 ) cross-dehydrogenative couplings, this reaction operates under redox-neutral conditions, with
Zubaoyi Yi et al.
The Journal of organic chemistry, 82(13), 6946-6957 (2017-06-16)
Pd-catalyzed arylation or benzylation of nitroazoles using aryl sulfonates or benzyl acetates is described. Electronically varied aryl tosylates and mesylates, as well as benzyl acetates, afford the arylated and benzylated products. Arylation of nitrobenzene is also reported. The relative rate
Aditya L Gottumukkala et al.
Chemistry (Weinheim an der Bergstrasse, Germany), 17(11), 3091-3095 (2011-02-10)
Ace of base: A catalytic system is presented that, solely by choice of the base, selectively switches between conjugate addition and the Mizoroki-Heck reaction of aryl halides with Michael acceptors (see scheme; R, R' = alkyl, aryl). For conjugate addition

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