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190780

Sigma-Aldrich

Sodium trichloroacetate

97%

Synonym(s):

NaTCA, TCA sodium salt, Trichloroacetic acid sodium salt

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About This Item

Linear Formula:
CCl3CO2Na
CAS Number:
650-51-1
Molecular Weight:
185.37
Beilstein:
3773249
EC Number:
211-479-2
MDL number:
MFCD00064198
UNSPSC Code:
12352302
PubChem Substance ID:
24851461
NACRES:
NA.22

Assay

97%

SMILES string

[Na+].[O-]C(=O)C(Cl)(Cl)Cl

InChI

1S/C2HCl3O2.Na/c3-2(4,5)1(6)7;/h(H,6,7);/q;+1/p-1

InChI key

SAQSTQBVENFSKT-UHFFFAOYSA-M

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Application

Sodium trichloroacetate with trichloroacetic acid (TCA) undergoes rapid decarboxylation in dimethylformamide (DMF) in the presence of aldehydes to form nucleophilic trichloromethyl anion, which then adds to the aldehydes to form trichloromethyl carbinols. It can also undergo thermal decarboxylation in aprotonic solvents in the presence of olefins to generate dichlorocarbene as an intermediate.

Pictograms

Exclamation markEnvironment
GHS07,GHS09

Signal Word

Warning

Hazard Statements

H335,H410

Hazard Classifications

Aquatic Acute 1 - Aquatic Chronic 1 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

11 - 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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Two effective procedures for the synthesis of trichloromethyl ketones, useful precursors of chiral ?-amino and ?-hydroxy acids.
Corey EJ
Tetrahedron Letters, 33(24), 3435-3438 (1992)
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The thermal decarboxylation of alkali trichloroacetates in aprotic solvents. II. Decarboxylation in the presence of olefins.
Wagner WM
Rec. Trav. Chim., 80(7), 740-746 (1961)
Pierre E Galand et al.
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