Trichloroacetic Acid

A carboxylic acid, C2HCl3O2, 163.387 g/mol. Boiling point 195.5 °C, melting point 57.5 °C, as published.

verified recordOrganic — carboxylic acid8 measured properties

Identifiers

Molecular formula: C₂HCl₃O₂
Molecular weight: 163.387 g/mol
Exact mass: 161.904212 g/mol
IUPAC name: 2,2,2-trichloroacetic acid
SMILES: O=C(O)C(Cl)(Cl)Cl
InChI: InChI=1S/C2HCl3O2/c3-2(4,5)1(6)7/h(H,6,7)
InChIKey: YNJBWRMUSHSURL-UHFFFAOYSA-N

Open in ReactionLens Use in reaction prediction

Measured properties

Published measurements, each with its source. Two readings of one property are both shown, in the units each used.

Boiling Point: 385 to 387 °F at 760 mmHg (NTP, 1992)measured · CAMEO Chemicals; 195.5 °Cmeasured · Hazardous Substances Data Bank (HSDB)
Melting Point: 135 to 136 °F (NTP, 1992)measured · CAMEO Chemicals; 57.5 °Cmeasured · Hazardous Substances Data Bank (HSDB)
Density: 1.62 at 77 °F (NTP, 1992) - Denser than water; will sinkmeasured · CAMEO Chemicals; 1.6126 at 64 °Cmeasured · Hazardous Substances Data Bank (HSDB)
Solubility: greater than or equal to 100 mg/mL at 72 °F (NTP, 1992)measured · CAMEO Chemicals; The acid has a solubility in water at 25 °C of 1,000 g/100 ml; it is soluble in ethanol and diethyl ether.measured · Hazardous Substances Data Bank (HSDB)
Vapor Pressure: 1 mmHg at 123.8 °F ; 5 mmHg at 168.8 °F (NTP, 1992)measured · CAMEO Chemicals; 0.06 [mmHg]measured · Haz-Map, Information on Hazardous Chemicals and Occupational Diseases
LogP: log Kow = 1.33measured · Hazardous Substances Data Bank (HSDB); 1.33measured · Human Metabolome Database (HMDB)
Flash Point: greater than 230 °F (NTP, 1992)measured · CAMEO Chemicals
Refractive Index: Clear liquid; odor resembling menthol. Specific gravity = 1.373 at 20 °C/4 °C. BP 169 °C. Index of refraction = 1.4507 at 20 °C/D. Miscible with alcohol, ether. /Ethyl ester/measured · O'Neil, M.J. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. 13th Edition, Whitehouse Station, NJ: Merck and Co., Inc., 2001., p. 1716; Index of refraction: 1.4603 at 61 °Cmeasured · Lide, D.R. (ed.). CRC Handbook of Chemistry and Physics. 76th ed. Boca Raton, FL: CRC Press Inc., 1995-1996., p. 3-9

Calculated properties

Derived from the structure, not from a sample; kept apart from the measurements above.

Molecular weight: 163.38 g/molcalculated · reference compound database; Average mass of one molecule, from reference compound database.
Exact mass: 161.904212 Dacalculated · reference compound database; Mass of the most common isotopic form.
XLogP3: 1.3calculated · reference compound database; Estimated oil/water partition, computed by reference compound database.
Polar surface area: 37.3 Å²calculated · reference compound database; Polar surface area as computed by reference compound database.
Complexity: 83calculated · reference compound database; A rough measure of how intricate the structure is.
H-bond donors: 1calculated · reference compound database
H-bond acceptors: 2calculated · reference compound database
logP: 1.4412calculated · chemistry engine; Estimated preference for oil over water. Higher means more oil-like.
Topological polar surface area: 37.3 Å²calculated · chemistry engine; Surface area from polar atoms; relates to how easily a molecule crosses membranes.
H-bond donors: 1calculated · chemistry engine; Atoms that can donate a hydrogen bond.
H-bond acceptors: 1calculated · chemistry engine; Atoms that can accept a hydrogen bond.
Rotatable bonds: 0calculated · chemistry engine; Single bonds the molecule can freely twist around.
Molar refractivity: 27.9258 cm³/molcalculated · chemistry engine; Relates to the molecule's polarisability.
Fraction sp³ carbons: 0.5calculated · chemistry engine; Share of carbon atoms with tetrahedral bonding.
QED drug-likeness: 0.5488calculated · chemistry engine; Quantitative estimate of drug-likeness (0–1).

What it is made of

Elements

Cl Chlorine3 atoms · 65.1% by mass
O Oxygen2 atoms · 19.6% by mass
C Carbon2 atoms · 14.7% by mass
H Hydrogen1 atom · 0.6% by mass

Percentages are of the molecular weight above, worked out the same way the molar mass calculator does it.

Structure

Heavy atoms, hydrogen excluded: 7
Total atoms, hydrogen included: 8
Rings: 0
Aromatic rings: 0
Stereocentres: 0
Formal charge: 0

Functional groups

Carboxylic acid
A carbon double-bonded to oxygen and bonded to an –OH group; acidic.
Halide (C–X)
A halogen atom attached to carbon.

Matched by structural pattern, not by a measurement.

The molecule in three dimensions

Rotate and inspect the atoms. Loaded only when you ask, so the page stays light.

The drawing above is a diagram of what is bonded to what. A molecule is not flat, and the model here is one low-energy shape generated from the connectivity — useful for seeing which groups can reach each other, and not a measured structure. A real sample is a population of conformations, interconverting.

Reactions it appears in

No documented reaction with a written procedure and a source involves Trichloroacetic Acid yet.

Other names for it

The systematic name on this record is 2,2,2-trichloroacetic acid.

The sources also call it Aceto-caustin, Acetic acid, trichloro-, Trichloroethanoic acid, Trichloracetic acid, Konesta, Trichloressigsaeure, Trichloroacetate, 2,2,2-trichloroacetic acid, Amchem grass killer, Acido tricloroacetico, Acide trichloracetique.

Structurally related

Molecules sharing this formula, or whose fingerprint is at least 40% similar to this one. Similarity is Tanimoto on Morgan fingerprints over this library only — it is a measure of structural overlap, not of how alike they behave.

1,1,1,3,3-Pentachloro-2-propanone

C3HCl5O

Where these values came from

reference compound database6421
compound record
chemistry engine
structure perception

compound record.

What this page does not claim

Identifiers are copied from the source record, measured values are reported as published, and calculated values are marked as calculated. Nothing here is a hazard, purity or handling assessment — how the library is checked.