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T4885

Sigma-Aldrich

Trichloroacetic acid

≥99.0% (titration)

Synonym(s):

TCA

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About This Item

Linear Formula:
Cl3CCOOH
CAS Number:
76-03-9
Molecular Weight:
163.39
Beilstein/REAXYS Number:
970119
EC Number:
200-927-2
MDL number:
MFCD00004177
UNSPSC Code:
12352100
PubChem Substance ID:
24900233
NACRES:
NA.21

vapor density

<1 (vs air)

Quality Level

200

vapor pressure

1 mmHg ( 51 °C)

assay

≥99.0% (titration)

refractive index

n20/D 1.62 (lit.)

bp

196 °C (lit.)

mp

54-58 °C (lit.)

solubility

H2O: 1 g/10 mL

density

1.62 g/mL at 25 °C (lit.)

storage temp.

2-8°C

SMILES string

OC(=O)C(Cl)(Cl)Cl

InChI

1S/C2HCl3O2/c3-2(4,5)1(6)7/h(H,6,7)

InChI key

YNJBWRMUSHSURL-UHFFFAOYSA-N

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Application

Trichloroacetic acid (TCA) can be used as a catalyst to synthesize:
  • β-enaminones via condensation reaction of 1,3-dicarbonyl compounds and amines.
  • 6-amino-3-methyl-1,4-diphenyl-1,4-dihydropyrano[2,3-c]pyrazole-5-carbonitrile derivatives via four-component condensation reaction of ethyl acetoacetate, phenylhydrazine, malononitrile, and aromatic aldehydes.
  • Tetrahydrobenzo[a]xanthen-11-ones by three-component reaction of aldehydes, 2-naphthol and dimedone.

Traditionally used to precipitate protein. Has been used to determine protein concentration by quantitative precipitation. Used as decalcifier and fixative in microscopy.

pictograms

CorrosionEnvironment
GHS05,GHS09

signalword

Danger

hcodes

H314,H410

Hazard Classifications

Aquatic Acute 1 - Aquatic Chronic 1 - Eye Dam. 1 - Skin Corr. 1A

Storage Class

8B - Non-combustible corrosive hazardous materials

wgk_germany

WGK 2

flash_point_f

>235.4 °F - closed cup

flash_point_c

> 113 °C - closed cup

ppe

Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges

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Certificates of Analysis (COA)

Lot/Batch Number
BCCL7958
BCCK7736
SLCP4587
SLCP4570
SLCP4584

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Expeditious, four-component synthesis of 1, 4-dihydropyrano [2, 3-c] pyrazole derivatives catalyzed by trichloroacetic acid or ceric sulfate
Jaberi ZK, et al.
Acta Chimica Slovenica, 60(1), 105-108 (2013)
Efficient Synthesis of β-Enaminones and β-Enamino Esters Using Tris (Hydrogensulfato) Boron or Trichloroacetic Acid as Catalysts
Karimi-Jaberi Z and Takmilifard Z
European Chemical Bulletin, 2, 211-213 (2013)
Efficient, one-pot synthesis of tetrahydrobenzo [a] xanthen-11-ones and dibenzo [a, j] xanthenes using trichloroacetic acid as a solid heterogeneous catalyst under solvent-free conditions
Jaber ZK, et al.
E-Journal of Chemistry, 8(4), 1895-1899 (2011)
Alan Mortensen et al.
Biomarkers : biochemical indicators of exposure, response, and susceptibility to chemicals, 18(1), 55-62 (2012-10-17)
The ratio of the nitric oxide synthase (NOS) cofactor tetrahydrobiopterin (BH(4)) to its oxidized form dihydrobiopterin (BH(2)) has been suggested as an index of endothelial dysfunction. Consequently, much effort has been put into preserving the in vivo equilibrium between these
Valentina Folgiero et al.
Oncotarget, 5(8), 2052-2064 (2014-06-07)
Microenvironmental factors contribute to the immune dysfunction characterizing acute myeloid leukemia (AML). Indoleamine 2,3-dioxygenase 1 (IDO1) is an interferon (IFN)-γ-inducible enzyme that degrades tryptophan into kynurenine, which, in turn, inhibits effector T cells and promotes regulatory T-cell (Treg) differentiation. It
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