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694037

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
NACRES:
NA.22
PubChem Substance ID:
329761643
UNSPSC Code:
12352302
MDL number:
MFCD10567040
Assay:
98%
Form:
powder
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Quality Level

100

assay

98%

form

powder

reaction suitability

core: Cesium

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

signalword

Warning

Hazard Classifications

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

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
SHBQ3944
SHBP3095
SHBP8087
SHBN0592
SHBL3414

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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
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Global Trade Item Number

SKUGTIN
694037-25G04061833510292
694037-5G04061833499887