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694037

Sigma-Aldrich

Cesium pivalate

98%

Synonym(s):

Cesium 2,2-dimethylpropanoate, Cesium trimethylacetate

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About This Item

Empirical Formula (Hill Notation):
C5H9O2Cs
CAS Number:
20442-70-0
Molecular Weight:
234.03
MDL number:
MFCD10567040
UNSPSC Code:
12352302
PubChem Substance ID:
329761643
NACRES:
NA.22

Assay

98%

form

powder

mp

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

InChI key

LGVUAXNPXVXCCW-UHFFFAOYSA-M

General description

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

Application

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.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

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

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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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
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
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
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
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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