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198323

Sigma-Aldrich

Cesium fluoride

99%

Synonym(s):

NSC 84270

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About This Item

Empirical Formula (Hill Notation):
CsF
CAS Number:
13400-13-0
Molecular Weight:
151.90
EC Number:
236-487-3
MDL number:
MFCD00010960
UNSPSC Code:
12352302
PubChem Substance ID:
24851873
NACRES:
NA.22

Assay

99%

form

liquid

mp

682 °C (lit.)

density

4.115 g/mL at 25 °C (lit.)

SMILES string

[F-].[Cs+]

InChI

1S/Cs.FH/h;1H/q+1;/p-1

InChI key

XJHCXCQVJFPJIK-UHFFFAOYSA-M

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General description

Cesium fluoride is an inorganic compound known to be a source of fluoride ion and a catalyst in organic synthesis. It has been used in many organic reactions like 1,4−elimination, desilylation, transesterification, acylation, nucleophilic aromatic substitution, etherification, cross−coupling reactions and so on.

Application

Cesium fluoride can be used as:
  • A base in the Suzuki cross-coupling synthesis of ortho-substituted biaryls.
  • A reagent for the nucleophilic fluorination of primary halides and sulfonates in protic media such as tert-butyl and tert-pentyl alcohols.

Reactant for:
  • Preparation of building blocks for synthesis of fluoroallylic compounds
  • Synthesis of alcohols via hydrolysis of alkyl silyl ethers at neutral pH in buffered mixed organic-aqueous solutions
  • Nucleophilic fluorination of alkynyliodonium salts to form fluorovinylic compounds
  • Nucleophilic aromatic substitution (SNAr) reactions
Used in the successful synthesis of a single-crystal Dion-Jacobson phase, CsLaTa2O7, that has applications in photocatalysis and superconductivity.

Signal Word

Danger

Hazard Statements

H302,H318,H361d,H373,H412

Hazard Classifications

Acute Tox. 4 Oral - Aquatic Chronic 3 - Eye Dam. 1 - Repr. 2 - STOT RE 2

Target Organs

Kidney,Adrenal gland

Supplementary Hazards

EUH032

Storage Class Code

13 - Non Combustible Solids

WGK

WGK 2

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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An efficient catalyst for the synthesis of ortho-substituted biaryls by the Suzuki cross-coupling: Triphenylphosphine adduct of cyclopalladated ferrocenylimine
Li H, et al.
Journal of Organometallic Chemistry, 691(26), 5688-5696 (2006)
Cesium Fluoride
e-EROS Encyclopedia of Reagents for Organic Synthesis. (2007)
A cesium fluoride promoted efficient and rapid multicomponent synthesis of functionalized 2-amino-3-cyano-4H-pyran and spirooxindole derivatives
Wagh YB, et al.
Chinese Chemical Letters = Zhongguo Hua Xue Kuai Bao, 26(10), 1273-1277 (2015)
A new class of SN2 reactions catalyzed by protic solvents: facile fluorination for isotopic labeling of diagnostic molecules
Kim DW, et al.
Journal of the American Chemical Society, 128(50), 16394-16397 (2006)
Dong Wook Kim et al.
Journal of the American Chemical Society, 128(50), 16394-16397 (2006-12-15)
Aprotic solvents are usually preferred for the SN2 reactions, because nucleophilicity and hence SN2 reactivity are severely retarded by the influence of the partial positive charge of protic solvents. In this work, we introduce a remarkable effect of using tertiary
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